Boronic Acids

Boronic Acids www.alfa.com

INCLUDING: • Boronic Esters • Oxazaborolidine Reagents • Coupling and Hydroboration Catalysts • Phosphine Ligands • Borylation Reagents

www.alfa.com Where Science Meets Service Quality Boronic Acids from Alfa Aesar

Alfa Aesar is known worldwide for a variety of chemical compounds used in research and development. Recognized for purity and quality, our products and brands are backed by technical and sales teams dedicated to providing you the best service possible.

In this catalog, you will find details on our line of boronic acids, esters and related compounds, which are manufactured to the same exacting standards as our full offering of over 33,000 products. Also included in this catalog is a 28-page introduction to boronic acids, their properties and applications.

This catalog contains only a selection of our wide range of chemicals and materials. Also included is a selection of novel coupling catalysts and ligands. Many more products, including high purity metals, analytical products, and labware are available in our main catalog or online at www.alfa.com. Table of Contents

About Us______II

How to Order/General Information______III

Introduction______1

Alkenylboronic acids and esters______29

Alkylboronic acids and esters______33

Alkyltrifluoroborate salts______38

Alkenyltrifluoroborate salts______39

Arylboronic acids______39

Arylboronic esters______107

Aryltrifluoroborate salts______128

Heterocyclic boronic acids______134

Heterocyclic boronic esters______144

Heterocyclic trifluoroborate salts______158

Oxazaborolidine reagents______159

Boronation reagents______161

Coupling catalysts______164

Phosphine ligands______174

Non-phosphine ligands______179

I About Us

GLOBAL INVENTORY

The majority of our boronic acids and related products are available in research and development quantities from stock. We also supply most products from stock in semi-bulk or bulk quantities. Many are in regular production and are available in bulk for next day shipment. Our experience in manufacturing, sourcing and handling a wide range of metals enables us to respond quickly and efficiently to your needs.

CUSTOM SYNTHESIS

We offer flexible custom manufacturing serviceswith the assurance of quality and confidentiality. We can deliver the chemical you need in sizes for research, pilot-scale and full- scale production applications.

CUSTOMER SERVICE

Our dedicated scientific and commercial teamsoffer full service from production to delivery. Most products are stocked in catalog pack sizes and the majority are available from stock in semi-bulk and bulk quantities as well. All specialty and bulk products are shipped with a batch specific certificate of analysis and material safety data sheet. Because we understand that specific packaging is often important, we offer custom packaging and labeling to meet your requirements.

QUALITY CONTROL

We employ advanced quality control for both in-process and final product testing phases. The high standard of our modern quality control and assurance facilities is matched by the expertise of our experienced staff.

II How to Order/ General Information

ORDERING of your receiving the materials. Restocking fees There is no minimum order. All orders are may be charged on authorized returns. accepted, regardless of size. TERMS OF SALE PRICING Full details of Terms and Conditions are listed Most current pricing may be found at our at the back of this catalog and on our website website: www.alfa.com. In cases where the (www.alfa.com). For health and safety reasons, selling price has changed significantly, we will we shall not supply chemicals to private contact you prior to filling your web, email or individuals or deliver to residential addresses. faxed order. Our payment terms are net 30 days Orders will be accepted from legitimate business of invoice. customers only.

SHIPPING NEW CUSTOMERS Whenever possible, we will ship products by the We welcome new customers and setting up an method specified on your order. account with Alfa Aesar is easy. Just call contact us and a customer service representative TECHNICAL SERVICE will assist you. At your request, we will furnish technical assistance and information with respect to our CONTACT US products. Our Technical Service Representatives WEBSITE are trained in specific product lines to answer www.alfa.com your questions regarding applications, Our webCatalysts catalog features up-to-date prices, specifications, product properties and handling. availability, MSDS, Certificates of Analysis and a user-friendly e-commerce system. MATERIAL SAFETY DATA SHEETS Each product ordered is automatically accompanied by a Material Safety Data Sheet (MSDS). If one is not immediately available, a copy will be sent via mail as soon as possible. If an MSDS is needed prior to shipment of a product please call us or visit our MSDS website at www.alfa.com/en/go160w.pgm#msds.

CERTIFICATES OF ANALYSIS Lot specific Certificates of analysis are available online at www.alfa.com. Please contact us by Pilot Plant/Custom phone, fax or email to request Certificates of Analysis as needed.

RETURN SHIPMENTS Some materials are not returnable. Returned shipments cannot be accepted unless prior arrangements have been made. Requests for return authorization must be made within 30 days

III Abbreviations and Codes The following abbreviations are used throughout our listing of products.

AAS Atomic absorption spectrometry N Normality of solution AES Atomic emission spectrometry Ë Refractive index for the sodium D line at ACS Chemicals meeting the specifications outlined 20 °C (or temperature indicated) by the American Chemical Society nm Nanometer APS Average particle size New product anhy Anhydrous NMR Nuclear magnetic resonance Å Angstrom OD Outer diameter ÷ Approximately optical gr. Suitable for optical applications approx. Approximately pc(s) Piece(s) Atm Atmospheres pH Value taken to represent the acidity or b.p. Boiling point in °C at 760mm pressure, unless alkalinity of an aqueous solution otherwise specified POR Price on request (c) Contained weight of active material ppb Parts per billion °C Celsius ppm Parts per million cc Cubic centimeter prec. Precipitated cm Centimeter Primary Analytical reagent of exceptional purity, cont. Contained Standard for standardizing volumetric solutions and cP Centipoise preparing reference standards cS Centistoke PTFE Poly(tetrafluoroethylene) d. Density Purified A grade of higher quality than technical, dec. Decomposes often used where there are no official dia. Diameter standards ea. Each P.T. Passes test eV Electron volt P.V. Pore volume °F Fahrenheit Reagent Reagent grade f.p. Flash point REM Rare earth metal FSSS Fisher sub-sieve sizer (REO) Rare earth oxide base - content of specific F.W. Formula weight rare earth element in comparison to total g Gram rare earths present g/l Grams per liter (gas density) S.A. Surface area GLC Suitable for use in gas liquid Sp.Gr. Specific gravity chromotography Sp.Rot. Specific rotation GC Gas chromotography subl. Sublimes HPLC High-performance liquid chromotography Tc Critical temperature ICP Inductively Coupled Plasma TLC Thin-layer chromotography ID Inner diameter TSCA Toxic Substance Control Act in Inch UN Hazardous material transportation incl Includes identification number IR Infrared œ Wavelength in nanometers J/mol.K Joule(s) per mole Kelvin wt Weight kg Kilogram w/w Weight/weight L or l Liter w/v Weight/volume lb Pound XRD X-ray diffraction m Meter È Air sensitive M Molarity of solution É Moisture sensitive mg Milligram Ê Hygroscopic æ Micro ß Light sensitive æg Microgram > Greater than meq Milliequivalent ² Greater than or equal to Merck The Merck Index < Less than æm Micrometer (micron) ³ Less than or equal to max Maximum [ ] Numbers in brackets after the chemical micron Micrometer description indicate the Chemical Abstract mm Millimeter Service Registry Number m.p. Melting point - mesh # 90% particles pass through screen having mol Mole a given mesh size mmol Millimole + mesh # 90% particles are retained by a screen M.W. Molecular weight having a given mesh size Mw Weighted averaged molecular weight Ì Denotes substance is listed in Toxic Mn Number averaged molecular weight Substance Control Act (TSCA) inventory Mw/Mn Monodispersity value 1 IA 18 VIIIA

1.00794 1 4.002602 2 Visit Our Website at

H1 He 1s 1s2 bp: -252.87°C bp: -268.9°C d: 0.089 g/ l www.alfa.com d: 0.179 g/l Hydrogen Helium 2 IIA 13 IIIA 14 IVA 15 VA 16 VIA 17 VIIA

6.941 3 9.012182 4 10.811 5 12.0107 6 14.0067 7 15.9994 8 18.9984032 9 20.1797 10

Li1 Be B 1 C N O F Ne [He] 2s [He] 2s2 [He] 2s2 2p [He] 2s2 2p2 [He] 2s2 2p3 [He] 2s2 2p4 [He] 2s2 2p5 [He] 2s2 2p6 mp: 180.5°C mp: 1287°C mp: 2076°C mp: 3527°C bp: -195.8°C bp: -182.9°C bp: -188.1°C bp: -246.1°C d: 0.53 g/cc d: 1.848 g/cc d: 2.46 g/cc d: 2.26 g/cc d: 1.25 g/l d: 1.43 g/l d: 1.696 g/l d: 0.8999 g/l Lithium Beryllium Boron Carbon Nitrogen Oxygen Fluorine Neon

22.989769 11 24.3050 12 26.981539 13 28.0855 14 30.973762 15 32.065 16 35.453 17 39.948 18 g Na1 M Al1 Si P S Cl Ar [Ne] 3s [Ne] 3s2 [Ne] 3s2 3p [Ne] 3s2 3p2 [Ne] 3s2 3p3 [Ne] 3s2 3p4 [Ne] 3s2 3p5 [Ne] 3s2 3p6 mp: 97.72°C mp: 650°C mp: 660.3°C mp: 1414°C mp: 44.2°C mp: 115.21°C bp: -34.0°C bp: -185.8°C d: 0.968 g /cc d: 1.738 g/cc d: 2.70 g/cc d: 2.33 g/cc d: 1.82 g/cc d: 1.96 g/cc d: 3.21 g/l d: 1.784 g/l Sodium Magnesium Periodic Table of Elements Aluminum Silicon Phosphorus Sulfur Chlorine Argon 3 IIIB 4 IVB 5 VB 6 VIB 7 VIIB 8 VIII 9 VIII 10 VIII 11 IB 12 IIB

39.0983 19 40.078 20 44.955912 21 47.867 22 50.9415 23 51.9961 24 54.938045 25 55.845 26 58.933195 27 58.6934 28 63.546 29 65.38 30 69.723 31 72.64 32 74.92160 33 78.96 34 79.904 35 83.798 36

K1 Ca Sc1 Ti V Cr1 Mn Fe Co Ni Cu1 Zn Ga1 Ge As Se Br Kr [Ar] 4s [Ar] 4s2 [Ar] 3d 4s2 [Ar] 3d2 4s2 [Ar] 3d3 4s2 [Ar] 3d5 4s [Ar] 3d5 4s2 [Ar] 3d6 4s2 [Ar] 3d7 4s2 [Ar] 3d8 4s2 [Ar] 3d10 4s [Ar] 3d10 4s2 [Ar] 3d10 4s2 4p [Ar] 3d10 4s2 4p2 [Ar] 3d10 4s2 4p3 [Ar] 3d10 4s2 4p4 [Ar] 3d10 4s2 4p5 [Ar] 3d10 4s2 4p6 mp: 63.4°C mp: 842°C mp: 1668°C mp: 1910°C mp: 1907°C mp: 1246°C mp: 1495°C mp: 1455°C mp: 1084°C mp: 419.5°C mp: 29.8°C mp: 938.3°C 817°C subl. mp: 221°C bp: 59.47°C bp: -157.36°C mp: 1541°C mp: 1538°C d: 0.856 g/cc d: 1.55 g/cc d: 4.507 g/cc d: 6.11 g/cc d: 7.14 g/cc d: 7.47 g/cc d: 8.90 g/cc d: 8.908 g/cc d: 8.92 g/cc d: 7.14 g/cc d: 5.90 g/cc d: 5.32 g/cc d: 5.73 g/cc d: 4.82 g/cc d: 3.12 g/cc 3.73 g/l d: 2.985 g /cc d: 7.87 g/cc Potassium Calcium Scandium Titanium Vanadium Chromium Manganese Iron Cobalt Nickel Copper Zinc Gallium Germanium Arsenic Selenium Bromine Krypton

85.4678 37 87.62 38 88.90585 39 91.224 40 92.90638 41 95.96 42 98 43 101.07 44 102.90550 45 106.42 46 107.8682 47 112.411 48 114.818 49 118.710 50 121.760 51 127.60 52 126.90447 53 131.293 54 g Rb1 Sr Y1 Zr Nb1 Mo1 Tc Ru1 Rh1 Pd A 1 Cd In 1 Sn Sb Te I Xe [Kr] 5s [Kr] 5s2 [Kr] 4d 5s2 [Kr] 4d2 5s2 [Kr] 4d4 5s [Kr] 4d5 5s [Kr] 4d5 5s2 [Kr] 4d7 5s [Kr] 4d8 5s [Kr] 4d10 [Kr] 4d10 5s [Kr] 4d10 5s2 [Kr] 4d10 5s2 5p [Kr] 4d10 5s2 5p2 [Kr] 4d10 5s2 5p3 [Kr] 4d10 5s2 5p4 [Kr] 4d10 5s2 5p5 [Kr] 4d10 5s2 5p6 mp: 39.3°C mp: 777°C mp: 1526°C mp: 1855°C mp: 2477°C mp: 2623°C mp: 2157°C mp: 2334°C mp: 1964°C mp: 1554.9°C mp: 961.8°C mp: 321.1°C mp: 156.6°C mp: 231.9°C mp: 630.6°C mp: 449.5°C mp: 113.7°C mp: -108°C d: 1.532 g/cc d: 2.64 g/cc d: 4.47 g/cc d: 6.51 g/cc d: 8.57 g/cc d: 10.28 g/cc d: 11.50 g/cc d: 12.37 g/cc d: 12.45 g/cc d: 12.02 g/cc d: 10.49 g/cc d: 8.65 g/cc d: 7.31 g/cc d: 7.31 g/cc d: 6.69 g /cc d: 6.24 g/cc d: 4.94 g/cc d: 5.89 g/l Rubidium Strontium Yttrium Zirconium Niobium Molybdenum Technetium Ruthenium Rhodium Palladium Silver Cadmium Indium Tin Antimony Tellurium Iodine Xenon

132.905452 55 137.327 56 57-71 178.49 72 180.94788 73 183.84 74 186.207 75 190.23 76 192.217 77 195.084 78 196.966569 79 200.59 80 204.3833 81 207.2 82 208.98040 83 [209] 84 [210] 85 [222] 86 g Cs1 Ba La- Hf Ta W Re Os Ir Pt Au1 H Tl 1 Pb Bi Po At Rn [Xe] 6s [Xe] 6s2 [Xe] 4f145d26s 2 [Xe] 4f14 5d3 6s2 [Xe] 4f14 5d4 6s2 [Xe] 4f14 5d5 6s2 [Xe] 4f14 5d6 6s2 [Xe] 4f14 5d7 6s2 [Xe] 4f14 5d9 6s [Xe] 4f14 5d10 6s [Xe] 4f14 5d10 6s2 [Xe] 4f14 5d10 6s26p [Xe] 4f14 5d10 6s2 6p2 [Xe] 4f14 5d10 6s2 6p3 [Xe] 4f14 5d10 6s2 6p4 [Xe] 4f14 5d10 6s2 6p5 [Xe] 4f14 5d10 6s2 6p6 mp: 28.4°C mp: 727°C mp: 2233°C mp: 3017°C mp: 3422°C mp: 3186°C mp: 3033°C mp: 2446°C mp: 1768.4°C mp: 1064.2°C bp: 356.73°C mp: 304°C mp: 327.5°C mp: 271.3°C mp: 254°C mp: 302°C bp: -61.7°C d: 1.88 g/cc d: 3.51 g/cc d: 13.31 g/cc d: 16.65 g/cc d: 19.25 g/cc d: 21.02 g/cc d: 22.61 g/cc d: 22.56 g/cc d: 21.09 g/cc d: 19.30 g/cc d: 13.534 g/cc d: 11.85 g/cc d: 11.34 g/cc d: 9.78 g/cc d: 9.20 g/cc d: none d: 9.73 g/cc Cesium Barium Lu Hafnium Tantalum Tungsten Rhenium Osmium Iridium Platinum Gold Mercury Thallium Lead Bismuth Polonium Astatine Radon

[223] 87 [226] 88 89-103 [261] 104 [262] 105 [266] 106 [264] 107 [277] 108 [268] 109 [271] 110 [272] 111 [285] 112 [284] 113 [289] 114 [288] 115 [293] 116 ISO 9001:2008 ISO 14001:2004 Ac- g Ds Rg Cn Uut Uuq Uup Uuh BS OHSAS 18001:2007 Fr1 Ra Rf Db S Bh Hs Mt [Rn] 7s [Rn] 7s2 [Rn] 5f14 6d2 7s2 [Rn] 5f14 6d3 7s2 [Rn] 5f14 6d4 7s2 [Rn] 5f14 6d5 7s2 [Rn] 5f14 6d6 7s2 [Rn] 5f14 6d7 7s2 [Rn] 5f14 6d9 7s1 [Rn] 5f14 6d10 7s1 [Rn] 5f14 6d10 7s2 [Rn] 5f14 6d10 7s2 7p1 [Rn] 5f14 6d10 7s2 7p2 [Rn] 5f14 6d10 7s2 7p3 [Rn] 5f14 6d10 7s2 7p4 Certified mp: 27°C mp: 700°C mp: none mp: none mp: none mp: none mp: none mp: none mp: none mp: none mp: none mp: none mp: none mp: none mp: none d: 2.29 g/cc d: 5.00 g/cc d: none d: none d: none d: none d: none d: none d: none d: none d: none d: none d: none d: none d: none Francium Radium Lr Rutherfordium Dubnium Seaborgium Bohrium Hassium Meitnerium Darmstadtium Roentgenium Copernicium Ununtrium Ununquadium Ununpentium Ununhexium

138.90547 57 140.116 58 140.90765 59 144.242 60 [145] 61 150.36 62 151.964 63 157.25 64 158.92535 65 162.500 66 164.93032 67 167.259 68 168.93421 69 173.054 70 174.9668 71 Key y La1 Ce Pr Nd Pm Sm Eu Gd1 Tb D Ho Er Tm Yb Lu [Xe] 5d 6s2 [Xe] 4f1 5d1 6s2 [Xe] 4f3 6s2 [Xe] 4f4 6s2 [Xe] 4f5 6s2 [Xe] 4f6 6s2 [Xe] 4f7 6s2 [Xe] 4f75d 6s2 [Xe] 4f9 6s2 [Xe] 4f10 6s2 [Xe] 4f11 6s2 [Xe] 4f12 6s2 [Xe] 4f13 6s2 [Xe] 4f14 6s2 [Xe] 4f14 5d 6s2 1.00794 1 mp: 920°C mp: 795°C mp: 935°C mp: 1024°C mp: 1100°C mp: 1072°C mp: 826°C mp: 1312°C mp: 1356°C mp: 1407°C mp: 1461°C mp: 1529°C mp: 1545°C mp: 824°C mp: 1652°C d: 6.15 g/cc d: 6.69 g/cc d: 6.64 g/cc d: 6.8 g/cc d: 7.26 g/cc d: 7.35 g/cc d: 5.24 g/cc d: 7.90 g/cc d: 8.22 g/cc d: 8.55 g/cc d: 8.79 g/cc d: 9.07 g/cc d: 9.32 g/cc d: 6.57 g/cc 9.84 g/cc Lanthanum Cerium Praseodymium Neodymium Promethium Samarium Europium Gadolinium Terbium Dysprosium Holmium Erbium Thulium Ytterbium Lutetium

H1 1s [227] 89 232.03806 90 231.03588 91 238.02891 92 [237] 93 [244] 94 [243] 95 [247] 96 [247] 97 [251] 98 [252] 99 [257] 100 [258] 101 [259] 102 [262] 103 bp: -259.3°C d: 0.088 g/ l Hydrogen p Ac1 Th Pa1 U1 N 1 Pu Am Cm1 Bk Cf Es Fm Md No Lr [Rn] 6d 7s2 [Rn] 6d2 7s2 [Rn] 5f26d 7s2 [Rn] 5f36d 7s2 [Rn] 5f46d 7s2 [Rn] 5f6 7s2 [Rn] 5f7 7s2 [Rn] 5f76d 7s2 [Rn] 5f9 7s2 [Rn] 5f10 7s2 [Rn] 5f11 7s2 [Rn] 5f12 7s2 [Rn] 5f13 7s2 [Rn] 5f14 7s2 [Rn] 5f14 6d 7s2 mp: 1050°C mp: 1842°C mp: 1568°C mp: 1132.3°C mp: 637°C mp: 639.4°C mp: 1176°C mp: 1340°C mp: 986°C mp: 900°C mp: 860°C mp: 1527°C mp: 827°C mp: 827°C mp: 1627°C d: 10.07 g/cc d: 11.72 g/cc d: 15.37 g/cc d: 19.05 g/cc d: 20.45 g/cc d: 19.81 g/cc d: 13.67 g/cc d: 13.51 g/cc d: 14.78 g/cc d: 15.10 g/cc d: 8.84 g/cc d: none d: none d: none d: none Actinium Thorium Protactinium Uranium Neptunium Plutonium Americium Curium Berkelium Californium Einsteinium Fermium Mendelevium Nobelium Lawrencium

Element Density Boiling or Melting Point in °C Electron Configuration Symbol Atomic Weight Atomic Number Boronic Acids

Humayan S Rashid, Alfa Aesar

A major role in modern chemistry is played by organoboron compounds, from which boronic acids have emerged in a leading position. With the discovery of a wealth of new chemistry, in particular the Suzuki-Miyaura cross-coupling reaction, together with their accessibility and ease of handling, boronic acids and boronates are now established as intermediates of great value and versatility. Applications abound in synthesis, catalysis, analytical chemistry and biological systems. Since the commercial introduction of a small range of boronic acids by the former Lancaster Synthesis Ltd., more than thirty years have elapsed during which the astonishing growth of interest in this area of chemistry has been paralleled by an enormous increase in the diversity of examples available from commercial sources, including Alfa Aesar. With a recently expanded range of well over 1500 boronic acids, esters and organotrifluoroborates, we can provide outstanding synthetic and analytical expertise in these products. This publication outlines the chemical properties and highlights the main synthetic uses of these versatile molecules.

1. Introduction Table 2: Typical covalent bond energies1,2 Bond Bond energy Elemental boron is rather difficult to isolate in a -1 -1 pure state, in which it is usually obtained as an kJ mol kcal mol extremely hard, dark brown or black powder, mp B-H 375 90 2075˚C. Its properties, such as electronegativity B-C 323 77 (Table 1), are those of a non-metal or metalloid, B-O 544 130 although organoboron compounds are often classed as organometallics, since they have B-F 659 158 certain similarities to compounds of some B-Cl 456 109 metallic elements. B-B 286 68 C-C 358 85 Table 1: Electronegativities (Pauling) Li-C 126 30 of representative elements1 Si-C 301 72 H 2.20 Li 0.98 Sn-C 225 54 Be 1.57 Mg 1.31 B 2.04 Al 1.61 Since trivalent boron has a vacant p-orbital, C 2.55 Si 1.90 organoboron compounds3 are Lewis acidic in N 3.04 P 2.19 character. They also tend to be air-sensitive, O 3.44 S 2.58 and in some cases pyrophoric. In 1859, before Mendeleev’s periodic classification of the F 3.98 Cl 3.16 elements, Frankland4 reported the reaction of Zn 1.65 Pd 2.20 pyrophoric diethylzinc with triethyl borate to Cu 1.90 Sn 1.96 form a new pyrophoric product, triethylborane, readily oxidized by air to diethylborinic acid

Table 2 shows a representative selection of Et2BOH. A second, slow oxidation step gave bond strengths involving boron, along with data a more stable, crystalline product, identified for related elements for comparison. as ethylboronic acid EtB(OH)2. This sequence, the first known synthesis of a boronic acid, is inconvenient and of limited scope, but even so, half a century elapsed before the publication 1 of Khotonsky and Melamed’s preparation of increase acidity, and electron-releasing groups benzeneboronic acid from phenylmagnesium decrease it.14 bromide and trimethyl borate,5 which was to OH O become the basis of the most generally useful RB + H2O RB + H O route to boronic acids. The procedure was 3 OH OH improved in the 1930s by Johnson,6 and in the 1950s by Washburn.8 Further details can be found in Section 4. OH OH RB + 2H2O RBOH + H3O Although organoboron chemistry became OH OH a focus of attention in the second half of the 20th century, largely due to the work of H. C. Scheme 1 Brown, boronic acid chemistry continued to be a relative backwater over 100 years after In this review, the reactions of boronic acids are Frankland’s initial disclosure, but from the 1970s divided into two broad categories, according to onwards, the level of interest has increased whether they involve retention or cleavage of dramatically, as new applications have come to the boron-carbon bond, which are discussed light. Whereas the chemistry of boronic acids in Sections 2 and 3 respectively. Section 4 could be covered by a 47-page review in 1964,9 outlines some of the preparative methods used a recent comprehensive monograph on the for boronic acids and boronates. subject runs to well over 500 pages.10

Most boronic acids are crystalline solids, easily 2. Reactions in which the B–C bond handled in the presence of air and moisture. is retained They are usually stable to long-term storage, but may undergo dehydration (see below) or, Boroxine formation in some cases, are prone to air oxidation or gradual degradation. Where these may present Most boronic acids readily undergo dehydration a problem, either the corresponding boronate (Scheme 2) to form the cyclic trimeric anhydride ester (Section 2) or trifluoroborate salt (Section (boroxine; 1,3,5,2,4,6-trioxatriborinane). This 3) usually offers a satisfactory alternative often tends to occur spontaneously at room which can undergo many of the reactions temperature, or in the course of drying, so of the boronic acid itself. Such evidence as that it may be difficult to obtain the acid free exists indicates that the boronic acid moiety from the anhydride. Apart from difficulties 11 is of relatively low intrinsic toxicity. Recent in characterization (variable analyses and 11 applications in medicine support this view. unreproducible melting points), this is rarely a From an environmental perspective, boronic serious problem, since in many applications, acids will degrade ultimately to the relatively the acid and the anhydride are essentially benign boric acid, although the fate of the rest indistinguishable. of the molecule will obviously depend on the nature of any substituents. R OH B -3H2O O O Chemical character 3 R B B B OH R O R Since the electron-deficient boron atom has a vacant p-orbital, boronic acids behave as mild Scheme 2 Lewis acids, which can coordinate to Lewis bases. Hence, in water they tend to coordinate However, if required, conversion of the boronic an OH group to form the tetrahedral anionic acid to a boronate ester with a suitable diol (see species, rather than acting as Brønsted acids below) will prevent the dehydration reaction. by losing a proton (Scheme 1).13 The measured acidity of arylboronic acids is comparable to phenols (benzeneboronic acid: pKa 8.9 in water); alkylboronic acids are weaker. Electron- withdrawing substituents on the aryl group 2 3 Boronate formation: protection of diols including the selective transport of sugars in lipophilic environments,28,29 and the design Boronic acids react with alcohols, with loss of artificial receptors, as discussed in several of water, to form boronic esters (boronates). reviews.30-34 With simple alcohols, the products are very susceptible to hydrolysis, but with 1,2- and Boronic derivatives as activating and 1,3-diols, the resulting cyclic boronates (1,3,2- directing groups dioxaborolanes and 1,3,2-dioxaborinanes) are stable enough to be isolated. The mild Lewis acidity of boronic acids, along with the ease of exchange around oxygen or The main early application was for protection nitrogen atoms attached to boron, has led to the and derivatization of 1,2- and 1,3-diols, application of the acids and their derivatives as 15 particularly in carbohydrate chemistry. These catalysts or temporary scaffolds in a variety of boronates have been widely used as volatile regio-, stereo- and enantioselective syntheses. derivatives for GC and GC-MS purposes. They Arylboronic acids can behave as water-, acid-, may be formed simply by stirring the boronic and base-tolerant, thermally stable Lewis acid and diol together at ambient temperature, acids. Yamamoto has found that a boronic or by warming, or, if necessary, with azeotropic acid with electron withdrawing substituents, in removal of water. A detailed examination particular 3,4,5-trifluorobenzeneboronic acid of boronic acid-diol complexation has been can be an effective catalyst for amidation and 16 published. Usually cleavage occurs readily esterification of carboxylic acids.35 The reaction under hydrolytic conditions, by exchange is thought to involve a 6-membered cyclic 17 with a glycol, or by treatment with hydrogen intermediate (Scheme 4). peroxide.18 Hindered boronic esters, such as

those of pinacol (2,3-dimethyl-2,3-butanediol),

H 1 2 O may be relatively stable to hydrolysis, and O O O R R ArB(OH)2 (1 mol%) N R1 can often be purified by chromatography. B H R N R OH toluene (azeotrope) R O Ar A useful application of boronate protection R2 is in the osmium(VIII) oxide catalyzed cis- dihydroxylation of alkenes under anhydrous Scheme 4 conditions in the presence of a boronic acid (Scheme 3).19,20 The amidation reaction has been extended to ureas.36 3,4,5-Trifluorobenzeneboronic O- Ph OH R2 ON acid also catalyzes the one-pot synthesis of 1 B R2 R CH3 30% H2O2 1 + O R O 2 acyl azides from carboxylic acids and sodium PhB(OH)2 OsO (0.2mol%) R EtOAc/acetone OH 4 R1 azide,37 and the one-pot reduction of carboxylic CH2Cl2 1:1 acids to alcohols with sodium borohydride.38 Scheme 3 In some reactions, 3-nitrobenzeneboronic acid may be an effective catalyst, as in the Further information on the applications of transesterification of á-keto esters.39 The use boronic acids as derivatizing and protecting of arylboron compounds as acid catalysts was agents can be found in various reviews21-23 and reviewed by Ishihara and Yamamoto.40 monographs.24-26 Benzeneboronic acid mediates the ortho- Other applications of diol boronates specific à-hydroxyalkylation of phenols by aldehydes.41 The key intermediate is a cyclic The formation of boronic esters with polymer- boronate, formed via a [3,3] sigmatropic bound diols has been utilized as a linker system rearrangement. This process was utilized in the mild syntheses of benzo-fused heterocycles, for solid phase synthesis, enabling modification 42 of the polymer-bound boronic acid, followed by including tetrahydrocannabinoids, and 2H- 43 mild deprotection with methanol.27 chromenes (Scheme 5).

Many other uses of boronates formed with carbohydrate molecules have been developed,

2 3 OH O OH Oxazaborolidines B PhB(OH)2 Ph H O O + toluene The reaction of a boronic acid with a chiral R (azeotrope) R 2-amino alcohol gives an oxazaborolidine. These derivatives were introduced by Corey, Bakshi R' 48 R' and Shibata (“CBS” reagents) as excellent O Ph catalysts for enantioselective borane reduction B R' of prochiral ketones (Scheme 7) with very high O O yield and enantiomeric excess (ee). R O O CO2Me BH3. THF R O MeO Ph R' Ph MeO

MeO O Scheme 5 N B MeO 98% (2 mol%) CH3 95% ee Chiral boronates Scheme 7 Matteson has carried out extensive work on cyclic boronates,44,46 formed from chiral diols, which undergo carbon insertion with LiCHCl2 The reagents derived from (R)- and (S)-à,à- in the presence of zinc chloride in up to 99% diphenylprolinol, usually with methylboronic acid: diastereomeric excess (de). Treatment of the (R)- and (S)-2-methyl-CBS-oxazaborolidine have resulting à-chloro boronic esters with various received the most attention, although the use nucleophiles leads to à-substituted boronic of other amino alcohols has been reported.49,50 esters which can be oxidatively cleaved with Reviews on the use of oxazaborolidines as hydrogen peroxide, or the sequence can be enantioselective catalysts,51-53 and the asymmetric repeated to introduce a second chiral carbon reduction of ketones54,55 are available. atom, as illustrated in Scheme 6. Diels-Alder reactions R O Cl2CH O R LiCHCl2 R1 B B 100o Boronic acids can form stable chiral acyloxyborane O - 1 O R R R (CAB) catalysts with tartaric acid derivatives. ZnCl2 0-25o These compounds have been developed by H Cl Cl O R R Yamamoto as catalysts for asymmetric Diels- R1 O 56 57 B Alder and hetero Diels-Alder reactions, for R2MgX or R2Li B R1 O 2 example between aldehydes and Danishefsky’s R o R O R -78 diene [1-methoxy-3-(trimethylsiloxy)-1,3-

H2O2, OH- 1. LiCHCl2 butadiene] to give, enantioselectively, dihydro-4- 2. ZnCl 58 R1 2 pyrone derivatives (Scheme 8). 3. R3MgX OH 1 4. H2O2, OH- i 2 R OPr O CO2H O R OMe 3 R O 2 R O O O O + i B OH OPr Me3SiO Ph H (20 mol%) Ar O Ph 80% yield Scheme 6 [Ar = 2-MeOC6H4] 79% ee

Scheme 8 Further aspects of this area of boronic ester chemistry have since been reviewed by 47 Matteson. Benzeneboronic acid itself can be used as a template for Diels-Alder reactions by forming boronate linkages with a hydroxy diene and a

4 5 hydroxy dieneophile,59 an approach which was undergo palladium-catalyzed cross-coupling applied successfully by Nicolaou to synthesize with aryl bromides and iodides in the presence the fully functionalized CD ring system of Taxol of a base (Scheme 10), which stimulated the (Scheme 9).60 greatest interest in the this reaction. As a result, a plethora of applications and variants have EtO2C EtO2C O PhB(OH)2 subsequently been developed leading to the + O O synthesis of unsymmetrical biaryls and many O O other types of coupled products.66 OH OH B O Ph O (Ph3P)4Pd (3 mol%) B(OH)2 + X O O EtO2C Z Z' 2Na2CO3 Z Z' H benzene/H2O + NaX HO OH EtO2C OH H O Scheme 10 O Early methods for biaryl synthesis generally Scheme 9 involved high temperatures (Ullmann coupling), or were low-yielding and unselective (Gomberg- The use of boron acids as protective agents Bachmann). Direct couplings of highly-reactive, and catalysts in synthesis has been reviewed moisture- and air-sensitive organometallic 23 by Duggan and Tyndall. reagents (Grignard, organolithium, organozinc, etc.) with aryl halides, generally in the presence of a transition metal catalyst, normally require strictly anhydrous conditions and an inert 3. Reactions involving B–C bond atmosphere, and are of limited scope, since the presence of many functional groups interferes. cleavage In contrast, Suzuki and Miyaura carried out the cross-coupling of boronic acids under In the reactions described in the following aqueous conditions, and the reaction tolerates sections, displacement of boron takes place a wide variety of functional groups. The with formation of a new carbon-carbon or widely-used Stille cross-coupling reaction,67 by carbon-heteroatom bond. comparison,68 is also extremely versatile, and in some ways complementary to the boronic coupling, but involves toxic, environmentally C–C bond-formation hazardous organotin species.

The Suzuki-Miyaura cross-coupling Recently, Kaboudin and co-workers,69 reaction demonstrated a reaction whereby homocoupling of arylboronic acid mediated by copper In comparison with typical organometallic (II) sulfate in DMF affords corresponding compounds of lithium, magnesium or symmetrical biaryls in good yield (scheme 11). the transition metals, the difference in

CuSO4 (1 equiv), 4 A MS electronegativity between boron and carbon 2 B(OH)2 is relatively small, and the boron-carbon R DMF, air, 50 0C, 1-5 h R R bond strong (see Tables 1,2). Organoboron up to 91% isolated compounds, therefore, in the absence of a catalyst, normally exhibit very low reactivity Scheme 11 towards electrophiles such as organic halides. Since its first disclosure, the cross-coupling In 1979, Suzuki and Miyaura reported the reaction of boronic acids (usually known as successful coupling of alkenyl-boranes and the Suzuki or Suzuki-Miyaura reaction) has catecholyl boronates, in the presence of a Pd(0) 61 62 been developed in methodology and scope catalyst and a base, with alkenyl and alkynyl, to become a cornerstone of modern synthetic aryl63 allyl and benzyl64 halides. However, 65 organic chemistry, from high-throughput it was their discovery, published in 1981, screening to full-scale production. Because of that stable, easily-handled arylboronic acids its versatility and the mild reaction conditions, 4 5 it has been widely adopted for solid-phase experimental procedures are described in synthesis on polymer supports.70-75 Organic Syntheses.95 Many reviews of the Suzuki-Miyaura and related reactions have Under the standard coupling conditions, been published, including those by Suzuki aryl bromides are the most frequently used and Miyaura,96,97 by Martin and Yang,92 with electrophilic coupling partners, but iodides, if particular emphasis on heteroaryl systems, available, are often preferred since they are and by Stanforth98 on biaryl synthesis via more reactive, as shown by the respective cross-coupling reactions. Nicolaou’s review99 bond energies (Table 3). features the use of palladium-catalyzed cross- couplings, including the Suzuki reaction, in Table 3: Bond dissociation energies of halobenzenes) selected total syntheses of natural products. More recent developments in the Suzuki cross- Bond Bond energy coupling have been reviewed by Kotha,100 and -1 -1 kJ mol kcal mol by Rossi.101 A review of palladium-catalyzed Ph-Cl 402 96 coupling reactions of aryl chlorides is also 102 Ph-Br 339 81 available, as is a general review of aryl-aryl bond formation.103 Ph-I 272 65

The coupling of unactivated aryl chlorides, Related coupling reactions which tend to be more readily available and cheaper, but are significantly less reactive, In early extensions of the biaryl coupling reaction, than the corresponding bromides or iodides, aryl- and heterorarylboronic acids were coupled has been achieved under modified conditions, with a variety of heterocyclic halides, including using a wide variety of palladium catalysts,76- thiophenes,104 furans, thiazoles,105 oxazoles,106 87 including systems developed by Johnson isoxazoles,107 pyridines,77,108-110 quinolines,108 Matthey chemists88 In some cases nickel-based pyrimidines,105,109,111 and pyrazines.109,110 Many catalysts have been successfully used.89,90 further examples have subsequently been published. A proposed catalytic cycle for the reaction91,92 is shown in Scheme 12. A detailed mechanistic Aryl112,113 or vinyl114 triflates also undergo boronic study has also been published.93 acid coupling, which usefully extends the scope of the reaction to phenols or enols. The relative Ar Ar' Pd(0) Ar'X reactivity of leaving groups is normally in the order I - > OTf - > Br - >> Cl (compare Table 3 above). Cross-coupling of boronate derivatives with aryl mesylates,115 and tosylates,116 Ar Pd Ar' Ar' Pd X catalyzed by nickel complexes, has also been described, as has palladium-catalyzed coupling with sulfonium salts117 or sulfonyl [B(OH) ]- Na+ 4 Ar'Pd OH chlorides.118 Coupling of arylboronic acids with heteroaryl thioethers has been brought OH- NaX ArB(OH)2 ArB(OH)3 about with a palladium catalyst, mediated by a Cu(I) carboxylate,119 while nickel-catalyzed Scheme 12 coupling with aryl quaternary ammonium salts has also been reported.120 Other substrates Suzuki and Miyaura’s initial publication was (Pd-catalyzed) for arylboronic acid cross- followed by a series of papers by Gronowitz et coupling include: benzyl bromides,121 à-bromo al,94 who showed that the deborylation found esters,122 vinyl halides,123-125 allylic bromides126 as a side reaction, particularly with electron- or acetates,127 allenic alcohols,128 propargylic rich boronic acids, could be minimized by alcohols,129 and allylic alcohols (Pd-catalyzed130 using dimethoxyethane (DME) as solvent in or Rh-catalyzed131). conjunction with aqueous Na2CO3. This system was found to be applicable to a variety of aryl As already stated, Suzuki and Miyaura’s and heteroaryl substrates, and has been widely earliest papers on the cross-coupling reaction adopted by other workers. Alternative illustrative 6 7 related to alkenylboranes and boronic esters by Pd(OAc)2 in dioxane or methanol, needed of catechol,62,63 and, although the use of free neither added base nor phosphine ligand.140 boronic acids now predominates, aryl and They applied similar conditions to the enol boronates, especially with pinacol (2,3- coupling of diazonium tetrafluoro-borates with dimethyl-2,3-butanediol), still find use in the potassium aryl trifluoroborates,141 which are air- reaction, particularly in examples where they are stable crystalline solids readily prepared from

more accessible via coupling or hydroboration arylboronic acids and KHF2, and potassium methods (see Section 4), or more stable, than vinyl trifluoro-borates,142 which are also readily the corresponding free boronic acids. This is isolable crystalline solids, more stable than the frequently an advantage in complex, multi-step corresponding vinylboronic acids. The cross- syntheses, where the boronate substituent coupling of potassium aryl and heteroaryl can be introduced under mild conditions, and trifluoroborates with aryl and heteroaryl halides may then be utilized to form a C–C bond with was subsequently described by Molander.143 a preformed electrophilic fragment. Scheme 13 For aryl and electron-rich heteroaryl (e.g. illustrates examples of boronate coupling.132,133 thiophene) trifluoroborates, these reactions

proceed in the presence of Pd(OAc)2 under O ligandless conditions. However he found that B Br N O (dppf)PdCl2, K2CO3 + for electron-deficient heteroaryl (e.g. pyridine) N DMF, 80oC N Cbz N Cbz 85% trifluoroborates, the use of a catalyst with a bulky liagnd, [1,1’-bis(diphenyl-phosphino)ferrocene]

OTBS O OTBS O palladium(II) chloride, was necessary to give TBSO TBSO 144 O NMe NMe satisfactory yields. Conditions for coupling B OMe OMe O I potassium aryl and heteroaryl trifluoroborates + (dppf)PdCl2, Ba(OH)2 with aryl and heteroaryl triflates have also 145 OTBS DMF, 45oC OTBS been reported. In general, trifluoroborate O 80% O salts are more nucleophilic than the equivalent boronic acids.141,146 Furthermore, they are often Scheme 13 more crystalline and more stable to long-term storage. There are relatively few accounts of boronic acids coupling with unactivated alkyl halides, Molander has reported that cross-coupling of although these have begun to appear, mainly aryl-trifluoroborates with benzylic halides is due to the work of Fu, who has described superior to that of the corresponding arylboronic conditions for Pd-catalyzed coupling of aryl-, acids.147 alkenyl- or alkylboronic acids with primary alkyl halides, in the presence of hindered phosphines, Molander has also demonstrated the coupling such as tricyclohexylphosphine or particularly of potassium alkenyl trifluoroborates with aryl (t-Bu) MeP,134 and also of the Ni-catalyzed 2 halides and triflates (Scheme 14).148 With coupling of aryl- and alkenylboronic acids with potassium vinyltrifluoroborate, which, unlike secondary alkyl bromides and iodides, in the 135 vinylboronic acid, is stable to polymerization, presence of a phenathroline ligand. high yields of Suzuki coupling products are obtained free from the products of Heck Improved syntheses and availability from coupling previously observed with vinylboronic commercial sources, including Alfa Aesar, of esters.149 boronic acids derived from electron-deficient

(dppf)PdCl2. CH2Cl2 hetereroaryl systems (e.g. pyridines) make their OTf + + BF3- K O Et3N, PrOH, reflux O use more attractive. There are several reviews 95% on the chemistry of these molecules.136-139 Scheme 14

Coupling reactions of Microwave-promoted rapid coupling with organotrifluoroborate salts alkenyl and alkynyl trifluoroborates and aryl iodides has been reported.150 Potassium Darses and Genêt showed that the alkenyltrifluoroborates also couple with alkenyl cross-coupling of arylboronic acids with bromides, affording, 1,3-dienes with retention arenediazonium tetrafluoroborates, catalyzed of double-bond geometry.151 6 7 Formation of carbonyl compounds C. N. Jera152 showed that the postassium vinyl and alkenyltrifluoroborates can be cross- Suzuki and Miyaura reported a variation of coupled with aryl and heteroaryl bromides the biaryl coupling reaction, shown in Scheme using Pd(OAc)2 as precatalyst, K2CO3 as 16, in which carbonylative cross-coupling of base and TBAB as additive to afford styrenes, arylboronic acids with aryl iodides occurs in the stilbenoids and alkenylbenzenes upon water presence of carbon monoxide at atmospheric reflux under conventional or microwave pressure, to give unsymmetrical substituted heating. These borates can be cross-coupled benzophenones.186 diastereoselectively with allyl and benzyl CO (1 atm) O (Ph3P)2PdCl2 chloride in the presence of KOH and 0.1 mol% (3 mol%) B(OH)2 + I Z Z' Pd to give the corresponding 1,4-diene and Z Z' K2CO3, allylarenes respectively. PhOMe, 80o

The chemistry of organotrifluoroborates has Scheme 16 been reviewed by Molander,153 Stefani,154 and by Darses and Genêt.155 In contrast, Uemura found that, in the absence of an aryl halide, carbonylation of an aryl- or Publications over the past few years into alkenylboronic acid, with a Pd(0) catalyst in Suzuki-Miyaura type cross-coupling reactions THF, leads to the corresponding symmetrical describe a diverse ranges of reagents including ketone. In methanol without added base, a substituted pyridines, indoles, pyrrolines, mixture of the ketone and the methyl aryl or tetrazoles, naphtholates and many more. The alkenyl carboxylic ester is formed, whereas in vast majority of the reactions reported achived the presence of sodium acetate, the methyl ester good yields, good regioselectivities and some is the major product.187 Unsymmetrical ketones were of one-pot synthesis.156-181 were subsequently prepared by reaction of arylboronic acids with acyl chlorides, catalyzed 188,189 190 Alkylboron couplings either by (Ph3P)4Pd, (Ph3P)2PdCl2, or 191,192 Pd(OAc)2 with no added ligand, and also 192 Suzuki-Miyaura coupling of alkylboronic acids with anhydrides, catalyzed by Pd(OAc)2 was described in a 2001 review as difficult to or rhodium complexes.193 A route to esters accomplish and limited in scope.182 However, and amides is available via the coupling of Molander subsequently reported conditions arylboronic acids with chloroformates (Scheme under which primary alkylboronic acids can be 17).194 coupled efficiently with aryl halides and triflates 183 (PPh3)4Pd (3 mol%), (Scheme 15). B(OH)2 CO2Et Cu2O (6 mol%) R + ClCO2Et R o K3PO4.3H2O, toluene, 80 C 21-78% O B(OH) 2 (dppf)PdCl CH Cl O 2. 2 2 Cs2CO3 or K2CO3 Scheme 17 + THF/H2O (10:1), reflux 91-97% TfO Similarly, tertiary amides have been prepared Scheme 15 by reaction of arylboronic acids156 or arylboronates195 with N,N-dialkylcarbamoyl This has been extended to the coupling of chlorides. potassium alkyl trifluoroborates with aryl halides 184 and triflates, catalyzed by (dppf)PdCl2. Doucet Coupling reactions of arylboronic acids with has reviewed Suzuki-Miyaura cross-coupling S-phenyl trifluorothioacetate, with Pd2(dba)3 reactions of alkylboronic acid derivatives and and a Cu(I) co-catalyst,196 or with phenyl alkyltrifluoroborates.185 trifluoroacetate, or the phenyl ester of another 197 perfluoroalkanoic acid, catalyzed by Pd(OAc)2 (Scheme 18), have been used to prepare the corresponding aryl perfluoroalkyl ketones.

8 9 O Pd(OAc)2 (5 mol%), Hindered ferrocene phosphines, such as 1,1’- B(OH)2 O (n-Bu)3P (15 mol%) CF3 bis(di-tert-butylphosphino)ferrocenepalladium + NMP, 80oC CH O PhO CF3 dichloride, have also been found to be effective 3 84% CH3O for challenging coupling reactions, including unactivated and hindered aryl chlorides.88 Scheme 18 As an alternative to phosphorus(III) derivatives, inexpensive 1,4-diazabicyclo[2.2.2]octane Catalyst systems (Dabco), in the presence of Pd(OAc)2 has been 222,223 65 found to be an effective ligand. Otherwise In the original biaryl coupling work, Suzuki and difficult couplings have also been successfully Miyaura employed the readily-available complex carried out with N-heterocyclic carbene (NHC) tetrakis(triphenyl-phosphine)palladium(0), ligands, usually generated in situ from 1,3-diaryl which continues to be the preferred catalyst imidazolium salts.86,87,223-225 in most routine syntheses. An extremely wide variety of alternative catalyst and ligand systems The use of tetrakis(triphenylphosphine) have been reported, with advantages in cost, platinum(0) instead of the palladium(0) complex efficiency or selectivity for particular applications. 107,186 permits selective coupling with an aryl iodide in Examples include: (Ph3P)2PdCl2, (dppb) 226 109,198 140,199,200 140,201,202 the presence of an aryl bromide. PdCl2, Pd(dba)n Pd(OAc)2, 110,203 110 Pd(OAc)2/(o-tol)3P, Pd(OAc)2/ dppf, 205 83 Attempts to minimize, or eliminate altogether, PdCl2/pyridine, PdCl2/PEG, Pd(dppf) 122,125,132,133,183,184 124 the use of palladium in the catalyst system have PdCl2, (PhCN)2-PdCl2/Ph3As, 186 130 been reported by Rothenburg, who successfully (CH3CN)2PdCl2, [Pd(allyl)Cl]2, palladium 227 78,108,206-208 209 utilized copper-based nanoclusters, and on carbon (review ), palladium on by Li and co-workers who have developed a a polymer support,77,84,210 (also the Johnson ® 211,212 palladium-free system consisting of CuI, Dabco Matthey FibreCat range ), palladium and TBAB, by means of which arylboronic acids nanoparticles,85 palladacycle complexes,213 214, 215 216 217 couple with vinyl bromides and iodides, mostly XPhos, S-Phos, (S)-KenPhos as well in good yields, and with several aryl iodides in as (Ph P) NiCl ,89 NiCl .6H O.90,218 3 2 2 2 2 moderate to good yields (Scheme 20).228 Low-cost trialkyl phosphites have also been 219,220 I B(OH)2 CuI (10 mol%) successfully used as ligands in palladium- Dabco (20 mol%) 219 + (n-Bu) NBr (1 eq) and nickel- catalyzed couplings. MeO 4 Cs2CO3 (2 eq) DMF, 125-130°C MeO 80 Pd2(dba)3/(t-Bu)3P, and the air-stable 81 equivalent Pd2(dba)3/[(t-Bu)3PH]BF4, Scheme 20 developed by Fu’s group, as well as Buchwald’s

biphenylphosphine systems, e.g. Pd(OAc)2/2- A comprehensive range of coupling catalyst 82 (di-tert-butylphosphino)biphenyl. are good systems, including most of those mentioned for coupling difficult substrates, including aryl above and some more specialized systems, chlorides, under mild conditions (Scheme 19). is available from Johnson Matthey Catalysts. These products are offered in research B(OH)2 O Pd2(dba)3 O (0.5-1.5 mol%) quantities through Alfa Aesar, and a selection is [(t-Bu)3PH]BF4 + (1-3.6 mol%) listed in the Product section of this publication. Cl KF, THF, rt Further technical information on the uses of 90% OMe these catalysts is available on request. MeO

t P(Bu )2 Bases

B(OH)2 + In contrast to the coupling reactions of organotin Pd(OAc)2, KF OMe Cl rt, 24h, 95% OMe or organozinc reagents, Suzuki and Miyaura found that the arylboronic acid coupling requires 2 equivalents of a base, originally aqueous Scheme 19 sodium carbonate.61,65 They also reported that 8 9 the stronger bases ethoxide or hydroxide gave (TBAB) behaves as an ionic liquid; mixtures poorer yields than carbonate, and that sodium with water have been utilized by Bedford for the acetate was ineffective, although its use under ligand-free Pd(OAc)2-catalyzed cross-coupling modified conditions has since been reported.229 of aryl chlorides.79 Many alternative bases have been introduced for these reactions, some of which offer Leadbeater studied the accelerating effect of advantages for particular substrates; examples microwaves on ligand-free Pd(OAc)2-catalyzed 107,230,,231-233 113,132,234 include: NaHCO3, K2CO3, Suzuki-type couplings in water, with or without 76,235 115,236 110 124 246 Cs2CO3, K3PO4, Et3N/DMF, Ag2O, TBAB. He also demonstrated Suzuki 134 133,237 KO-t-Bu, Ba(OH)2, good for sterically- coupling of aryl chlorides using palladium hindered biaryls, and CsF,238 compatible on carbon catalyst in water with microwave with readily-hydrolyzed functionality, such as heating and simultaneous cooling.247 Yu has esters. The use of TlOH, Tl2CO3 or TlOEt has reported improved yields with aryl chlorides also been found to give superior results with using a Pd-phosphine complex in aqueous sensitive substrates, particularly in multi-step media.248 Leadbeater’s claim249 to have total syntheses.99,239 achieved microwave-promoted, transition metal-free coupling was later retracted, with the Other reaction conditions detection of traces of palladium in the sodium carbonate base.250 The use of microwave Many Suzuki-Miyaura biaryl coupling reactions heating in conjunction with FibreCat® described in the literature use an aqueous supported palladium catalysts has also been mixed solvent with a water-miscible component recommended in high throughput synthesis such as DME or 1,4-dioxane. Examples techniques.212 Microwave irradiation enables have appeared of the use of poly(ethylene cross-coupling of organotrifluoroborates with glycol)85,192,222,240,242 or poly(ethylene oxide)242 ultra-low (ppm) catalyst loadings.251 It has also as co-solvent, potentially replacing volatile been recommended for the preparation of diaryl organic solvents, and facilitating recycling of ketones from Arylboronic acids and benzoyl the catalyst system. chlorides.189 “Environmentally friendly” Suzuki reactions have been reviewed.252 The coupling reaction of arylboronic acids with aryl bromides is dramatically accelerated A novel catalytic activity for Suzuki-Miyaura by using the ionic liquid, 1-n-butyl-3- cross coupling reaction in water mediated methylimidazolium tetrafluoroborate [bmim] with gold nanoparticles was reported by 253 [BF4] as the reaction medium; improved yields Guo. It was shown that high yields of with reduced catalyst loading of (Ph3P)4Pd are biaryls can be achieved with aryl halides or claimed.243 4-Iodophenol immobilized on Wang boronic acids bearing various substituents. resin undergoes accelerated coupling with the This new finding will undoubtedly broaden same catalyst in [bmim][BF ].71 The application 4 the application of gold nanoparticles in of ultrasound, also in [bmim][BF ], with ligand- 4 organic catalytic reactions. (Scheme 21) free Pd(OAc)2 as catalyst and NaOAc as base, has been found to promote rapid coupling at Cl B(OH)2 ambient temperature under extremely mild Au catalysts (0.05 mol%) 186 conditions. Water dramatically accelerates + o NaOH (4 eq), H2O, 80 C, 4h the Pd(OAc)2-catalyzed coupling of aryl halides in [bmim][BF4] and [bmim][PF6], enabling 244 Scheme 21 multiple recycling of the catalyst system. A Scheme 21 short review article on palladium-catalyzed C-C coupling reactions in ionic liquids is available.245

Arylboronic acids also undergo rhodium- catalyzed, copper-mediated coupling with 131 allylic alcohols in [bmim][PF6]. At elevated temperatures, the simple phase-transfer catalyst tetra-n-butylammonium bromide 10 11 Additions to carbonyl compounds have led to improved results under milder conditions (Scheme 23).267 New results in this 268 Palladium-catalyzed reactions field continue to appear on a regular basis.

Rh[(R)-BINAP](nbd) Uemura reported palladium-catalyzed 1,4- B(OH)2 (3 mol%) 254 + O addition of arylboronic acids to enones, Et3N, dioxane/water o 97% O 25 , 6h but yields were generally poor. Ohta later 99% ee OCH3 demonstrated 1,2-addition of arylboronic [nbd = 2,5-norbornadiene] OCH3 acids to aldehydes, catalyzed by Pd(0), but useful yields of secondary alcohols were only Scheme 23 obtained in the presence of chloroform.255 Organoboronic acids also undergo 1,4-addition Rh(I)-catalyzed addition of aryl- and to à,á-unsaturated ketones with a Pd phosphine alkenylboronic acids to isocyanates affords 269 complex and chloroform.256 More recently, Wu secondary amides. Rhodium-catalyzed and Cheng demonstrated a dramatic increase C-C bond-forming reactions of organometallic compounds have been reviewed.270 in yield for the PdCl2-catalyzed, chloroform- free 1,2-addition of aryl and heteroarylboronic acids to aldehydes, by adding tri(1-naphthyl) Mizoroki-Heck and other transition phosphine;257 other phosphine ligands were metal-catalyzed reactions with alkenes

much less effective. Pd(OAc)2-catalyzed 1,2- and alkynes addition to nitriles, in the presence of 2,2’- bipyridine, gives ketones in moderate to good Uemura reported the Pd(OAc) -catalyzed cross- 258 2 yields. coupling of arylboronic and alkenylboronic acids with alkenes in acetic acid to give aryl-substituted Rhodium-catalyzed reactions alkenes and conjugated dienes respectively, by oxidative addition of the B-C bond to an in Miyaura and Hayashi described the conjugate situ formed Pd(0) species.271 Subsequently, addition of arylboronic acids to enones, Mori described a Pd(II)-catalyzed pathway,

catalyzed by a rhodium(I) complex and a employing catalytic Pd(OAc)2 with Cu(OAc)2 chelating phosphine, to give good yields of as stoichiometric co-oxidant.272 Treatment of saturated ketones.259 Under similar conditions, a variety of alkenes with arylboronic acids both aryl- and alkenylboronic acids can add to thus affords á-arylated products in good yield aldehydes to give secondary alcohols in high (Scheme 24). The reaction conditions were yield (Scheme 22).260 also adapted to permit the coupling of sodium tetraphenylborate or alkenylboronates. B(OH)2 O CO2Bu

4-CF3C6H4CHO Pd(OAc)2 (5 mol%) Rh(acac)(CO) Rh(acac)(CO)2 PhB(OH)2 Ph 2 o (3 mol%) Cu(OAc) , LiOAc, DMF, 100 CO2Bu (3 mol%) OH 2 dppf O dppb 84% MeOH/H2O DME/H2O 50o 80o 82% 97% CF3 O

Scheme 22 OPh Ph

82% O An extension of these reactions to the addition CO2Et Ph OPh of potassium alkenyl- and aryltrifluoroborates to Ph CO Et aldehydes and enones has been described.261,262 2 79% 62% Miyaura and Hayashi utilized the Rh(I)- catalyzed 1,4-addition reaction of boronic Scheme 24 acids to à,á-unsaturated ketones,263 esters264 or amides,265 in the presence of a chiral BINAP Jung has demonstrated the palladium-catalyzed ligand, in enantioselective syntheses of the oxygen-promoted coupling of a number of aryl corresponding saturated ketones and esters. and heteroaryl boronic acids and boronates 266 with a variety of olefins in good yields under This area was reviewed by Hayashi. Further 273 investigations of the 1,4-addition reactions mild conditions (Scheme 25).

10 11 Zou (see Scheme 26).284 The regioselectivity of palladium-catalyzed hydroarylation of t CO2Bu unsymmetrical internal alkynes has been 285 O2, Pd(OAc)2 (10 mol%) studied by Oh. Ar o t ArB(OH)2 Na2CO3, DMF, 50 CO2Bu

OBu (CH2)4OH HO (Ph3P)4Pd, Ar AcOH, dioxane OBu 80o Ph 93% Ph Ph (CH2)5CH3 PhB(OH)2 (dppf)PdCl , Ar 2 Ph Ag2O, K2CO3 Ar Ph CH2Cl2, rt

90% Ph (CH2)5CH3 Scheme 25 Scheme 26 In contrast, with electron-rich olefins (vinyl ethers and N-vinylamides), the use of a phenanthroline Internal alkynes undergo addition with arylboronic acids, providing tetrasubstituted ligand promotes Pd-catalyzed Heck arylation at 286 the internal (heteroatom-substituted) position.274 olefins. Arylboronic acids also undergo aerobic Pd- catalyzed Heck-type coupling with phenyl vinyl Metal-promoted cross-couplings and metal- sulfones275 and vinylphosphonates.276 catalysed allylations represent two of the most widely used reactions in contemporary synthetic chemistry. However, cross-coupling reactions Conditions for Heck-type reactions of involving allylic electrophiles appear not been arylboronic acids with acrylate esters to give thoroughly investigated. Pigge287 published a cinnamic esters have been described by Brown, review which explores in some detail metal- with a ruthenium catalyst in the presence of a catalysed allylation of organoboranes and Cu(II) oxidant,277 and by Zou, with a rhodium organoboronic acids with emphasis on regio catalyst.278 Xiao has reported an oxygen and base-free Heck reaction of both electron-rich and stereoselective allyation procedures. and electron-deficient olefins, catalyzed by ortho-Substitution of aromatic ketones Pd(OAc)2 in the presence of dppp and acetone, which acts as a hydrogen acceptor.279 A variety of aryl alkyl ketones react with boronic Lautens has investigated the rhodium esters in the presence of a catalytic amount of catalyzed coupling of boronic acids with RuH2(CO)(PPh3)3, with ortho-specific C–H bond alkenes and alkynes in aqueous systems. In cleavage to give the ortho-aryl ketone (Scheme 27).288 the presence of [Rh(COD)Cl]2 and a water- soluble phosphine ligand, arylboronic acids undergo a Heck-type reaction with styrenes O Ar O to give trans-stilbenes, whereas, with vinyl- RuH2(CO)(PPh3)3 (2 mol%) O substituted pyridines, quinolines or pyrazine, + pinacolone, reflux B hydroarylation of the olefinic bond gives the Ar O 75-98% saturated 2-arylethyl heterocycle.280 Alkynyl Scheme 27 heteroaromatic compounds under analogous conditions also undergo hydroarylation to Neopentyl glycol esters were found to give the 2-arylvinyl derivatives.281 Stereoselective best results. Pinacol and other boronic esters rhodium-catalyzed hydroarylation of internal gave lower yields but free boronic acids were alkynes had previously been demonstrated by recovered essentially unchanged. The reaction Hayashi.282 Terminal alkynes with a palladium has been extended to the ortho-alkenylation catalyst can undergo either hydroarylation by using alkenylboronic esters.289 arylboronic acids, reported by Oh,283 or Heck- type coupling under oxidative conditions, by 12 13 Cyanation and Carboxylation Utilization of aminophosphonates in the Petasis boronic acid Mannich reaction Preparation of aryl nitriles by classical routes by Kukhar and co-workers.295 With the (Sandmeyer or Rosenmund-von Braun) use of à-aminophosphonates, several involves highly toxic inorganic cyanides (Cu N-phosphonomethylglycine derivatives were or Zn). Arylboronic acids undergo a copper(I)- prepared in modest to good yields and high mediated, Pd(0) catalyzed coupling reaction diastereoselectivities, as shown in scheme 31. with an organic thiocyanate to give high yields 290 of benzonitriles (Scheme 28). The reaction P(O)(OEt)2 B(OH)2 O P(O)(OEt)2 can also be applied to heteroaryl and alkenyl EtOAc N OH OH P(O)(OEt)2 + H + systems. S N P(O)(OEt) H 2 Reflux, 4h O O B(OH)2 (Ph3P)4Pd (3 mol%) CN CuTC (1.5-3 eq) S R + PhCH2SCN R dioxane, 100°C Scheme 31 CuTC = Cu(I) thiophene-2-carboxylate Scheme 31

Harwood and co-workers demonstrated the Scheme 28 use of a chiral secondary amine as a template Arylboronic and alkenylboronic esters can be in a diastereo-controlled Mannich reaction converted to benzoic acids by Rh(I)-catalyzed with furan-2-boronic acid, to give substituted furfurylamines with high de.296 The Petasis reaction with CO2 at atmospheric pressure (Scheme 29).291 reaction has been investigated with one of the three components anchored to a polymer support, and found to give satisfactory results CO2 (1 atm) O [Rh(OH)(COD]2 (3 mol%) 297 dppp (7 mol%) in most cases. The reaction has also been R B R CO2H O CsF (3 eq.), dioxane, 60oC successfully extended to pinacolyl boronic esters,298 with chiral induction achievable via a homochiral boronic ester.299 Scheme 29 Petasis has reported an analogous stereocontrolled three-component Transition metal-free C–C condensation, involving a boronic acid, an condensations amine and an à-hydroxy aldehyde, to yield the anti-á-amino alcohol.300 This route has been The Boron-Mannich (Petasis) reaction adapted to give the product enantioselectively with high ee.301 Petasis initially described the Mannich- type reaction of alkenylboronic acids with The Petasis reaction has been extended to the paraformaldehyde and secondary amines,292 more reactive potassium organotrifluoroborates affording allylamines in good yield with retention (aryl, vinyl and allyl), which condense with an of double-bond geometry. Subsequently, he aldehyde and an amine, in the presence of developed the three-component Mannich a Lewis acid.302 Alkenyl, aryl and heteroaryl reaction of an alkenylboronic acid with glyoxylic pinacol boronates react slowly or not at all in the acid and an amine to give á,Ž-unsaturated Petasis reaction in aprotic solvents. In alcohols à-amino acid derivatives,293 which was extended such as methanol or hexafluoroisopropanol, to the synthesis à-aryl and à-heteroaryl glycines the reaction proceeds well to give amino acid from the corresponding boronic acids,294 as derivatives, mostly in high yield.303 shown in Scheme 30. F. Lamaty 304 developed a new solvent Ph et. al. Ph free microwave-assisted procedure for the B(OH)2 O Ph CH Cl , 25o HN OH OH 2 2 Petasis multicomponent reaction. Their + H + H2N Ph 92% O method is applicable to various boronic acids S O and secondary amines. The advantage S of this method is that the reaction time is Scheme 30 somewhat reduced, giving an excellent yield 12 13 R1 and with no purification step other than an B(OH)2 R1 N Cu(OAc)2, Et3N or pyridine R2 + N H 2 aqueous washing. R CH2Cl2 R R

Allylation reactions B(OH)2 OH Cu(OAc)2, Et3N or pyridine O + CH2Cl2 R R' R R' Allylboronic esters can add stereoselectively to aldehydes, in the absence of a catalyst, to give Scheme 33 homoallylic alcohols.41b Ishiyama and Miyaura have shown that the reaction of pinacolyl This methodology provides a mild alternative allylboronates is dramatically accelerated, and to classical Ullmann-type chemistry, normally the chemoselectivity increased, by a catalytic carried out at elevated temperatures. The next amount of a Lewis acid (Scheme 32).305 The two papers in the same issue are by Evans,311 potential for modest enantioselectivity was describing more detailed studies of the phenol demonstrated in the presence of a BINOL co- arylation reaction, and by Chan and Lam,312 catalyst. on the N-arylation of imidazoles, triazoles, tetrazoles and similar heteroaromatics. Subsequent publications have provided Catalyst Temp Yield% 3:4 many more examples of what is sometimes none r.t. 89 81:19 referred to as the Chan-Lam coupling reaction, 313 none -78o 0 including arylation of N-hydroxyphthalimide, amines,314,315 amides and imides.315 The C-N AlCl (10 mol%) -78o 57 99:1 3 coupling reaction has been applied to solid- o 316 Sc(OTf)3 (10 mol%) -78 72 99:1 phase synthesis of N-heterocycles. The formation of unsymmetrical thioethers from arylboronic acids and thiols, mediated by O 317 4-CF3C6H4CHO + 4-MeOC6H4CHO + Cu(OAc) has been reported. Alkyl and aryl B toluene, 16h 2 (1.1eq) (1.1eq) O 1 2 (1 eq) sulfinic acid salts also react with arylboronic

OH OH acids, in the presence of Cu(OAc)2, to give good 318,319 + yields of aryl sulfones. Copper-promoted 4-CF3C6H4 4-MeOC6H4 34C-heteroatom bond cross-coupling reactions have been reviewed by Chan and Lam,320 Scheme 32 giving a first-hand insight into the development of this type of reaction. Ley and Thomas have Kobayashi has described allylation of ketones, also published a review of Copper mediated catalyzed by In(I) salts.306 Hall has published a aryl C-O, C-N and C-S bond formation.321 review of Lewis and Brønsted acid catalyzed allylboration of carbonyl compounds.307 As originally described, these reactions required stoichiometric amounts of Cu(II). C–O, C–N and C–S bond forming Buchwald reported a catalytic procedure for amination utilizing molecular oxygen as reactions reoxidant for copper,322 and Batey has since developed improved oxygen-mediated catalytic Oxidative cleavage of organoboron compounds procedures for the formation of ethers from to give alcohols or phenols is well known. In the trifluoroborate salts (or, in reduced yield, case of boronic acids and esters, conditions 323 18,308 ® 309 boronic acids) and aliphatic alcohols, and utilizing hydrogen peroxide or Oxone also for amination of both boronic acids and have been described. trifluoroborates (Scheme 34).324

Of much greater synthetic interest was Chan’s publication in 1998,310 describing the ambient temperature arylation with arylboronic acids of N-H groups in amines, amides, imides, ureas, sulfonamides and carbamates, and of O-H groups in phenols, promoted by Cu(II) acetate and triethylamine or pyridine (Scheme 33).

14 15 1 1 Ar BF3K (i) Cu(OAc)2.H2O (10 mol%) Ar O R R = alkyl reactions, affording high yields of the required DMAP (20 mol%), or or CH2Cl2, 4A MS, rt 1 products. Potassium aryltrifluoroborates salts R R R R = alkyl, aryl BF3K (ii) R1 OH, O , rt O 2 R1 = alkyl undergo ipso-iodinations using a combination of sodium iodide and Chloramine-T.342 Ar B(OH)2 (i) Cu(OAc)2.H2O (10 mol%) 1 CH Cl , 4A MS, rt R or 2 2 Arylboronic acids have been converted, via Ar N (ii) R1R2NH, O , 40o Ar BF3K 2 R2 the N-methyldiethanolamine cyclic esters, to R1 = alkyl, aryl aryl fluorides using cesium fluoroxysulfate.343 R2 = H 344 or R1 = R2 = cycloalkyl, pyrrole Widdowson and co-workers have demonstrated the facile conversion of Scheme 34 arylboronic acids to diaryliodonium triflates in

the presence of PhI(OAc)2/TfOH. Diaryl and Arylboronic acids undergo reductive amination heteroaryl (phenyl)iodonium tosylates can also with arylnitroso compounds, mediated by be readily prepared from the corresponding Cu(I), providing a route to unsymmetrical boronic acid and Koser’s reagent [PhI(OH)OTs]. diarylamines.325 This approach is preferable to the previous route via toxic stannanes. The displacement reaction Numerous publications in the area of copper of iodonium salts with fluoride ion provides a promoted coupling reactions with boronic acids, mild synthesis of aryl fluorides, including 18F boronates and trifluoroboronate salts have labelled derivatives, which can be employed in appeared in the literature in recent years.326- positron emission tomography. 334, A one-pot copper catalysed synthesis of N-functionalised pyrazoles from boronic acids Vinylboronic acids can be converted to that are difficult to access via conventional vinyl halides, with retention of double-bond methods was recently reported.335 configuration, using NCS, NBS or NIS.345 Vinyl and alkynyl trifluoroborates can be iodinated with Unsymmetrical diaryl or aryl heteroaryl sulfones sodium iodide/ Chloramine-T.346 Fluorination of have been prepared via a ligand-free, palladium vinylboronic acids occurs with 1-chloromethyl- chloride-catalyzed coupling of arylboronic 4-fluoro-1,4-diazoniabicyclo[2.2.2]octane acids with arenesulfonyl chlorides.336 Sulfones bis(tetrafluoroborate) [Selectfluor®], but are also available by cross-coupling of aryl- or better results have been obtained starting alkenylboronic acids with aryl or alkyl sulfinate from the corresponding potassium alkenyl 337 347 salts, promoted by stoichiometric Cu(OAc)2, trifluoroborates. 338 or catalytic Cu(OAc)2/1,10-phenathroline. Arylboronic acids undergo ipso-nitration with ammonium nitrate/ trifluoroacetic anhydride348 (Crivello’s reagent: in situ trifluoroacetyl Miscellaneous displacement reactions of nitrate), or, more selectively, with a nitrate salt boronic acids and TMS chloride,349 to give the boron-free aryl nitro compound, in contrast to conventional Many other examples can be found of boronic nitration which tends to give mainly the m-nitro acid chemistry involving displacement of benzeneboronic acid. boron: With lead(IV) acetate, catalyzed by mercury(II) Reaction of arylboronic acids with copper(II) acetate, arylboronic acids are transmetallated chloride or bromide to give the corresponding to the aryllead triacetates, used in situ for aryl halide with loss of boron has long been electrophilic arylation, for example of active known.339 More recently, ipso-bromination or methylene compounds,350 or with sodium azide -iodination of arylboronic acids with NBS or in DMSO for the preparation of aryl azides, NIS in acetonitrile has been described.340 The providing a useful two-step route for the reaction has been further developed utilizing preparation of these from aryl halides.351 1,3-dibromo-5,5-dimethylhydantoin and the dichloro analogue, providing convenient Transmetallation of an arylboronic acid to an access to “abnormally” substituted bromo arylzinc species in situ has been achieved with and chloro aromatics.341 A catalytic amount of diethylzinc.352 sodium methoxide was found to minimize side

14 15 4. Preparative routes to boronic better results for a range of substrates were claimed by an ortho-lithiation-silylation-ipso- acids and esters boro-desilylation361 sequence with boron tribromide (Scheme 35). Borylation of organometallics

NEt2 NEt2 NEt2

Boronic acids are still most often prepared O O O O O O o (i) n-BuLi (i) BBr3/CH2Cl2, -78 from the corresponding organomagnesium or SiMe3 B(OH)2 (ii) Me3SiCl (ii) MeOH, rt organolithium reagent and a trialkyl borate, (iii) HCl, H2O followed by acidic hydrolysis of the resulting dialkyl boronate. The original conditions of Kotinsky and Melamed,5 addition of trimethyl Scheme 35 borate to an ether solution of phenylmagnesium bromide, were repeated by Gilman,353 who Other workers362 have utilized ipso- claimed yields of benzeneboronic acid as high borodesilylation with either BBr3 or BCl3 in the as 86%. However, most other workers were formation of boronic acids and esters. Neopentyl unable to reproduce this, and often obtained esters have been ortho-lithiated with LDA and only very low yields, mainly due to the formation reacted with triisopropyl borate in situ to give of large amounts of diphenylborinic acid. Johnson subsequently used a reverse-addition good yields of arylboronic acids, isolated via technique, adding the ethereal phenyl Grignard the diethanolamine esters.363 to trimethyl borate at -12˚C (ca 30% yield),6 or to tributyl borate at -70 to -75˚C, (50-60% yield).7 Organotrifluoroborates are a unique class of Washburn later undertook a more detailed organoboron compounds that have emerged study of the synthesis of benzeneboronic acid as promising synthetic reagents. The from phenylmagnesium bromide and trimethyl tetracoordinated nature of boron in these borate,8 confirming that the yield of boronic complexes coupled with strong boron-fluorine acid is much improved by carrying out the bonds makes the organotrifluoroboronates borylation of the Grignard at low temperatures essentially a protected boronic acid or boronate (generally below -50oC). As the reaction esters.364-366 The most convenient method for temperature approaches ambient, increasing the preparation of these compounds from amounts of the ester of diphenylborinic acid are boronic acids and derivatives utilises the readily formed by further attack of the Grignard on the available and inexpensive KHF2 as described by intermediate dimethyl benzeneboronate. He Vedejs and co-workers.367,368 In combination with also demonstrated that simultaneous addition of this process, potassium organotrifluoroborates the borate and Grignard to a vessel containing can be readily prepared by transmetalation of ether stirred at low temperature tended to organolithium or organomagnesium reagents minimize formation of diphenylborinic acid. In with trialkylborates.369 Alternatively, they can be a second key paper,354 Washburn discussed synthesised by various catalysed hydroboration further experimental and mechanistic aspects of alkynes or alkenes.370-372 The utilisation of the reaction of phenyl- and substituted of organofluoroborates in organic synthesis phenylmagnesium halides with trialkyl borates. led to the preparation of more functionalised His optimal procedure for benzeneboronic compounds. A short review by R. A. Oliverira373 acid is detailed in Organic Syntheses.355 The outlines many of the reactions involving results of other workers indicate that the use potassium organotrifluoroborate salts. of triisopropyl borate356 or isopropyl pinacol borate (2-isopropoxy-4,4,5,5-tetramethyl-1,3,2- Hydroboration methods dioxaborolane)357 instead of trimethyl borate may have advantages in particular cases. Hydroboration of alkenes with catecholborane to give alkylboronic esters374 usually requires Snieckus has developed directed metallation358 forcing conditions. Improved results can be routes to boronic acids. His initial publication359 375 obtained by catalysis with LiBH4, or with described ortho-lithiation of N,N-dialkyl Rh(I)376,377 or Ir(I)377 complexes. Hydroboration of benzamides, followed by borylation with alkynes with catecholborane occurs somewhat trimethyl borate. In a subsequent paper,360 more readily, affording alkenylboronic 16 17 esters, often regio- and stereoselectively.374 has been adapted to borylation of polymer- Nevertheless, catalysis with, for example supported aryl iodides, allowing in situ coupling Rh(I),376 Ni(II)378 or Pd(II)379 complexes, may to give unsymmetrical biaryls.386 Microwave permit reaction under milder conditions, with irradiation has been found to offer dramatic greater selectivity. Alkenes can undergo Rh(I)- rate enhancements and improved yields in the catalyzed hydroboration with pinacolborane, to formation of otherwise difficult electron-rich give the alkylboronate,380 or, with a phosphine- boronates.387 In a further detailed examination free Rh(I) complex, the alkenylboronate381 by of the borylation reaction, Zhang has shown

dehydrogenative borylation. Vinylboronates are that ligandless Pd(OAc)2 is a highly effective also formed from alkynes and pinacolborane catalyst with advantages of lower cost, ease (2 eq.) under mild conditions.382 High yields of work-up, and the ability to couple the are obtained with 1 eq. of the reagent in the boronate in situ with a suitable electrophile.388 presence of Rh or Ni catalysts380 (Scheme 36). Buchwald has demonstrated the high-yield borylation of aryl chlorides using the hindered ligand 2-dicyclohexyl-phosphino-2’,4’,6’- [(COD)RhCl]2 O R triisopropylbiphenyl.389 85-95% B R O (Ph3P)3RhCl 50-99% The preparation of pinacolyl arylboronates O + (Ph3P)3RhCl B 98-99% by palladium-catalyzed coupling of aryl H O iodides, triflates or, less readily, bromides O R with pinacolborane has been described by B R O Masuda.390 In this reaction, the arene, formed by reduction of the aryl halide, was often found Scheme 36 as a significant by-product. This method has been adapted to a one-pot conversion of aryl bromides to unsymmmetrical biaryls via the Transition metal catalyzed B–C pinacol boronates.391 Aryl iodides can also be coupling converted to the pinacol boronates in acceptable yield in a Pd-free, CuI catalyzed reaction, along As well as the need for low temperatures, the with a strong base, preferably NaH.392 Masuda use of reactive organometallics, RMgX or RLi, has reported the Pt(0)-catalyzed regio- and as boronic acid precursors is generally limited stereoselective synthesis of allylboronates from to substrates lacking functional groups which allyl halides and pinacolborane.393 could react with the organometallic species. A major advance in the synthesis of arylboronic Borylation with bis(pinacolato)diboron, esters came with the publication by Miyaura383 of catalyzed by Pd complexes, has been extended the palladium-catalyzed coupling of aryl halides to alkenyl halides and triflates,394,395 benzyl with diboron esters, especially bis(pinacolato) halides396,397 and allyl acetates.398 Miyaura diboron, by cleavage of the B-B bond, enabling has also reported coupling with allyl halides, access to boronic acid derivatives without mediated by copper(I) chloride.399 protection of functionalities such as ester, ketone, cyano or nitro groups (Scheme 37). The reaction with alkynes, catalyzed by Pt(0) affords cis-bis-boryl alkenes.400,401 Cu(I)- mediated 1,2-addition to terminal alkynes has O O also been described.399 Stereoselective Pt(0)- Br B (dppf)PdCl2 catalyzed addition to 1,3-dienes gives 1,4-bis- O O KOAc 401 + BB boryl 2-alkenes, (Scheme 38). o O O DMSO, 80 80%

O O (Ph3P)4Pt O O O O + BB B B toluene, O O O O 80o 93% Scheme 37 (Z) > 99%

Aryl triflates are also converted to pinacol arylboronates under similar conditions,384 as Scheme 38 are arenediazonium salts.385 The reaction 16 17 A detailed discussion of diboration reactions palladium-catalyzed cross-coupling with halides with diboron derivatives has been published by can take place in either Suzuki (loss of boron) Marder and Norman.403 or Heck (retention of boron) modes.149 However, use of the more nucleophilic vinyltrifluoroborate Marder and Norman first reported 1,4-addition salt in the Suzuki coupling may be preferable of bis(pinacolato)diboron to enones, catalyzed (see Section 3).148 With the pinacol ester, by a Pt(0) complex.404 Other authors have Whiting has developed reaction conditions described a variety conditions for this type of which facilitate the Heck coupling, providing reaction, promoted by Pt(0),347 Cu(I)399,406 or a route to styryl and other 2-substituted Rh(I)407 systems (Scheme 39). vinylboronates (Scheme 41).417,418

O Pd(OAc)2 (2.5 mol%), O O O O PhI + O Ph3P (5 mol%) O + BB B O + Ph 1 2 R R B Et N, MeCN B O O O 3 Ph O 1 2 R R 66% yield >95 : 5

Scheme 39 Scheme 41

Alkylbenzenes can be borylated on the side- Improved dimethylzinc-promoted vinylation chain with either bis(pinacolato)diboron or of nitrones with vinylboronic esters was pinacolborane, in the presence of Pd/C catalyst, reported.419 Nucleophilic addition of the vinyl providing a direct route to benzylboronates.408 group derived from 4, 4, 6-trimethyl-[1,3,2] dioxaborinane onto nitrones providing a route A development of considerable interest is the to N-allylic hydroxylamines in moderate yields. direct borylation of aromatic rings, which has been achieved by Smith using pinacolborane Homologated alkenylboronates are available via in the presence of a rhodium complex,409 Grubbs ruthenium-catalyzed cross-metathesis or by Ishiyama, Miyaura and Hartwig using with terminal alkenes.420 The olefinic double bis(pinacolato)diboron with an iridium(I) bond of a vinylboronate can also undergo complex (Scheme 40).410 cycloaddition reactions with 1,3-dipoles, such as isoxazolines from nitrile oxides,421.422 and OMe OMe various free-radical reactions,423-425 leading to O O O [(COD)IrCl]2 substituted boronates. BB + B bipy, 80o O O O o : m : p 1 :74:25

Scheme 40

The Ir-catalyzed reaction has been extended to the regio-selective borylation of heteroaromatics,411 to selective ortho-borylation of aromatic nitriles,412 and to ferrocenes.413 Further reactions of arylboronates obtained by this method have provided access to “abnormally” substituted aromatics, including anilines, aryl ethers414 and aryl bromides.415

Vinylboronate reactions

Vinylboronic acid polymerizes too readily for convenient isolation. The pinacol ester, on the other hand, is stable enough to be stored for limited periods,416 and can undergo a variety of useful reactions. Whiting has shown that

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Commun., 1997, 2051 Soc., 1992, 114, 6671; D. A. Evans, G. C. Fu, B. 405 H. A. Ali, I. Goldberg, M. Srebnik, A. Anderson, J. Am. Chem. Soc., 1992, 114, Organometallics, 2001, 20, 3962. 6674. 406 H. Ito, H. Yamanaka, J. Tateiwa, A. Hosomi, 378 I. D. Gridnev, N. Miyaura, A. Suzuki, Tetrahedron Lett., 2000, 41, 6821. Organometallics, 1993, 12, 589. 407 G. W. Kabalka, B. C. Das, S. Das, Tetrahedron 379 I. D. Gridnev, N. Miyaura, A. Suzuki, J. Org. Lett., 2002, 43, 2323. Chem., 1993, 58, 5351. 408 T.Ishiyama, K. Ishida, J. Takagi, N. Miyaura, 380 S. Pereira, M. Srebnik, Tetrahedron Lett., 1996, Chem. Lett., 2001, 1082. 37, 3283. 409 M. K. Tse, J.-Y. Cho, M. R. Smith, Org. Lett., 381 M. Murata, S. Watanabe, Y. Masuda, Tetrahedron 2001, 3, 2831. Lett., 1999, 40, 2585; M. Murata, K. Kawakita, 410 T. Ishiyama, J. Tagaki, K. Ishida, N. Miyaura, N. T. Asana, S. Watanabe, Y. Masuda, Bull. Chem. R. Anastasi, J. F. Hartwig, J. Am. Chem. Soc., Soc. Jpn., 2002, 75, 825. 2002, 124, 390. 382 C. E. Tucker, J. Davidson, P. Knochel, J. Org. 411 J. Tagaki, K. Sato, J. F. Hartwig, T. Ishiyama, N. Chem., 1992, 57, 3482. Miyaura,Tetrahedron Lett., 2002, 43, 5649. 383 T. Ishiyama, M. Murata, N. Miyaura, J. Org. 412 G. A. Chotana, M. A. Rak, M. R. Smith, J. Am. Chem., 1995, 60, 7508. Chem. Soc., 2005, 127, 10539. 384 T. Ishiyama, Y. Itoh, T. Kitano, N. Miyaura, 413 A. Datta, A. Köllhofer, H. Plenio, Chem. Commun., Tetrahedron Lett., 1997, 38, 3447. 2004, 1508. 385 D. M. Willis, R. M. Strongin, Tetrahedron Lett., 414 C. C. Tzschucke, J. M. Murphy, J. F. Hartwig, Org. 2000, 41, 8683. Lett., 2006, 9, 761. 386 S. R. Piettre, S. Balzer, Tetrahedron Lett., 1997, 415 J. M. Murphy, X. Liao, J. F. Hartwig, J. Am. Chem. 38, 1197. Soc., 2007, 129, 15434. 387 P. Appukkuttan, E. Van der Eycken, W. Dehaen, 416 The ester with 2-methyl-2,4-pentanediol [4,4,6- Synlett, 2003, 1204. trimethyl-2-vinyl-1,3,2-dioxaborinane] is claimed 388 L. Zhu, J. Duquette, M. Zhang, J. Org. Chem., to be more stable: A. P. Lightfoot, S. J. R. 2003, 68, 3729. Twiddle, A, Whiting, Synlett, 2005, 529. 389 K. L. Billingsley, T. E. Barder, S. L. Buchwald, 417 S. K. Stewart. A. Whiting, J. Organomet. Chem., Angew. Chem. Int. Ed., 2007, 46, 5359. 1994, 482, 293; Tetrahedron Lett., 1995, 36, 390 M. Murata, S. Watanabe, Y. Masuda, J. Org. 3925; N. Henaff, A. Whiting, Tetrahedron, 2000, Chem., 1997, 62,6458; M. Murata, T. Oyama, S. 56, 5193. Watanabe, Y. Masuda, J. Org. Chem., 2000, 65, 418 K. Tonogaki, K. Soga, K. Itami, J. Yoshida, 164. Synlett, 2005, 1802. 391 P.-E. Brontin, I. Cerna, M. Campaniello, F. Leroux, 419 N. PreveenGanesh, C. De Candia, A. Memboeuf, F. Colobert, Org. Lett., 2004, 6, 4419. G. Lendvay, Y. Gimbert, P. Y. Chavant, J. 392 W. Zhu, D. Ma, Org. Lett., 2006, 8, 261. Organomet. Chem., 2010, 695, 2377. 393 M. Murata, S. Watanabe, Y. Masuda, Tetrahedron 420 H. E. Blackwell, D. J. O’Leary, A. K. Chatterjee, Lett., 2000, 41, 5877. R. A. Washenfelder, D. A. Bussmann, R. H. 394 K. Takahashi, J. Takagi, T. Ishiyama, N. Miyaura, Grubbs, J. Am. Chem. Soc., 2000, 122, 58. Chem. Lett., 2000, 126. 421 R. H. Wallace, K. K. Zong, Tetrahedron Lett., 395 J. Tagaki, A. Kamon, T. Ishiyama, N. Miyaura, 1992, 33, 6941. Synlett, 2002, 1880. 422 M. Jazouli, S. Baba, B. Carboni, R. Carrie, M. 26 27 Soufiaoui, J. Organomet. Chem., 1995, 498, 229; Tetrahedron Lett., 1997, 38, 6665. 423 N. Guennouni, F. Lhermitte, S. Cochard, B. Carboni, Tetrahedron, 1995, 51, 6999. 424 A. McCarroll, J. C. Walton, R. Nziengui, B. Carboni, Chem. Commun., 1997, 2075; J. C. Walton, A. J. McCarroll, Q. Chen, B. Carboni, R. Nziengui, J. Am. Chem. Soc., 2000, 122, 5255. 425 H. Lopez-Ruiz, S. Z. Zard, Chem. Commun., 2001, 2618.

© Copyright Alfa Aesar 2011

26 27 28 Alkenylboronic Acids and Esters

Stock # Description Standard Selling Sizes L19700 3-Acetoxy-1-propenylboronic acid pinacol ester, 97% 250mg 1g

[2-(3-Acetoxy-1-propenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane]

[161395-97-7], C11H19BO4, F.W. 226.08, Colourless liquid, Ë 1.4485, BRN 6923397, MDL MFCD03788751 Undergoes 1,3-cycloaddition with aryl nitrile oxides which, on oxidation with t-BuOOH, gave 4-hydroxy- Ð 2 -isoxazolines in good yield: Tetrahedron Lett., 35, 7493 (1994). H31412 trans-4-Bromo-á-styrylboronic acid pinacol ester, 96% 250mg [2-[(E)-2-(4-Bromophenyl)vinyl- 1g ]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane] 5g

C14H18BBrO2, F.W. 309.01, White crystalline powder, m.p. 85-87ø, MDL MFCD12546200 Alkenylboronic

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53282 4-tert-Butylcyclohexene-1-boronic acid, 97% 250mg

[850567-91-8], C10H19BO2, F.W. 182.07, Off-white solid, m.p. 166-170ø, MDL MFCD06659856

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52627 2-tert-Butyl-trans-vinylboronic acid, 97% 250mg [3,3-Dimethyl-1-butenylboronic acid] 1g

[86595-37-1], C6H13BO2, F.W. 127.98, White solid, m.p. 78-80ø,

MDL MFCD01074624 Acids

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52617 1-(4-Chlorophenyl)vinylboronic acid pinacol ester, 97% 250mg

[850567-54-3], C14H18BClO2, F.W. 264.56, Off-white solid, m.p. 53-56ø, MDL MFCD06659924

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H51692 4-Chloro-á-styrylboronic acid pinacol ester, 97% 1g [2-[2-(4-Chlorophenyl)vinyl- 5g ]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane]

C14H18BClO2, F.W. 264.56, Pale yellow solid, MDL MFCD15144834

H53116 Cycloheptene-1-boronic acid, 97% 250mg

[835882-35-4], C7H13BO2, F.W. 139.99, White solid, m.p. 110-116ø, MDL MFCD04115655

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H51036 1-Cyclohexene-1-boronic acid pinacol ester, 95% 250mg

[141091-37-4], C12H21BO2, F.W. 208.10, MDL MFCD05663845 1g

H52531 Cyclopentene-1-boronic acid, 97% 250mg

[850036-28-1], C5H9BO2, F.W. 111.94, Off-white solid, m.p. 134-140ø, MDL MFCD02179496

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L19579 3,3-Diethoxy-trans-1-propenylboronic acid pinacol ester, 250mg 97% 1g [2-[(1E)-3,3-Diethoxy-1-propen-1-yl- ]-4,4,5,5,-tetramethyl-1,3,2-dioxaborolane]

[153737-25-8], C13H25BO4, F.W. 256.15, Colorless liquid, Ë 1.4410, MDL MFCD03788737 H52763 4,4-Dimethylcyclohexa-1,5-diene-1-boronic acid monosodium 250mg salt, 96%

[871329-70-3], C8H12BNaO2, F.W. 173.98, White solid, m.p. 300-302ø, MDL MFCD16036162

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Bulk and Specialty Sizes Available 1 Alkenylboronic Acids and Esters Stock # Description Standard Selling Sizes H52914 4,4-Dimethylcyclohexa-1,5-diene-1-boronic acid pinacol 250mg ester, 96%

[871333-97-0], C14H23BO2, F.W. 234.15, White solid, m.p. 32-34ø, MDL MFCD07363842

H52955 4,4-Dimethylcyclohexene-1-boronic acid, 96% 250mg

[865869-28-9], C8H15BO2, F.W. 154.02, White solid, m.p. 152-154ø, MDL MFCD07363758

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52606 1,4-Dioxaspiro[4,5]dec-7-en-8-boronic acid, 96% 250mg [4-Borono-3-cyclohexen-1-one ethylene glycol ketal]

[850567-90-7], C8H13BO4, F.W. 184.00, Pale brown solid, m.p. 154-158ø, MDL MFCD06659855

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53205 1,4-Dioxaspiro[4,5]dec-7-en-8-boronic acid pinacol ester, 250mg 96%

[680596-79-6], C14H23BO4, F.W. 266.14, Off-white solid, m.p. 60-62ø, MDL MFCD04115656 Acids H52983 4-Ethylcyclohexene-1-boronic acid, 98% 250mg

[871329-72-5], C8H15BO2, F.W. 154.02, Off-white solid, MDL MFCD07783854

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H30744 4-Ethyl-trans-á-styrylboronic acid pinacol ester, 97% 250mg [2-[trans-2-(4-Ethylphenyl)vinyl]-4,4,5,5-tetramethyl- 1g [1,3,2]dioxaborolane] 5g

[870717-91-2], C16H23BO2, F.W. 258.17, White crystalline Alkenylboronic solid, m.p. 46-48ø, f.p. >110ø(230øF), MDL MFCD08276837 H52584 1-(4-Fluorophenyl)vinylboronic acid pinacol ester, 97% 250mg

[850567-55-4], C14H18BFO2, F.W. 248.10, Yellow solid, m.p. 38-42ø, MDL MFCD06659925

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H30578 4-Fluoro-trans-á-styrylboronic acid pinacol ester, 97% 250mg [2-[trans-2-(4-Fluorophenyl)vinyl]-4,4,5,5-tetramethyl- 1g [1,3,2]dioxaborolane] 5g

[504433-86-7], C14H18BFO2, F.W. 248.11, White crystalline granules, MDL MFCD12546189

L19649 (E)-1-Heptene-1,2-diboronic acid bis(pinacol) ester, 1g 98% 5g [1-cis-1,2-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- heptene]

[307531-74-4], C19H36B2O4, F.W. 350.12, Colorless to yellow liquid, b.p. 108ø/0.08mm, f.p. >110ø(230øF), d. 0.949, Ë 1.4560, BRN 8859280, MDL MFCD02683463 H52590 trans-1-Hepten-1-ylboronic acid, 98% 1g

[57404-76-9], C7H15BO2, F.W. 142.00, Grey solid, 5g m.p. 107-111ø, MDL MFCD01074600

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27876 trans-1-Hepten-1-ylboronic acid pinacol ester, 95% 5g [E-2-(1-Heptenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane]

[169339-75-7], C13H25BO2, F.W. 224.15, Colorless to pale yellow liquid, b.p. 73-77ø/0.5mm, f.p. 106ø(223øF), d. 0.875, Ë 1.445, MDL MFCD05663884 L19650 (E)-1-Hexene-1,2-diboronic acid bis(pinacol) ester, 98% 1g [1-cis-1,2-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 5g hexene]

[185427-48-9], C18H34B2O4, F.W. 336.09, Colorless liquid, b.p. 102-104ø/0.08mm, f.p. >110ø(230øF), d. 0.954, Ë 1.4560, BRN 7768251, MDL MFCD03093898

2 www.alfa.com Alkenylboronic Acids and Esters Stock # Description Standard Selling Sizes H52613 trans-1-Hexen-1-ylboronic acid, 98% 1g

[42599-18-8], C6H13BO2, F.W. 127.98, White or off-white solid, 5g m.p. 62-63ø, MDL MFCD01074553

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H30373 4-Methoxy-trans-á-styrylboronic acid pinacol ester, 250mg 98% 1g [2-[trans-2-(4-Methoxyphenyl)vinyl]-4,4,5,5-tetramethyl- 5g [1,3,2]dioxaborolane]

[149777-83-3], C15H21BO3, F.W. 260.14, White waxy solid, MDL MFCD04038966 H52759 4-Methylcyclohexene-1-boronic acid, 97% 250mg

[850567-92-9], C7H13BO2, F.W. 139.99, Off-white solid, m.p. 162-166ø, MDL MFCD06659857

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27655 4-Methyl-1-pentenylboronic acid, 97% 50mg

[214907-33-2], C6H13BO2, F.W. 127.98, White cryst powder, 250mg m.p. 99-102ø, MDL MFCD01074680

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Alkenylboronic L19704 4-Methyl-á-styrylboronic acid diethanolamine ester, 97% 100mg

[608534-31-2], C13H18BNO2, F.W. 231.10, White cryst powder, m.p. 205-213ø, MDL MFCD03788755

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H30073 3-Methyl-á-styrylboronic acid pinacol ester, 97% 1g [4,4,5,5-Tetramethyl-2-(trans-2-m-tolylvinyl)[1,3,2]dioxaborolane] 5g

C15H21BO2, F.W. 244.14, Clear colorless liquid, 25g b.p. 114ø/0.3mm, Ë 1.5235, MDL MFCD12546181 Acids

L19698 4-Methyl-á-styrylboronic acid pinacol ester, 98% 250mg

[149777-84-4], C15H21BO2, F.W. 244.14, White solid, 1g m.p. 56-58ø, BRN 7204616, MDL MFCD03788749

H53221 2-Norbornene-2-boronic acid 250mg [Bicyclo[2.2.1]hept-2-en-2-ylboronic acid, 95%]

[871333-98-1], C7H11BO2, F.W. 137.97, White solid, m.p. 124-126ø, MDL MFCD07783853

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52634 trans-1-Octenylboronic acid, 98% 250mg

[42599-16-6], C8H17BO2, F.W. 156.03, White solid, 1g m.p. 96-98ø, MDL MFCD02093734

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L19705 4-Octen-4-ylboronic acid diethanolamine ester, 97% 100mg

[608534-40-3], C12H24BNO2, F.W. 225.14, White cryst powder, m.p. 160-167ø, MDL MFCD03788756

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

L19697 trans-1-Octenylboronic acid pinacol ester, 97% 250mg 1g

[(E)-2-(1-Octenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane]

[83947-55-1], C14H27BO2, F.W. 238.18, Colorless liquid, Ë 1.4460, BRN 7291389, MDL MFCD03453667 L19699 4-Octen-4-ylboronic acid pinacol ester, 98% 250mg

[177949-95-0], C14H27BO2, F.W. 238.18, Colorless liquid, 1g Ë 1.4480, BRN 9128681, MDL MFCD03788750

H52495 5-Oxocyclopentene-1-boronic acid, 97% 250mg [2-Borono-2-cyclopentenone]

[871329-71-4], C5H7BO3, F.W. 125.92, White solid, m.p. 106-108ø, MDL MFCD08056354

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Bulk and Specialty Sizes Available 3 Alkenylboronic Acids and Esters Stock # Description Standard Selling Sizes L19648 (E)-1-Pentene-1,2-diboronic acid bis(pinacol) ester, 98% 1g [1-cis-1,2-Bis(4,4,5,5-tetramethyl-1,3,2-dioxoboralan-2-yl)pentene] 5g

[307531-75-5], C17H32B2O4, F.W. 322.06, Colorless to pale yellow liquid, b.p. 301-303ø, f.p. 76ø(168øF), d. 0.954, Ë 1.4550, MDL MFCD03093909 H:H227, P:P210-P280-P370+P378a-P403+P235-P501a L19677 1-Pentenylboronic acid, 98% 250mg

[104376-24-1], C5H11BO2, F.W. 113.95, m.p. 79-81ø, BRN 2038297, 1g MDL MFCD01074677 5g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27749 (E)-1-Pentenylboronic acid pinacol ester, 98% 1g [(E)-2-(1-Pentenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 5g 2-Hexyl-4,4,5,5-tetramethyl[1,3,2]dioxaborolane] 25g

[161395-96-6], C11H21BO2, F.W. 196.10, Colorless liquid, b.p. 110-111ø/28mm, f.p. 82ø(180øF), d. 0.884, Ë 1.441, MDL MFCD05663882

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L19701 5-Phenyl-1-pentenylboronic acid pinacol ester, 96% 250mg

[154820-97-0], C17H25BO2, F.W. 272.20, Colorless liquid, 1g Ë 1.4980, BRN 7295229, MDL MFCD03788752 Acids H53227 trans-2-Phenylvinylboronic acid, 97% 1g [trans-Phenylethenylboronic acid] 5g

[6783-05-7], C8H9BO2, F.W. 147.97, White or cream solid, m.p. 163-164ø, MDL MFCD00963621

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53216 1-Phenylvinylboronic acid pinacol ester, 95% 250mg

[143825-84-7], C14H19BO2, F.W. 230.11, White solid, m.p. 40-42ø, 1g MDL MFCD06659923 Alkenylboronic

L19573 cis-Stilbeneboronic acid diethanolamine ester, 98% 100mg [cis-(1,2-Diphenylethenyl)boronic acid diethanolamine cyclic ester]

[501014-42-2], C18H20BNO2, F.W. 293.18, m.p. 239-241ø, MDL MFCD03788731

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

L19576 cis-Stilbeneboronic acid pinacol ester, 99% 250mg [cis-(1,2-Diphenylethenyl)boronic acid pinacol cyclic ester] 1g

[264144-59-4], C20H23BO2, F.W. 306.22, White solid, m.p. 92-94ø, BRN 9269561, MDL MFCD03788734

L19652 (Z)-Stilbenediboronic acid bis(pinacol) ester, 98% 1g [cis-1,2-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)stilbene] 5g

[221006-76-4], C26H34B2O4, F.W. 432.18, White to cream powder, m.p. 176-179ø, BRN 9081275, MDL MFCD02683500

L19651 (E)-à,á-Styrenediboronic acid bis(pinacol) ester, 98% 1g [cis-1,2-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)styrene] 5g

[173603-23-1], C20H30B2O4, F.W. 356.08, White to yellow solid, m.p. 69-73ø, BRN 8855562, MDL MFCD02683500

L19571 á-Styrylboronic acid diethanolamine ester, 99% 100mg

[411222-52-1], C12H16BNO2, F.W. 217.08, m.p. 196-198ø, MDL MFCD03788729

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

4 www.alfa.com Alkylboronic Acids and Esters Stock # Description Standard Selling Sizes L19529 trans-á-Styrylboronic acid pinacol ester, 99% 250mg

[83947-56-2], C14H19BO2, F.W. 230.12, m.p. 27-33ø, 1g b.p. 128ø/4mm, f.p. >110ø(230øF), Ë 1.5290, BRN 8617179, MDL MFCD03453666

H52956 (1S)-1,7,7-Trimethylnorborn-2-ene-2-boronic acid, 95% 250mg [(1S)-1,7,7-Trimethylbicyclo[2.2.1]hept-2-en-2-ylboronic acid]

[871333-99-2], C10H17BO2, F.W. 180.05, White solid, m.p. 205-207ø, MDL MFCD08705231

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H51689 trans-3-Trimethylsiloxy-1-propenylboronic acid pinacol 1g ester, 96% 5g

C12H25BO3Si, F.W. 256.22, Liquid, MDL MFCD12547729 25g

L19577 2-(Trimethylsilyl)vinylboronic acid pinacol ester, 95% É 250mg

[126688-99-1], C11H23BO2Si, F.W. 226.20, Colorless liquid, 1g Ë 1.4467, BRN 8616829, MDL MFCD03788735

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Alkylboronic H28703 Vinylboronic anhydride pyridine complex, 95% 1g [O'Shea's reagent, Trivinylboroxin pyridine complex] 5g

[95010-17-6], C6H9B3O3, F.W. 161.57, White to cream powder, m.p. 44-52ø, MDL MFCD03839940

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Stable equivalent of the readily-polymerizable vinylboronic acid, first

reported by Matteson: J. Org. Chem., 27, 3712 (1962), and more recently adopted by O'Shea Acids as a vinylboron unit for Suzuki cross-coupling reactions with aryl halides to give substituted styrenes: J. Org. Chem., 67, 4968 (2002). The reaction has been applied to the formation of ortho-Boc-amino styrenes, further reaction of which has been developed as a route to diversely functionalized indoles: J. Am. Chem. Soc., 125, 4054 (2003). Copper(II) acetate mediated coupling with phenols affords an efficient synthesis of aryl vinyl ethers: J. Org. Chem., 69, 5087 (2004).

Stock # Description Standard Selling Sizes L16232 Allylboronic acid pinacol ester, 98+% 1g [2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane] 5g

[72824-04-5], C9H17BO2, F.W. 168.05, Colorless liquid, b.p. 50-53ø/5mm, f.p. 60ø(140øF), d. 0.890, Ë 1.4270, UN3272, BRN 4244068, MDL MFCD00013347

H:H226, P:P210-P241-P280-P240-P303+P361+P353-P501a Reacts with carboxylic acids, in the presence of tri-n-butyltin hydride, to give homoallylic alcohols in good yield: Synthesis, 1573 (2001):

Homoallylic alcohols can also be formed by allylboration of aldehydes; the reaction has been

found to be accelerated by Lewis acids, e.g. AlCl3 or Sc(OTf)3: J. Am. Chem. Soc., 124, 12414 (2002). H32523 Benzylboronic acid pinacol ester, 96% 1g

[87100-28-5], C13H19BO2, F.W. 218.1, Liquid, b.p. 65ø/0.15mm, 5g d. 0.98, MDL MFCD05663841 25g

H27097 4-Bromobutylboronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol 250mg ester, 95% 1g [(1S,2S,3R,5S)-(+)-2,3-Pinanediol 4-bromobutylboronate]

[165881-36-7], C14H24BBrO2, F.W. 315.06, Colorless to pale yellow liquid, Ë 1.4960, MDL MFCD09037500 H30646 3-Bromopropylboronic acid pinacol ester, 98% 1g [2-(3-Bromopropyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane] 5g

[124215-44-7], C9H18BBrO2, F.W. 248.96, Colorless liquid, 25g b.p. 61-64ø/0.35mm, d. 1.177, MDL MFCD10567053

H:H315-H319, P:P280g-P305+P351+P338

Bulk and Specialty Sizes Available 5 Alkylboronic Acids and Esters Stock # Description Standard Selling Sizes A13725 1-Butylboronic acid, 98% È Ê 1g [n-Butaneboronic acid] 5g

[4426-47-5], CH3CH2CH2CH2B(OH)2, F.W. 101.94, White crystals, m.p. 92-96ø, 25g EINECS 224-607-7, BRN 1733489, MDL MFCD00002106

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Reagent for preparation of volatile derivatives of diols, e.g. carbohydrates, for GC and mass spectrometry: J. Chromat., 54, 193 (1971); J. Chromat. Sci., 9, 18 (1971); Gas Chromat., 129 (1968). In combination with (S)-(-)-à,à-Diphenylprolinol, L09217, p. 132, or its enantiomer (9218), oxazaborolidine catalysts are generated in situ, for use in highly enantioselective reductions: Tetrahedron Lett., 33, 4141 (1992). The same system has been employed in the synthesis of chiral monosubstituted oxiranes: Tetrahedron Lett., 34, 5227 (1993). See also (S)-2-Methyl-CBS-oxazaborolidine monohydrate, L09219, p. 133, and Appendix 5. H27661 1-Butylboronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester, 250mg 95% 1g [(1S,2S,3R,5S)-(+)-2,3-Pinanediol butylboronate]

[85167-10-8], C14H25BO2, F.W. 236.17, Colorless to pale yellow liquid, Ë 1.4629, MDL MFCD09037499 H27051 2-(4-tert-Butylphenyl)ethylboronic acid pinacol ester, 1g 95% 5g [2-[2-(4-tert-Butylphenyl)ethyl- 25g ]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane]

C18H29BO2, F.W. 288.24, White solid, Acids MDL MFCD09953477 L19575 2-(9-Carbazolyl)ethylboronic acid diethanolamine ester, 98% 100mg

[501014-45-5], C18H21BN2O2, F.W. 308.19, White crytalline powder, m.p. 244-248ø, MDL MFCD03788733 Alkylboronic L19580 2-(9-Carbazolyl)ethylboronic acid pinacol ester, 98% 250mg

[608534-41-4], C20H24BNO2, F.W. 321.23, White powder, 1g m.p. 111-113ø, MDL MFCD03788738

H30464 2-(3-Chlorophenyl)ethylboronic acid pinacol ester, 97% 1g [2-[2-(3-Chlorophenyl)ethyl- 5g ]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane]

C14H20BClO2, F.W. 266.58, Clear colorless liquid, Ë 1.4965, MDL MFCD12546188

H30303 2-(4-Chlorophenyl)ethylboronic acid pinacol ester, 98% 1g [2-[2-(4-Chlorophenyl)ethyl- 5g ]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane]

[444094-88-6], C14H20BClO2, F.W. 266.58, White fused solid, m.p. 34-38ø, MDL MFCD12546184

H27126 3-Cyano-1-propylboronic acid pinacol ester, 96% 1g [4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)butyronitrile] 5g

[238088-16-9], C10H18BNO2, F.W. 195.07, Colorless liquid, 25g Ë 1.4370, UN3276, MDL MFCD09953480

H:H302-H312-H332, P:P261-P280-P302+P352-P304+P340-P322-P501a H31156 2-Cyclohexylethylboronic acid pinacol ester, 96% 1g [2-(2-Cyclohexylethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane] 5g

[167692-95-7], C14H27BO2, F.W. 238.18, Colorless liquid, MDL MFCD12546193

H27081 Cyclopentylboronic acid, 95% 1g

[63076-51-7], C5H11BO2, F.W. 113.95, White solid, MDL MFCD01074541 10g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H31158 3-Cyclopentylpropylboronic acid pinacol ester, 97% 1g [2-(3-Cyclopentylpropyl)-4,4,5,5-tetramethyl[1,3,2]dioxaborolane] 5g

C14H27BO2, F.W. 238.18, Colorless liquid, b.p. 114ø/5mm, 25g MDL MFCD12546194

6 www.alfa.com Alkylboronic Acids and Esters Stock # Description Standard Selling Sizes H26254 Cyclopropylboronic acid, tech. 85% 1g

[411235-57-9], C3H7BO2, F.W. 85.90, White to cream cryst powder, 5g m.p. 90-95ø, MDL MFCD04038750

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27642 Cyclopropylboronic acid pinacol ester, 96% É 1g [2-Cyclopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane] 5g

[126689-01-8], C9H17BO2, F.W. 168.04, Colorless liquid, b.p. 146ø, f.p. 40ø(104øF), d. 0.922, UN3272, MDL MFCD05663847

H:H226, P:P210-P241-P280-P240-P303+P361+P353-P501a L19957 1-Decylboronic acid, 98% 1g [n-Decaneboronic acid] 5g

[24464-63-9], CH3(CH2)9B(OH)2, F.W. 186.10, m.p. 86-89ø, BRN 1743934, 25g MDL MFCD01074638

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H30403 1-Decylboronic acid pinacol ester, 98% 1g [2-(n-Decyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane] 5g

[141091-38-5], C16H33BO2, F.W. 268.25, Liquid, 25g MDL MFCD12546186 L19532 3,3-Diethoxy-1-propylboronic acid pinacol ester, 97% 250mg Alkylboronic

[165904-27-8], C13H27BO4, F.W. 258.17, Colorless liquid, 1g Ë 1.4280, MDL MFCD03788723

H27267 3,3-Dimethylbicyclo[2.2.1]hept-2-ylmethylboronic acid pinacol 1g ester, mixture of isomers, 90+% 5g

[2-(3,3-Dimethylbicyclo[2.2.1]hept-2-yl- 25g Acids methyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane]

C16H29BO2, F.W. 264.22, White low-melting solid, MDL MFCD09953482 L19533 2-(1,3-Dioxolan-2-on-4-yl)-1-ethylboronic acid pinacol 250mg ester, 97% 1g

[501014-47-7], C11H19BO5, F.W. 242.08, Colorless liquid, Ë 1.5430, MDL MFCD03788724

H26071 2-(1,3-Dioxolan-2-yl)ethylboronic acid pinacol ester, 97% 1g

C11H21BO4, F.W. 228.10, Colorless liquid, b.p. 100ø/1.5mm, 5g MDL MFCD03788722

L19703 2,2-Diphenylethylboronic acid diethanolamine ester, 97% 100mg

[608534-43-6], C18H22BNO2, F.W. 295.19, m.p. 189-191ø, MDL MFCD03788754

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L19958 1-Dodecylboronic acid, 98% È 1g [n-Dodecaneboronic acid, Laurylboronic acid] 5g

[3088-79-7], C12H27BO2, F.W. 214.16, White to cream cryst, m.p. 91-93ø, BRN 1750795, 25g MDL MFCD04039322

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H31186 1-Dodecylboronic acid pinacol ester, 98% 1g [2-n-Dodecyl-4,4,5,5-tetramethyl[1,3,2]dioxaborolane] 5g

[177035-82-4], C18H37BO2, F.W. 296.31, Liquid, 25g b.p. 123ø/0.2mm, MDL MFCD12546195 L19959 Ethylboronic acid, 98% È 1g [Ethaneboronic acid] 5g

[4433-63-0], C2H7BO2, F.W. 73.89, White powder or flakes, m.p. 84-88ø, BRN 1731546, 25g MDL MFCD01074536

H:H315-H319-H335, P:P280g-P305+P351+P338 B22446 1-Hexylboronic acid, 97% È 10g [n-Hexaneboronic acid]

[16343-08-1], CH3(CH2)5B(OH)2, F.W. 130.00, White to pale cream cryst powder, m.p. 85-90ø, BRN 1736080, MDL MFCD01074641

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Bulk and Specialty Sizes Available 7 Alkylboronic Acids and Esters Stock # Description Standard Selling Sizes H27831 1-Hexylboronic acid pinacol ester, 98% 1g [2-n-Hexyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane] 5g

[86308-26-1], C12H25BO2, F.W. 212.14, Colorless liquid, 25g f.p. 84ø(183øF), d. 1.167, Ë 1.426, MDL MFCD08457665 H:H227, P:P210-P280-P370+P378a-P403+P235-P501a H27153 3-(2-Hydroxyphenyl)propylboronic acid pinacol ester, 1g 97% 5g [2-[3-(2-Hydroxyphenyl)propyl- 25g ]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane]

C15H23BO3, F.W. 262.16, White powder, m.p. 61-64ø, MDL MFCD09953481

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L19574 2-Indanylboronic acid diethanolamine ester, 98% 100mg

[501014-44-4], C13H18BNO2, F.W. 231.10, m.p. 218-221ø, MDL MFCD03788732

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L19535 2-Indanylboronic acid pinacol ester, 95% 250mg

[608534-44-7], C15H21BO2, F.W. 244.14, Colorless liquid, 1g Ë 1.5040, MDL MFCD03788726

Acids H27698 Isobutylboronic acid, 97% 1g [(2-Methylpropyl)boronic acid] 5g

[84110-40-7], (CH3)2CHCH2B(OH)2, F.W. 101.94, White cryst powder, m.p. 108-110ø, MDL MFCD00134156

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L19962 Isopropylboronic acid, 98% Ê 1g [2-Propaneboronic acid] 5g

[80041-89-0], C3H9BO2, F.W. 87.91, BRN 1731883, MDL MFCD01319021 25g Alkylboronic

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H28557 3-(4-Methoxyphenyl)-1-propylboronic acid pinacol 250mg ester, 97% 1g [2-[3-(4-Methoxyphenyl)propyl- 5g ]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane]

C16H25BO3, F.W. 276.19, Colorless liquid, MDL MFCD09953503 L15589 Methylboronic acid, 97% Ê 1g [Methaneboronic acid] 5g

[13061-96-6], CH5BO2, F.W. 59.86, White to pale cream cryst powder, m.p. 89-94ø, BRN 1731087, MDL MFCD00002105

H:H315-H319-H335, P:P280g-P305+P351+P338 H52460 (5-Methylthio-3-pyridylthio)methylboronic acid, 95% 250mg

[913835-66-2], C7H10BNO2S2, F.W. 215.09, Yellow solid, m.p. 142-144ø, MDL MFCD08436048

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H30191 3-(4-Morpholinyl)propyl-1-boronic acid pinacol ester, 98% 1g [4-[3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)propyl- 5g ]morpholine]

C13H26BNO3, F.W. 255.17, Pale brown liquid, Ë 1.4585, MDL MFCD12546182

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L19964 1-Octylboronic acid, 97% È 1g [Caprylboronic acid, n-Octaneboronic acid] 5g

[28741-08-4], CH3(CH2)7B(OH)2, F.W. 158.05, m.p. 81-85ø, BRN 1739759, 25g MDL MFCD01074560

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H31154 3-Pentafluorophenyl-1-propylboronic acid pinacol ester, 250mg 96% 1g [4,4,5,5-Tetramethyl-2-[3-(pentafluorophenyl)propyl- 5g ]-1,3,2-dioxaborolane]

C15H18BF5O2, F.W. 336.11, Clear colorless liquid, b.p. 126-128ø/1.5mm, Ë 1.4412, MDL MFCD12546192

H:H315-H319, P:P280-P305+P351+P338-P302+P352-P321-P362-P332+P313

8 www.alfa.com Alkylboronic Acids and Esters Stock # Description Standard Selling Sizes H31401 2-(4-Phenoxyphenyl)ethylboronic acid diethanolamine 1g ester, 97% 5g

C18H22BNO3, F.W. 311.19, White powder, m.p. 164-167ø, 25g MDL MFCD12546199

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52502 2-Phenylethylboronic acid, 98% 1g [Phenethylboronic acid] 5g

[34420-17-2], C8H11BO2, F.W. 149.98, White solid, m.p. 82-84ø, MDL MFCD01631226

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L19706 2-Phenylethyl-1-boronic acid diethanolamine ester, 98+% 100mg

[4848-04-8], C12H18BNO2, F.W. 219.09, White solid, m.p. 133-137ø, MDL MFCD03788757

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

L19530 2-Phenylethyl-1-boronic acid pinacol ester, 99% 250mg

[165904-22-3], C14H21BO2, F.W. 232.13, Colorless liquid, 1g Ë 1.4860, BRN 8258927, MDL MFCD03788721 Alkylboronic

H26931 2-Phenyl-1-propylboronic acid pinacol ester, 97% 250mg [4,4,5,5-Tetramethyl-2-(2-phenylpropyl)-1,3,2-dioxaborolane] 1g

[280559-30-0], C15H23BO2, F.W. 246.16, Colorless liquid, 5g MDL MFCD09953475

H28985 3-Phenyl-1-propylboronic acid pinacol ester, 97% 250mg Acids [4,4,5,5-Tetramethyl-2-(3-phenylpropyl)-1,3,2-dioxaborolane] 1g

[329685-40-7], C15H23BO2, F.W. 246.16, Colurless liquid, 5g MDL MFCD09953505 H31838 3-(Phenylsulfonyl)propylboronic acid diethanolamine ester 1g [3-(Benzenesulfonyl)propylboronic acid diethanolamine ester, 5g 2-[3-(Phenylsulfonyl)propyl]-1,3,6,2-dioxazaborocane]

C13H20BNO4S, F.W. 297.18, White solid, m.p. 164-166ø, MDL MFCD12546197

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L19965 1-Propylboronic acid, 98% È Ê 1g [Propaneboronic acid] 5g

[17745-45-8], CH3(CH2)2B(OH)2, F.W. 87.91, m.p. 105-108ø, BRN 1731884, 25g MDL MFCD01074564

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H30441 1-Propylboronic acid pinacol ester, 98% 1g [4,4,5,5-Tetramethyl-2-n-propyl-1,3,2-dioxaborolane] 5g

[67562-19-0], C9H19BO2, F.W. 170.06, Clear colorless liquid, 25g b.p. 166-168ø, f.p. 47ø(117øF), Ë 1.4140, UN1993, MDL MFCD12546187

H:H226, P:P210-P241-P280-P240-P303+P361+P353-P501a L19966 1-Tetradecylboronic acid 1g [Myristylboronic acid, n-Tetradecaneboronic acid] 5g

[100888-40-2], CH3(CH2)13B(OH)2, F.W. 242.21, m.p. 72-76ø, BRN 1757986, 25g MDL MFCD00093676

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H31355 Tetrahydrothiophene-1,1-dioxide-3-boronic acid diethanolamine 250mg ester, 97% 1g

C8H16BNO4S, F.W. 233.10, Cream powder, m.p. 242-244ø, 5g MDL MFCD12546196

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H30323 3-(2-Trimethylsiloxyphenyl)-1-propylboronic acid pinacol 1g ester, 95% É 5g [4,4,5,5-Tetramethyl-2-[3-(2-trimethylsiloxyphenyl)propyl- 25g ]-1,3,2-dioxaborolane]

C18H31BO3Si, F.W. 334.34, Clear colorless liquid, Ë 1.4799, MDL MFCD12546185

Bulk and Specialty Sizes Available 9 Alkyltrifluoroborate Salts Stock # Description Standard Selling Sizes L19572 2-Trimethylsilyl-1-ethylboronic acid diethanolamine ester, 98% 100mg É

[501014-43-3], C9H22BNO2Si, F.W. 215.18, m.p. 183-186ø, MDL MFCD03788730

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L19534 2-Trimethylsilyl-1-ethylboronic acid pinacol ester, 97% É 250mg

[165904-20-1], C11H25BO2Si, F.W. 228.22, Colorless liquid, 1g Ë 1.4310, BRN 8683473, MDL MFCD03788725

H28413 3-Trimethylsilyl-1-propylboronic acid pinacol ester, 94% 250mg [4,4,5,5-Tetramethyl-2-(3-trimethylsilylpropyl)-1,3,2-dioxoborolane] 1g

C12H27BO2Si, F.W. 242.24, Colorless liquid, 5g MDL MFCD09953502

Stock # Description Standard Selling Sizes

Salts H32215 Potassium N-benzyl-N-methyl-aminomethyltrifluoroborate, 95% 250mg

[936329-96-3], C9H12BF3KN, F.W. 241.11, White to orange cryst powder 1g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H31672 Potassium (4-Boc-1-piperazinyl)methyltrifluoroborate, 95% 1g [Potassium (4-tert-butoxycarbonyl-1-piperazinyl)methyl- 5g trifluoroborate]

[936329-97-4], C10H19BF3KN2O2, F.W. 306.18, Pale yellow cryt powder

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H32168 Potassium bromomethyltrifluoroborate, 95% 1g

[888711-44-2], CH2BBrF3K, F.W. 200.84, White cryst powder 250mg

Alkyltrifluoroborate 5g H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H32077 Potassium (tert-butylaminomethyl)trifluoroborate, 95% 250mg

C5H12BF3KN, F.W. 193.07, White cryst powder 1g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H31878 Potassium (cyclohexylaminomethyl)trifluoroborate, 95% 250mg

[888711-52-2], C7H14BF3KN, F.W. 219.11, White cryst powder 1g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H32025 Potassium N-cyclohexyl-N-methylaminomethyltrifluoroborate, 250mg 95% 1g

C8H16BF3KN, F.W. 233.13, White to yellow solid

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H32674 Potassium methoxymethyltrifluoroborate, 95% 500mg

[910251-11-5], C2H5BF3KO, F.W. 151.97, White cryst powder 2g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H32957 Potassium (4-morpholinyl)methyltrifluoroborate, 95% 1g

[936329-94-1], C5H10BF3KNO, F.W. 207.05, White cryst powder 5g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H32030 Potassium phenoxymethyltrifluoroborate, 95% 250mg

C7H7BF3KO, F.W. 214.04, White cryst powder 1g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H25930 Potassium 2-phenylethyltrifluoroborate, 98% 1g [Potassium phenethyltrifluoroborate] 5g

[329976-74-1], C8H9BF3K, F.W. 212.06, White cryst powder, m.p. 173-175ø, MDL MFCD09039257

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

10 www.alfa.com Alkenyltrifluoroborate Salts

Stock # Description Standard Selling Sizes L17973 Potassium 4-methyl-á-styryltrifluoroborate, 95% 1g [4-Methyl-á-styryltrifluoroboric acid potassium salt] 5g

[219718-86-2], C9H9BF3K, F.W. 224.08, BRN 7783635, MDL MFCD02093982

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L17971 Potassium trans-á-styryltrifluoroborate, 98% 1g [á-Styryltrifluoroboric acid potassium salt] 5g

[201852-49-5], C8H7BF3K, F.W. 210.05, m.p. >300ø, BRN 7782992, MDL MFCD02093981

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Undergoes cross-coupling reactions with arenediazonium tetrafluoroborates, catalyzed by the palladacycle trans-Di-mu-acetatobis[2-(di-o-tolylphosphino)benzyl]dipalladium(II),

L16948, p. 140, to give substituted stilbenes in high yield: Tetrahedron Lett., 39, 5045 (1998); Alkenyltrifluoroborate Eur. J. Org. Chem., 1875 (1999). L17970 Potassium vinyltrifluoroborate, 97% Ê 1g [Vinyltrifluoroboric acid potassium salt] 5g

[13682-77-4], C2H3BF3K, F.W. 133.95, m.p. 230ø dec., BRN 7777570, MDL MFCD02093335

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Stable vinylating agent. Darses et al, reported the cross-coupling reaction with arenediazonium

tetrafluoroborates to give styrenes in high yield, catalyzed by Pd(OAc)2 (ligand-free) or the palladacycle trans-Di-mu-acetatobis[2-(di-o-tolylphosphino)benzyl]dipalladium(II), L16948, p. 140: Tetrahedron Lett., 39, 5045 (1998); Eur. J. Org. Chem., 1875 (1999). Molander has since described the direct cross-coupling of the reagent with aryl halides and triflates, catalyzed by [1,1'-Bis(diphenylphosphino)ferrocene]palladium(II) chloride, 41225, p. 137: Org. Lett., 4, 107 (2002): Salts

Stock # Description Standard Selling Sizes H53302 2-Acetamidobenzeneboronic acid, 96% 250mg [2-Acetylaminophenylboronic acid] 1g

[169760-16-1], C8H10BNO3, F.W. 178.98, White to brown solid, m.p. >300ø, MDL MFCD02179474

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B23833 3-Acetamidobenzeneboronic acid, 98% 1g [3-Acetamidophenylboronic acid] 5g

[78887-39-5], C8H10BNO3, F.W. 178.98, White to pale brown cryst 25g powder, m.p. ca 263ø dec., BRN 3278316, MDL MFCD00236013

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52987 4-Acetamidobenzeneboronic acid, 96% 1g [4-Acetylaminophenylboronic acid] 5g

[101251-09-6], C8H10BNO3, F.W. 178.98, Grey-pale brown powder, m.p. 215-220ø, MDL MFCD02179451

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53349 3-Acetamido-5-carboxybenzeneboronic acid, 98% 250mg [3-Acetamido-5-boronobenzoic acid] 1g

[108749-15-1], C9H10BNO5, F.W. 222.99, White solid, m.p. 240-243ø, MDL MFCD08436066

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53252 3-(Acetamidomethyl)benzeneboronic acid, 97% 250mg [3-(Acetylaminomethyl)phenylboronic acid] 1g

[850568-42-2], C9H12BNO3, F.W. 193.01, White solid, m.p. 253-255ø, MDL MFCD06659819

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52602 4-(Acetamidomethyl)benzeneboronic acid, 97% 250mg [4-(Acetylaminomethyl)phenylboronic acid] 1g

[850568-41-1], C9H12BNO3, F.W. 193.01, White solid, m.p. 278-280ø, MDL MFCD06659818

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Bulk and Specialty Sizes Available 11 Arylboronic Acids Stock # Description Standard Selling Sizes H53348 3-Acetamido-2-nitrobenzeneboronic acid, 96% 250mg [3-Acetylamino-2-nitrophenylboronic acid]

[78887-38-4], C8H9BN2O5, F.W. 223.98, Yellow solid, m.p. 161-162ø, MDL MFCD06659828

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53135 5-Acetamido-2-nitrobenzeneboronic acid, 96% 250mg [5-Acetylamino-2-nitrophenylboronic acid]

[78887-36-2], C8H9BN2O5, F.W. 223.98, Yellow solid, m.p. 193-196ø, MDL MFCD06659829

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52879 4-Acetoxybenzeneboronic acid, 97% 250mg [4-Acetyloxyphenylboronic acid] 1g

[177490-82-3], C8H9BO4, F.W. 179.97, Pale brown solid, m.p. 220-224ø, MDL MFCD09027198

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52966 4-Acetoxymethylbenzeneboronic acid, 97% 250mg

[326496-51-9], C9H11BO4, F.W. 193.99, White solid, m.p. 81-83ø, 1g MDL MFCD08235082

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27327 2-Acetylbenzeneboronic acid, 97% 5g [2-Acetylphenylboronic acid, 2'-Boronoacetophenone] 25g

[308103-40-4], C8H9BO3, F.W. 163.97, White to pale yellow powder, Acids m.p. ca 170ø dec., MDL MFCD01321263

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B23478 3-Acetylbenzeneboronic acid, 97% 1g [3-Acetylphenylboronic acid, 3'-Boronoacetophenone] 5g

[204841-19-0], C8H9BO3, F.W. 163.97, White to cream powder, 25g m.p. ca 200-205ø, BRN 8255673, MDL MFCD01074678

Arylboronic H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B23234 4-Acetylbenzeneboronic acid, 98% 1g [4-Acetylphenylboronic acid, 4'-Boronoacetophenone] 5g

[149104-90-5], C8H9BO3, F.W. 163.97, White to pale brown cryst 25g powder, m.p. ca 240ø dec., BRN 7869162, MDL MFCD01074667

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53151 4-(Acetylsulfamoyl)benzeneboronic acid, 97% 250mg [N-Acetyl 4-boronobenzenesulfonamide]

[913835-52-6], C8H10BNO5S, F.W. 243.04, White solid, m.p. 130-134ø, MDL MFCD08436010

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53104 3-(1-Adamantyl)-4-methoxybenzeneboronic acid, 96% 250mg

[459423-32-6], C17H23BO3, F.W. 286.18, Yellow solid, m.p. 239-242ø, MDL MFCD08056355

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H53237 3-Allylcarbamoylbenzeneboronic acid, 96% 250mg [N-Allyl 3-boronobenzamide] 1g

[850567-29-2], C10H12BNO3, F.W. 205.02, Off-white solid, m.p. 92-96ø, MDL MFCD04115702

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52961 4-Allylcarbamoylbenzeneboronic acid, 97% 250mg [N-Allyl 4-boronobenzamide] 1g

[850568-20-6], C10H12BNO3, F.W. 205.02, White solid, m.p. 196-200ø, MDL MFCD04115674

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52535 4-Amidoximobenzeneboronic acid, 95% 250mg [4-(N-Hydroxycarbamimidoyl)benzeneboronic acid] 1g

[913835-61-7], C7H9BN2O3, F.W. 179.97, White solid, MDL MFCD08436061

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L18069 2-Aminobenzeneboronic acid, 96% 100mg [2-Aminophenylboronic acid] 1g

[5570-18-3], C6H8BNO2, F.W. 136.95, m.p. 188-190ø, BRN 2962939, 5g MDL MFCD01074645

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

12 www.alfa.com Arylboronic Acids Stock # Description Standard Selling Sizes A18189 3-Aminobenzeneboronic acid monohydrate, 97% Ê 1g [3-Aminophenylboronic acid monohydrate] 5g

[206658-89-1], C6H8BNO2ùH2O, F.W. 154.96 (136.95anhy), 25g Crystalline, m.p. 93-97ø, EINECS 250-189-0, BRN 2936342, MDL MFCD00149554

H:H315-H319, P:P280-P305+P351+P338-P302+P352-P321-P362-P332+P313 H52909 3-Aminobenzeneboronic acid, 98% 1g

[30418-59-8], C6H8BNO2, F.W. 136.95, Off-white solid, m.p. 138-143ø, 5g EINECS 250-189-0, MDL MFCD00007755 25g A17240 3-Aminobenzeneboronic acid hemisulfate, 98+% Ê 1g [3-Aminophenylboronic acid hemisulfate] 5g

[66472-86-4], C6H8BNO2ù0.5H2SO4, F.W. 185.98, Powder, m.p. >300ø, 25g EINECS 266-376-5, BRN 8094151, MDL MFCD00013111

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Has been used in the preparation of polymers containing the benzeneboronate function for use in chromatography: J. Chromat., 176, 239 (1979). H52595 3-Aminobenzeneboronic acid hydrochloride, 98% 1g [3-Aminophenylboronic acid hydrochloride] 5g

[85006-23-1], C6H8BNO2ùHCl, F.W. 173.41, Off-white to brown solid, m.p. >300ø, EINECS 285-052-4, MDL MFCD00191748 Arylboronic H27479 4-Aminobenzeneboronic acid hydrochloride, 97% Ê 100mg [4-Aminophenylboronic acid hydrochloride, 4-Boronoaniline hydrochloride] 500mg

[80460-73-7], C6H8BNO2ùHCl, F.W. 173.41, White cryst powder, m.p. 125-132ø, MDL MFCD03001333

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H53076 3-Amino-5-carboxybenzeneboronic acid, 98% 250mg Acids [3-Amino-5-carboxyphenylboronic acid] 1g

[116378-40-6], C7H8BNO4, F.W. 180.95, Grey solid, m.p. 210-212ø, MDL MFCD02179466

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52888 2-Amino-4-carboxybenzeneboronic acid hydrochloride, 96% 250mg [3-Amino-4-boronobenzoic acid hydrochloride, 2-Amino-4-carboxyphenylboronic acid hydrochloride]

[850568-60-4], C7H8BNO4ùHCl, F.W. 217.42, Off-white solid, m.p. >300ø, MDL MFCD06656012

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52893 3-Amino-4-chlorobenzeneboronic acid hydrochloride, 95% 250mg [3-Amino-4-chlorophenylboronic acid hydrochloride] 1g

[850568-45-5], C6H7BClNO2ùHCl, F.W. 207.85, Brown, m.p. 278-288ø, MDL MFCD04115643

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52695 2-Amino-4-cyanobenzeneboronic acid hydrochloride, 97% 250mg [2-Amino-4-cyanophenylboronic acid hydrochloride]

[850568-47-7], C7H7BN2O2ùHCl, F.W. 198.42, White solid, m.p. 214-218ø, MDL MFCD06659820

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52455 3-Amino-5-cyanobenzeneboronic acid hydrochloride, 97% 250mg [3-Amino-5-cyanophenylboronic acid hydrochloride] 1g

[913835-26-4], C7H7BN2O2ùHCl, F.W. 198.42, White solid, m.p. 123-125ø, MDL MFCD08436033

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52629 5-Amino-2-(hydroxymethyl)benzeneboronic acid hemiester 250mg hydrochloride, 95% 1g [6-Amino-1-hydroxy-2,1-benzoxaborolane hydrochloride, 5-Amino-2-(hydroxymethyl)benzeneboronic acid cyclic monoester hydrochloride]

[117098-93-8], C7H8BNO2ùHCl, F.W. 185.42, Grey solid, m.p. 300ø, MDL MFCD04115645

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53234 2-Amino-4-(methoxycarbonyl)benzeneboronic acid 250mg hydrochloride, 95% 1g [Methyl 3-amino-4-boronobenzoate hydrochloride]

[380430-55-7], C8H10BNO4ùHCl, F.W. 231.44, Off-white solid, m.p. 200-204ø, MDL MFCD02258941

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Bulk and Specialty Sizes Available 13 Arylboronic Acids Stock # Description Standard Selling Sizes H52904 3-Amino-5-(methoxycarbonyl)benzeneboronic acid 250mg hydrochloride, 97% 1g [Methyl 3-Amino-5-boronobenzoate hydrochloride]

[380430-56-8], C8H10BNO4ùHCl, F.W. 231.44, White solid, m.p. 220-226ø, MDL MFCD04971992

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L17695 3-Amino-4-methylbenzeneboronic acid, 98% 1g [3-Amino-4-methylphenylboronic acid, 3-Amino-p-tolylboronic acid] 5g

[22237-12-3], C7H10BNO2, F.W. 150.98, m.p. ca 250ø, MDL MFCD01074640

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53284 3-(Aminomethyl)benzeneboronic acid hydrochloride, 96% 250mg [3-(Aminomethyl)phenylboronic acid hydrochloride] 1g

[352525-94-1], C7H10BNO2ùHCl, F.W. 187.43, White or cream solid, m.p. 248-250ø, MDL MFCD02093050

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52855 4-(Aminomethyl)benzeneboronic acid hydrochloride, 96% 1g [4-(Aminomethyl)phenylboronic acid hydrochloride, 4-Boronobenzylamine 5g hydrochloride]

[75705-21-4], C7H10BNO2ùHCl, F.W. 187.43, White or cream solid, m.p. 240-250ø, MDL MFCD01632199

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Acids H52926 2-Aminomethyl-4-fluorobenzeneboronic acid hydrochloride, 250mg 95% 1g [2-Aminomethyl-4-fluorophenylboronic acid hydrochloride, 2-Borono-5-fluorobenzylamine hydrochloride]

[850568-02-4], C7H9BFNO2ùHCl, F.W. 205.42, Off-white solid, m.p. >300ø, MDL MFCD04973742

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Arylboronic H53097 2-Aminomethyl-5-fluorobenzeneboronic acid hydrochloride, 250mg 95% 1g [2-Aminomethyl-5-fluorophenylboronic acid hydrochloride, 2-Borono-4-fluorobenzylamine hydrochloride]

[850568-03-5], C7H9BFNO2ùHCl, F.W. 205.42, Off-white solid, m.p. 152-158ø, MDL MFCD04115666

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52651 3-Amino-5-nitrobenzeneboronic acid, 97% 250mg [3-Amino-5-nitrophenylboronic acid, 3-Borono-5-nitroaniline] 1g

[89466-05-7], C6H7BN2O4, F.W. 181.94, Pink solid, MDL MFCD08436012

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52674 3-Amino-5-nitrobenzeneboronic acid hydrochloride, 96% 250mg [3-Amino-5-nitrophenylboronic acid hydrochloride]

[389621-79-8], C6H7BN2O4ùHCl, F.W. 218.40, White to off-white solid, m.p. 136-141ø, MDL MFCD03411933

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L19630 Anthracene-9-boronic acid, 99% 100mg [9-Anthrylboronic acid] 500mg

[100622-34-2], C14H11BO2, F.W. 222.06, m.p. ca 215ø dec., BRN 3301031, MDL MFCD03425925

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53088 4-(1-Azetidinylsulfonyl)benzeneboronic acid, 96% 250mg [4-(1-Azetidinylsulfonyl)phenylboronic acid, 1-(4-Boronophenylsulfonyl)- 1g azetidine]

[871329-68-9], C9H12BNO4S, F.W. 241.07, White solid, m.p. 140-144ø, MDL MFCD07363756

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52456 4-Benzamidobenzeneboronic acid, 95% 250mg [4-Benzamidophenylboronic acid] 1g

[397843-80-0], C13H12BNO3, F.W. 241.05, Brown solid, m.p. 194-196ø, MDL MFCD08235089

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

14 www.alfa.com Arylboronic Acids Stock # Description Standard Selling Sizes A14257 Benzeneboronic acid, 98+% 10g [Phenylboric acid, Phenylboronic acid] 50g

[98-80-6], C6H7BO2, F.W. 121.93, White to cream cryst powder, 250g m.p. 214-219ø, Merck 14,1068, Fieser 1,833 2,317 3,221 5,513 7,284 9,23 15,254 20,303, EINECS 202-701-9, RTECS CY8575000, BRN 970972, MDL MFCD00002103, Ì

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Reagent for protection of diols as their cyclic boronates: J. Am. Chem. Soc., 80, 2443 (1958); Tetrahedron, 25, 477 (1969), which are also useful in GC and GC-MS. This has been utilized to trap cis-diols, in order to prevent over-oxidation during dihydroxylation reactions catalyzed by Osmium(VIII) oxide, 12103, p. ?: Chem. Lett., 1721 (1988); J. Org. Chem., 63, 7322 (1998). Promotes the ortho-hydroxalkylation of phenols by aldehydes. The cyclic boronate, formed via a [3,3] sigmatropic rearrangement, is the key intermediate: Synthesis, 365 (1979):

With citronellal, hexahydrocannabinoids are formed: J. Chem. Soc., Perkin 1, 605 (1992). Acts as a template for Diels-Alder reactions, by forming boronate linkages with a hydroxydiene and a hydroxydienophile: Synthesis 1171 (1991); for Nicolaou's application to synthesis of Arylboronic the CD ring system of taxol, see: J. Chem. Soc., Chem. Commun., 1118 (1992); J. Am. Chem. Soc., 117, 634 (1995): Acids

For use in the formation of an oxazaborolidine catalyst for use in enantioselective reductions, see note under (S)-(-)-à,à-Diphenylprolinol, L09217, p. 132. Forms a stable chiral acyloxyborane (CAB) catalyst with tartaric acid derivatives, which catalyze hetero Diels-Alder reactions, e.g. between aldehydes and 1-Methoxy-3-trimethyl- siloxy-1,3-butadiene, L06100, p. ?, to give enantioselectively, dihydro-4-pyrone derivatives: Tetrahedron, 50, 979 (1994). The most widely-used reaction of arylboronic acids is the Pd-catalyzed Suzuki synthesis of unsymmetrical biaryls: Synth. Commun., 11, 513 (1981):

For illustrative example, see: Org. Synth., 75, 53 (1997). For a brief feature on uses of this reagent in Organic synthesis, see: Synlett, 2679 (2006). For further information and reviews on boronic acid chemistry, see Appendix 5. L19459 Benzeneboronic acid, polymer-supported, 2.6-3.2 mmol/g 1g [4-Boronopolystyrene, Phenylboronic acid, polymer-supported] 5g MDL MFCD03456184 25g Useful in the resolution of sugars: Makromol. Chem., 178, 2799 (1977). For the selective removal of cis-diols in the presence of trans-diols, see: Tetrahedron Lett., 3669 (1976). B24903 1,3-Benzenediboronic acid, 97% 1g [1,3-Phenylenediboronic acid] 5g

[4612-28-6], C6H8B2O4, F.W. 165.75, White to cream powder, 25g m.p. >300ø, MDL MFCD03092915

H:H302, P:P264-P270-P301+P312-P330-P501a B24064 1,4-Benzenediboronic acid, 96% 1g [1,4-Phenylenediboronic acid] 5g

[4612-26-4], C6H8B2O4, F.W. 165.75, White to cream powder, 25g m.p. >300ø, BRN 2836921, MDL MFCD00236018

H:H302, P:P264-P270-P301+P312-P330-P501a L20296 1,4-Benzodioxane-6-boronic acid, 97% 1g [2,3-Dihydro-1,4-benzodioxin-6-ylboronic acid, 3,4-(Ethylenedioxy)- 5g benzeneboronic acid]

[164014-95-3], C8H9BO4, F.W. 179.97, White to cream cryst powder, BRN 7478648, MDL MFCD01009696

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52506 3-Benzylamino-5-nitrobenzeneboronic acid hydrochloride, 95% 250mg [3-Benzylamino-5-nitrophenylboronic acid hydrochloride]

[913835-78-6], C13H13BN2O4ùHCl, F.W. 308.53, Off-white solid, m.p. 210-212ø, MDL MFCD08689484

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Bulk and Specialty Sizes Available 15 Arylboronic Acids Stock # Description Standard Selling Sizes H52474 3-(Benzylcarbamoyl)benzeneboronic acid, 98% 1g [3-(Benzylaminocarbonyl)phenylboronic acid] 5g

[625470-96-4], C14H14BNO3, F.W. 255.08, White solid, m.p. 224-230ø, MDL MFCD04115688

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52486 4-(Benzylcarbamoyl)benzeneboronic acid, 98% 250mg [4-(Benzylaminocarbonyl)phenylboronic acid, N-Benzyl 1g 4-boronobenzamide]

[252663-47-1], C14H14BNO3, F.W. 255.08, White solid, m.p. 212-218ø, MDL MFCD03411953

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52598 3-Benzylcarbamoyl-4-fluorobenzeneboronic acid, 98% 250mg [3-Benzylcarbamoyl-4-fluorophenylboronic acid, N-Benzyl 1g 5-borono-2-fluorobenzamide]

[874219-22-4], C14H13BFNO3, F.W. 273.07, White solid, m.p. 237-239ø, MDL MFCD08235041

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52527 3-Benzylcarbamoyl-5-fluorobenzeneboronic acid, 98% 250mg [3-Benzylcarbamoyl-5-fluorophenylboronic acid, N-Benzyl 1g 3-borono-5-fluorobenzamide]

[874219-41-7], C14H13BFNO3, F.W. 273.07, White solid, m.p. 263-265ø, MDL MFCD08235058 Acids H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52982 4-Benzylcarbamoyl-3-fluorobenzeneboronic acid, 97% 250mg [4-Benzylcarbamoyl-3-fluorophenylboronic acid, N-Benzyl 1g 4-borono-2-fluorobenzamide]

[874289-19-7], C14H13BFNO3, F.W. 273.07, Off-white solid, m.p. 113-116ø, MDL MFCD08689501

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Arylboronic H52684 5-Benzylcarbamoyl-2-fluorobenzeneboronic acid, 97% 250mg [5-Benzylcarbamoyl-2-fluorophenylboronic acid, N-Benzyl 1g 3-borono-4-fluorobenzamide]

[874289-53-9], C14H13BFNO3, F.W. 273.07, Pale pink solid, m.p. 224-226ø, MDL MFCD08436031

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53206 3-Benzylcarbamoyl-5-nitrobenzeneboronic acid, 98% 250mg [3-Benzylaminocarbonyl-5-nitrophenylboronic acid, N-Benzyl 1g 3-borono-5-nitrobenzamide]

[871332-90-0], C14H13BN2O5, F.W. 300.08, White solid, m.p. 246-248ø, MDL MFCD07783882

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52978 4-[Benzyl(ethyl)carbamoyl]benzeneboronic acid, 98% 250mg [N-Benzyl-N-ethyl-4-boronobenzamide, 4-[Benzyl(ethyl)carbamoyl- 1g ]phenylboronic acid]

[913835-41-3], C16H18BNO3, F.W. 283.13, White solid, m.p. 140-145ø, MDL MFCD09027215

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52917 4-[Benzyl(4-methoxybenzyl)sulfamoyl- 250mg ]benzeneboronic acid, 97% 1g [4-[Benzyl(4-methoxybenzyl)sulfamoyl]phenylboronic acid, N-Benzyl-N-(4-methoxybenzyl) 4-boronobenzenesulfonamide]

[913835-95-7], C21H22BNO5S, F.W. 411.28, Off-white solid, m.p. 95-98ø, MDL MFCD08689526

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52941 3-[Benzyl(methyl)carbamoyl]benzeneboronic acid, 97% 250mg [3-[Benzyl(methyl)carbamoyl]phenylboronic acid] 1g

[874460-01-2], C15H16BNO3, F.W. 269.11, Off-white solid, m.p. 127-130ø, MDL MFCD09027200

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52857 4-[Benzyl(methyl)carbamoyl]benzeneboronic acid, 96% 250mg [4-[Benzyl(methyl)carbamoyl]phenylboronic acid, 1g 4-(N-Benzyl-N-methylaminocarbonyl)phenylboronic acid]

[874219-49-5], C15H16BNO3, F.W. 269.11, Off-white solid, MDL MFCD08235067

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

16 www.alfa.com Arylboronic Acids Stock # Description Standard Selling Sizes L20100 2-Benzyloxybenzeneboronic acid, 96% 1g [2-Benzyloxyphenylboronic acid] 5g

[190661-29-1], C13H13BO3, F.W. 228.06, White to pale brown cryst powder, m.p. 96-99ø, BRN 7813704, MDL MFCD01632206

H:H315-H319-H335, P:P261-P280g-P305+P351+P338 L17474 3-Benzyloxybenzeneboronic acid, 98+% 1g [3-Benzyloxyphenylboronic acid] 5g

[156682-54-1], C13H13BO3, F.W. 228.06, m.p. 122-124ø, BRN 6808244, MDL MFCD02093063

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B24351 4-Benzyloxybenzeneboronic acid, 97% 250mg [4-Benzyloxyphenylboronic acid] 1g

[146631-00-7], C13H13BO3, F.W. 228.06, White to cream powder, 5g m.p. 193-198ø, MDL MFCD01075705

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52690 4-(Benzyloxycarbonylamino)benzeneboronic acid, 96% 1g [4-Cbz-aminophenyboronic acid, 4-(Benzyloxycarbonylamino)phenyl- 5g boronic acid]

[192804-36-7], C14H14BNO4, F.W. 271.08, White solid, m.p. 168-169ø, MDL MFCD02093055 Arylboronic

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52931 4-Benzyloxycarbonylamino-3-fluorobenzeneboronic acid, 250mg 98% 1g [Benzyl 4-borono-2-fluorophenylcarbamate, 4-Benzyloxycarbonyl- amino-3-fluorophenylboronic acid]

[874290-60-5], C14H13BFNO4, F.W. 289.07, Pale brown solid, m.p. 197-199ø, MDL MFCD08235098 Acids

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52536 3-Benzyloxycarbonylamino-5-nitrobenzeneboronic acid, 98% 250mg [3-Benzyloxycarbonylamino-5-nitrophenylboronic acid, Benzyl 1g (3-borono-5-nitro)phenylcarbamate]

[874219-56-4], C14H13BN2O6, F.W. 316.08, Pale yellow solid, m.p. 218-220ø, MDL MFCD08235090

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53128 3-(Benzyloxycarbonyl)benzeneboronic acid, 98% 250mg [3-(Benzyloxycarbonyl)phenylboronic acid, Benzyl 3-boronobenzoate] 1g

[380430-52-4], C14H13BO4, F.W. 256.06, White solid, m.p. 138-146ø, MDL MFCD02179445

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27675 4-(Benzyloxycarbonyl)benzeneboronic acid, 95% 100mg [4-(Benzyloxycarbonyl)phenylboronic acid, Benzyl 4-boronobenzoate] 500mg

[184000-11-1], C14H13BO4, F.W. 256.06, White powder, m.p. 187-192ø, MDL MFCD02179442

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52938 3-Benzyloxycarbonyl-5-nitrobenzeneboronic acid, 95% 250mg [3-Benzyloxycarbonyl-5-nitrophenylboronic acid, Benzyl 1g 3-borono-5-nitrobenzoate]

[380430-62-6], C14H12BNO6, F.W. 301.06, Off-white solid, m.p. 140-148ø, MDL MFCD03411934

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52969 4-Benzyloxycarbonyl-2-nitrobenzeneboronic acid, 95% 250mg [4-Benzyloxycarbonyl-2-nitrophenylboronic acid, Benzyl 1g 4-borono-3-nitrobenzoate]

[850568-58-0], C14H12BNO6, F.W. 301.06, White solid, m.p. 192-200ø, MDL MFCD02179461

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52447 2-Benzyloxy-5-chlorobenzeneboronic acid, 96% 250mg [2-Benzyloxy-5-chlorophenylboronic acid] 1g

[612832-83-4], C13H12BClO3, F.W. 262.50, White solid, m.p. 108-110ø, MDL MFCD04039000

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53033 4-Benzyloxy-3-chlorobenzeneboronic acid, 98% 1g [4-Benzyloxy-3-chlorophenylboronic acid] 5g

[845551-44-2], C13H12BClO3, F.W. 262.50, White solid, m.p. 154-162ø, MDL MFCD04115642

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Bulk and Specialty Sizes Available 17 Arylboronic Acids Stock # Description Standard Selling Sizes H53002 2-Benzyloxy-4-fluorobenzeneboronic acid, 98% 1g [2-Benzyloxy-4-fluorophenylboronic acid] 5g

[848779-87-3], C13H12BFO3, F.W. 246.04, White solid, m.p. 110-116ø, 25g MDL MFCD03788402

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H25880 2-Benzyloxy-5-fluorobenzeneboronic acid, 98% 250mg [2-Benzyloxy-5-fluorophenylboronic acid] 1g

[779331-47-4], C13H12BFO3, F.W. 246.05, White to cream powder, 5g m.p. 117-120ø, MDL MFCD03788403

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52704 3-Benzyloxy-5-fluorobenzeneboronic acid, 98% 250mg [3-Benzyloxy-5-fluorophenylboronic acid] 1g

[850589-56-9], C13H12BFO3, F.W. 246.04, White solid, m.p. 156-162ø, MDL MFCD07363782

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L18521 4-Benzyloxy-2-fluorobenzeneboronic acid, 96% 250mg [4-Benzyloxy-2-fluorophenylboronic acid] 1g

[166744-78-1], C13H12BFO3, F.W. 246.05, MDL MFCD02093064 5g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L18520 4-Benzyloxy-3-fluorobenzeneboronic acid, 98% 250mg [4-Benzyloxy-3-fluorophenylboronic acid] 1g

[133057-83-7], C13H12BFO3, F.W. 246.05, m.p. 129-131ø, Acids MDL MFCD00994627

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52462 4-Benzyloxy-3-methoxybenzeneboronic acid, 98% 250mg [4-Benzyloxy-3-methoxyphenylboronic acid] 1g

[243990-53-6], C14H15BO4, F.W. 258.08, White solid, m.p. 200-203ø, MDL MFCD09027252

Arylboronic H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53266 4-Benzyloxy-2-methylbenzeneboronic acid, 98% 1g [4-Benzyloxy-2-methylphenylboronic acid, 5-Benzyloxytoluene-2-boronic 5g acid]

[847560-49-0], C14H15BO3, F.W. 242.08, White solid, m.p. 154-158ø, MDL MFCD03788404

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53073 4-Benzyloxy-3-methylbenzeneboronic acid, 96% 1g [4-Benzyloxy-3-methylphenylboronic acid] 5g

[338454-30-1], C14H15BO3, F.W. 242.08, Off-white solid, m.p. 102-106ø, MDL MFCD06409944

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52918 2-Benzyloxy-5-(trifluoromethyl)benzeneboronic acid, 97% 250mg [2-Benzyloxy-5-(trifluoromethyl)phenylboronic acid] 1g

[612833-41-7], C14H12BF3O3, F.W. 296.05, White solid, m.p. 122-126ø, MDL MFCD06409944

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52521 3-(Benzylsulfamoyl)benzeneboronic acid, 95% 250mg [N-Benzyl 3-boronobenzenesulfonamide, 3-(Benzylsulfamoyl)phenyl- 1g boronic acid]

[690662-91-0], C13H14BNO4S, F.W. 291.12, White solid, m.p. 194-196ø, MDL MFCD07783857

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53105 4-(Benzylsulfamoyl)benzeneboronic acid, 95% 250mg [N-Benzyl 4-boronobenzenesulfonamide, 4-(Benzylsulfamoyl)phenyl- 1g boronic acid]

[548769-96-6], C13H14BNO4S, F.W. 291.12, White solid, m.p. 148-150ø, MDL MFCD06659845

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53142 3-Benzylsulfamoyl-4-methoxybenzeneboronic acid, 93% 250mg [N-Benzyl 5-borono-2-methoxybenzenesulfonamide, 3-Benzyl- sulfamoyl-4-methoxyphenylboronic acid]

[874219-51-9], C14H16BNO5S, F.W. 321.15, White solid, m.p. 134-136ø, MDL MFCD08235069

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

18 www.alfa.com Arylboronic Acids Stock # Description Standard Selling Sizes H52919 5-Benzylsulfamoyl-2-methylbenzeneboronic acid, 97% 250mg [N-Benzyl 3-borono-4-methylbenzenesulfonamide, 5-Benzyl- sulfamoyl-2-methylphenylboronic acid]

[871329-73-6], C14H16BNO4S, F.W. 305.16, White solid, m.p. 118-122ø, MDL MFCD07363760

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L17547 Biphenyl-2-boronic acid, 95% 1g [2-Phenylbenzeneboronic acid]

[4688-76-0], C12H11BO2, F.W. 198.03, m.p. 177-180ø, BRN 3031806, MDL MFCD00136929

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L17552 Biphenyl-3-boronic acid, 98% 1g [3-Phenylbenzeneboronic acid] 5g

[5122-95-2], C12H11BO2, F.W. 198.03, m.p. 206-211ø, BRN 2836311, MDL MFCD01318102

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Fluorescent PET receptor useful in saccharide detection: Tetrahedron Lett., 36, 4825 (1995); Pure Appl. Chem., 68, 2179 (1996). For boronic acid chemistry, see Appendix 5. B23703 Biphenyl-4-boronic acid, 98+% 1g [4-Phenylbenzeneboronic acid, 4-Phenylphenylboronic acid] 5g Arylboronic

[5122-94-1], C12H11BO2, F.W. 198.03, White powder, 25g m.p. 238-247ø, BRN 2937410, MDL MFCD00093311

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a The absolute configuration of 1-arylethane-1,2-diols has been determined by analysis of the CD spectra of the 4-biphenylboronates: Org. Lett., 1, 2093 (1999). L13328 Biphenyl-4,4'-diboronic acid, 95% 1g [Biphenyl-4,4'-diylbisboronic acid] 5g Acids

[4151-80-8], C12H12B2O4, F.W. 241.85, m.p. ca 300ø dec., BRN 2941876, MDL MFCD00151795

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53207 4-[Bis(4-methoxybenzyl)sulfamoyl- 250mg ]benzeneboronic acid, 98% 1g [4-[N,N-Bis(4-methoxybenzyl)sulfamoyl]phenylboronic acid, N,N-Bis(4-methoxybenzyl) 4-boronobenzenesulfonamide]

[913835-48-0], C22H24BNO6S, F.W. 441.31, White solid, m.p. 104-106ø, MDL MFCD09027223

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52844 2,2'-Bis(methoxymethoxy)-1,1'-binaphthyl-3,3'-diboronic acid, 250mg 97%

[957111-26-1], C24H24B2O8, F.W. 462.07, MDL MFCD09027264

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

L18161 2,4-Bis(trifluoromethyl)benzeneboronic acid, 97% 1g [2,4-Bis(trifluoromethyl)phenylboronic acid] 5g

[153254-09-2], C8H5BF6O2, F.W. 257.93, MDL MFCD01631349

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L19952 2,6-Bis(trifluoromethyl)benzeneboronic acid, 97% 250mg [2,6-Bis(trifluoromethyl)phenylboronic acid] 1g

[681812-07-7], C8H5BF6O2, F.W. 257.93, m.p. ca 150ø, 5g MDL MFCD04039321

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a A11373 3,5-Bis(trifluoromethyl)benzeneboronic acid, 97+% 1g [3,5-Bis(trifluoromethyl)phenylboronic acid] 5g

[73852-19-4], C8H5BF6O2, F.W. 257.93, White to pale brown cryst 25g powder, m.p. 219-224ø, BRN 7379990, MDL MFCD00051850

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a GC reagent for diols: J. Chromat., 158, 33 (1978); 186, 307 (1979). Has been used to protect a 1,3-diamine as the 2-aryl-1,3,2-diazaborinane, permitting selective reaction at a remote amine function: J. Am. Chem. Soc., 118, 1569 (1996). Has been used to form chiral catalysts for use in enantioselective Diels-Alder reactions; see, for example: J. Org. Chem., 62, 3026 (1997) and references therein. See Appendix 5.

Bulk and Specialty Sizes Available 19 Arylboronic Acids Stock # Description Standard Selling Sizes H52448 2-(Boc-amino)benzeneboronic acid, 96% 250mg [2-(Boc-amino)phenylboronic acid, 2-(tert-Butoxycarbonylamino)phenyl- 1g boronic acid]

[115377-94-1], C11H16BNO4, F.W. 237.06, Off-white solid, m.p. 123-125ø, MDL MFCD02179450

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27258 3-(Boc-amino)benzeneboronic acid, 95% 1g [3-(Boc-amino)phenylboronic acid, 3-[(tert-Butoxycarbonyl)- 5g amino]phenylboronic acid]

[380430-68-2], C11H16BNO4, F.W. 237.06, White to pale brown powder, m.p. ca 155ø dec., MDL MFCD03411945

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H28799 4-(Boc-amino)benzeneboronic acid, 97% 1g [4-(tert-Butoxycarbonylamino)phenylboronic acid] 5g

[380430-49-9], C11H16BNO4, F.W. 237.06, Solid, m.p. ca 200ø dec., MDL MFCD02093054

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53051 3-(Boc-amino)-5-carboxybenzeneboronic acid, 98% 250mg [3-(Boc-amino)-5-carboxyphenylboronic acid, 1g 3-Borono-5-(tert-butoxycarbonylamino)benzoic acid]

[913835-72-0], C12H16BNO6, F.W. 281.07, White solid, m.p. >300ø, MDL MFCD08689482 Acids H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52681 3-(Boc-amino)-4-chlorobenzeneboronic acid, 97% 250mg [3-(tert-Butoxycarbonylamino)-4-chlorophenylboronic acid, 3-(Boc-amino)-4-chlorophenylboronic acid]

[871329-57-6], C11H15BClNO4, F.W. 271.51, Off-white solid, m.p. 180-182ø, MDL MFCD08056353

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Arylboronic H52890 5-(Boc-amino)-2-(hydroxymethyl)benzeneboronic acid 250mg hemiester, 98+% [6-(Boc-amino)-1-hydroxy-2,1-benzoxaborolane, 5-(Boc-amino)-2-(hydroxymethyl)benzeneboronic acid cyclic monoester]

[850568-79-5], C12H16BNO4, F.W. 249.07, Off-white solid, m.p. 134-138ø, MDL MFCD06659853

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52453 3-(Boc-aminomethyl)benzeneboronic acid, 97% 250mg [3-(Boc-aminomethyl)phenylboronic acid] 1g

[199609-62-6], C12H18BNO4, F.W. 251.08, Off-white solid, m.p. 188-190ø, MDL MFCD06246052

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52548 3-(Boc-amino)-4-methylbenzeneboronic acid, 98% 250mg [3-(Boc-amino)-4-methylphenylboronic acid, 1g 3-tert-Butoxycarbonylamino-4-methylphenylboronic acid]

[850568-81-9], C12H18BNO4, F.W. 251.09, Off-white solid, m.p. 300ø, MDL MFCD04115654

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53225 4-(Boc-aminomethyl)benzeneboronic acid, 97% 250mg [4-(Boc-aminomethyl)phenylboronic acid] 1g

[489446-42-6], C12H18BNO4, F.W. 251.09, White solid, m.p. 204-206ø, MDL MFCD04115637

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53057 2-(Boc-aminomethyl)-4-fluorobenzeneboronic acid, 97% 250mg [2-(Boc-aminomethyl)-4-fluorophenylboronic acid] 1g

[850568-64-8], C12H17BFNO4, F.W. 269.08, White solid, m.p. 90-94ø, MDL MFCD06659826

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53275 2-(Boc-aminomethyl)-5-fluorobenzeneboronic acid, 96% 250mg [2-(Boc-aminomethyl)-5-fluorophenylboronic acid, 1g 2-tert-Butoxycarbonylaminomethyl-5-fluorophenylboronic acid]

[850568-43-3], C12H17BFNO4, F.W. 269.08, White solid, m.p. 98-102ø, MDL MFCD04115639

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

20 www.alfa.com Arylboronic Acids Stock # Description Standard Selling Sizes L18581 2-Bromobenzeneboronic acid, 98% 1g [2-Bromophenylboronic acid] 5g

[244205-40-1], C6H6BBrO2, F.W. 200.83, m.p. 108-110ø, BRN 8542615, MDL MFCD01114672

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L16354 3-Bromobenzeneboronic acid, 98+% 1g [3-Bromophenylboronic acid] 5g

[89598-96-9], C6H6BBrO2, F.W. 200.83, m.p. 164-168ø, BRN 3127104, 25g MDL MFCD00239386

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L01565 4-Bromobenzeneboronic acid, 97+% 1g [4-Bromophenylboronic acid] 5g

[5467-74-3], C6H6BBrO2, F.W. 200.83, m.p. 282-286ø, 25g EINECS 226-779-9, RTECS CY8650000, BRN 2936347, MDL MFCD00002104

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a GC reagent for diols: J. Chromat., 158, 33 (1978); 186, 307 (1979). Carbonylative cross-coupling with iodobenzenes and CO, catalyzed by trans-Dichlorobis(triphenylphosphine)palladium(II), 10491, p. 142, gives unsymmetrical diaryl ketones: Tetrahedron Lett., 34, 7595 (1993); J. Org. Chem., 63, 4726 (1998). For Arylboronic reactions of boronic acids, see Appendix 5. H53311 3-Bromo-5-carboxybenzeneboronic acid, 97% 250mg [3-Bromo-5-carboxyphenylboronic acid, 3-Borono-5-bromobenzoic acid] 1g

[913835-73-1], C7H6BBrO4, F.W. 244.84, White solid, m.p. 290-292ø, MDL MFCD08689487

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53058 4-Bromo-2-chloro-5-methoxybenzeneboronic acid, 97% 250mg Acids [4-Bromo-2-chloro-5-methoxyphenylboronic acid, 1g 2-Bromo-4-chloroanisole-5-boronic acid]

[850567-94-1], C7H7BBrClO3, F.W. 265.30, White solid, m.p. 260-268ø, MDL MFCD06659862

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L18516 4-Bromo-2,3-difluorobenzeneboronic acid, 98% 250mg [4-Bromo-2,3-difluorophenylboronic acid] 1g

[374790-99-5], C6H4BBrF2O2, F.W. 236.81, m.p. ca 225ø, MDL MFCD02093065

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53278 4-Bromo-2,5-dimethybenzeneboronic acid, 96% 250mg [4-Bromo-2,5-dimethylphenylboronic acid] 1g

[130870-00-7], C8H10BBrO2, F.W. 228.88, White solid, m.p. 194-202ø, MDL MFCD04115647

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52939 4-(2-Bromoethoxy)benzeneboronic acid, 95% 250mg [4-(2-Bromoethoxy)phenylboronic acid] 1g

[913836-06-3], C8H10BBrO3, F.W. 244.88, Brown solid, m.p. 149-156ø, MDL MFCD09027232

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53240 3-Bromo-5-(ethoxycarbonyl)benzeneboronic acid, 97% 250mg [Ethyl 3-borono-5-bromobenzoate, 3-Bromo-5-(ethoxycarbonyl)phenyl- 1g boronic acid]

[913835-88-8], C9H10BBrO4, F.W. 272.89, White solid, m.p. 155-157ø, MDL MFCD08689516

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53185 2-(2-Bromoethyl)benzeneboronic acid, 95% 250mg [2-(2-Bromoethyl)phenylboronic acid]

[850568-82-0], C8H10BBrO2, F.W. 228.88, White solid, m.p. 146-148ø, MDL MFCD06659854

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53071 2-Bromo-6-fluorobenzeneboronic acid, 98% 1g [2-Bromo-6-fluorophenylboronic acid] 5g

[913835-80-0], C6H5BBrFO2, F.W. 218.82, White solid, m.p. 142-145ø, 25g MDL MFCD05664309

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Bulk and Specialty Sizes Available 21 Arylboronic Acids Stock # Description Standard Selling Sizes H52878 3-Bromo-5-fluorobenzeneboronic acid, 95% 1g [3-Bromo-5-fluorophenylboronic acid] 5g

[849062-37-9], C6H5BBrFO2, F.W. 218.82, White solid, m.p. >300ø, MDL MFCD06411356

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L17468 4-Bromo-2-fluorobenzeneboronic acid, 98+% 1g [4-Bromo-2-fluorophenylboronic acid] 5g

[216393-64-5], C6H5BBrFO2, F.W. 218.82, m.p. 238-242ø, MDL MFCD01318110

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L18514 4-Bromo-3-fluorobenzeneboronic acid, 95% 250mg [4-Bromo-3-fluorophenylboronic acid] 1g

[374790-97-3], C6H5BBrFO2, F.W. 218.82, m.p. >300ø, MDL MFCD02093066

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52962 5-Bromo-2-fluorobenzeneboronic acid, 98% 1g [5-Bromo-2-fluorophenylboronic acid] 5g

[112204-57-6], C6H5BBrFO2, F.W. 218.82, White solid, m.p. 220-224ø, MDL MFCD05664307

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52911 4-Bromo-1-fluoronaphthalene-2-boronic acid, 98% 250mg

[913836-09-6], C10H7BBrFO2, F.W. 268.88, Off-white solid, m.p. >300ø, 1g Acids MDL MFCD09027236

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H52937 5-Bromo-2-hydroxybenzeneboronic acid, 97% 250mg [5-Bromo-2-hydroxyphenylboronic acid, 2-Borono-4-bromophenol] 1g

[89598-97-0], C6H6BBrO3, F.W. 216.83, White solid, m.p. 196-200ø, Arylboronic MDL MFCD00093408

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52972 2-Bromo-5-methoxybenzeneboronic acid, 97% 250mg [2-Bromo-5-methoxyphenylboronic acid] 1g

[89694-44-0], C7H8BBrO3, F.W. 230.85, Off-white solid, m.p. 214-216ø, MDL MFCD06659859

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52497 5-Bromo-2-methoxybenzeneboronic acid, 97% 1g [5-Bromo-2-methoxyphenylboronic acid, 4-Bromoanisole-2-boronic acid] 5g

[89694-45-1], C7H8BBrO3, F.W. 230.85, White solid, m.p. 129-131ø, MDL MFCD00093409

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53223 3-Bromo-5-(methoxycarbonyl)benzeneboronic acid, 96% 250mg [Methyl 3-borono-5-bromobenzoate, 3-Bromo-5-(methoxycarbonyl)- 1g phenylboronic acid]

[913835-87-7], C8H8BBrO4, F.W. 258.86, White solid, m.p. 166-168ø, MDL MFCD08689544

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52467 2-(Bromomethyl)benzeneboronic acid, 97% 250mg [2-(Bromomethyl)phenylboronic acid, 2-Boronobenzyl bromide] 1g

[91983-14-1], C7H8BBrO2, F.W. 214.85, White to cream solid, 5g m.p. 145-148ø, MDL MFCD01318941

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L20102 3-(Bromomethyl)benzeneboronic acid, 95% 1g [3-Boronobenzyl bromide, 3-(Bromomethyl)phenylboronic acid] 5g

[51323-43-4], C7H8BBrO2, F.W. 214.85, m.p. 214-216ø, UN3261, 25g BRN 3246618, MDL MFCD01632207 H:H314, P:P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501a H53070 3-Bromo-5-methylbenzeneboronic acid, 97% 1g [3-Bromo-5-methylphenylboronic acid] 5g

[849062-36-8], C7H8BBrO2, F.W. 214.85, White solid, m.p. 276-278ø, MDL MFCD06411355

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

22 www.alfa.com Arylboronic Acids Stock # Description Standard Selling Sizes L19953 4-(Bromomethyl)benzeneboronic acid, tech. 85% 1g [4-Boronobenzyl bromide, 4-(Bromomethyl)phenylboronic acid] 5g

[68162-47-0], C7H8BBrO2, F.W. 214.85, m.p. ca 145-150ø, UN3261, BRN 3030979, MDL MFCD01318113 H:H314, P:P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501a Has been employed in the synthesis of para-substituted boronated stilbenes via the Wittig reaction: J. Am. Chem. Soc., 117, 8982 (1995), which were subsequently employed as highly selective fluorescent probes for glucose: J. Phys. Chem. A, 105, 6834 (2001). H53276 2-Bromomethyl-4-fluorobenzeneboronic acid, 97% 250mg [2-Bromomethyl-4-fluorophenylboronic acid, 2-Borono-5-fluorobenzyl bromide] 1g

[850568-01-3], C7H7BBrFO2, F.W. 232.84, White solid, m.p. 169-171ø, MDL MFCD06659867

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52623 3-Bromo-5-nitrobenzeneboronic acid, 95% 250mg [3-Bromo-5-nitrophenylboronic acid]

[380430-48-8], C6H5BBrNO4, F.W. 245.83, White to off-white solid, m.p. 238-248ø, MDL MFCD03411929

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53112 3-(2-Bromophenylcarbamoyl)benzeneboronic acid, 98% 250mg

[3-Borono-N-(2-bromophenyl)benzamide, 3-(2-Bromophenyl- 1g Arylboronic carbamoyl)phenylboronic acid]

[874288-30-9], C13H11BBrNO3, F.W. 319.95, White solid, m.p. 252-255ø, MDL MFCD09027206

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52905 4-(2-Bromophenylcarbamoyl)benzeneboronic acid, 95% 250mg [4-(2-Bromophenylcarbamoyl)phenylboronic acid] 1g

[874288-01-4], C13H11BBrNO3, F.W. 319.95, Off-white solid, Acids m.p. 233-235ø, MDL MFCD09027202

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53174 4-(4-Bromophenylcarbamoyl)benzeneboronic acid, 250mg 98% 1g [N-4-Bromophenyl 4-boronobenzamide, 4-(4-Bromophenyl- carbamoyl)phenylboronic acid]

[874287-99-7], C13H11BBrNO3, F.W. 319.95, White solid, m.p. 268-275ø, MDL MFCD09027201

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53006 3-(3-Bromophenylsulfonamido)benzeneboronic acid, 250mg 95% 1g [3-(3-Bromophenylsulfonamido)phenylboronic acid, 3-Boronophenyl 3-bromobenzenesulfonamide]

[913835-31-1], C12H11BBrNO4S, F.W. 360.00, Off-white solid, m.p. 97-100ø, MDL MFCD08436047

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52516 3-(3-Bromopropylcarbamoyl)benzeneboronic acid, 250mg 97% 1g [N-(3-Bromopropyl) 3-boronobenzamide, 3-[(3-Bromopropyl)- carbamoyl]phenylboronic acid]

[850567-42-9], C10H13BBrNO3, F.W. 285.93, Off-white solid, m.p. 97-99ø, MDL MFCD06659892

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53130 4-(3-Bromopropylcarbamoyl)benzeneboronic acid, 250mg 97% 1g [N-(3-Bromopropyl) 4-Boronobenzamide, 4-[(3-Bromopropyl)- carbamoyl]phenylboronic acid]

[850567-41-8], C10H13BBrNO3, F.W. 285.93, White solid, m.p. 124-128ø, MDL MFCD06659891

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52898 3-Bromo-5-(trifluoromethyl)benzeneboronic acid, 98% 250mg [3-Bromo-5-(trifluoromethyl)phenylboronic acid] 1g

[913835-64-0], C7H5BBrF3O2, F.W. 268.82, White solid, m.p. 177-180ø, MDL MFCD08436051

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52865 4-n-Butoxybenzeneboronic acid, 98% 1g [4-n-Butoxyphenylboronic acid] 5g

[105365-51-3], C10H15BO3, F.W. 194.04, White solid, m.p. 102-104ø, MDL MFCD03427054

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Bulk and Specialty Sizes Available 23 Arylboronic Acids Stock # Description Standard Selling Sizes H53007 3-(tert-Butoxycarbonyl)benzeneboronic acid, 98% 1g [3-(tert-Butoxycarbonyl)phenylboronic acid, tert-Butyl 5g 3-boronobenzoate]

[220210-56-0], C11H15BO4, F.W. 222.05, White solid, m.p. 96-102ø, MDL MFCD01630855

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53198 4-(tert-Butoxycarbonyl)benzeneboronic acid, 95% 250mg [4-(tert-Butoxycarbonyl)phenylboronic acid, tert-Butyl 1g 4-boronobenzoate]

[850568-54-6], C11H15BO4, F.W. 222.05, White solid, m.p. 100-106ø, MDL MFCD03411946

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52446 3-(tert-Butoxycarboxy)benzeneboronic acid, 97% 250mg [3-(tert-Butoxycarbonyloxy)phenylboronic acid] 1g

[380430-69-3], C11H15BO5, F.W. 238.05, White solid, m.p. 104-106ø, MDL MFCD03095133

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52469 4-(tert-Butoxycarboxy)benzeneboronic acid, 97% 250mg [4-(tert-Butoxycarbonyloxy)phenylboronic acid] 1g

[380430-70-6], C11H15BO5, F.W. 238.05, White to off-white solid, m.p. 140-146ø, MDL MFCD03095144

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Acids L15584 4-n-Butylbenzeneboronic acid, 98% 1g [4-n-Butylphenylboronic acid] 5g

[145240-28-4], C10H15BO2, F.W. 178.04, m.p. 103-106ø, BRN 6920034, MDL MFCD02093926

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53358 4-sec-Butylbenzeneboronic acid, 98% 250mg [4-sec-Butylphenylboronic acid, 4-(1-Methylpropyl)phenylboronic acid] Arylboronic 1g

[850568-56-8], C10H15BO2, F.W. 178.04, White to off-white solid, m.p. 96-100ø, MDL MFCD02179456

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B24408 4-tert-Butylbenzeneboronic acid, 97% 1g [4-tert-Butylphenylboronic acid] 5g

[123324-71-0], C10H15BO2, F.W. 178.04, White to cream cryst powder, m.p. 191-196ø, BRN 5330959, MDL MFCD01009697

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52693 3-(n-Butylcarbamoyl)benzeneboronic acid, 97% 250mg [3-(n-Butylaminocarbonyl)phenylboronic acid] 1g

[397843-70-8], C11H16BNO3, F.W. 221.06, White solid, m.p. 216-224ø, MDL MFCD04115691

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53303 3-(tert-Butylcarbamoyl)benzeneboronic acid, 97% 250mg [3-(tert-Butylaminocarbonyl)phenylboronic acid] 1g

[183158-30-7], C11H16BNO3, F.W. 221.06, Off-white solid, m.p. 120-126ø, MDL MFCD04115693

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53012 4-(n-Butylcarbamoyl)benzeneboronic acid, 97% 1g [4-(n-Butylaminocarbonyl)phenylboronic acid, N-n-Butyl 5g 4-boronobenzamide]

[252663-48-2], C11H16BNO3, F.W. 221.06, White solid, m.p. 206-210ø, MDL MFCD03788412

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53301 4-(tert-Butylcarbamoyl)benzeneboronic acid, 97% 1g [4-(tert-Butylaminocarbonyl)phenylboronic acid, N-tert-Butyl 5g 4-boronobenzamide]

[850568-14-8], C11H16BNO3, F.W. 221.06, White solid, m.p. 230-246ø, MDL MFCD03788413

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52616 3-n-Butylcarbamoyl-4-fluorobenzeneboronic acid, 98% 250mg [3-n-Butylcarbamoyl-4-fluorophenylboronic acid, N-n-Butyl 1g 5-borono-2-fluorobenzamide]

[874219-23-5], C11H15BFNO3, F.W. 239.05, White solid, m.p. 242-244ø, MDL MFCD08235042

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

24 www.alfa.com Arylboronic Acids Stock # Description Standard Selling Sizes H52594 3-tert-Butylcarbamoyl-4-fluorobenzeneboronic acid, 98% 250mg [3-tert-Butylcarbamoyl-4-fluorophenylboronic acid, N-tert-Butyl 1g 5-borono-2-fluorobenzamide]

[874219-26-8], C11H15BFNO3, F.W. 239.05, White solid, m.p. 218-220ø, MDL MFCD08235045

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53115 4-n-Butylcarbamoyl-3-fluorobenzeneboronic acid, 98% 250mg [N-n-Butyl 4-borono-2-fluorobenzamide, 4-n-Butyl- 1g carbamoyl-3-fluorophenylboronic acid]

[874289-17-5], C11H15BFNO3, F.W. 239.05, White solid, m.p. 130-133ø, MDL MFCD08689527

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52930 4-tert-Butylcarbamoyl-3-fluorobenzeneboronic acid, 98% 250mg [N-tert-Butyl 4-borono-2-fluorobenzamide, 4-tert-Butyl- 1g carbamoyl-3-fluorophenylboronic acid]

[874289-18-6], C11H15BFNO3, F.W. 239.05, White solid, m.p. 140-143ø, MDL MFCD08689525

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53228 5-n-Butylcarbamoyl-2-fluorobenzeneboronic acid, 98% 250mg [N-n-Butyl 3-borono-4-fluorobenzamide, 5-n-Butyl- 1g Arylboronic carbamoyl-2-fluorophenylboronic acid]

[874289-50-6], C11H15BFNO3, F.W. 239.05, White solid, m.p. 174-176ø, MDL MFCD08235104

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53080 5-tert-Butylcarbamoyl-2-fluorobenzeneboronic acid, 97% 250mg [N-tert-Butyl 3-borono-4-fluorobenzamide, 5-tert-Butyl- 1g carbamoyl-2-fluorophenylboronic acid] Acids

[874289-51-7], C11H15BFNO3, F.W. 239.05, White solid, m.p. 142-144ø, MDL MFCD08436054

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53257 3-n-Butylcarbamoyl-5-nitrobenzeneboronic acid, 97% 250mg [3-(n-Butylaminocarbonyl)-5-nitrophenylboronic acid, N-n-Butyl 1g 3-borono-5-nitrobenzamide]

[871332-89-7], C11H15BN2O5, F.W. 266.06, Off-white solid, m.p. 190-192ø, MDL MFCD07783881

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53034 3-tert-Butylcarbamoyl-5-nitrobenzeneboronic acid, 98% 250mg [3-(tert-Butylaminocarbonyl)-5-nitrophenylboronic acid, N-tert-butyl 1g 3-borono-5-nitrobenzamide]

[871332-87-5], C11H15BN2O5, F.W. 266.06, Off-white solid, m.p. 177-179ø, MDL MFCD07783879

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H28378 3-(tert-Butyldimethylsiloxy)benzeneboronic acid, tech. 90% 1g É 5g [3-(tert-Butyldimethylsiloxy)phenylboronic acid]

[261621-12-9], C12H21BO3Si, F.W. 252.19, Solid, m.p. 86-91ø, MDL MFCD03701505

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53339 2-[2-(tert-Butyldimethylsiloxy)ethyl]benzeneboronic acid, 96% 250mg [2-[2-(tert-Butyldimethylsilyloxy)ethyl]phenylboronic acid]

[913835-62-8], C14H25BO3Si, F.W. 280.25, White solid, m.p. 92-94ø, MDL MFCD08436049

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52604 4-tert-Butyldimethylsiloxy-3-methoxybenzeneboronic acid, 250mg 98% 1g [4-tert-Butyldimethylsilyloxy-3-methoxyphenylboronic acid]

[957060-93-4], C13H23BO4Si, F.W. 282.22, White solid, m.p. 220-223ø, MDL MFCD09027250

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53322 6-(tert-Butyldimethysiloxy)naphthalene-2-boronic acid, 250mg 98% 1g [6-(tert-Butyldimethylsilyloxy)naphthalene-2-boronic acid, 6-TBDMSO-2-naphthaleneboronic acid]

[179942-45-1], C16H23BO3Si, F.W. 302.25, Off-white solid, m.p. 224-232ø, MDL MFCD04115644

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Bulk and Specialty Sizes Available 25 Arylboronic Acids Stock # Description Standard Selling Sizes H53156 4-(N-[2-(tert-Butyldimethylsilyloxy)ethyl]sulfamoyl)- 250mg benzeneboronic acid, 96% 1g [4-(N-[2-(TBDMSO)ethyl]sulfamoyl)phenylboronic acid, N-[2-(tert-Butyldimethylsilyloxy)ethyl] 4-boronobenzenesulfonamide]

[913835-53-7], C14H26BNO5SSi, F.W. 359.32, White solid, m.p. 106-108ø, MDL MFCD08436009

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L20415 5-tert-Butyl-2-methoxybenzeneboronic acid 250mg [5-tert-Butyl-2-methoxyphenylboronic acid] 1g

[128733-85-7], C11H17BO3, F.W. 208.07, m.p. 103-106ø, BRN 4181890, MDL MFCD06201034

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53277 4-[n-Butyl(4-methoxybenzyl)sulfamoyl- 250mg ]benzeneboronic acid, 98% 1g [4-[N-Butyl-N-(4-methoxybenzyl)sulfamoyl]phenylboronic acid, N-Butyl-N-(4-methoxybenzyl) 4-boronobenzenesulfonamide]

[913835-97-9], C18H24BNO5S, F.W. 377.26, White solid, m.p. 103-106ø, MDL MFCD09027227

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52944 4-[tert-Butyl(4-methoxybenzyl)sulfamoyl- 250mg

Acids ]benzeneboronic acid, 98% 1g [4-[N-tert-Butyl-N-(4-methoxybenzyl)sulfamoyl]phenyl- boronic acid, N-tert-Butyl-N-(4-methoxybenzyl) 4-boronobenzenesulfonamide]

[957060-86-5], C18H24BNO5S, F.W. 377.26, White solid, m.p. 135-137ø, MDL MFCD09027251

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Arylboronic H53352 3-tert-Butyl-5-methylbenzeneboronic acid, 96% 250mg [3-tert-Butyl-5-methylphenylboronic acid]

[193905-93-0], C11H17BO2, F.W. 192.06, White solid, m.p. 158-160ø, MDL MFCD03411938

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52883 4-tert-Butyl-3-nitrobenzeneboronic acid, 98% 250mg [4-tert-Butyl-3-nitrophenylboronic acid] 1g

[871329-54-3], C10H14BNO4, F.W. 223.04, Off-white solid, m.p. 52-54ø, MDL MFCD07363743

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52484 3-(n-Butylsulfamoyl)benzeneboronic acid, 95% 250mg [N-n-Butyl 3-boronobenzenesulfonamide, 3-N-n-Butylsulfamoyl- phenylboronic acid]

[871329-78-1], C10H16BNO4S, F.W. 257.11, White solid, m.p. 92-94ø, MDL MFCD07783858

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52655 3-(tert-Butylsulfamoyl)benzeneboronic acid, 97% 250mg [tert-Butyl 3-boronobenzenesulfonamide, 3-tert-Butylsulfamoylphenyl- boronic acid]

[221290-14-8], C10H16BNO4S, F.W. 257.11, White solid, m.p. 120-124ø, MDL MFCD06659842

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53218 4-(n-Butylsulfamoyl)benzeneboronic acid, 97% 250mg [N-n-Butyl 4-boronobenzenesulfonamide, 4-N-n-Butylsulfamoyl- 1g phenylboronic acid]

[850589-32-1], C10H16BNO4S, F.W. 257.11, White solid, m.p. 124-126ø, MDL MFCD07363753

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52923 4-(tert-Butylsulfamoyl)benzeneboronic acid, 97% 250mg [tert-Butyl 4-boronobenzenesulfonamide, 4-(tert-Butylaminosulfonyl)- 1g phenylboronic acid]

[208516-15-8], C10H16BNO4S, F.W. 257.11, White solid, m.p. 128-132ø, MDL MFCD06659841

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

26 www.alfa.com Arylboronic Acids Stock # Description Standard Selling Sizes H53316 5-tert-Butylsulfamoyl-2-methylbenzeneboronic acid, 95% 250mg [N-tert-Butyl 3-borono-4-methylbenzenesulfonamide, 5-tert-Butyl- sulfamoyl-2-methylphenylboronic acid]

[874219-47-3], C11H18BNO4S, F.W. 271.14, White solid, m.p. 142-145ø, MDL MFCD08235063

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52600 3-Carbamothioylbenzeneboronic acid, 97% 250mg [3-Boronothiobenzamide, 3-Carbamothioylphenylboronic acid] 1g

[850568-10-4], C7H8BNO2S, F.W. 181.02, Yellow solid, m.p. 188-192ø, MDL MFCD06659873

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53095 4-(2-Carbamothioylhydrazinocarbonyl)benzeneboronic 250mg acid, 98% 1g [2-(4-Boronobenzoyl)hydrazinecarbothioamide, 4-(2-Carbamothioylhydrazinecarbonyl)phenylboronic acid]

[957060-76-3], C8H10BN3O3S, F.W. 239.06, White solid, m.p. 183-184ø, MDL MFCD09027244

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52642 2-Carbamoylbenzeneboronic acid, 96% 250mg [2-Aminocarbonylphenylboronic acid, 2-Carbamoylphenylboronic acid] 1g Arylboronic

[380430-54-6], C7H8BNO3, F.W. 164.96, White to off-white solid, m.p. 226-230ø, MDL MFCD02179454

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52869 3-Carbamoylbenzeneboronic acid, 98% 1g [3-Aminocarbonylphenylboronic acid, 3-Carbamoylphenylboronic acid] 5g

[351422-73-6], C7H8BNO3, F.W. 164.96, White solid, m.p. 232-238ø, MDL MFCD03411948 Acids

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53345 4-Carbamoylbenzeneboronic acid, 98% 1g [4-Aminocarbonylphenylboronic acid, 4-Carbamoylphenylboronic acid] 5g

[123088-59-5], C7H8BNO3, F.W. 164.96, White solid, m.p. 242-252ø, MDL MFCD03411940

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52641 4-Carbamoyl-3-chlorobenzeneboronic acid, 96% 250mg [4-Carbamoyl-3-chlorophenylboronic acid, 1g 4-Aminocarbonyl-3-chlorophenylboronic acid]

[850589-52-5], C7H7BClNO3, F.W. 199.40, White solid, m.p. 152-158ø, MDL MFCD07363777

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53102 3-Carbamoyl-4-fluorobenzeneboronic acid, 97% 250mg [3-Carbamoyl-4-fluorophenylboronic acid, 5-Borono-2-fluorobenzamide] 1g

[874219-34-8], C7H7BFNO3, F.W. 182.95, Off-white solid, m.p. 257-259ø, MDL MFCD08235053

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52663 3-Carbamoyl-5-fluorobenzeneboronic acid, 98% 250mg [3-Carbamoyl-5-fluorophenylboronic acid, 3-Borono-5-fluorobenzamide] 1g

[871332-66-0], C7H7BFNO3, F.W. 182.95, Off-white solid, m.p. 280-286ø, MDL MFCD08056357

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53010 5-Carbamoyl-2-fluorobenzeneboronic acid, 95% 250mg [3-Borono-4-fluorobenzamide, 5-Carbamoyl-2-fluorophenylboronic acid] 1g

[874289-39-1], C7H7BFNO3, F.W. 182.95, White solid, m.p. 192-194ø, MDL MFCD08436055

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52709 3-Carbamoyl-5-nitrobenzeneboronic acid, 98% 250mg [3-Aminocarbonyl-5-nitrophenylboronic acid, 3-Borono-5-nitrobenzamide] 1g

[102170-51-4], C7H7BN2O5, F.W. 209.95, White solid, m.p. 269-271ø, MDL MFCD07783870

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53320 3,3'-Carbonylbis(azanediyl)bis(3,1-phenylene)- 250mg diboronic acid, 97% 1g [1,3-Bis(3-boronophenyl)urea]

[957060-87-6], C13H14B2N2O5, F.W. 299.88, White solid, m.p. 225-226ø, MDL MFCD09027259

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Bulk and Specialty Sizes Available 27 Arylboronic Acids Stock # Description Standard Selling Sizes L16301 2-Carboxybenzeneboronic acid, 95% 250mg [2-Boronobenzoic acid, 2-Carboxyphenylboronic acid] 1g

[149105-19-1], C7H7BO4, F.W. 165.94, m.p. ca 220ø, BRN 2835407, 5g MDL MFCD01318118

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B25315 3-Carboxybenzeneboronic acid 1g [3-Boronobenzoic acid, 3-Carboxyphenylboronic acid] 5g

[25487-66-5], C7H7BO4, F.W. 165.94, m.p. ca 240ø dec., RTECS CY8750000, BRN 2967400, MDL MFCD00036833

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B20954 4-Carboxybenzeneboronic acid, 97% 1g [4-Boronobenzoic acid, 4-Carboxyphenylboronic acid] 5g

[14047-29-1], C7H7BO4, F.W. 165.94, White to pale cream powder, 25g m.p. ca 220ø dec., RTECS CY8925000, BRN 3031088, MDL MFCD00151801

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53043 2-Carboxy-4-chlorobenzeneboronic acid, 96% 250mg [2-Carboxy-4-chlorophenylboronic acid, 2-Borono-5-chlorobenzoic acid] 1g

[850568-07-9], C7H6BClO4, F.W. 200.39, White solid, m.p. >300ø, MDL MFCD06659869

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52698 2-Carboxy-5-chlorobenzeneboronic acid, 97% 250mg Acids [2-Carboxy-5-chlorophenylboronic acid, 2-Borono-4-chlorobenzoic acid] 1g

[874290-67-2], C7H6BClO4, F.W. 200.39, White solid, m.p. 236-238ø, MDL MFCD08235091

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52764 3-Carboxy-4-chlorobenzeneboronic acid, 98% 250mg [5-Borono-2-chlorobenzoic acid, 3-Carboxy-4-chlorophenylboronic acid] 1g

Arylboronic [913835-32-2], C7H6BClO4, F.W. 200.39, White solid, m.p. 223-225ø, MDL MFCD06801689

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52489 4-Carboxy-2-chlorobenzeneboronic acid, 97% 1g [4-Carboxy-2-chlorophenylboronic acid, 4-Borono-3-chlorobenzoic acid] 5g

[851335-09-6], C7H6BClO4, F.W. 200.39, White solid, m.p. 208-210ø, MDL MFCD07363763

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H28999 4-Carboxy-3-chlorobenzeneboronic acid, 97% 1g [4-Borono-2-chlorobenzoic acid, 4-Carboxy-3-chlorophenylboronic acid] 5g

[136496-72-5], C7H6BClO4, F.W. 200.38, White cryst powder, MDL MFCD06656268

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52583 5-Carboxy-2-chlorobenzeneboronic acid, 98% 250mg [5-Carboxy-2-chlorophenylboronic acid, 3-Borono-4-chlorobenzoic acid] 1g

[913835-75-3], C7H6BClO4, F.W. 200.39, White solid, m.p. 228-244ø, MDL MFCD08689491

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52977 3-(2-Carboxyethyl)benzeneboronic acid, 96% 250mg [3-(2-Carboxyethyl)phenylboronic acid, 3-(3-Boronophenyl)propionic 1g acid]

[693803-17-7], C9H11BO4, F.W. 193.99, Off-white solid, m.p. 166-169ø, MDL MFCD04115649

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L17485 4-(2-Carboxyethyl)benzeneboronic acid, 97% 1g [3-(4-Boronophenyl)propionic acid, 4-(2-Carboxyethyl)phenylboronic 5g acid]

[166316-48-9], C9H11BO4, F.W. 194.00, m.p. 146-148ø, BRN 9198524, MDL MFCD01318119

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53180 2-Carboxy-4-fluorobenzeneboronic acid, 97% 250mg [2-Borono-5-fluorobenzoic acid, 2-Carboxy-4-fluorophenylboronic acid] 1g

[874290-63-8], C7H6BFO4, F.W. 183.93, White solid, m.p. 183-186ø, MDL MFCD08235078

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

28 www.alfa.com Arylboronic Acids Stock # Description Standard Selling Sizes H28313 3-Carboxy-4-fluorobenzeneboronic acid, 97% 1g [5-Borono-2-fluorobenzoic acid, 3-Carboxy-4-fluorophenylboronic acid] 10g

[872460-12-3], C7H6BFO4, F.W. 183.93, White powder, m.p. 217-219ø, MDL MFCD03095129

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52886 3-Carboxy-5-fluorobenzeneboronic acid, 98% 250mg [3-Carboxy-5-fluorophenylboronic acid] 1g

[871329-84-9], C7H6BFO4, F.W. 183.93, White solid, m.p. 264-266ø, MDL MFCD07363791

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53285 4-Carboxy-3-fluorobenzeneboronic acid, 98% 1g [4-Carboxy-3-fluorophenylboronic acid, 4-Borono-2-fluorobenzoic acid] 5g

[120153-08-4], C7H6BFO4, F.W. 183.93, White solid, m.p. 236-240ø, MDL MFCD01114671

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53323 3-Carboxy-2-methoxybenzeneboronic acid, 98% 250mg [3-Borono-2-methoxybenzoic acid, 3-Carboxy-2-methoxyphenylboronic acid] 1g

[913836-10-9], C8H9BO5, F.W. 195.97, White solid, m.p. 152-155ø, MDL MFCD09027237 Arylboronic

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53005 3-Carboxy-4-methoxybenzeneboronic acid, 98% 250mg [5-Borono-2-methoxybenzoic acid, 3-Carboxy-4-methoxyphenylboronic 1g acid]

[913836-12-1], C8H9BO5, F.W. 195.97, White solid, m.p. 176-177ø, MDL MFCD06203322

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Acids H52929 5-Carboxy-2-methoxybenzeneboronic acid, 98% 250mg [3-Borono-4-methoxybenzoic acid, 5-Carboxy-2-methoxyphenylboronic 1g acid]

[730971-32-1], C8H9BO5, F.W. 195.97, White solid, m.p. 207-210ø, MDL MFCD06203261

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53199 3-Carboxymethoxy-5-fluorobenzeneboronic acid, 96% 250mg [3-Carboxymethoxy-5-fluorophenylboronic acid, 1g 2-(3-Borono-5-fluorophenoxy)acetic acid]

[913835-56-0], C8H8BFO5, F.W. 213.96, Off-white solid, m.p. 230-232ø, MDL MFCD08436015

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H29348 3-Carboxy-5-nitrobenzeneboronic acid, 97% 1g [3-Borono-5-nitrobenzoic acid, 3-Carboxy-5-nitrophenylboronic acid] 5g

[101084-81-5], C7H6BNO6, F.W. 210.94, Pale cream powder, MDL MFCD00757433

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52757 4-Carboxy-2-nitrobenzeneboronic acid, 97% 1g [4-Carboxy-2-nitrophenylboronic acid, 4-Borono-3-nitrobenzoic acid] 5g

[85107-54-6], C7H6BNO6, F.W. 210.94, White to cream solid, m.p. 265-268ø, MDL MFCD00448780

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53327 4-(4-Carboxy-1-piperidinoyl)benzeneboronic acid, 98% 250mg [1-(4-Boronobenzoyl)piperidine-4-carboxylic acid, 1g N-(4-Carboxy)piperidinyl 4-boronobenzamide]

[850593-02-1], C13H16BNO5, F.W. 277.08, White solid, m.p. 110-114ø, MDL MFCD07363784

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L16368 2-(2-Carboxyvinyl)benzeneboronic acid, 98% 50mg [2-Boronocinnamic acid] 250mg

[374105-86-9], C9H9BO4, F.W. 191.98, m.p. 170-172ø, MDL MFCD02093067

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L16369 3-(2-Carboxyvinyl)benzeneboronic acid, 97% 250mg [3-Boronocinnamic acid] 1g

[216144-91-1], C9H9BO4, F.W. 191.98, m.p. ca 218ø, MDL MFCD01075738

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Bulk and Specialty Sizes Available 29 Arylboronic Acids Stock # Description Standard Selling Sizes L15586 4-(2-Carboxyvinyl)benzeneboronic acid, 95% 250mg [4-Boronocinnamic acid] 1g

[151169-68-5], C9H9BO4, F.W. 191.98, m.p. ca 190-196ø, 5g BRN 9196727, MDL MFCD01075704

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53103 4-(trans-2-Carboxyvinyl)benzeneboronic acid, 96% 250mg [4-(trans-2-Carboxyvinyl)phenylboronic acid, 4-Boronocinnamic 1g acid]

[159896-15-8], C9H9BO4, F.W. 191.98, Off-white solid, m.p. 222-224ø, MDL MFCD01075704

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B23324 2-Chlorobenzeneboronic acid, 97% 1g [2-Chlorophenylboronic acid] 5g

[3900-89-8], C6H6BClO2, F.W. 156.38, White to pale cream cryst powder, 25g m.p. ca 95-100ø, BRN 3030414, MDL MFCD00674012

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B24444 3-Chlorobenzeneboronic acid, 97% 1g [3-Chlorophenylboronic acid] 5g

[63503-60-6], C6H6BClO2, F.W. 156.38, White cryst powder, 25g m.p. 180-185ø, BRN 2936343, MDL MFCD00161354

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a A15657 4-Chlorobenzeneboronic acid, 98+% 1g Acids [4-Chlorophenylboronic acid] 5g

[1679-18-1], C6H6BClO2, F.W. 156.38, White to pale cream powder, 25g m.p. 268-277ø, EINECS 216-845-5, RTECS CY8950000, BRN 2936346, MDL MFCD00039137

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a GC reagent for diols: J. Chromat., 158, 33 (1978); 186, 307 (1979). See also Appendix 5.

Arylboronic H53334 3-Chloro-4-(benzylcarbamoyl)benzeneboronic acid, 98% 250mg [3-Chloro-4-(benzylcarbamoyl)phenylboronic acid, N-Benzyl 1g 2-chloro-4-boronobenzamide]

[850589-42-3], C14H13BClNO3, F.W. 289.53, White solid, m.p. 126-128ø, MDL MFCD07363769

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53069 3-Chloro-4-(tert-butylcarbamoyl)benzeneboronic acid, 98% 250mg [3-Chloro-4-(N-tert-butylcarbamoyl)phenylboronic acid, 1g N-tert-Butyl 4-borono-2-chlorobenzamide]

[850589-46-7], C11H15BClNO3, F.W. 255.51, White solid, m.p. 130-134ø, MDL MFCD07363771

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52967 4-Chloro-3-(n-butylcarbamoyl)benzeneboronic acid, 250mg 98% 1g [4-Chloro-3-(n-butylaminocarbonyl)phenylboronic acid, N-n-Butyl 5-borono-2-chlorobenzamide]

[871332-94-4], C11H15BClNO3, F.W. 255.51, White solid, m.p. 214-216ø, MDL MFCD07783886

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52975 4-Chloro-3-(tert-butylcarbamoyl)benzeneboronic acid, 97% 250mg [4-Chloro-3-(tert-butylcarbamoyl)phenylboronic acid, N-tert-Butyl 1g 5-borono-2-chlorobenzamide]

[871332-72-8], C11H15BClNO3, F.W. 255.51, White solid, m.p. 250-256ø, MDL MFCD07783864

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53333 4-Chloro-3-carbamoylbenzeneboronic acid, 98% 250mg [2-Chloro-5-boronobenzamide, 3-Carbamoyl-4-chlorophenylboronic acid] 1g

[871332-67-1], C7H7BClNO3, F.W. 199.40, White solid, m.p. 242-246ø, MDL MFCD07363796

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52722 3-Chlorocarbonylbenzeneboronic anhydride, tech. 1g 90% 5g [3-Chlorocarbonylphenylboronic anhydride, 3-Boronobenzoyl chloride]

[332154-58-2], C7H4BClO2, F.W. 166.37, White solid, m.p. 252-254ø, MDL MFCD06801675

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

30 www.alfa.com Arylboronic Acids Stock # Description Standard Selling Sizes H52852 4-Chlorocarbonylbenzeneboronic anhydride, tech. 1g 90% 5g [4-Chlorocarbonylphenylboronic anhydride, 4-Boronobenzoyl chloride]

[332154-57-1], C7H4BClO2, F.W. 166.37, Off-white solid, m.p. >300ø, MDL MFCD06801674

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52908 3-Chloro-4-chlorocarbonylbenzeneboronic 250mg anhydride, tech. 90% 1g [3-Chloro-4-chlorocarbonylphenylboronic anhydride, 2-Chloro-4-boronobenzoyl chloride, dehydrate]

[850589-38-7], C7H3BCl2O2, F.W. 200.82, Off-white solid, m.p. 243-245ø, MDL MFCD07363765

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53001 4-Chloro-3-cyanobenzeneboronic acid, 98% 250mg [4-Chloro-3-cyanophenylboronic acid, 5-Borono-2-chlorobenzonitrile] 1g

[871332-95-5], C7H5BClNO2, F.W. 181.39, White solid, m.p. 300-304ø, MDL MFCD08056360

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53032 4-Chloro-3-(cyclohexylcarbamoyl)benzeneboronic acid, 250mg Arylboronic 98% 1g [4-Chloro-3-(cyclohexylaminocarbonyl)phenylboronic acid, N-Cyclohexyl 5-borono-2-chlorobenzamide]

[871332-92-2], C13H17BClNO3, F.W. 281.55, White solid, m.p. 252-256ø, MDL MFCD07783884

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52910 3-Chloro-4-(cyclopropylcarbamoyl)benzeneboronic acid, 250mg Acids 97% 1g [3-Chloro-4-(cyclopropylcarbamoyl)phenylboronic acid, N-Cyclopropyl 2-chloro-4-boronobenzamide]

[850589-44-5], C10H11BClNO3, F.W. 239.46, Off-white solid, m.p. 216-220ø, MDL MFCD07363770

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52551 4-Chloro-3-(cyclopropylcarbamoyl)benzeneboronic acid, 250mg 98% 1g [4-Chloro-3-(cyclopropylcarbamoyl)phenylboronic acid, N-Cyclopropyl 5-borono-2-chlorobenzamide]

[871332-73-9], C10H11BClNO3, F.W. 239.46, White solid, m.p. 238-242ø, MDL MFCD07783865

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52656 3-Chloro-4-(diethylcarbamoyl)benzeneboronic acid, 98% 250mg [3-Chloro-4-(diethylcarbamoyl)phenylboronic acid, N,N-Diethyl 1g 2-chloro-4-boronobenzamide]

[850589-48-9], C11H15BClNO3, F.W. 255.51, Yellow solid, m.p. 148-152ø, MDL MFCD07363773

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53077 4-Chloro-3-(diethylcarbamoyl)benzeneboronic acid, 98% 250mg [4-Chloro-3-(diethylcarbamoyl)phenylboronic acid, N,N-Diethyl 1g 5-borono-2-chlorobenzamide]

[871332-68-2], C11H15BClNO3, F.W. 255.51, White solid, m.p. 130-134ø, MDL MFCD07363797

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H25923 5-Chloro-2,4-difluorobenzeneboronic acid, 97% 250mg [5-Chloro-2,4-difluorophenylboronic acid] 1g

[911645-24-4], C6H4BClF2O2, F.W. 192.36, White to cream powder, m.p. 218-222ø, MDL MFCD04038751

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53131 3-Chloro-4-(dimethylcarbamoyl)benzeneboronic acid, 98% 250mg [3-Chloro-4-(dimethylcarbamoyl)phenylboronic acid, N,N-Dimethyl 1g 2-chloro-4-boronobenzamide]

[850589-47-8], C9H11BClNO3, F.W. 227.45, Off-white solid, m.p. 126-132ø, MDL MFCD07363772

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Bulk and Specialty Sizes Available 31 Arylboronic Acids Stock # Description Standard Selling Sizes H52519 4-Chloro-3-(dimethylcarbamoyl)benzeneboronic acid, 98% 250mg [4-Chloro-3-(dimethylaminocarbonyl)phenylboronic acid, 1g N,N-Dimethyl 5-borono-2-chlorobenzamide]

[871332-76-2], C9H11BClNO3, F.W. 227.45, White solid, m.p. 164-166ø, MDL MFCD07783868

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52990 2-Chloro-4-ethoxybenzeneboronic acid, 95% 250mg [2-Chloro-4-ethoxyphenylboronic acid] 1g

[313545-44-7], C8H10BClO3, F.W. 200.43, White solid, m.p. 104-108ø, MDL MFCD02684318

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53154 2-Chloro-5-ethoxybenzeneboronic acid, 97% 250mg [2-Chloro-5-ethoxyphenylboronic acid] 1g

[913835-30-0], C8H10BClO3, F.W. 200.43, White solid, m.p. 98-100ø, MDL MFCD08235081

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53114 3-Chloro-4-ethoxybenzeneboronic acid, 97% 1g [3-Chloro-4-ethoxyphenylboronic acid] 5g

[279261-81-3], C8H10BClO3, F.W. 200.43, White solid, m.p. 230-236ø, MDL MFCD03701556

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52861 4-Chloro-2-ethoxybenzeneboronic acid, 98% 250mg Acids [4-Chloro-2-ethoxyphenylboronic acid] 1g

[850568-80-8], C8H10BClO3, F.W. 200.43, Off-white solid, m.p. 154-158ø, MDL MFCD03094940

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53312 5-Chloro-2-ethoxybenzeneboronic acid, 97% 1g [5-Chloro-2-ethoxyphenylboronic acid] 5g

Arylboronic [352534-86-2], C8H10BClO3, F.W. 200.43, White solid, m.p. 110-114ø, MDL MFCD03427055

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52963 2-Chloro-4-(ethoxycarbonyl)benzeneboronic acid, 98% 250mg [Ethyl 4-borono-3-chlorobenzoate, 2-Chloro-4-(ethoxycarbonyl)phenyl- 1g boronic acid]

[913835-94-6], C9H10BClO4, F.W. 228.44, White solid, m.p. 115-118ø, MDL MFCD08689531

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53031 2-Chloro-5-(ethoxycarbonyl)benzeneboronic acid, 98% 250mg [Ethyl 3-borono-4-chlorobenzoate, 2-Chloro-5-(ethoxycarbonyl)phenyl- 1g boronic acid]

[913835-93-5], C9H10BClO4, F.W. 228.44, White solid, m.p. 236-240ø, MDL MFCD08689529

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53153 4-Chloro-2-(ethoxycarbonyl)benzeneboronic acid, 95% 250mg [4-Chloro-2-(ethoxycarbonyl)phenylboronic acid, Ethyl 1g 2-borono-5-chlorobenzoate]

[850568-61-5], C9H10BClO4, F.W. 228.44, White solid, m.p. 132-134ø, MDL MFCD06659823

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52668 4-Chloro-3-(ethoxycarbonyl)benzeneboronic acid, 96% 250mg [4-Chloro-3-(ethoxycarbonyl)phenylboronic acid, Ethyl 1g 5-borono-2-chlorobenzoate]

[874219-46-2], C9H10BClO4, F.W. 228.44, Off-white solid, m.p. 162-164ø, MDL MFCD08235062

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53016 5-Chloro-2-(ethoxycarbonyl)benzeneboronic acid, 98% 250mg [5-Chloro-2-(ethoxycarbonyl)phenylboronic acid, Ethyl 1g 2-borono-4-chlorobenzoate]

[871329-55-4], C9H10BClO4, F.W. 228.44, White solid, m.p. 106-108ø, MDL MFCD07363744

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53342 3-(2-Chloroethylcarbamoyl)benzeneboronic acid, 96% 250mg [N-(2-Chloroethyl) 3-boronobenzamide, 3-(2-Chloroethylcarbamoyl)- 1g phenylboronic acid]

[874288-12-7], C9H11BClNO3, F.W. 227.45, White solid, m.p. 250-252ø, MDL MFCD08436013

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

32 www.alfa.com Arylboronic Acids Stock # Description Standard Selling Sizes H53162 3-Chloro-4-(ethylcarbamoyl)benzeneboronic acid, 97% 250mg [3-Chloro-4-(ethylcarbamoyl)phenylboronic acid, N-Ethyl 1g 2-chloro-4-boronobenzamide]

[850589-40-1], C9H11BClNO3, F.W. 227.45, Off-white solid, m.p. 142-146ø, MDL MFCD07363767

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52452 4-(2-Chloroethylcarbamoyl)benzeneboronic acid, 95% 250mg [N-(2-Chloroethyl) 4-boronobenzamide, 4-(2-Chloroethylcarbamoyl)- 1g phenylboronic acid]

[874460-05-6], C9H11BClNO3, F.W. 227.45, White solid, m.p. 173-175ø, MDL MFCD08436019

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53175 4-Chloro-3-(ethylcarbamoyl)benzeneboronic acid, 98% 250mg [4-Chloro-3-(ethylcarbamoyl)phenylboronic acid, N-Ethyl 1g 5-borono-2-chlorobenzamide]

[871332-69-3], C9H11BClNO3, F.W. 227.45, White solid, m.p. 220-224ø, MDL MFCD07783861

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52591 2-Chloro-3-fluorobenzeneboronic acid, 95% 250mg [2-Chloro-3-fluorophenylboronic acid] 1g Arylboronic

[871329-52-1], C6H5BClFO2, F.W. 174.37, White solid, m.p. 80-84ø, MDL MFCD07363741

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27591 2-Chloro-4-fluorobenzeneboronic acid, 98% 1g [2-Chloro-4-fluorophenylboronic acid] 5g

[313545-72-1], C6H5BClFO2, F.W. 174.37, Solid, MDL MFCD02684295 25g Acids

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52906 2-Chloro-5-fluorobenzeneboronic acid, 98% 1g [2-Chloro-5-fluorophenylboronic acid] 5g

[444666-39-1], C6H5BClFO2, F.W. 174.37, Off-white solid, m.p. 78-82ø, MDL MFCD06656272

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53079 2-Chloro-6-fluorobenzeneboronic acid, 97% 1g [2-Chloro-6-fluorophenylboronic acid] 5g

[313545-32-3], C6H5BClFO2, F.W. 174.37, White solid, m.p. 131-135ø, MDL MFCD04039892

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52665 3-Chloro-2-fluorobenzeneboronic acid, 97% 1g [3-Chloro-2-fluorophenylboronic acid] 5g

[352535-82-1], C6H5BClFO2, F.W. 174.37, White solid, m.p. 240-242ø, MDL MFCD05664224

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B22755 3-Chloro-4-fluorobenzeneboronic acid, 98% 1g [3-Chloro-4-fluorophenylboronic acid] 5g

[144432-85-9], C6H5BClFO2, F.W. 174.37, White to pale cream powder, 25g m.p. 255-260ø, BRN 7369789, MDL MFCD00051800

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H32137 3-Chloro-5-fluorobenzeneboronic acid, 95% 1g

[328956-61-2], C6H5BClFO2, F.W. 174.37, Solid, MDL MFCD06801741 5g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H28872 4-Chloro-2-fluorobenzeneboronic acid, 97% 1g [4-Chloro-2-fluorophenylboronic acid] 10g

[160591-91-3], C6H5BClFO2, F.W. 174.37, White cryst powder, MDL MFCD02684293

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53325 4-Chloro-3-fluorobenzeneboronic acid, 97% 1g [4-Chloro-3-fluorophenylboronic acid] 5g

[137504-86-0], C6H5BClFO2, F.W. 174.37, Off-white solid, m.p. 198-204ø, MDL MFCD01319010

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53108 5-Chloro-2-fluorobenzeneboronic acid, 97% 1g [5-Chloro-2-fluorophenylboronic acid] 5g

[352535-83-2], C6H5BClFO2, F.W. 174.37, Pale brown solid, m.p. 182-188ø, MDL MFCD05664225

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Bulk and Specialty Sizes Available 33 Arylboronic Acids Stock # Description Standard Selling Sizes H52643 3-Chloro-4-fluoro-5-nitrobenzeneboronic acid, 95% 250mg [3-Chloro-4-fluoro-5-nitrophenylboronic acid] 1g

[850568-73-9], C6H4BClFNO4, F.W. 219.36, Pale brown solid, m.p. 120-124ø, MDL MFCD06659837

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27725 3-Chloro-4-formylbenzeneboronic acid, 95% È 250mg [4-Borono-2-chlorobenzaldehyde, 3-Chloro-4-formylphenylboronic acid] 1g

[1072952-53-4], C7H6BClO3, F.W. 184.39, White to cream or pink powder, m.p. 210-214ø, MDL MFCD08274473

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52549 4-Chloro-2-formylbenzeneboronic acid, 98% È 250mg [4-Chloro-2-formylphenylboronic acid, 2-Borono-5-chlorobenzaldehyde] 1g

[913835-76-4], C7H6BClO3, F.W. 184.39, White solid, m.p. 132-134ø, MDL MFCD08689492

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52476 3-Chloro-4-(hydrazinocarbonyl)benzeneboronic acid, 97% 250mg [4-Borono-2-chlorobenzhydrazide, 3-Chloro-4-(hydrazinecarbonyl)- 1g phenylboronic acid]

[850589-37-6], C7H8BClN2O3, F.W. 214.42, White solid, m.p. 144-150ø, MDL MFCD07363764

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53330 2-Chloro-5-hydroxybenzeneboronic acid, 98% 250mg Acids [2-Chloro-5-hydroxyphenylboronic acid] 1g

[913835-71-9], C6H6BClO3, F.W. 172.37, White solid, m.p. 263-265ø, MDL MFCD08689478

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53075 5-Chloro-2-hydroxybenzeneboronic acid, 97% 250mg [5-Chloro-2-hydroxyphenylboronic acid, 2-Borono-4-chlorophenol] 1g

Arylboronic [89488-25-5], C6H6BClO3, F.W. 172.37, White solid, m.p. 166-170ø, MDL MFCD06659863

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52968 3-Chloro-4-(isopropylcarbamoyl)benzeneboronic acid, 250mg 98% 1g [3-Chloro-4-(isopropylcarbamoyl)phenylboronic acid, N-Isopropyl 4-borono-2-chlorobenzamide]

[850589-41-2], C10H13BClNO3, F.W. 241.48, White solid, m.p. 184-190ø, MDL MFCD07363768

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52679 4-Chloro-3-(isopropylcarbamoyl)benzeneboronic acid, 250mg 98% 1g [4-Chloro-3-(isopropylcarbamoyl)phenylboronic acid, N-Isopropyl 5-borono-2-chlorobenzamide]

[871332-74-0], C10H13BClNO3, F.W. 241.48, Off-white solid, m.p. 254-260ø, MDL MFCD07783866

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H26917 2-Chloro-4-methoxybenzeneboronic acid, 95% 1g [2-Chloro-4-methoxyphenylboronic acid] 5g

[219735-99-6], C7H8BClO3, F.W. 186.40, White powder, m.p. ca 202ø, MDL MFCD03411935

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53359 2-Chloro-5-methoxybenzeneboronic acid, 98% 1g [2-Chloro-5-methoxyphenylboronic acid] 5g

[89694-46-2], C7H8BClO3, F.W. 186.40, Off-white crystalline solid, m.p. 106-110ø, MDL MFCD06659858

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52468 3-Chloro-4-methoxybenzeneboronic acid, 97% 1g [3-Chloro-4-methoxyphenylboronic acid] 5g

[175883-60-0], C7H8BClO3, F.W. 186.40, Off-white crystalline solid, m.p. 224-230ø, MDL MFCD04039888

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27442 3-Chloro-5-methoxybenzeneboronic acid, 94% 250mg [3-Chloro-5-methoxyphenylboronic acid] 1g

[915201-07-9], C7H8BClO3, F.W. 186.40, White to pale cream powder, m.p. 185-189ø, MDL MFCD03095046

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

34 www.alfa.com Arylboronic Acids Stock # Description Standard Selling Sizes H52529 4-Chloro-2-methoxybenzeneboronic acid, 98% 250mg [4-Chloro-2-methoxyphenylboronic acid] 1g

[762287-57-0], C7H8BClO3, F.W. 186.40, White solid, m.p. 128-134ø, MDL MFCD02684317

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27127 5-Chloro-2-methoxybenzeneboronic acid, 97% 5g [5-Chloro-2-methoxyphenylboronic acid] 25g

[89694-48-4], C7H8BClO3, F.W. 186.40, White to cream powder, m.p. 134-141ø, MDL MFCD01318966

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52999 2-Chloro-5-(methoxycarbonyl)benzeneboronic acid, 98% 250mg [Methyl 3-borono-4-chlorobenzoate, 2-Chloro-5-(methoxycarbonyl)- 1g phenylboronic acid]

[913835-92-4], C8H8BClO4, F.W. 214.41, White solid, m.p. 230-232ø, MDL MFCD08689528

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53271 3-Chloro-4-(methoxycarbonyl)benzeneboronic acid, 97% 250mg [3-Chloro-4-(methoxycarbonyl)phenylboronic acid, Methyl 1g 4-borono-2-chlorobenzoate] Arylboronic [603122-82-3], C8H8BClO4, F.W. 214.41, White solid, m.p. 174-178ø, MDL MFCD06659874

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52854 4-Chloro-3-(methoxycarbonyl)benzeneboronic acid, 98% 250mg [4-Chloro-3-(methoxycarbonyl)phenylboronic acid, Methyl 1g 5-borono-2-chlorobenzoate]

[874219-45-1], C8H8BClO4, F.W. 214.41, Off-white solid, m.p. 136-138ø, MDL MFCD06801690 Acids

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H28604 2-Chloro-4-methylbenzeneboronic acid, 97% 1g [2-Chloro-4-methylphenylboronic acid, 2-Chloro-p-tolylboronic acid] 5g

[145349-62-8], C7H8BClO2, F.W. 170.40, White cryst powder, 25g m.p. 198-202ø, MDL MFCD03411936

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53166 2-Chloro-5-methylbenzeneboronic acid, 96% 1g [2-Chloro-5-methylphenylboronic acid] 5g

[193353-35-4], C7H8BClO2, F.W. 170.40, White solid, m.p. 203-205ø, MDL MFCD06659822

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H30893 3-Chloro-2-methylbenzeneboronic acid, 97% 250mg [3-Chloro-2-methylphenylboronic acid] 1g

[313545-20-9], C7H8BClO2, F.W. 170.40, White powder, MDL MFCD04115641

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H28288 3-Chloro-4-methylbenzeneboronic acid, 97% 1g [3-Chloro-4-methylphenylboronic acid, 3-Chloro-p-tolylboronic acid] 5g

[175883-63-3], C7H8BClO2, F.W. 170.40, White cryst powder, m.p. 224-230ø, MDL MFCD04039010

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53179 3-Chloro-5-methylbenzeneboronic acid, 98% 250mg [3-Chloro-5-methylphenylboronic acid] 1g

[913836-14-3], C7H8BClO2, F.W. 170.40, White solid, m.p. 235-238ø, MDL MFCD09027241

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53328 4-Chloromethylbenzeneboronic acid, 95% 250mg [4-Chloromethylphenylboronic acid, 4-Boronobenzyl chloride] 1g

[164413-77-8], C7H8BClO2, F.W. 170.40, White solid, m.p. 186-192ø, MDL MFCD07363850

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B23688 4-Chloro-2-methylbenzeneboronic acid, 98% 1g [4-Chloro-2-methylphenylboronic acid, 4-Chloro-o-tolylboronic acid] 5g

[209919-30-2], C7H8BClO2, F.W. 170.40, White powder, m.p. 193-195ø, 25g MDL MFCD02683107

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Bulk and Specialty Sizes Available 35 Arylboronic Acids Stock # Description Standard Selling Sizes B23179 4-Chloro-3-methylbenzeneboronic acid, 98% 1g [4-Chloro-3-methylphenylboronic acid, 4-Chloro-m-tolylboronic acid] 5g

[161950-10-3], C7H8BClO2, F.W. 170.40, White powder, m.p. 238-242ø, 25g MDL MFCD02683104

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52994 5-Chloro-2-methylbenzeneboronic acid, 97% 1g [5-Chloro-2-methylphenylboronic acid] 5g

[148839-33-2], C7H8BClO2, F.W. 170.40, White powder, m.p. 162-166ø, MDL MFCD03411939

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52721 3-Chloro-4-(methylcarbamoyl)benzeneboronic acid, 96% 250mg [N-Methyl 2-chloro-4-boronobenzamide, 3-Chloro-4-(methylcarbamoyl)- 1g phenylboronic acid]

[850589-39-8], C8H9BClNO3, F.W. 213.43, Off-white solid, m.p. 164-170ø, MDL MFCD07363766

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52659 4-Chloro-3-(methylcarbamoyl)benzeneboronic acid, 98% 250mg [4-Chloro-3-(methylcarbamoyl)phenylboronic acid, N-Methyl 1g 5-borono-2-chlorobenzamide]

[871332-65-9], C8H9BClNO3, F.W. 213.43, White solid, m.p. 294-298ø, MDL MFCD07363795

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Acids H52958 5-Chloro-2-methyl-3-nitrobenzeneboronic acid, 97% 250mg [5-Chloro-2-methyl-3-nitrophenylboronic acid] 1g

[957060-80-9], C7H7BClNO4, F.W. 215.40, Yellow solid, m.p. 110-112ø, MDL MFCD09027246

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52706 3-(2-Chloro-4-methylphenylcarbamoyl)benzeneboronic 250mg

Arylboronic acid, 98% 1g [3-Borono-N-(2-chloro-4-methylphenyl)benzamide, 3-(2-Chloro-4-methylphenylcarbamoyl)phenylboronic acid]

[957060-97-8], C14H13BClNO3, F.W. 289.53, White solid, m.p. 294-297ø, MDL MFCD09027260

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53343 4-(2-Chloro-4-methylphenylcarbamoyl)benzeneboronic 250mg acid, 98% 1g [N-(2-Chloro-4-methylphenyl) 4-boronobenzamide, 4-(2-Chloro-4-methylphenylcarbamoyl)phenylboronic acid]

[913835-39-9], C14H13BClNO3, F.W. 289.53, White solid, m.p. 234-236ø, MDL MFCD09027213

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53015 4-(3-Chloro-4-methylphenylcarbamoyl)benzeneboronic 250mg acid, 98% 1g [N-(3-Chloro-4-methylphenyl) 4-boronobenzamide, 4-(3-Chloro-4-methylphenylcarbamoyl)phenylboronic acid]

[913835-37-7], C14H13BClNO3, F.W. 289.53, Off-white solid, m.p. 217-219ø, MDL MFCD09027211

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53315 3-Chloro-4-(4-morpholinylcarbonyl)benzeneboronic acid, 250mg 98% 1g [4-(4-Borono-2-chlorobenzoyl)morpholine]

[850589-49-0], C11H13BClNO4, F.W. 253.49, White solid, m.p. 182-186ø, MDL MFCD07363774

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53336 4-Chloro-3-(4-morpholinylcarbonyl)benzeneboronic acid, 250mg 98% 1g [4-Chloro-3-(4-morpholinylcarbonyl)phenylboronic acid]

[871332-71-7], C11H13BClNO4, F.W. 253.49, White solid, m.p. 146-150ø, MDL MFCD07783863

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52657 2-Chloro-5-nitrobenzeneboronic acid, 97% 1g [2-Chloro-5-nitrophenylboronic acid]

[867333-29-7], C6H5BClNO4, F.W. 201.37, White solid, m.p. 236-238ø, MDL MFCD03095323

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

36 www.alfa.com Arylboronic Acids Stock # Description Standard Selling Sizes H27093 4-Chloro-3-nitrobenzeneboronic acid, 97% 100mg [4-Chloro-3-nitrophenylboronic acid] 500mg

[151169-67-4], C6H5BClNO4, F.W. 201.37, Cream powder, m.p. ca 275ø dec., MDL MFCD02258950

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53338 4-(4-Chlorophenylcarbamoyl)benzeneboronic acid, 250mg 97% 1g [4-(4-Chlorophenylcarbamoyl)phenylboronic acid]

[874288-02-5], C13H11BClNO3, F.W. 275.50, Pale yellow solid, m.p. 248-250ø, MDL MFCD09027203

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52685 3-Chloro-4-(1-piperidinylcarbonyl)benzeneboronic acid, 98% 250mg [1-(4-Borono-2-chlorobenzoyl)piperidine] 1g

[850589-50-3], C12H15BClNO3, F.W. 267.52, Off-white solid, m.p. 160-163ø, MDL MFCD07363775

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53196 4-Chloro-3-(1-piperidinylcarbonyl)benzeneboronic acid, 98% 250mg [(5-Borono-2-chlorophenyl)carbonylpiperidine] 1g

[871332-70-6], C12H15BClNO3, F.W. 267.52, Cream solid, m.p. 152-156ø, MDL MFCD07783862 Arylboronic

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52461 3-(3-Chloropropylcarbamoyl)benzeneboronic acid, 98% 250mg [N-(3-Chloropropyl) 3-boronobenzamide, 3-(3-Chloropropyl- 1g carbamoyl)phenylboronic acid]

[874288-10-5], C10H13BClNO3, F.W. 241.48, White solid, m.p. 218-220ø, MDL MFCD08436014 Acids

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53098 4-(3-Chloropropylcarbamoyl)benzeneboronic acid, 97% 250mg [4-(3-Chloropropylcarbamoyl)phenylboronic acid] 1g

[874460-03-4], C10H13BClNO3, F.W. 241.48, White solid, m.p. 169-171ø, MDL MFCD08235077

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53211 4-Chloro-3-(n-propylcarbamoyl)benzeneboronic acid, 250mg 98% 1g [4-Chloro-3-(n-propylaminocarbonyl)phenylboronic acid, N-n-Propyl 5-borono-2-chlorobenzamide]

[871332-93-3], C10H13BClNO3, F.W. 241.48, White solid, m.p. 237-239ø, MDL MFCD07783885

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53099 4-(3-Chloropropylsulfamoyl)benzeneboronic acid, 98% 250mg [N-(3-Chloropropyl) 4-boronobenzenesulfonamide, 4-[N-(3-Chloropropyl)sulfamoyl]phenylboronic acid]

[874219-48-4], C9H13BClNO4S, F.W. 277.53, White solid, m.p. 243-245ø, MDL MFCD08235065

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52723 3-(3-Chloropropylsulfonamido)benzeneboronic acid, 250mg 98% 1g [3-(3-Chloropropylsulfonamido)phenylboronic acid, N-(3-Boronophenyl) 3-chloropropanesulfonamide]

[913835-50-4], C9H13BClNO4S, F.W. 277.53, Pale brown solid, m.p. 114-116ø, MDL MFCD08436041

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52949 3-Chloro-4-(1-pyrrolidinylcarbonyl)benzeneboronic acid, 95% 250mg [1-(4-Borono-2-chlorobenzoyl)pyrrolidine] 1g

[850589-51-4], C11H13BClNO3, F.W. 253.49, Yellow solid, m.p. 152-155ø, MDL MFCD07363776

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52769 4-Chloro-3-(1-pyrrolidinylcarbonyl)benzeneboronic acid, 95% 250mg [4-Chloro-3-(pyrrolidine-1-carbonyl)phenylboronic acid, 1g (5-Borono-2-chlorophenyl)carbonylpyrrolidine]

[871332-75-1], C11H13BClNO3, F.W. 253.49, Off-white solid, m.p. 159-163ø, MDL MFCD07783867

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Bulk and Specialty Sizes Available 37 Arylboronic Acids Stock # Description Standard Selling Sizes L20103 2-Chloro-4-(trifluoromethyl)benzeneboronic acid, 96% 1g [2-Chloro-4-(trifluoromethyl)phenylboronic acid] 5g

[254993-59-4], C7H5BClF3O2, F.W. 224.38, m.p. 110-112ø, BRN 9263388, MDL MFCD02684337

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L20104 2-Chloro-5-(trifluoromethyl)benzeneboronic acid, 96% 1g [2-Chloro-5-(trifluoromethyl)phenylboronic acid] 5g

[182344-18-9], C7H5BClF3O2, F.W. 224.38, MDL MFCD00797335

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53120 3-Chloro-4-(trifluoromethyl)benzeneboronic acid, 97% 250mg [3-Chloro-4-(trifluoromethyl)phenylboronic acid] 1g

[847756-88-1], C7H5BClF3O2, F.W. 224.38, Off-white solid, m.p. 206-212ø, MDL MFCD03788417

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H28351 4-Chloro-2-(trifluoromethyl)benzeneboronic acid, 97% 1g [4-Chloro-2-(trifluoromethyl)phenylboronic acid] 10g

[313545-41-4], C7H5BClF3O2, F.W. 224.38, White cryst powder, m.p. 180-182ø, MDL MFCD04973086

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L20105 4-Chloro-3-(trifluoromethyl)benzeneboronic acid, 96% 1g [4-Chloro-3-(trifluoromethyl)phenylboronic acid] 5g

[176976-42-4], C7H5BClF3O2, F.W. 224.38, MDL MFCD03094999 Acids

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52609 2-Cyanobenzeneboronic acid 1g [2-Boronobenzonitrile, 3-Cyanophenylboronic acid] 5g

[138642-62-3], C7H6BNO2, F.W. 146.94, White to cream solid, m.p. 250-254ø, MDL MFCD01632208

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Arylboronic L19635 3-Cyanobenzeneboronic acid, 98+% 250mg [3-Boronobenzonitrile, 3-Cyanophenylboronic acid] 1g

[150255-96-2], C7H6BNO2, F.W. 146.94, m.p. ca 298ø dec., 5g BRN 6136720, MDL MFCD01318967

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L18007 4-Cyanobenzeneboronic acid, 98% 1g [4-Boronobenzonitrile, 4-Cyanophenylboronic acid] 5g

[126747-14-6], C7H6BNO2, F.W. 146.94, m.p. >300ø, BRN 6593772, MDL MFCD01318968

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52586 3-(2-Cyanoethylaminocarbonyl)benzeneboronic acid 250mg [3-(2-Cyanoethylaminocarbonyl)phenylboronic acid] 1g

[762262-11-3], C10H11BN2O3, F.W. 218.02, White solid, m.p. 226-236ø, MDL MFCD04115697

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52692 4-(2-Cyanoethylaminocarbonyl)benzeneboronic acid 250mg [4-(2-Cyanoethylaminocarbonyl)phenylboronic acid] 1g

[850568-16-0], C10H11BN2O3, F.W. 218.02, White solid, m.p. 166-170ø, MDL MFCD04115669

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53041 3-Cyano-4-fluorobenzeneboronic acid 250mg [2-Fluoro-5-boronobenzonitrile] 1g

[214210-21-6], C7H5BFNO2, F.W. 164.93, White solid, m.p. >300ø, MDL MFCD03095130

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27710 4-Cyano-3-fluorobenzeneboronic acid, 97% 1g [4-Cyano-3-fluorophenylboronic acid, 4-Borono-2-fluorobenzonitrile] 5g

[843663-18-3], C7H5BFNO2, F.W. 164.93, Yellow powder, m.p. >300ø, 25g MDL MFCD03411549

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53157 5-Cyano-2-fluorobenzeneboronic acid 250mg [5-Cyano-2-fluorophenylboronic acid] 1g

[468718-30-1], C7H5NO2BF, F.W. 164.93, White solid, m.p. >300ø, MDL MFCD03095147

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

38 www.alfa.com Arylboronic Acids Stock # Description Standard Selling Sizes H53337 3-(Cyanomethyl)benzeneboronic acid, 96% 250mg

[220616-39-7], C8H8BNO2, F.W. 160.97, White solid, m.p. 85-88ø, MDL MFCD03788026

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L19955 4-(Cyanomethyl)benzeneboronic acid, 98% 1g [4-Boronophenylacetonitrile, 4-(Cyanomethyl)phenylboronic acid] 5g

[91983-26-5], C8H8BNO2, F.W. 160.97, Pale yellow or cream powder, m.p. ca 196-200ø, BRN 3031323, MDL MFCD01632200

H:H302-H315-H319-H335, P:P280h-P305+P351+P338 H53244 3-Cyano-5-nitrobenzeneboronic acid, 98% 250mg [3-Borono-5-nitrobenzonitrile] 1g

[913835-33-3], C7H5BN2O4, F.W. 191.94, Off-white solid, m.p. 230-233ø, MDL MFCD03411554

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52478 4-Cyano-2-nitrobenzeneboronic acid, 95% 250mg

[850568-46-6], C7H5BN2O4, F.W. 191.94, Yellow solid, m.p. 110-116ø, 1g MDL MFCD04115646

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H53145 3-(4-Cyanophenylcarbamoyl)benzeneboronic acid, 250mg Arylboronic 95% 1g

[850567-36-1], C14H11BN2O3, F.W. 266.06, Off-white solid, m.p. 232-238ø, MDL MFCD06659886

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53173 4-(2-Cyano-2-propyl)benzeneboronic acid, 97% 250mg

[2-(4-Boronophenyl)-2-methylpropionitrile] Acids

[850568-67-1], C10H12BNO2, F.W. 189.02, White solid, m.p. 146-148ø, MDL MFCD06659832

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52652 2-(trans-2-Cyanovinyl)benzeneboronic acid, 95% 250mg [3-(2-Boronophenyl)acrylonitrile] 1g

[850568-63-7], C9H8BNO2, F.W. 172.98, Off-white solid, MDL MFCD06659825

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53270 3-(trans-2-Cyanovinyl)benzeneboronic acid, 95% 250mg [3-(3-Boronophenyl)acrylonitrile] 1g

[850568-53-5], C9H8NBO2, F.W. 172.98, White to off-white solid, MDL MFCD04973741

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L18076 4-Cyclohexylbenzeneboronic acid, 98% 250mg [4-Cyclohexylphenylboronic acid] 1g

[374538-04-2], C12H17BO2, F.W. 204.08, m.p. ca 220ø, 5g MDL MFCD02093068

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53122 3-(Cyclohexylcarbamoyl)benzeneboronic acid, 98% 1g

[850567-25-8], C13H18BNO3, F.W. 247.10, White solid, 5g m.p. 174-178ø, MDL MFCD04115696

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52839 4-(Cyclohexylcarbamoyl)benzeneboronic acid, 97% 1g

[762262-07-7], C13H18BNO3, F.W. 247.10, White solid, 5g m.p. 174-178ø, MDL MFCD03411956

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H52753 3-Cyclohexylcarbamoyl-4-fluorobenzeneboronic acid, 98% 250mg

[874219-24-6], C13H17BFNO3, F.W. 265.09, White solid, 1g m.p. 231-233ø, MDL MFCD08235043

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H52682 3-Cyclohexylcarbamoyl-5-fluorobenzeneboronic acid, 98% 250mg

[874219-42-8], C13H17BFNO3, F.W. 265.09, White solid, m.p. 239-241ø, 1g MDL MFCD08235059

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Bulk and Specialty Sizes Available 39 Arylboronic Acids Stock # Description Standard Selling Sizes H52922 4-Cyclohexylcarbamoyl-3-fluorobenzeneboronic acid, 95% 250mg

[874289-11-9], C13H17BFNO3, F.W. 265.09, White solid, 1g m.p. 157-159ø, MDL MFCD08436036

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H53297 5-Cyclohexylcarbamoyl-2-fluorobenzeneboronic acid, 98% 250mg

[874289-44-8], C13H17BFNO3, F.W. 265.09, White solid, 1g m.p. 164ø, MDL MFCD08235096

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H53176 3-Cyclohexylcarbamoyl-5-nitrobenzeneboronic acid, 97% 250mg [3-Cyclohexylaminocarbonyl-5-nitrophenylboronic acid] 1g

[871332-85-3], C13H17BN2O5, F.W. 292.10, White solid, MDL MFCD07783877

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53053 4-[Cyclohexyl(4-methoxybenzyl)sulfamoyl- 250mg ]benzeneboronic acid, 97% 1g

[913836-13-2], C20H26BNO5S, F.W. 403.30, White solid, MDL MFCD09027240

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Acids H53107 4-[Cyclohexyl(methyl)carbamoyl]benzeneboronic acid, 250mg 98% 1g

[913835-84-4], C14H20BNO3, F.W. 261.13, White solid, MDL MFCD09027224

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52915 3-(Cyclohexylsulfamoyl)benzeneboronic acid, 97% 250mg

[871329-79-2], C12H18BNO4S, F.W. 283.15, White solid, Arylboronic MDL MFCD07783859

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52703 4-(Cyclohexylsulfamoyl)benzeneboronic acid, 95% 250mg

[871329-66-7], C12H18BNO4S, F.W. 283.15, White solid, 1g m.p. 270-276ø, MDL MFCD07363754

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H53125 3-(Cyclopentylcarbamoyl)benzeneboronic acid, 98% 250mg [N-Cyclopentyl-3-boronobenzamide] 1g

[850567-24-7], C12H16BNO3, F.W. 233.07, White solid, MDL MFCD04115695

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52500 4-(Cyclopentylcarbamoyl)benzeneboronic acid, 97% 1g [N-Cyclopentyl 4-boronobenzamide] 5g

[850568-15-9], C12H16BNO3, F.W. 233.07, White solid, m.p. 196-200ø, MDL MFCD03788418

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53262 3-(Cyclopropylcarbamoyl)benzeneboronic acid, 97% É 250mg

[850567-23-6], C10H12BNO3, F.W. 205.02, Solid, m.p. 220-226ø, 1g MDL MFCD04115694

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53036 4-(Cyclopropylcarbamoyl)benzeneboronic acid, 97% 250mg

[515140-26-8], C10H12BNO3, F.W. 205.02, White solid, 1g m.p. 202-206ø, MDL MFCD03788419

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52440 3-Cyclopropylcarbamoyl-5-nitrobenzeneboronic acid, 98% 250mg [3-Cyclopropylaminocarbonyl-5-nitrophenylboronic acid] 1g

[871332-86-4], C10H11BN2O5, F.W. 250.02, Off-white solid, m.p. 126-128ø, MDL MFCD07783878

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

40 www.alfa.com Arylboronic Acids Stock # Description Standard Selling Sizes H52845 3-[Cyclopropyl(4-methoxybenzyl)sulfamoyl- 250mg ]benzeneboronic acid, 98% 1g [N-Cyclopropyl-N-(4-methoxybenzyl) 3-boronobenzenesulfonamide]

[913836-07-4], C17H20BNO5S, F.W. 361.22, Off-white solid, MDL MFCD09027233

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52614 4-[Cyclopropyl(4-methoxybenzyl)sulfamoyl- 250mg ]benzeneboronic acid, 98% 1g [N-Cyclopropyl-N-(4-methoxybenzyl) 4-boronobenzenesulfonamide]

[913835-89-9], C17H20BNO5S, F.W. 361.22, Off-white solid, MDL MFCD09027226

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52441 3-(Cyclopropylsulfamoyl)benzeneboronic acid, 98% 250mg

[913835-28-6], C9H12BNO4S, F.W. 241.07, White solid, 1g m.p. 126-128ø, MDL MFCD08436035

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53170 4-(Cyclopropylsulfamoyl)benzeneboronic acid, 98% 250mg Arylboronic [871329-67-8], C9H12BNO4S, F.W. 241.07, White solid, 1g m.p. 142-144ø, MDL MFCD07363755

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27550 4-(Dibenzylamino)benzeneboronic acid, 95% 250mg [4-(Dibenzylamino)phenylboronic acid] 1g

[159191-44-3], C20H20BNO2, F.W. 317.19, White powder,

m.p. 184-188ø, MDL MFCD06798225 Acids

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B23863 3,5-Dibromobenzeneboronic acid, 97% 1g [3,5-Dibromophenylboronic acid] 5g

[117695-55-3], C6H5BBr2O2, F.W. 279.73, White to cream powder, 25g m.p. >300ø, BRN 6645285, MDL MFCD01075725

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52866 2,4-Dibromo-5-methoxybenzeneboronic acid, 97% 250mg

[89677-46-3], C7H7BBr2O3, F.W. 309.75, White solid, m.p. 300ø, 1g MDL MFCD06659860

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53261 2,6-Dibromo-3-methoxybenzeneboronic acid, 97% 250mg

[850567-93-0], C7H7BBr2O3, F.W. 309.75, White solid, m.p. 106-110ø, 1g MDL MFCD06659861

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

B22781 2,3-Dichlorobenzeneboronic acid, 98% 1g [2,3-Dichlorophenylboronic acid] 5g

[151169-74-3], C6H5BCl2O2, F.W. 190.82, White to cream cryst powder, 25g m.p. 233-242ø, MDL MFCD01075703

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L01563 2,4-Dichlorobenzeneboronic acid, 98+% 1g [2,4-Dichlorophenylboronic acid, 2,4-Dichlorobenzeneboron dihydroxide] 5g

[68716-47-2], C6H5BCl2O2, F.W. 190.82, m.p. 242-245ø, BRN 4983878, MDL MFCD00013930

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a GC reagent for diols: J. Chromat., 158, 33 (1978); 186, 307 (1979). For reactions of boronic acids, see Appendix 5. B22984 2,5-Dichlorobenzeneboronic acid, 98% 1g [2,5-Dichlorophenylboronic acid] 5g

[135145-90-3], C6H5BCl2O2, F.W. 190.82, White powder, m.p. ca 25g 210-216ø, BRN 4801290, MDL MFCD01863182

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L19816 2,6-Dichlorobenzeneboronic acid, 95% 250mg [2,6-Dichlorophenylboronic acid] 1g

[73852-17-2], C6H5BCl2O2, F.W. 190.82, m.p. 151-152ø, BRN 4802506, MDL MFCD00064869

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Bulk and Specialty Sizes Available 41 Arylboronic Acids Stock # Description Standard Selling Sizes B24292 3,4-Dichlorobenzeneboronic acid, 97% 1g [3,4-Dichlorophenylboronic acid] 5g

[151169-75-4], C6H5BCl2O2, F.W. 190.82, White to cream powder, 25g m.p. 270-274ø, BRN 7369790, MDL MFCD01074646

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B22765 3,5-Dichlorobenzeneboronic acid, 98+% 1g [3,5-Dichlorophenylboronic acid] 5g

[67492-50-6], C6H5BCl2O2, F.W. 190.82, White to cream powder, 25g m.p. ca 315ø dec., BRN 7581091, MDL MFCD00051935

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Reagent for derivatization of diols and diamines for GC: Chromatographia, 11, 347 (1978). For reactions of boronic acids, see Appendix 5. H53281 3-[2-(Diethylamino)ethylcarbamoyl]benzeneboronic 250mg acid hydrochloride, 97% 1g [3-[2-(Diethylamino)ethylaminocarbonyl]phenylboronic acid hydrochloride]

[957061-01-7], C13H21BN2O3ùHCl, F.W. 300.59, Off-white solid, MDL MFCD09027256

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52871 4-[2-(Diethylamino)ethylcarbamoyl]benzeneboronic 250mg acid hydrochloride 1g [4-[2-(Diethylamino)ethylaminocarbonyl]phenylboronic acid hydrochloride]

Acids [913835-46-8], C13H22BClN2O3, F.W. 300.59, White solid, m.p. 65-67ø, MDL MFCD09027220

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52951 2-(Diethylcarbamoyl)benzeneboronic acid, 95% 250mg [2-(Diethylaminocarbonyl)phenylboronic acid] 1g

[129112-21-6], C11H16BNO3, F.W. 221.06, White solid, m.p. 64-70ø, MDL MFCD01318988 Arylboronic H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53061 3-(Diethylcarbamoyl)benzeneboronic acid, 98% 1g [3-(Diethylaminocarbonyl)phenylboronic acid] 5g

[237413-05-7], C11H16BNO3, F.W. 221.06, Off-white solid, m.p. 132-136ø, MDL MFCD04115684

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52986 4-(Diethylcarbamoyl)benzeneboronic acid, 98% 1g [4-(Diethylaminocarbonyl)phenylboronic acid] 5g

[389621-80-1], C11H16BNO3, F.W. 221.06, White solid, m.p. 138-142ø, MDL MFCD03411949

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52667 3-Diethylcarbamoyl-4-fluorobenzeneboronic acid, 98% 250mg [5-Borono-N,N-diethyl-2-fluorobenzamide] 1g

[874219-28-0], C11H15BFNO3, F.W. 239.05, White solid, m.p. 133-135ø, MDL MFCD08235047

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52646 4-Diethylcarbamoyl-3-fluorobenzeneboronic acid, 98% 250mg

[874289-14-2], C11H15BFNO3, F.W. 239.05, White solid, 1g m.p. 158-160ø, MDL MFCD08436057

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52507 5-Diethylcarbamoyl-2-fluorobenzeneboronic acid, 98% 250mg

[874289-47-1], C11H15BFNO3, F.W. 239.05, Off-white solid, 1g m.p. 136-138ø, MDL MFCD08436045

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52837 4-Diethylcarbamoyl-2-methoxybenzeneboronic acid, 96% 250mg [4-Borono-N,N-diethyl-3-methoxybenzamide]

[913835-34-4], C12H18BNO4, F.W. 251.09, Yellow solid, MDL MFCD09027199

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52490 3-Diethylcarbamoyl-5-nitrobenzeneboronic acid, 98% 250mg [3-Diethylaminocarbonyl-5-nitrophenylboronic acid] 1g

[871332-82-0], C11H15BN2O5, F.W. 266.06, White solid, m.p. 170-173ø, MDL MFCD07783874

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52593 3-(Diethylsulfamoyl)benzeneboronic acid, 98% 250mg

[871329-58-7], C10H16BNO4S, F.W. 257.11, White solid, 1g m.p. 120-123ø, MDL MFCD07363746

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

42 www.alfa.com Arylboronic Acids Stock # Description Standard Selling Sizes H52473 4-(Diethylsulfamoyl)benzeneboronic acid, 98% 250mg

[850568-76-2], C10H16BNO4S, F.W. 257.11, White solid, 1g m.p. 120-124ø, MDL MFCD06659846

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52770 3-Diethylsulfamoyl-4-methoxybenzeneboronic acid, 95% 250mg

[871333-03-8], C11H18BNO5S, F.W. 287.14, White solid, 1g m.p. 110-112ø, MDL MFCD08056367

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52509 5-Diethylsulfamoyl-2-methylbenzeneboronic acid, 97% 250mg

[871329-80-5], C11H18BNO4S, F.W. 271.14, White solid, 1g m.p. 146-152ø, MDL MFCD08056356

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L18012 2,3-Difluorobenzeneboronic acid, 98% 1g [2,3-Difluorophenylboronic acid] 5g

[121219-16-7], C6H5BF2O2, F.W. 157.91, m.p. ca 225ø dec., BRN 6594341, 25g MDL MFCD01863170

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B23821 2,4-Difluorobenzeneboronic acid, 97% 1g

[2,4-Difluorophenylboronic acid] 5g Arylboronic

[144025-03-6], C6H5BF2O2, F.W. 157.91, m.p. 247-250ø, BRN 8616257, 25g MDL MFCD01318998

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B24113 2,5-Difluorobenzeneboronic acid, 96% 1g [2,5-Difluorophenylboronic acid] 5g

[193353-34-3], C6H5BF2O2, F.W. 157.91, White powder, BRN 8833254, 25g MDL MFCD01863171 Acids

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B22805 2,6-Difluorobenzeneboronic acid, 98% 1g [2,6-Difluorophenylboronic acid] 5g

[162101-25-9], C6H5BF2O2, F.W. 157.91, White to pale brown cryst powder, 25g m.p. ca 140ø dec., BRN 8545931, MDL MFCD00792436

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B22799 3,4-Difluorobenzeneboronic acid, 98% 1g [3,4-Difluorophenylboronic acid] 5g

[168267-41-2], C6H5BF2O2, F.W. 157.91, White cryst powder, m.p. >300ø, 25g BRN 7369788, MDL MFCD00807405

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L17425 3,5-Difluorobenzeneboronic acid, 97+% 1g [3,5-Difluorophenylboronic acid] 5g

[156545-07-2], C6H5BF2O2, F.W. 157.91, m.p. >300ø, BRN 6800882, MDL MFCD01318138

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53251 2,3-Difluoro-4-methoxybenzeneboronic acid, 98% 1g

[170981-41-6], C7H7BF2O3, F.W. 187.94, White solid, 5g MDL MFCD07368234

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L19773 3,5-Difluoro-2-methoxybenzeneboronic acid, 97% 250mg [3,5-Difluoro-2-methoxyphenylboronic acid] 1g

[737000-76-9], C7H7BF2O3, F.W. 187.94, m.p. 112-115ø, 5g MDL MFCD03095353

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52585 2,3-Difluoro-5-nitrobenzeneboronic acid, 98% 250mg

[957060-82-1], C6H4BF2NO4, F.W. 202.91, Yellow solid, 1g MDL MFCD09027242

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53039 2,4-Difluoro-5-nitrobenzeneboronic acid, 98% 250mg

[325786-11-6], C6H4BF2NO4, F.W. 202.91, Pale brown solid, 1g m.p. 225-227ø, MDL MFCD03095253

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53062 4-(5,6-Dihydro-4H-1,3-oxazin-2-yl)benzeneboronic acid, 96% 250mg [2-(4-Boronophenyl)-5,6-dihydro-4H-1,3-oxazine] 1g

[850568-68-2], C10H12BNO3, F.W. 205.02, White solid, m.p. 180-182ø, MDL MFCD06659833

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Bulk and Specialty Sizes Available 43 Arylboronic Acids Stock # Description Standard Selling Sizes H52439 3-(Diisopropylcarbamoyl)benzeneboronic acid, 98% 250mg [3-(Diisopropylaminocarbonyl)phenylboronic acid] 1g

[850567-40-7], C13H20BNO3, F.W. 249.12, White solid, m.p. 170-174ø, MDL MFCD06659890

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52924 4-(Diisopropylcarbamoyl)benzeneboronic acid, 98% 250mg [4-(Diisopropylaminocarbonyl)phenylboronic acid] 1g

[850568-33-1], C13H20BNO3, F.W. 249.12, White solid, m.p. 228-234ø, MDL MFCD06659884

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B24125 2,3-Dimethoxybenzeneboronic acid, 98% 1g [2,3-Dimethoxyphenylboronic acid] 5g

[40972-86-9], C8H11BO4, F.W. 181.99, m.p. 67-71ø, BRN 3051295, 25g MDL MFCD02683112

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B24374 2,4-Dimethoxybenzeneboronic acid, 98% 1g [2,4-Dimethoxyphenylboronic acid] 5g

[133730-34-4], C8H11BO4, F.W. 181.99, White to cream powder, 25g m.p. 115-120ø, BRN 4744213, MDL MFCD01074590

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B24571 2,5-Dimethoxybenzeneboronic acid, 98% 1g [2,5-Dimethoxyphenylboronic acid] 5g Acids [107099-99-0], C8H11BO4, F.W. 181.99, m.p. 92-94ø, BRN 2969872, 25g MDL MFCD01318181

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B24305 2,6-Dimethoxybenzeneboronic acid, 98% 1g [2,6-Dimethoxyphenylboronic acid] 5g

[23112-96-1], C8H11BO4, F.W. 181.99, m.p. 106-108ø, BRN 3032352, 25g

Arylboronic MDL MFCD01318987

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B24240 3,4-Dimethoxybenzeneboronic acid, 98% 1g [3,4-Dimethoxyphenylboronic acid] 5g

[122775-35-3], C8H11BO4, F.W. 181.99, White to cream powder, 25g m.p. ca 240ø, BRN 5334877, MDL MFCD01074574

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Suzuki coupling (see Appendix 5) with 1-amino-2-bromonaphthalene derivatives has been used in a versatile synthesis of benzo[c]phenanthridine alkaloids: J. Chem. Soc., Perkin 1, 1647 (1996). H52965 3,5-Dimethoxybenzeneboronic acid, 98% 1g

[192182-54-0], C8H11BO4, F.W. 181.98, Off-white solid, m.p. 205-207ø, 5g MDL MFCD03095127

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53140 (S)-2,2'-Dimethoxy-1,1'-binaphthyl-3,3'-diboronic acid, 97% 250mg

[220204-00-2], C22H20B2O6, F.W. 402.02, White solid, MDL MFCD09027249

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H52498 3-[2-(Dimethylamino)ethylcarbamoyl]benzeneboronic 250mg acid, 96% 1g [3-[2-(Dimethylaminoethyl)aminocarbonyl]phenylboronic acid]

[850567-31-6], C11H17BN2O3, F.W. 236.08, Off-white solid, m.p. 42-45ø, MDL MFCD04115706

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52933 4-[2-(Dimethylamino)ethylcarbamoyl]benzeneboronic 250mg acid hydrochloride, 97% 1g [4-[2-(Dimethylaminoethyl)aminocarbonyl]phenylboronic acid hydrochloride]

[850568-22-8], C11H17BN2O3ùHCl, F.W. 272.54, White solid, m.p. 186-190ø, MDL MFCD06656014

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

44 www.alfa.com Arylboronic Acids Stock # Description Standard Selling Sizes H52632 4-[5-(4-Dimethylaminophenyl)-2-oxazolyl- 250mg ]benzeneboronic acid, 97% [5-(4-Dimethylaminophenyl)-2-(4-boronophenyl)- oxazole]

[380499-66-1], C17H17BN2O3, F.W. 308.14, Yellow to cream solid, MDL MFCD08689479

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B23942 2,3-Dimethylbenzeneboronic acid, 98% 1g [2,3-Dimethylphenylboronic acid] 5g

[183158-34-1], C8H11BO2, F.W. 149.99, m.p. ca 175ø, BRN 8050763, 25g MDL MFCD01863524

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B23076 2,4-Dimethylbenzeneboronic acid, 97% 1g [2,4-Dimethylphenylboronic acid] 5g

[55499-44-0], C8H11BO2, F.W. 149.99, White to cream powder, 25g m.p. 204-208ø, MDL MFCD02683101

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B23740 2,5-Dimethylbenzeneboronic acid, 98% 1g [2,5-Dimethylphenylboronic acid] 5g Arylboronic [85199-06-0], C8H11BO2, F.W. 149.99, White to cream powder, m.p. ca 25g 180ø, BRN 3241785, MDL MFCD01863525

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B24613 2,6-Dimethylbenzeneboronic acid, 97% 1g [2,6-Dimethylphenylboronic acid] 5g

[100379-00-8], C8H11BO2, F.W. 149.99, m.p. 104-106øC (dec.), 25g m.p. 104-106ø dec., MDL MFCD01009693 Acids

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L17461 3,4-Dimethylbenzeneboronic acid, 98+% 1g [3,4-Dimethylphenylboronic acid] 5g

[55499-43-9], C8H11BO2, F.W. 149.99, m.p. ca 220ø, BRN 2963858, MDL MFCD01009694

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B23434 3,5-Dimethylbenzeneboronic acid, 98% 1g [3,5-Dimethylphenylboronic acid] 5g

[172975-69-8], C8H11BO2, F.W. 149.99, m.p. 235-237ø, BRN 7368658, 25g MDL MFCD00185689

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52765 2-(Dimethylcarbamoyl)benzeneboronic acid, 95% 250mg [2-(Dimethylaminocarbonyl)phenylboronic acid] 1g

[874219-16-6], C9H12BNO3, F.W. 193.01, White solid, m.p. 108-110ø, MDL MFCD03425959

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52545 3-(Dimethylcarbamoyl)benzeneboronic acid, 96% 250mg [3-(Dimethylaminocarbonyl)phenylboronic acid] 1g

[373384-14-6], C9H12BNO3, F.W. 193.01, White solid, m.p. 122-128ø, MDL MFCD03412066

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53363 4-(Dimethylcarbamoyl)benzeneboronic acid, 97% 1g [4-(Dimethylaminocarbonyl)phenylboronic acid] 5g

[405520-68-5], C9H12BNO3, F.W. 193.01, White solid, m.p. 130-136ø, MDL MFCD02258943

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52988 3-Dimethylcarbamoyl-4-fluorobenzeneboronic acid, 98% 250mg [3-Dimethylaminocarbonyl-4-fluorophenylboronic acid] 1g

[874219-27-9], C9H11BFNO3, F.W. 211.00, White solid, m.p. 146-148ø, MDL MFCD08235046

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53117 4-Dimethylcarbamoyl-3-fluorobenzeneboronic acid, 98% 250mg [4-Dimethylaminocarbonyl-3-fluorophenylboronic acid] 1g

[874289-13-1], C9H11BFNO3, F.W. 211.00, Off-white solid, m.p. 147-149ø, MDL MFCD08436060

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53045 5-Dimethylcarbamoyl-2-fluorobenzeneboronic acid, 98% 250mg [5-Dimethylcarbamoyl-2-fluorophenylboronic acid] 1g

[874289-46-0], C9H11BFNO3, F.W. 211.00, White solid, m.p. 143-147ø, MDL MFCD08235102

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Bulk and Specialty Sizes Available 45 Arylboronic Acids Stock # Description Standard Selling Sizes H53100 5-Dimethylcarbamoyl-3-fluorobenzeneboronic acid, 98% 250mg [5-Dimethylaminocarbonyl-3-fluorophenylboronic acid] 1g

[874219-39-3], C9H11BFNO3, F.W. 211.00, Pink solid, m.p. 111-113ø, MDL MFCD08235056

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52688 3-Dimethylcarbamoyl-5-nitrobenzeneboronic acid, 98% 250mg [3-Dimethylaminocarbonyl-5-nitrophenylboronic acid] 1g

[874219-44-0], C9H11BN2O5, F.W. 238.01, Off-white solid, m.p. 160-162ø, MDL MFCD08235061

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52767 3,5-Dimethyl-4-ethoxybenzeneboronic acid, 98% 1g [4-Ethoxy-3,5-dimethylphenylboronic acid] 5g

[850568-59-1], C10H15BO3, F.W. 194.04, White solid, m.p. 210-212ø, MDL MFCD02179463

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52762 3-(2,3-Dimethylphenylcarbamoyl)benzeneboronic 250mg acid, 96% 1g [3-(2,3-Dimethylphenylaminocarbonyl)phenylboronic acid]

[957060-99-0], C15H16BNO3, F.W. 269.11, White solid, MDL MFCD09027262

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53293 3-(2,4-Dimethylphenylcarbamoyl)benzeneboronic 250mg Acids acid, 98% 1g [3-(2,4-Dimethylphenylaminocarbonyl)phenylboronic acid]

[957060-98-9], C15H16BNO3, F.W. 269.11, White solid, MDL MFCD09027261

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52504 3-(2,5-Dimethylphenylcarbamoyl)benzeneboronic 250mg

Arylboronic acid, 98% 1g [3-(2,5-Dimethylphenylaminocarbonyl)phenylboronic acid]

[957061-00-6], C15H16BNO3, F.W. 269.11, White solid, MDL MFCD09027263

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53189 4-(2,3-Dimethylphenylcarbamoyl)benzeneboronic acid, 250mg 98% 1g [4-(2,3-Dimethylphenylaminocarbonyl)phenylboronic acid]

[913835-36-6], C15H16BNO3, F.W. 269.11, Off-white solid, MDL MFCD09027210

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53356 4-(2,4-Dimethylphenylcarbamoyl)benzeneboronic 250mg acid, 98% 1g [4-(2,4-Dimethylphenylaminocarbonyl)phenylboronic acid]

[913835-38-8], C15H16BNO3, F.W. 269.11, White solid, MDL MFCD09027212

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52850 4-(2,5-Dimethylphenylcarbamoyl)benzeneboronic 250mg acid, 96% 1g [4-(2,5-Dimethylphenylaminocarbonyl)phenylboronic acid]

[913835-40-2], C15H16BNO3, F.W. 269.11, Off-white solid, MDL MFCD09027214

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53294 3,5-Dimethyl-4-n-propoxybenzeneboronic acid, 98% 1g

[357611-51-9], C11H17BO3, F.W. 208.06, White solid, 5g m.p. 170-173ø, MDL MFCD05865178

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53235 3-(Dimethylsulfamoylamino)benzeneboronic acid, 98% 250mg

[277295-50-8], C8H13BN2O4S, F.W. 244.07, White solid, 1g m.p. 129-132ø, MDL MFCD08235107

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52838 3-(Dimethylsulfamoyl)benzeneboronic acid, 98% 250mg

[871329-59-8], C8H12BNO4S, F.W. 229.06, White solid, 1g m.p. 88-92ø, MDL MFCD07363747

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

46 www.alfa.com Arylboronic Acids Stock # Description Standard Selling Sizes H52936 4-(Dimethylsulfamoyl)benzeneboronic acid, 95% 250mg

[486422-59-7], C8H12BNO4S, F.W. 229.06, White solid, 1g m.p. 140-144ø, MDL MFCD06659849

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52996 5-Dimethylsulfamoyl-2-methylbenzeneboronic acid, 98% 250mg

[871332-99-9], C9H14BNO4S, F.W. 243.08, White solid, 1g m.p. 86-92ø, MDL MFCD08056363

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52611 3,5-Dinitro-2-methylbenzeneboronic acid, 96% 1g

[24341-76-2], C7H7BN2O6, F.W. 225.95, Pale yellow solid, 5g m.p. 122-128ø, MDL MFCD00757434

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H25773 3,5-Dinitro-4-methylbenzeneboronic acid, 97% 1g [3,5-Dinitro-4-methylphenylboronic acid, 3,5-Dinitro-p-tolueneboronic acid] 5g

[28249-49-2], C7H7BN2O6, F.W. 225.95, Cream powder, m.p. ca 280ø 25g dec., MDL MFCD08060935

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H52902 4-(Diphenylamino)benzeneboronic acid, 98% 250mg Arylboronic [4-(Diphenylamino)phenylboronic acid] 1g

[201802-67-7], C18H16BNO2, F.W. 289.14, Off-white solid, m.p. 110-115ø, MDL MFCD06798117

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53191 3-(Di-n-propylcarbamoyl)benzeneboronic acid, 98% 250mg [3-(Di-n-propylaminocarbonyl)phenylboronic acid] 1g

[850567-39-4], C13H20BNO3, F.W. 249.12, White solid, Acids m.p. 118-120ø, MDL MFCD06659889

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52514 4-(Di-n-propylcarbamoyl)benzeneboronic acid, 98% 250mg [4-(Di-n-propylaminocarbonyl)phenylboronic acid] 1g

[850568-32-0], C13H20BNO3, F.W. 249.12, Solid, m.p. 120-124ø, MDL MFCD06659883

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B23644 2-Ethoxybenzeneboronic acid, 98% 1g [2-Ethoxyphenylboronic acid] 5g

[213211-69-9], C8H11BO3, F.W. 165.99, White to pale brown cryst powder, 25g m.p. 98-101ø, MDL MFCD00674027

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B24485 3-Ethoxybenzeneboronic acid, 98% 1g [3-Ethoxyphenylboronic acid] 5g

[90555-66-1], C8H11BO3, F.W. 165.99, White to cream cryst powder, 25g m.p. 142-146ø, MDL MFCD00274219

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B23683 4-Ethoxybenzeneboronic acid, 98% 1g [4-Ethoxyphenylboronic acid] 5g

[22237-13-4], C8H11BO3, F.W. 165.99, White to cream cryst powder, 25g m.p. 165-168ø, BRN 3530408, MDL MFCD00674028

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H25867 2-(Ethoxycarbonyl)benzeneboronic acid, 98% 1g [2-(Ethoxycarbonyl)phenylboronic acid, Ethyl 2-boronobenzoate] 5g

[380430-53-5], C9H11BO4, F.W. 193.99, White to yellow cryst powder, m.p. 130-133ø, MDL MFCD02179453

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H26615 3-(Ethoxycarbonyl)benzeneboronic acid, 97% 1g [3-Ethoxycarbonylphenylboronic acid, Ethyl 3-boronobenzoate] 5g

[4334-87-6], C9H11BO4, F.W. 193.99, White powder, m.p. 135-139ø, MDL MFCD02179444

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H26356 4-(Ethoxycarbonyl)benzeneboronic acid, 94% 1g [4-Ethoxycarbonylphenylboronic acid, Ethyl 4-boronobenzoate] 5g

[4334-88-7], C9H11BO4, F.W. 193.99, White powder, m.p. 137-140ø, MDL MFCD02179441

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Bulk and Specialty Sizes Available 47 Arylboronic Acids Stock # Description Standard Selling Sizes H52896 4-Ethoxycarbonyl-3-chlorobenzeneboronic acid, 98% 250mg [Ethyl 4-borono-2-chlorobenzoate] 1g

[850568-11-5], C9H10BClO4, F.W. 228.44, White solid, m.p. 122-126ø, MDL MFCD06659875

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53268 3-[2-(Ethoxycarbonyl)ethyl]benzeneboronic acid, 97% 250mg [Ethyl 3-(3-boronophenyl)propionate] 1g

[913835-82-2], C11H15BO4, F.W. 222.05, White solid, m.p. 94-96ø, MDL MFCD08689511

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52640 4-[2-(Ethoxycarbonyl)ethyl]benzeneboronic acid, 96% 250mg [Ethyl 3-(4-boronophenyl)propionate] 1g

[660440-57-3], C11H15BO4, F.W. 222.05, Off-white solid, m.p. 80-84ø, MDL MFCD04115652

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52528 3-Ethoxycarbonyl-4-fluorobenzeneboronic acid, 98% 250mg [Ethyl 5-borono-2-fluorobenzoate] 1g

[874219-36-0], C9H10BFO4, F.W. 211.98, White solid, m.p. 149-152ø, MDL MFCD08061836

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52620 4-Ethoxycarbonyl-3-fluorobenzeneboronic acid, 95% 250mg [Ethyl 4-borono-2-fluorobenzoate] 1g Acids [874288-38-7], C9H10BFO4, F.W. 211.98, White solid, m.p. 158-161ø, MDL MFCD06656274

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53134 5-Ethoxycarbonyl-2-fluorobenzeneboronic acid, 97% 250mg [Ethyl 3-borono-4-fluorobenzoate] 1g

[874219-60-0], C9H10BFO4, F.W. 211.98, White solid, m.p. 97-99ø,

Arylboronic MDL MFCD08235094

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52873 3-Ethoxycarbonyl-5-nitrobenzeneboronic acid, 97% 1g [Ethyl 3-borono-5-nitrobenzoate] 5g

[850568-37-5], C9H10BNO6, F.W. 238.99, White to off-white solid, m.p. 158-163ø, MDL MFCD03788422

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52912 4-Ethoxycarbonyl-2-nitrobenzeneboronic acid, 97% 250mg [Ethyl 4-borono-3-nitrobenzoate] 1g

[5785-70-6], C9H10BNO6, F.W. 238.99, Off-white solid, m.p. 116-118ø, MDL MFCD02179460

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52451 3-Ethoxy-5-fluorobenzeneboronic acid, 95% 250mg

[850589-53-6], C8H10BFO3, F.W. 183.97, White solid, m.p. 155-158ø, 1g MDL MFCD07363779

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52465 4-Ethoxy-3-fluorobenzeneboronic acid, 98% 1g

[279263-10-4], C8H10BFO3, F.W. 183.97, White solid, 5g m.p. 108-113C, MDL MFCD04115667 25g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53269 2-(Ethoxymethyl)benzeneboronic acid, 97% 250mg

[871329-56-5], C9H13BO3, F.W. 180.01, White solid, m.p. 60-63ø, 1g MDL MFCD07363844

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53340 2-Ethoxy-5-methylbenzeneboronic acid, 95% 1g

[123291-97-4], C9H13BO3, F.W. 180.01, White solid, m.p. 98-101ø, 5g MDL MFCD00196832

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52538 4-Ethoxy-2-methylbenzeneboronic acid, 98% 1g

[313545-31-2], C9H13BO3, F.W. 180.01, Off-white solid, 5g m.p. 163-168ø, MDL MFCD04115659

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53308 4-Ethoxy-3-methylbenzeneboronic acid, 97% 250mg

[850568-08-0], C9H13BO3, F.W. 180.01, Off-white solid, 1g m.p. 168-172ø, MDL MFCD06659870

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

48 www.alfa.com Arylboronic Acids Stock # Description Standard Selling Sizes H52872 6-Ethoxynaphthalene-2-boronic acid, 98% 1g

[352525-98-5], C12H13BO3, F.W. 216.04, Off-white solid, 5g m.p. 240-242ø, MDL MFCD03427009

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52669 4-(2-Ethoxy-2-oxoethoxy)benzeneboronic acid, 98% 250mg [Ethyl (4-boronophenoxy)acetate] 1g

[282116-97-6], C10H13BO5, F.W. 224.02, Off-white solid, m.p. 145-147ø, MDL MFCD08235079

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52755 3-(trans-3-Ethoxy-3-oxo-1-propen-1-yl)benzeneboronic 250mg acid, 98% 1g [Ethyl 3-boronocinnamate]

[913835-51-5], C11H13BO4, F.W. 220.03, Off-white solid, m.p. 141-143ø, MDL MFCD08689480

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52552 4-(trans-3-Ethoxy-3-oxo-1-propen-1-yl)benzeneboronic 1g acid, 96% 5g [Ethyl 4-boronocinnamate]

[850568-49-9], C11H13BO4, F.W. 220.03, Off-white solid, m.p. 130-134ø, MDL MFCD04115651 Arylboronic

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52539 3-[(3-Ethoxy-3-oxopropyl)carbamoyl- 250mg ]benzeneboronic acid, 97% 1g [Ethyl 3-(3-boronobenzamido)propionate]

[850567-28-1], C12H16BNO5, F.W. 265.07, Off-white solid, m.p. 128-132ø, MDL MFCD04115701 Acids

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52464 4-[(3-Ethoxy-3-oxopropyl)carbamoyl- 250mg ]benzeneboronic acid, 97% 1g [Ethyl 3-(4-boronobenzamido)propionate]

[850568-19-3], C12H16BNO5, F.W. 265.07, White solid, m.p. 128-132ø, MDL MFCD04115673

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52541 2-Ethoxy-5-(trifluoromethyl)benzeneboronic acid, 98% 250mg

[850593-10-1], C9H10BF3O3, F.W. 233.98, White solid, m.p. 100-104ø, 1g MDL MFCD06801695

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52989 3-Ethoxy-5-(trifluoromethyl)benzeneboronic acid, 98% 250mg

[871332-96-6], C9H10BF3O3, F.W. 233.98, White solid, m.p. 173-176ø, 1g MDL MFCD08056361

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52524 4-Ethoxy-3-(trifluoromethyl)benzeneboronic acid, 98% 250mg

[871329-83-8], C9H10BF3O3, F.W. 233.98, Off-white solid, 1g MDL MFCD07363789

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L17719 2-Ethylbenzeneboronic acid, 98+% 1g [2-Ethylphenylboronic acid] 5g

[90002-36-1], C8H11BO2, F.W. 149.99, m.p. 96-98ø, BRN 2963801, MDL MFCD02093075

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B24656 4-Ethylbenzeneboronic acid, 97% 1g [4-Ethylphenylboronic acid] 5g

[63139-21-9], C8H11BO2, F.W. 149.99, White powder, 25g m.p. 150-154ø, BRN 3030638, MDL MFCD00859377

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52696 3-(Ethylcarbamoyl)benzeneboronic acid, 97% 250mg

[850567-21-4], C9H12BNO3, F.W. 193.01, White solid, 1g m.p. 106-116ø, MDL MFCD04115689

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53226 4-(Ethylcarbamoyl)benzeneboronic acid, 98% 250mg

[850568-12-6], C9H12BNO3, F.W. 193.01, White solid, 1g m.p. 143-146ø, MDL MFCD03411954

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Bulk and Specialty Sizes Available 49 Arylboronic Acids Stock # Description Standard Selling Sizes H52683 3-Ethylcarbamoyl-4-fluorobenzeneboronic acid, 98% 250mg

[874219-20-2], C9H11BFNO3, F.W. 211.00, White solid, 1g m.p. 260-262ø, MDL MFCD08235039

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53273 4-Ethylcarbamoyl-3-fluorobenzeneboronic acid, 98% 250mg

[874289-12-0], C9H11BFNO3, F.W. 211.00, White solid, 1g m.p. 157-160ø, MDL MFCD08436070

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53056 5-Ethylcarbamoyl-2-fluorobenzeneboronic acid, 97% 250mg

[874289-45-9], C9H11BFNO3, F.W. 211.00, Off-white solid, 1g m.p. 141-143ø, MDL MFCD08436027

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53326 5-Ethylcarbamoyl-3-fluorobenzeneboronic acid, 98% 250mg

[874219-38-2], C9H11BFNO3, F.W. 211.00, White solid, 1g m.p. 288-290ø, MDL MFCD08235055

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52501 3-Ethylcarbamoyl-5-nitrobenzeneboronic acid, 98% 250mg [3-Ethylaminocarbonyl-5-nitrophenylboronic acid] 1g

[871332-79-5], C9H11BN2O5, F.W. 238.01, Off-white solid, m.p. 187-191ø, MDL MFCD07783872

Acids H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52485 4-[Ethyl(4-methoxybenzyl)sulfamoyl- 250mg ]benzeneboronic acid, 98% 1g

[913835-55-9], C16H20BNO5S, F.W. 349.21, White solid, m.p. 98-102ø, MDL MFCD08689489

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Arylboronic H52530 3-[Ethyl(methyl)carbamoyl]benzeneboronic acid, 98% 250mg [3-(N-Ethyl-N-methylaminocarbonyl)phenylboronic acid] 1g

[871333-07-2], C10H14BNO3, F.W. 207.04, White solid, m.p. 73-76ø, MDL MFCD08056369

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52713 4-[Ethyl(methyl)carbamoyl]benzeneboronic acid, 98% 250mg [4-(N-Ethyl-N-methylaminocarbonyl)phenylboronic acid] 1g

[871333-04-9], C10H14BNO3, F.W. 207.04, Off-white solid, m.p. 257-259ø, MDL MFCD08056368

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53362 3-(Ethylsulfamoyl)benzeneboronic acid, 97% 250mg

[871329-76-9], C8H12BNO4S, F.W. 229.06, White solid, MDL MFCD07783855

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52840 4-(Ethylsulfamoyl)benzeneboronic acid, 97% 250mg

[871329-65-6], C8H12BNO4S, F.W. 229.06, White solid, 1g m.p. 132-136ø, MDL MFCD07363751

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L17814 4-(Ethylsulfonyl)benzeneboronic acid, 98+% 250mg [4-(Ethanesulfonyl)benzeneboronic acid, 4-(Ethylsulfonyl)phenyl- 1g boronic acid]

[352530-24-6], C8H11BO4S, F.W. 214.05, m.p. 135-139ø, MDL MFCD02093076

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53350 2-(Ethylthio)benzeneboronic acid, 97% 1g

[362045-33-8], C8H11BO2S, F.W. 182.04, White solid, m.p. 42-46ø, 5g MDL MFCD03095256

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L17623 4-(Ethylthio)benzeneboronic acid, 98% 1g [4-(Ethylthio)phenylboronic acid] 5g

[145349-76-4], C8H11BO2S, F.W. 182.05, m.p. 104-106ø, BRN 8763159, MDL MFCD01318146

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52268 Fluoranthene-3-boronic acid, 95% 1g

[359012-63-8], C16H11BO2, F.W. 246.07, White to off-white solid, 5g MDL MFCD16660041

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

50 www.alfa.com Arylboronic Acids Stock # Description Standard Selling Sizes B23103 2-Fluorobenzeneboronic acid, 98% 1g [2-Fluorophenylboronic acid] 5g

[1993-03-9], C6H6BFO2, F.W. 139.92, White to cream cryst powder, 25g m.p. 100-108ø, BRN 3030413, MDL MFCD00674013

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B21247 3-Fluorobenzeneboronic acid, 97% 1g [3-Fluorophenylboronic acid] 5g

[768-35-4], C6H6BFO2, F.W. 139.92, White/pale yellow/cream powder, 25g m.p. 212-215ø, BRN 3030632, MDL MFCD00236042

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a A15991 4-Fluorobenzeneboronic acid, 97% 1g [4-Fluorophenylboronic acid] 5g

[1765-93-1], C6H6BFO2, F.W. 139.92, White to pale brown cryst powder, 25g m.p. 260-265ø, BRN 2829653, MDL MFCD00039136

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a GC reagent for diols: J. Chromat., 158, 33 (1978); 186, 307 (1979). For reactions of boronic acids, see Appendix 5. L15634 2-Fluorobiphenyl-4-boronic acid, 97% 1g [3-Fluoro-4-phenylbenzeneboronic acid] 5g Arylboronic [178305-99-2], C12H10BFO2, F.W. 216.02, m.p. ca 242-250ø, MDL MFCD01075707

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53004 2-Fluoro-5-carboxybenzeneboronic acid, 96% 250mg [3-Borono-4-fluorobenzoic acid] 1g

[874219-59-7], C7H6BFO4, F.W. 183.93, White solid, m.p. 224-226ø, MDL MFCD08436065 Acids

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53052 3-Fluoro-5-(diethylcarbamoyl)benzeneboronic acid, 98% 250mg

[871332-64-8], C11H15BFNO3, F.W. 239.05, White solid, 1g MDL MFCD07363794

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52444 3-Fluoro-5-ethoxycarbonylbenzeneboronic acid, 97% 250mg [Ethyl 3-borono-5-fluorobenzoate] 1g

[871329-85-0], C9H10BFO4, F.W. 211.98, White solid, m.p. 146-150ø, MDL MFCD07363792

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H28857 2-Fluoro-5-formylbenzeneboronic acid, 97% È 1g [3-Borono-4-fluorobenzaldehyde, 2-Fluoro-5-formylphenylboronic acid] 5g

[352534-79-3], C7H6BFO3, F.W. 167.93, White powder, m.p. 168-171ø, MDL MFCD03095100

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L17851 3-Fluoro-4-formylbenzeneboronic acid, 98% 1g [4-Borono-3-fluorobenzaldehyde, 3-Fluoro-4-formylphenylboronic acid]

[248270-25-9], C7H6BFO3, F.W. 167.93, m.p. ca 240ø, MDL MFCD02093051

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L17808 4-Fluoro-3-formylbenzeneboronic acid, 98+% È 1g [5-Borono-2-fluorobenzaldehyde, 4-Fluoro-3-formylphenylboronic acid] 250mg

[374538-01-9], C7H6BFO3, F.W. 167.93, m.p. ca 240ø, BRN 9046762, MDL MFCD02093074

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53072 2-Fluoro-5-(hydrazinocarbonyl)benzeneboronic acid, 95% 250mg [3-Borono-4-fluorobenzhydrazide] 1g

[874289-56-2], C7H8BFN2O3, F.W. 197.96, Off-white solid, m.p. 183-185ø, MDL MFCD08436072

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53106 3-Fluoro-4-(hydrazinocarbonyl)benzeneboronic acid, 96% 250mg

[850568-06-8], C7H8BFN2O3, F.W. 197.96, White to off-white solid, 1g MDL MFCD04973743

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53110 3-Fluoro-4-hydroxybenzeneboronic acid, 97% 250mg

[182344-14-5], C6H6BFO3, F.W. 155.92, Off-white solid, m.p. 252-256ø, 1g MDL MFCD06659838

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Bulk and Specialty Sizes Available 51 Arylboronic Acids Stock # Description Standard Selling Sizes H52619 3-Fluoro-5-hydroxybenzeneboronic acid, 98% 250mg

[871329-82-7], C6H6BFO3, F.W. 155.92, Off-white solid, m.p. 54-62ø, 1g MDL MFCD07363778

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53304 4-Fluoro-2-hydroxybenzeneboronic acid, 97% 250mg

[850568-00-2], C6H6BFO3, F.W. 155.92, White solid, m.p. 176-180ø, 1g MDL MFCD04115662

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52550 4-Fluoro-3-hydroxybenzeneboronic acid, 98% 250mg

[913835-74-2], C6H6BFO3, F.W. 155.92, Pale brown solid, 1g m.p. 264-266ø, MDL MFCD08689483

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52716 5-Fluoro-2-hydroxybenzeneboronic acid, 97% 250mg

[259209-20-6], C6H6BFO3, F.W. 155.92, Gray solid, m.p. 160-166ø, 1g MDL MFCD03095357

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52596 3-Fluoro-4-(2-hydroxyethylcarbamoyl)benzeneboronic 250mg acid, 98% 1g [3-Fluoro-4-(2-hydroxyethylaminocarbonyl)phenylboronic acid]

[874289-21-1], C9H11BFNO4, F.W. 227.00, Off-white solid, m.p. 217-219ø, MDL MFCD08689535 Acids H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52934 4-Fluoro-3-(2-hydroxyethylcarbamoyl)benzeneboronic 250mg acid, 98% 1g

[874219-25-7], C9H11BFNO4, F.W. 227.00, White solid, m.p. 89-91ø, MDL MFCD08235044

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Arylboronic H29251 2-Fluoro-5-(hydroxymethyl)benzeneboronic acid, 98% 1g [3-Borono-4-fluorobenzyl alcohol, 2-Fluoro-5-(hydroxymethyl)phenyl- 10g boronic acid]

C7H8BFO3, F.W. 169.95, White powder, m.p. 70-72ø, MDL MFCD06656276

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52487 4-Fluoro-3-(hydroxymethyl)benzeneboronic acid, 98% 250mg

[481681-02-1], C7H8BFO3, F.W. 169.95, White solid, m.p. 124-126ø, 1g MDL MFCD08235075

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52921 3-Fluoro-5-isobutoxybenzeneboronic acid, 98% 250mg

[850589-57-0], C10H14BFO3, F.W. 212.03, Off-white solid, 1g m.p. 130-134ø, MDL MFCD07363783

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53351 3-Fluoro-5-isopropoxybenzeneboronic acid, 98% 250mg

[850589-54-7], C9H12BFO3, F.W. 198.00, White solid, 1g m.p. 130-134ø, MDL MFCD07363781

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52605 2-Fluoro-5-(isopropylcarbamoyl)benzeneboronic acid, 98% 250mg [2-Fluoro-5-(isopropylaminocarbonyl)phenylboronic acid] 1g

[874289-49-3], C10H13BFNO3, F.W. 225.03, White solid, m.p. 130-134ø, MDL MFCD08235103

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53361 3-Fluoro-4-(isopropylcarbamoyl)benzeneboronic acid, 98% 250mg [3-Fluoro-4-(isopropylaminocarbonyl)phenylboronic acid] 1g

[874289-16-4], C10H13BFNO3, F.W. 225.03, White solid, m.p. 137-139ø, MDL MFCD08436040

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53030 4-Fluoro-3-(isopropylcarbamoyl)benzeneboronic acid, 98% 250mg [4-Fluoro-3-(isopropylaminocarbonyl)phenylboronic acid] 1g

[874219-21-3], C10H13BFNO3, F.W. 225.03, White solid, m.p. 263-265ø, MDL MFCD08235040

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

52 www.alfa.com Arylboronic Acids Stock # Description Standard Selling Sizes L19655 2-Fluoro-3-methoxybenzeneboronic acid, 97% 1g [2-Fluoro-3-methoxyphenylboronic acid] 5g

[352303-67-4], C7H8BFO3, F.W. 169.95, BRN 9191510, MDL MFCD02094728

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L19960 2-Fluoro-4-methoxybenzeneboronic acid, 98% 1g [2-Fluoro-4-methoxyphenylboronic acid] 5g

[162101-31-7], C7H8BFO3, F.W. 169.95, White to cream crystalline powder, BRN 9192698, MDL MFCD04039323

H:H315-H319-H335, P:P280g-P305+P351+P338 H26064 2-Fluoro-6-methoxybenzeneboronic acid, 98% 1g [2-Fluoro-6-methoxyphenylboronic acid] 5g

[78495-63-3], C7H8BFO3, F.W. 169.95, White crystalline powder, m.p. 124-126ø, MDL MFCD02179483

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L19818 3-Fluoro-4-methoxybenzeneboronic acid, 98+% 1g [3-Fluoro-4-methoxyphenylboronic acid] 5g

[149507-26-6], C7H8BFO3, F.W. 169.95, m.p. 237-239ø, BRN 7370120, MDL MFCD00807404 Arylboronic

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52768 3-Fluoro-5-methoxybenzeneboronic acid, 98% 1g

[609807-25-2], C7H8BFO3, F.W. 169.95, Off-white solid, m.p. 168-172ø, 5g MDL MFCD07363780

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H52976 4-Fluoro-2-methoxybenzeneboronic acid, 98% 1g Acids [4-Fluoro-2-methoxyphenylboronic acid] 5g

[179899-07-1], C7H8BFO3, F.W. 169.95, White solid, m.p. 131-136ø, MDL MFCD03788423

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52635 4-Fluoro-3-methoxybenzeneboronic acid, 98% 250mg [4-Fluoro-3-methoxyphenylboronic acid] 1g

[854778-31-7], C7H8BFO3, F.W. 169.95, White solid, m.p. 189-191ø, MDL MFCD08056358

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H32748 5-Fluoro-2-methoxybenzeneboronic acid, 98% 5g [5-Fluoro-2-methoxyphenylboronic acid] 25g

[179897-94-0], C7H8BFO3, F.W. 169.95, Solid, MDL MFCD01863526

H:H315-H319-H335, P:P280g-P305+P351+P338 H53049 3-Fluoro-4-(4-methoxybenzyloxycarbamoyl)- 250mg benzeneboronic acid, 98% 1g [3-Fluoro-4-(4-methoxybenzyloxyaminocarbonyl)- phenylboronic acid]

[913835-49-1], C15H15BFNO5, F.W. 319.10, Pale brown solid, m.p. 150-152ø, MDL MFCD08235097

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53249 2-Fluoro-5-(methoxycarbamoyl)benzeneboronic acid, 98% 250mg [2-Fluoro-5-(methoxyaminocarbonyl)phenylboronic acid] 1g

[874289-58-4], C8H9BFNO4, F.W. 212.97, Off-white solid, m.p. 122-124ø, MDL MFCD08436032

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52610 3-Fluoro-4-(methoxycarbamoyl)benzeneboronic acid, 97% 250mg [3-Fluoro-4-(methoxyaminocarbonyl)phenylboronic acid] 1g

[913835-58-2], C8H9BFNO4, F.W. 212.97, Off-white solid, m.p. 161-163ø, MDL MFCD08436059

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52875 4-Fluoro-3-(methoxycarbamoyl)benzeneboronic acid, 98% 250mg [4-Fluoro-3-(methoxyaminocarbonyl)phenylboronic acid] 1g

[913835-47-9], C8H9BFNO4, F.W. 212.97, White solid, m.p. 213-215ø, MDL MFCD08235105

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52971 2-Fluoro-4-(methoxycarbonyl)benzeneboronic acid, 98% 250mg [Methyl 4-borono-3-fluorobenzoate] 1g

[603122-84-5], C8H8BFO4, F.W. 197.96, Brown solid, m.p. 173-175ø, MDL MFCD08436034

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Bulk and Specialty Sizes Available 53 Arylboronic Acids Stock # Description Standard Selling Sizes H52900 2-Fluoro-5-(methoxycarbonyl)benzeneboronic acid, 97% 250mg [Methyl 3-borono-4-fluorobenzoate] 1g

[850568-04-6], C8H8BFO4, F.W. 197.96, White solid, m.p. 210-212ø, MDL MFCD06659868

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52510 3-Fluoro-4-(methoxycarbonyl)benzeneboronic acid, 97% 250mg [Methyl 4-borono-2-fluorobenzoate] 1g

[505083-04-5], C8H8BFO4, F.W. 197.96, White solid, m.p. 180-184ø, 5g MDL MFCD04115665

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53084 3-Fluoro-5-(methoxycarbonyl)benzeneboronic acid, 95% 250mg [Methyl 3-borono-5-fluorobenzoate] 1g

[871329-62-3], C8H8BFO4, F.W. 197.96, White solid, m.p. 138-142ø, MDL MFCD07363749

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53254 4-Fluoro-2-(methoxycarbonyl)benzeneboronic acid, 95% 250mg [Methyl 2-borono-5-fluorobenzoate]

[871329-81-6], C8H8BFO4, F.W. 197.96, White solid, m.p. 86-90ø, MDL MFCD07363762

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53123 4-Fluoro-3-(methoxycarbonyl)benzeneboronic acid, 98% 250mg [Methyl 5-borono-2-fluorobenzoate] 1g Acids [874219-35-9], C8H8BFO4, F.W. 197.96, White solid, m.p. 253-255ø, MDL MFCD06801688

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52756 5-Fluoro-2-(methoxycarbonyl)benzeneboronic acid, 97% 250mg [Methyl 2-borono-4-fluorobenzoate] 1g

[850568-05-7], C8H8BFO4, F.W. 197.96, White solid, m.p. 146-148ø,

Arylboronic MDL MFCD03095367

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53267 2-Fluoro-5-[methoxy(methyl)carbamoyl]benzeneboronic 250mg acid, 98% 1g [2-Fluoro-5-[methoxy(methyl)aminocarbonyl]phenylboronic acid]

[874289-59-5], C9H11BFNO4, F.W. 227.00, Pale brown solid, m.p. 146-148ø, MDL MFCD08436038

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53324 3-Fluoro-4-[methoxy(methyl)carbamoyl]benzeneboronic 250mg acid, 98% 1g [3-Fluoro-4-[methoxy(methyl)aminocarbonyl]phenylboronic acid]

[913835-59-3], C9H11BFNO4, F.W. 227.00, White solid, m.p. 154-156ø, MDL MFCD08689477

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52512 4-Fluoro-3-[methoxy(methyl)carbamoyl]benzeneboronic 250mg acid, 98% 1g [4-Fluoro-3-[methoxy(methyl)aminocarbonyl]phenylboronic acid]

[874290-69-4], C9H11BFNO4, F.W. 227.00, White solid, m.p. 160-163ø, MDL MFCD08235106

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53265 2-Fluoro-4-methylbenzeneboronic acid, 97% 1g [2-Fluoro-4-methylphenylboronic acid, 2-Fluoro-p-tolylboronic acid] 5g

[170981-26-7], C7H8BFO2, F.W. 153.95, White to off-white solid, m.p. 228-233ø, MDL MFCD05664239

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52714 2-Fluoro-5-methylbenzeneboronic acid, 95% 1g [2-Fluoro-5-methylphenylboronic acid, 6-Fluoro-m-tolylboronic acid] 5g

[166328-16-1], C7H8BFO2, F.W. 153.95, White solid, m.p. 77-82ø, MDL MFCD03428512

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52752 3-Fluoro-2-methylbenzeneboronic acid, 98% 250mg [3-Fluoro-2-methylphenylboronic acid, 3-Fluoro-o-tolylboronic acid] 1g

[163517-61-1], C7H8BFO2, F.W. 153.95, White solid, m.p. 142-144ø, MDL MFCD07368679

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

54 www.alfa.com Arylboronic Acids Stock # Description Standard Selling Sizes B24512 3-Fluoro-4-methylbenzeneboronic acid, 98% 1g [3-Fluoro-4-methylphenylboronic acid, 3-Fluoro-p-tolylboronic acid] 5g

[168267-99-0], C7H8BFO2, F.W. 153.95, m.p. 234ø, BRN 8544594, 25g MDL MFCD02683115

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53111 3-Fluoro-5-methylbenzeneboronic acid, 98% 250mg [3-Fluoro-5-methylphenylboronic acid, 5-Fluoro-m-tolylboronic acid] 1g

[850593-06-5], C7H8BFO2, F.W. 153.95, White solid, m.p. 216-222ø, MDL MFCD07363785

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B24117 4-Fluoro-2-methylbenzeneboronic acid, 98% 1g [4-Fluoro-2-methylphenylboronic acid, 4-Fluoro-o-tolylboronic acid] 5g

[139911-29-8], C7H8BFO2, F.W. 153.95, m.p. 199-201ø, 25g MDL MFCD02093072

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L18753 4-Fluoro-3-methylbenzeneboronic acid, 98% 1g [4-Fluoro-3-methylphenylboronic acid, 4-Fluoro-m-tolylboronic acid] 5g

[139911-27-6], C7H8BFO2, F.W. 153.95, m.p. 208-211ø, BRN 7474834, MDL MFCD01863527 Arylboronic

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L19819 5-Fluoro-2-methylbenzeneboronic acid, 99% 1g [5-Fluoro-2-methylphenylboronic acid, 5-Fluoro-o-tolylboronic acid] 5g

[163517-62-2], C7H8BFO2, F.W. 153.95, m.p. 148-149ø, MDL MFCD03095047

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H53178 2-Fluoro-5-(methylcarbamoyl)benzeneboronic acid, 98% 250mg Acids [2-Fluoro-5-(methylaminocarbonyl)phenylboronic acid] 1g

[874289-40-4], C8H9BFNO3, F.W. 196.97, Pale pink solid, m.p. 174-176ø, MDL MFCD08436028

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53289 3-Fluoro-4-(methylcarbamoyl)benzeneboronic acid, 98% 250mg [3-Fluoro-4-(methylaminocarbonyl)phenylboronic acid] 1g

[849833-86-9], C8H9BFNO3, F.W. 196.97, Off-white solid, m.p. 173-175ø, MDL MFCD08436026

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53149 3-Fluoro-5-(methylcarbamoyl)benzeneboronic acid, 98% 250mg [3-Fluoro-5-(methylaminocarbonyl)phenylboronic acid] 1g

[871332-63-7], C8H9BFNO3, F.W. 196.97, White solid, MDL MFCD07363793

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53101 4-Fluoro-3-(methylcarbamoyl)benzeneboronic acid, 96% 250mg [4-Fluoro-3-(methylaminocarbonyl)phenylboronic acid] 1g

[874219-19-9], C8H9BFNO3, F.W. 196.97, White solid, m.p. 226-228ø, MDL MFCD08235038

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53306 2-Fluoro-4-(methylsulfonyl)benzeneboronic acid, 98% 250mg

[957060-85-4], C7H8BFO4S, F.W. 218.01, White solid, MDL MFCD09027248

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53064 2-Fluoro-4-(methylthio)benzeneboronic acid, 98% 250mg [4-Borono-3-fluorothioanisole]

[957060-84-3], C7H8BFO2S, F.W. 186.01, White solid, MDL MFCD09027247

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52454 3-Fluoro-5-(4-morpholinylcarbonyl)benzeneboronic acid, 250mg 98% 1g

[874219-40-6], C11H13BFNO4, F.W. 253.04, White solid, m.p. 145-147ø, MDL MFCD08235057

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H52523 4-Fluoro-3-(4-morpholinylcarbonyl)benzeneboronic acid, 250mg 98% 1g

[874219-29-1], C11H13BFNO4, F.W. 253.04, White solid, m.p. 138-140ø, MDL MFCD08235048

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Bulk and Specialty Sizes Available 55 Arylboronic Acids Stock # Description Standard Selling Sizes H52707 4-Fluoronaphthalene-1-boronic acid, 98% 250mg

[182344-25-8], C10H8BFO2, F.W. 189.98, White solid, m.p. 240-242ø, 1g MDL MFCD04039221

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H52711 2-Fluoro-5-(phenylcarbamoyl)benzeneboronic acid, 98% 250mg [2-Fluoro-5-(phenylaminocarbonyl)phenylboronic acid] 1g

[874289-41-5], C13H11BFNO3, F.W. 259.04, White solid, m.p. 252-256ø, MDL MFCD08235095

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53347 3-(2-Fluorophenylcarbamoyl)benzeneboronic acid, 98% 250mg [3-Borono-N-(2-fluorophenyl)benzamide] 1g

[874288-35-4], C13H11BFNO3, F.W. 259.04, White solid, MDL MFCD09027208

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52959 3-(3-Fluorophenylcarbamoyl)benzeneboronic acid, 98% 250mg [3-Borono-N-(3-fluorophenyl)benzamide] 1g

[874288-34-3], C13H11BFNO3, F.W. 259.04, White solid, MDL MFCD09027207

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53011 3-(4-Fluorophenylcarbamoyl)benzeneboronic acid, 97% 250mg Acids [3-Borono-N-(4-fluorophenyl)benzamide] 1g

[850567-35-0], C13H11BFNO3, F.W. 259.04, Off-white solid, m.p. 232-238ø, MDL MFCD04115712

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52849 3-Fluoro-4-(phenylcarbamoyl)benzeneboronic acid, 98% 250mg [3-Fluoro-4-(phenylaminocarbonyl)phenylboronic acid] 1g

[874288-40-1], C13H11BFNO3, F.W. 259.04, White solid, Arylboronic m.p. 219-221ø, MDL MFCD08436025

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53164 4-(2-Fluorophenylcarbamoyl)benzeneboronic acid, 98% 250mg [4-Borono-N-(2-fluorophenyl)benzamide] 1g

[874288-06-9], C13H11BFNO3, F.W. 259.04, White solid, MDL MFCD09027205

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53192 4-(3-Fluorophenylcarbamoyl)benzeneboronic acid, 98% 250mg [4-Borono-N-(3-fluorophenyl)benzamide] 1g

[874288-05-8], C13H11BFNO3, F.W. 259.04, White solid, MDL MFCD09027204

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52662 4-Fluoro-3-(phenylcarbamoyl)benzeneboronic acid, 98% 250mg [5-Borono-2-fluoro-N-phenylbenzamide] 1g

[874219-33-7], C13H11BFNO3, F.W. 259.04, Off-white solid, m.p. 252-254ø, MDL MFCD08235052

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52670 4-(4-Fluorophenylcarbamoyl)benzeneboronic acid, 250mg 97% 1g [N-4-Fluorophenyl 4-boronobenzamide]

[850568-27-3], C13H11BFNO3, F.W. 259.04, Off-white solid, m.p. 234-240ø, MDL MFCD06659878

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52993 2-Fluoro-5-(1-piperidinylcarbonyl)benzeneboronic acid, 97% 250mg

[874289-43-7], C12H15BFNO3, F.W. 251.06, White solid, 1g MDL MFCD08436068

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52680 3-Fluoro-4-(1-piperidinylcarbonyl)benzeneboronic acid, 98% 250mg

[874289-10-8], C12H15BFNO3, F.W. 251.06, White solid, 1g m.p. 162-164ø, MDL MFCD08436039

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52766 3-Fluoro-5-(1-piperidinylcarbonyl)benzeneboronic acid, 98% 250mg

[874219-43-9], C12H15BFNO3, F.W. 251.06, Off-white solid, 1g m.p. 133-135ø, MDL MFCD08235060

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

56 www.alfa.com Arylboronic Acids Stock # Description Standard Selling Sizes H52973 4-Fluoro-3-(1-piperidinylcarbonyl)benzeneboronic acid, 98% 250mg

[874219-30-4], C12H15BFNO3, F.W. 251.06, Off-white solid, 1g m.p. 155-157ø, MDL MFCD08235049

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53280 2-Fluoro-5-(n-propylcarbamoyl)benzeneboronic acid, 250mg 97% 1g [2-Fluoro-5-(n-propylaminocarbonyl)phenylboronic acid]

[874289-48-2], C10H13BFNO3, F.W. 225.03, Off-white solid, m.p. 147-149ø, MDL MFCD08436029

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52892 3-Fluoro-5-(n-propylcarbamoyl)benzeneboronic acid, 250mg 98% 1g [N-Propyl 3-borono-5-fluorobenzamide]

[874219-37-1], C10H13BFNO3, F.W. 225.03, Off-white solid, m.p. 95-97ø, MDL MFCD08235054

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52841 4-Fluoro-3-(n-propylcarbamoyl)benzeneboronic acid, 250mg 98% 1g

[4-Fluoro-3-(n-propylaminocarbonyl)phenylboronic acid] Arylboronic

[874219-32-6], C10H13BFNO3, F.W. 225.03, White solid, m.p. 105-107ø, MDL MFCD08235051

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53346 2-Fluoro-5-(1-pyrrolidinylcarbonyl)benzeneboronic acid, 98% 250mg

[874289-42-6], C11H13BFNO3, F.W. 237.04, Off-white solid, 1g m.p. 146-148ø, MDL MFCD08436030 Acids H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53183 3-Fluoro-4-(1-pyrrolidinylcarbonyl)benzeneboronic acid, 98% 250mg

[874289-09-5], C11H13BFNO3, F.W. 237.04, White solid, 1g m.p. 107-109ø, MDL MFCD08436024

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52481 4-Fluoro-3-(1-pyrrolidinylcarbonyl)benzeneboronic acid, 98% 250mg

[874219-31-5], C11H13BFNO3, F.W. 237.04, White solid, 1g m.p. 152-154ø, MDL MFCD08235050

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52449 2-Fluoro-5-(trifluoromethoxy)benzeneboronic acid, 97% 250mg

[881402-22-8], C7H5BF4O3, F.W. 223.92, Off-white solid, 1g MDL MFCD09027234

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53364 2-Fluoro-3-(trifluoromethyl)benzeneboronic acid, 97% 1g

[157834-21-4], C7H5BF4O2, F.W. 207.92, White solid, m.p. 56-58ø, 5g MDL MFCD07784336

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H28788 2-Fluoro-4-(trifluoromethyl)benzeneboronic acid, 97% 1g [2-Fluoro-4-(trifluoromethyl)phenylboronic acid] 5g

[503309-11-3], C7H5BF4O2, F.W. 207.92, White cryst powder, m.p. 113-115ø, MDL MFCD03094995

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H28144 2-Fluoro-5-(trifluoromethyl)benzeneboronic acid, 98% 1g [2-Fluoro-5-(trifluoromethyl)phenylboronic acid] 5g

[352535-96-7], C7H5BF4O2, F.W. 207.92, White to pale yellow cryst powder, m.p. 104-109ø, MDL MFCD03701538

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52526 3-Fluoro-5-(trifluoromethyl)benzeneboronic acid, 97% 250mg

[159020-59-4], C7H5BF4O2, F.W. 207.92, Off-white solid, 1g MDL MFCD06657735

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H26144 4-Fluoro-2-(trifluoromethyl)benzeneboronic acid, 98% 250mg [4-Fluoro-2-(trifluoromethyl)phenylboronic acid] 1g

[182344-16-7], C7H5BF4O2, F.W. 207.92, White to pale yellow powder, m.p. 183-186ø, MDL MFCD08062379

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Bulk and Specialty Sizes Available 57 Arylboronic Acids Stock # Description Standard Selling Sizes H52483 4-Fluoro-3-(trifluoromethyl)benzeneboronic acid, 98% 1g

[182344-23-6], C7H5BF4O2, F.W. 207.92, White solid, m.p. 170-174ø, 5g MDL MFCD07363787

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B25434 2-Formylbenzeneboronic acid, 97% È 1g [2-Boronobenzaldehyde, 2-Formylphenylboronic acid] 5g

[40138-16-7], C7H7BO3, F.W. 149.94, White to cream crystalline powder, m.p. ca 115-120ø, BRN 3030776, MDL MFCD00151822

H:H315-H319-H335, P:P280g-P305+P351+P338 Used in combination with (R)- or (S)-1,1'-bi-2-naphthol in a protocol for determining the enantiomeric excess of primary amines by NMR: Org. Lett., 8, 609 (2006). B25437 3-Formylbenzeneboronic acid È 1g [3-Boronobenzaldehyde, 3-Formylphenylboronic acid] 5g

[87199-16-4], C7H7BO3, F.W. 149.94, White to pale brown powder, 25g m.p. 109-113ø, BRN 3030769, MDL MFCD00161356

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B25199 4-Formylbenzeneboronic acid, 97% È 1g [4-Boronobenzaldehyde, 4-Formylphenylboronic acid] 5g

[87199-17-5], C7H7BO3, F.W. 149.94, White to cream/pale yellow 25g powder, m.p. 260-266ø, EINECS 438-670-5, BRN 3030770, MDL MFCD00151823, Ì

H:H317, P:P280g-P262 Acids H52477 3-Formyl-2-methoxybenzeneboronic acid, 98% 1g [3-Borono-o-anisaldehyde, 3-Borono-2-methoxybenzaldehyde] 5g

[480424-49-5], C8H9BO4, F.W. 179.97, Pale brown solid, m.p. 122-125ø, MDL MFCD08689486

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L17850 3-Formyl-4-methoxybenzeneboronic acid, 98% È 1g

Arylboronic [5-Borono-o-anisaldehyde, 5-Borono-2-methoxybenzaldehyde] 5g

[121124-97-8], C8H9BO4, F.W. 179.97, m.p. ca 240ø dec., BRN 7423998, MDL MFCD02093661

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L19059 5-Formyl-2-methoxybenzeneboronic acid, 98% È 250mg [3-Borono-p-anisaldehyde, 3-Borono-4-methoxybenzaldehyde] 1g

[127972-02-5], C8H9BO4, F.W. 179.97, White powder, m.p. ca 160ø, 5g BRN 5334095, MDL MFCD01319044

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52666 2-Formyl-4,5-(methylenedioxy)benzeneboronic acid, 96% 250mg

[94838-88-7], C8H7BO5, F.W. 193.95, Orange solid, m.p. 231-233ø, 1g MDL MFCD01319005

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53143 4-Formylnaphthalene-1-boronic acid, 95% 250mg

[332398-52-4], C11H9BO3, F.W. 200.00, White to cream solid, m.p. 230ø, MDL MFCD01632205

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H26988 4-Formyl-3-(trifluoromethyl)benzeneboronic acid, 95% È 250mg [4-Borono-2-(trifluoromethyl)benzaldehyde, 4-Formyl-3-(trifluoromethyl)- 1g phenylboronic acid]

[1072944-24-1], C8H6BF3O3, F.W. 217.94, White powder, m.p. 200-202ø, MDL MFCD09037498

H:H315-H319-H335, P:P280g-P305+P351+P338 H52992 3-(Furfurylcarbamoyl)benzeneboronic acid, 97% 250mg [N-Furfuryl 3-boronobenzamide] 1g

[850567-27-0], C12H12BNO4, F.W. 245.04, White solid, m.p. 216-220ø, MDL MFCD04115700

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52970 4-(Furfurylcarbamoyl)benzeneboronic acid, 97% 250mg [N-Furfuryl 4-boronobenzamide] 1g

[850568-18-2], C12H12BNO4, F.W. 245.04, White solid, m.p. 134-140ø, MDL MFCD04115672

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53066 4-n-Heptyloxybenzeneboronic acid, 97% 1g

[136370-19-9], C13H21BO3, F.W. 236.12, White solid, 5g MDL MFCD04039169

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

58 www.alfa.com Arylboronic Acids Stock # Description Standard Selling Sizes H52874 4-n-Hexyloxybenzeneboronic acid, 96% 1g

[121219-08-7], C12H19BO3, F.W. 222.09, White solid, 5g MDL MFCD04039027

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53365 3-(Hydrazinocarbonyl)benzeneboronic acid, 97% 250mg [3-Boronobenzhydrazide] 1g

[913835-79-7], C7H9BN2O3, F.W. 179.97, Off-white solid, m.p. 149-151ø, MDL MFCD08689505

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53017 4-(Hydrazinocarbonyl)benzeneboronic acid, 95% 250mg [4-Boronobenzhydrazide] 1g

[850567-95-2], C7H9BN2O3, F.W. 179.97, White solid, m.p. 236-240ø, MDL MFCD06659865

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L19400 2-Hydroxybenzeneboronic acid, 97% 1g [2-Boronophenol, 2-Hydroxyphenylboronic acid] 5g

[89466-08-0], C6H7BO3, F.W. 137.93, m.p. ca 185ø, BRN 2962938, MDL MFCD01074581

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Arylboronic L19061 3-Hydroxybenzeneboronic acid, 97% 1g [3-Boronophenol, 3-Hydroxyphenylboronic acid] 5g

[87199-18-6], C6H7BO3, F.W. 137.93, m.p. 208-210ø, BRN 3240771, MDL MFCD01074603

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L15594 4-Hydroxybenzeneboronic acid, 97% 1g [4-Boronophenol, 4-Hydroxyphenylboronic acid] 5g Acids

[71597-85-8], C6H7BO3, F.W. 137.93, m.p. ca 285ø dec., BRN 2963491, MDL MFCD01074628

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52974 3-(2-Hydroxyethyl)benzeneboronic acid, 98% 250mg

[647853-32-5], C8H11BO3, F.W. 165.98, White solid, MDL MFCD03095123

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52672 2-(2-Hydroxyethyl)benzeneboronic acid hemiester, 95% 250mg [3,4-Dihydro-1H-benzo[c][1,2]oxaborinin-1-ol, 2-(2-Hydroxyethyl)benzeneboronic acid dehydrate]

[19206-51-0], C8H9BO2, F.W. 147.97, White solid, m.p. 70-72ø, MDL MFCD08436050

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52608 4-(2-Hydroxyethylcarbamoyl)benzeneboronic acid, 98% 250mg

[850593-04-3], C9H12BNO4, F.W. 209.01, Off-white solid, 1g m.p. 228-230ø, MDL MFCD06659848

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52533 4-[4-(2-Hydroxyethyl)-1-piperazinylcarbonyl- 250mg ]benzeneboronic acid, 97% 1g

[913835-44-6], C13H19BN2O4, F.W. 278.11, White solid, m.p. 100-102ø, MDL MFCD09027218

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53087 3-[4-(2-Hydroxyethyl)-1-piperazinylcarbonyl- 250mg ]benzeneboronic acid hydrochloride, 97% 1g

[957060-95-6], C13H19BN2O4ùHCl, F.W. 314.58, White solid, MDL MFCD09027253

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52637 3-(2-Hydroxyethylsulfamoyl)benzeneboronic acid, 98% 250mg

[913835-57-1], C8H12BNO5S, F.W. 245.06, White solid, m.p. 228-230ø, MDL MFCD08436067

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52719 4-(2-Hydroxyethylsulfamoyl)benzeneboronic acid, 95% 250mg

[850568-77-3], C8H12BNO5S, F.W. 245.06, White solid, m.p. 278-284ø, MDL MFCD07363750

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52442 2-Hydroxymethylbenzeneboronic acid, 97% 1g

[87199-14-2], C7H9BO3, F.W. 151.96, Off-white crystalline solid 5g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Bulk and Specialty Sizes Available 59 Arylboronic Acids Stock # Description Standard Selling Sizes L15193 3-(Hydroxymethyl)benzeneboronic acid, 98% 1g [3-(Hydroxymethyl)phenylboronic acid] 5g

[87199-15-3], C7H9BO3, F.W. 151.96, m.p. 93-98ø, BRN 8832019, MDL MFCD01317846

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L15194 4-(Hydroxymethyl)benzeneboronic acid, 98% 1g [4-(Hydroxymethyl)phenylboronic acid] 5g

[59016-93-2], C7H9BO3, F.W. 151.96, m.p. ca 280ø, BRN 2831413, 25g MDL MFCD00792672

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53068 4-Hydroxy-2-methylbenzeneboronic acid, 98% 250mg

[493035-82-8], C7H9BO3, F.W. 151.96, Off-white solid, m.p. 100-104ø, 1g MDL MFCD03788424

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L15192 2-(Hydroxymethyl)benzeneboronic acid hemiester, 98+% 250mg [1-Hydroxy-2,1-benzoxaborolane, 2-(Hydroxymethyl)phenylboronic acid 1g hemiester]

[5735-41-1], C7H7BO2, F.W. 133.94, m.p. 98-100ø, BRN 4333, MDL MFCD01075677

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53212 2-Hydroxymethyl-5-nitrobenzeneboronic acid hemiester, 96% 250mg [1-Hydroxy-6-nitro-2,1-benzoxaborolane, 1g Acids 2-Hydroxymethyl-5-nitrobenzeneboronic acid cyclic monoester]

[118803-40-0], C7H6BNO4, F.W. 178.94, Off-white solid, MDL MFCD04115657

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53074 6-Hydroxynaphthalene-2-boronic acid, 98% 250mg

[173194-95-1], C10H9BO3, F.W. 187.99, Off-white solid, 1g

Arylboronic m.p. 218-224ø, MDL MFCD00092986

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52592 3-(3-Hydroxypropyl)benzeneboronic acid, 96% 250mg

[736989-98-3], C9H13BO3, F.W. 180.01, White solid, MDL MFCD04115650

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52518 4-(3-Hydroxypropyl)benzeneboronic acid, 96% 250mg

[850568-48-8], C9H13BO3, F.W. 180.01, White to off-white solid, m.p. 70-74ø, MDL MFCD04973734

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53177 4-(3-Hydroxypropylcarbamoyl)benzeneboronic acid, 250mg 97% 1g

[913835-29-7], C10H14BNO4, F.W. 223.04, White solid, m.p. 224-226ø, MDL MFCD08235076

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H51112 3-Iodobenzeneboronic acid, 97% ß 1g [3-Iodophenylboronic acid] 5g

[221037-98-5], C6H6BIO2, F.W. 247.83, Colorless solid, 25g MDL MFCD01319015

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H51119 4-Iodobenzeneboronic acid, 97% ß 1g [4-Iodophenylboronic acid] 5g

[5122-99-6], C6H6BIO2, F.W. 247.83, Cream solid, MDL MFCD02093073 25g

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52603 4-Isobutylbenzeneboronic acid, 98% 1g [4-(2-Methylpropyl)phenylboronic acid] 5g

[153624-38-5], C10H15BO2, F.W. 178.04, White to cream solid, 25g m.p. 117-120ø, MDL MFCD01632198

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53233 3-(Isobutylcarbamoyl)benzeneboronic acid, 97% 1g [3-Borono-N-isobutylbenzamide] 5g

[723282-09-5], C11H16BNO3, F.W. 221.06, White solid, m.p. 224-230ø, MDL MFCD04115692

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

60 www.alfa.com Arylboronic Acids Stock # Description Standard Selling Sizes H52947 4-(Isobutylcarbamoyl)benzeneboronic acid, 97% 250mg [4-Borono-N-isobutylbenzamide] 1g

[850568-13-7], C11H16BNO3, F.W. 221.06, White solid, m.p. 206-216ø, MDL MFCD03411955

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53152 4-Isobutyl-3-nitrobenzeneboronic acid, 97% 250mg

[850568-57-9], C10H14BNO4, F.W. 223.04, Off-white solid, 1g m.p. 168-174ø, MDL MFCD04115653

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53300 3-Isobutyramidobenzeneboronic acid, 98% 250mg

[874459-76-4], C10H14BNO3, F.W. 207.04, Off-white solid, 1g m.p. 275-277ø, MDL MFCD08235080

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53147 4-Isobutyramidobenzeneboronic acid, 98% 250mg

[874219-50-8], C10H14BNO3, F.W. 207.04, White solid, 1g m.p. 235ø, MDL MFCD08235068

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53085 4-Isopropoxybenzene-1,3-bisboronic acid, 98% 250mg

[4-Isopropoxy-1,3-phenylenebisboronic acid] 1g Arylboronic

[850568-40-0], C9H14B2O5, F.W. 223.83, White solid, m.p. 104-108ø, MDL MFCD04115638

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53168 2-Isopropoxybenzeneboronic acid, 95% 1g

[138008-97-6], C9H13BO3, F.W. 180.01, Pale yellow solid, m.p. 30-35ø, 5g b.p. 199ø, f.p. 110ø(230øF), d. 1.075, Ë 1.5090, MDL MFCD03427050 Acids H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52981 3-Isopropoxybenzeneboronic acid, 97% 1g

[216485-86-8], C9H13BO3, F.W. 180.01, Off-white solid, 5g m.p. 76-81ø, MDL MFCD03701512 25g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52675 4-Isopropoxybenzeneboronic acid, 97% 1g

[153624-46-5], C9H13BO3, F.W. 180.01, White to off-white solid, 5g m.p. 150-154ø, MDL MFCD03427051 25g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52758 3-(Isopropoxycarbonyl)benzeneboronic acid, 98% 250mg [Isopropyl 3-boronobenzoate] 1g

[342002-80-6], C10H13BO4, F.W. 208.02, Off-white solid, m.p. 127-129ø, MDL MFCD02093047

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53335 4-(Isopropoxycarbonyl)benzeneboronic acid, 98% 1g [Isopropyl 4-boronobenzoate] 5g

[342002-82-8], C10H13BO4, F.W. 208.02, White solid, m.p. 111ø, MDL MFCD02259385

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53132 4-Isopropoxy-2-methylbenzeneboronic acid, 98% 250mg

[871126-21-5], C10H15BO3, F.W. 194.04, White solid, 1g m.p. 112-116ø, MDL MFCD07363788

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52862 4-Isopropoxy-3-methylbenzeneboronic acid, 97% 1g

[850568-09-1], C10H15BO3, F.W. 194.04, White solid, 5g m.p. 128-132ø, MDL MFCD06659871

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53121 2-Isopropoxy-5-(trifluoromethyl)benzeneboronic acid, 98% 250mg

[850593-12-3], C10H12BF3O3, F.W. 248.01, White solid, m.p. 66-68ø, 1g MDL MFCD07363786

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27800 4-(Isopropylamino)benzeneboronic acid, 95% È 250mg [4-(Isopropylamino)phenylboronic acid] 1g

[219945-56-9], C9H14BNO2, F.W. 179.03, White to pale brown powder, m.p. ca 140ø dec., MDL MFCD06798224

H:H315-H319-H335, P:P280g-P305+P351+P338

Bulk and Specialty Sizes Available 61 Arylboronic Acids Stock # Description Standard Selling Sizes L20110 2-Isopropylbenzeneboronic acid, 97% 250mg [2-Cumylboronic acid, 2-Isopropylphenylboronic acid] 1g

[89787-12-2], C9H13BO2, F.W. 164.01, m.p. 85-86ø, BRN 3090298, 5g MDL MFCD03411937

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L15530 3-Isopropylbenzeneboronic acid, 99% 250mg [3-Cumylboronic acid, 3-Isopropylphenylboronic acid] 1g

[216019-28-2], C9H13BO2, F.W. 164.01, m.p. ca 75-80ø, 5g f.p. >110ø(230øF), BRN 3090001, MDL MFCD01074634

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L17459 4-Isopropylbenzeneboronic acid, 98+% 1g [4-Cumylboronic acid, 4-Isopropylphenylboronic acid] 5g

[16152-51-5], C9H13BO2, F.W. 164.01, m.p. 142-144ø, BRN 2830262, MDL MFCD01074614

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53172 3-(Isopropylcarbamoyl)benzeneboronic acid, 95% 250mg [3-(Isopropylaminocarbonyl)phenylboronic acid] 1g

[397843-69-5], C10H14BNO3, F.W. 207.04, White solid, m.p. 252-260ø, MDL MFCD04115690

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52925 4-(Isopropylcarbamoyl)benzeneboronic acid, 95% 250mg [4-(Isopropylaminocarbonyl)phenylboronic acid] 1g Acids [397843-67-3], C10H14BNO3, F.W. 207.04, White solid, m.p. 162-167ø, MDL MFCD04039353

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52754 3-Isopropylcarbamoyl-5-nitrobenzeneboronic acid, 98% 250mg [3-(Isopropylaminocarbonyl)-5-nitrophenylboronic acid] 1g

[871332-83-1], C10H13BN2O5, F.W. 252.03, White solid,

Arylboronic m.p. 198-201ø, MDL MFCD07783875

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L17460 5-Isopropyl-2-methoxybenzeneboronic acid, 98+% 1g [5-Isopropyl-2-methoxyphenylboronic acid] 5g

[216393-63-4], C10H15BO3, F.W. 194.04, m.p. 85-87ø, BRN 9193266, MDL MFCD01318154

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53184 4-[Isopropyl(4-methoxybenzyl)sulfamoyl- 250mg ]benzeneboronic acid, 98% 1g [4-Borono-N-isopropyl-N-(4-methoxybenzyl)- benzenesulfonamide]

[913835-96-8], C17H22BNO5S, F.W. 363.24, Off-white solid, m.p. 114-116ø, MDL MFCD08689524

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53236 3-(Isopropylsulfamoyl)benzeneboronic acid, 95% 250mg [3-(Isopropylaminosulfonyl)phenylboronic acid]

[871329-77-0], C9H14BNO4S, F.W. 243.08, White solid, MDL MFCD07783856

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53029 4-(Isopropylsulfamoyl)benzeneboronic acid, 98% 250mg [4-(Isopropylaminosulfonyl)phenylboronic acid] 1g

[850589-31-0], C9H14BNO4S, F.W. 243.08, White solid, m.p. 136-140ø, MDL MFCD07363752

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52880 4-Isopropylsulfonylbenzeneboronic acid, 97% 250mg

[850567-98-5], C9H13BO4S, F.W. 228.07, White solid, m.p. 126-128ø, 1g MDL MFCD06659866

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52960 4-Isopropylthiobenzeneboronic acid, 97% 1g

[380427-38-3], C9H13BO2S, F.W. 196.07, White solid, m.p. 82-88ø, MDL MFCD03411947 5g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B21071 2-Methoxybenzeneboronic acid, 97% 1g [2-Boronoanisole, 2-Methoxyphenylboronic acid] 5g

[5720-06-9], C7H9BO3, F.W. 151.96, White to pale brown cryst powder, 25g m.p. 102-106ø, BRN 3030981, MDL MFCD00236047

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

62 www.alfa.com Arylboronic Acids Stock # Description Standard Selling Sizes B24412 3-Methoxybenzeneboronic acid, 97% 1g [3-Boronoanisole, 3-Methoxyphenylboronic acid] 5g

[10365-98-7], C7H9BO3, F.W. 151.96, White cryst powder, 25g m.p. 158-162ø, BRN 2831223, MDL MFCD00161359

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a A14462 4-Methoxybenzeneboronic acid, 97+% 1g [4-Boronoanisole, 4-Methoxyphenylboronic acid] 5g

[5720-07-0], C7H9BO3, F.W. 151.96, White to pale brown powder, 25g m.p. 202-208ø, RTECS CY8975000, BRN 2936912, MDL MFCD00039139

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a GC reagent for diols: J. Chromat., 158, 33 (1978), 186, 307 (1979). For an illustrative example of the silver oxide promoted Suzuki coupling with sensitive à-halo enones, under extremely mild conditions, see: Org. Synth., 75, 69 (1997):

H52856 3-(4-Methoxybenzyloxy)-5-(trifluoromethyl)benzeneboronic 250mg acid, 98% 1g Arylboronic

[913835-77-5], C15H14BF3O4, F.W. 326.08, White solid, MDL MFCD08689490

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52494 3-(4-Methoxybenzylsulfamoyl)benzeneboronic 250mg acid, 96% 1g

[913836-05-2], C14H16BNO5S, F.W. 321.15, White solid, m.p. 110-112ø, MDL MFCD08689541 Acids

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52985 4-(4-Methoxybenzylsulfamoyl)benzeneboronic 250mg acid, 98% [4-(4-Methoxybenzylaminosulfonyl)phenylboronic acid]

[957060-91-2], C14H16BNO5S, F.W. 321.15, White solid, MDL MFCD09027228

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53023 4'-Methoxybiphenyl-4-boronic acid, 96% 250mg [4-(4-Methoxyphenyl)phenylboronic acid]

[156642-03-4], C13H13BO3, F.W. 228.05, White solid, m.p. 209-211ø, MDL MFCD04039030

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53171 3-(Methoxycarbamoyl)benzeneboronic acid, 97% 250mg [3-(Methyloxyaminocarbonyl)phenylboronic acid] 1g

[850567-26-9], C8H10BNO4, F.W. 194.98, Off-white solid, MDL MFCD04115698

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53188 4-(Methoxycarbamoyl)benzeneboronic acid, 97% 250mg [4-(Methoxyaminocarbonyl)phenylboronic acid] 1g

[850568-17-1], C8H10BNO4, F.W. 194.98, White solid, m.p. 130-136ø, MDL MFCD04115670

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53027 4-(Methoxycarbonylamino)benzeneboronic acid, 97% 250mg [4-(Methoxycarbonylamino)phenylboronic acid] 1g

[850567-96-3], C8H10BNO4, F.W. 194.98, White solid, m.p. 234-236ø, MDL MFCD03788425

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L17958 2-(Methoxycarbonyl)benzeneboronic acid, 97% 250mg [2-Carbomethoxybenzeneboronic acid, Methyl 2-boronobenzoate] 1g

[374538-03-1], C8H9BO4, F.W. 179.97, m.p. 68-70ø, BRN 8313459, 5g MDL MFCD02179452

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27444 3-(Methoxycarbonyl)benzeneboronic acid, 97% 1g [3-(Methoxycarbonyl)phenylboronic acid, Methyl 3-boronobenzoate] 5g

[99769-19-4], C8H9BO4, F.W. 179.97, Solid, m.p. 136ø, MDL MFCD02093046

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Bulk and Specialty Sizes Available 63 Arylboronic Acids Stock # Description Standard Selling Sizes H27627 4-(Methoxycarbonyl)benzeneboronic acid, 97% 1g [4-(Methoxycarbonyl)phenylboronic acid, Methyl 4-boronobenzoate] 5g

[99768-12-4], C8H9BO4, F.W. 179.97, White to pale cream powder, m.p. 220-225ø, MDL MFCD01632203

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52542 3-(2-Methoxycarbonylethyl)benzeneboronic acid, 97% 250mg [Methyl 3-(3-boronophenyl)propionate] 1g

[833472-82-5], C10H13BO4, F.W. 208.02, Off-white solid, m.p. 96-100ø, MDL MFCD04115648

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53243 4-(2-Methoxycarbonylethyl)benzeneboronic acid, 97% 250mg [Methyl 3-(4-boronophenyl)propionate] 1g

[850568-44-4], C10H13BO4, F.W. 208.02, White solid, m.p. 90-94ø, MDL MFCD04115640

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52525 4-(Methoxycarbonylmethylcarbamoyl)benzeneboronic 250mg acid, 97% 1g [Methyl (4-boronobenzoylamino)acetate, 4-(2-Methoxy-2-oxoethylcarbamoyl)phenylboronic acid]

[850568-24-0], C10H12BNO5, F.W. 237.02, Off-white solid, m.p. 124-130ø, MDL MFCD04115681

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Acids H52935 3-Methoxycarbonyl-5-nitrobenzeneboronic acid, 98% 1g [Methyl 3-borono-5-nitrobenzoate, Methyl 3-borono-5-nitrobenzoate] 5g

[117342-20-8], C8H8BNO6, F.W. 224.96, White to off-white solid, m.p. 250-255ø, MDL MFCD02179469

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52863 4-Methoxycarbonyl-2-nitrobenzeneboronic acid, 97% 1g [Methyl 4-borono-3-nitrobenzoate, 4-Methoxycarbonyl-2-nitrophenyl- Arylboronic 5g boronic acid]

[85107-55-7], C8H8BNO6, F.W. 224.96, White or cream solid, m.p. 160-171ø, MDL MFCD01632202

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53355 4-Methoxy-2,6-dimethylbenzeneboronic acid, 95% 250mg [4-Methoxy-2,6-dimethylphenylboronic acid] 1g

[361543-99-9], C9H13BO3, F.W. 180.01, White solid, m.p. 168-172ø, MDL MFCD03452755

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L19820 4-Methoxy-3,5-dimethylbenzeneboronic acid, 98% 1g [3,5-Dimethyl-4-methoxybenzeneboronic acid, 4-Methoxy-3,5-dimethyl- 5g phenylboronic acid]

[301699-39-8], C9H13BO3, F.W. 180.01, m.p. ca 237ø, BRN 8205051, MDL MFCD01114648

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52920 3-(2-Methoxyethylcarbamoyl)benzeneboronic acid, 97% 250mg [3-(2-Methoxyethylaminocarbonyl)phenylboronic acid] 1g

[850567-33-8], C10H14BNO4, F.W. 223.04, Off-white powder, m.p. 130-132ø, MDL MFCD04115710

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53155 4-(2-Methoxyethylcarbamoyl)benzeneboronic acid, 98% 250mg [4-(2-Methoxyethylaminocarbonyl)phenylboronic acid] 1g

[850589-34-3], C10H14BNO4, F.W. 223.04, Off-white solid, m.p. 120-124ø, MDL MFCD04115682

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52858 2-(Methoxymethyl)benzeneboronic acid, 97% 250mg

[126617-98-9], C8H11BO3, F.W. 165.99, MDL MFCD03412110 1g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53059 2-Methoxy-5-methylbenzeneboronic acid, 95% 1g

[127972-00-3], C8H11BO3, F.W. 165.99, White solid, m.p. 80-84ø, 5g MDL MFCD02179465

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H28753 3-Methoxy-4-methylbenzeneboronic acid, 97% 1g [3-Methoxy-4-methylphenylboronic acid, 3-Methoxy-p-tolylboronic acid] 5g

[917757-15-4], C8H11BO3, F.W. 165.99, Cream powder, m.p. 192-194ø, MDL MFCD08274479

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

64 www.alfa.com Arylboronic Acids Stock # Description Standard Selling Sizes L20112 4-Methoxy-2-methylbenzeneboronic acid, 98% 1g [4-Methoxy-2-methylphenylboronic acid] 5g

[208399-66-0], C8H11BO3, F.W. 165.99, m.p. 191ø, BRN 8111222, MDL MFCD02684315

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L19821 4-Methoxy-3-methylbenzeneboronic acid, 98+% 1g [4-Methoxy-3-methylphenylboronic acid] 5g

[175883-62-2], C8H11BO3, F.W. 165.99, White to cream powder, m.p. ca 215ø, BRN 7475212, MDL MFCD02179464

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53354 3-[Methoxy(methyl)carbamoyl]benzeneboronic acid, 97% 250mg [3-(N,O-Dimethylhydroxylaminocarbonyl)benzeneboronic acid, 1g 3-Borono-N-methoxy-N-methylbenzamide]

[723281-57-0], C9H12BNO4, F.W. 209.01, White solid, m.p. 66-70ø, MDL MFCD04115699

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53256 4-[Methoxy(methyl)carbamoyl]benzeneboronic acid, 97% 250mg [4-(N,O-Dimethylhydroxylaminocarbonyl)benzeneboronic acid, 1g 4-Borono-N-methoxy-N-methylbenzamide] Arylboronic [179055-26-6], C9H12BNO4, F.W. 209.01, White solid, m.p. 118-124ø, MDL MFCD04115671

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52964 3-[Methoxy(methyl)carbamoyl]-5-nitrobenzeneboronic acid, 98% 250mg [3-[Methoxy(methyl)aminocarbonyl]-5-nitrophenylboronic acid] 1g

[871332-84-2], C9H11BN2O6, F.W. 254.01, White solid, m.p. 156-160ø, MDL MFCD07783876 Acids

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H53329 4-Methoxy-3-(4-morpholinylsulfonyl)benzeneboronic acid, 250mg 95% 1g

[871333-02-7], C11H16BNO6S, F.W. 301.12, White solid, m.p. 270-276ø, MDL MFCD08056366

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L19060 6-Methoxy-2-naphthaleneboronic acid, 95% 1g [6-Methoxy-2-naphthylboronic acid] 5g

[156641-98-4], C11H11BO3, F.W. 202.02, m.p. ca 245ø dec., BRN 7636998, MDL MFCD03093087

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52631 2-(trans-3-Methoxy-3-oxo-1-propen-1-yl)benzeneboronic acid, 250mg 95% 1g [Methyl 2-boronocinnamate]

[372193-68-5], C10H11BO4, F.W. 206.00, Off-white solid, m.p. 180-186ø, MDL MFCD02179475

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53089 3-(trans-3-Methoxy-3-oxo-1-propen-1-yl)benzeneboronic 250mg acid, 95% 1g [Methyl 3-boronocinnamate]

[380430-59-1], C10H11BO4, F.W. 206.00, Cream solid, m.p. 126-130ø, MDL MFCD02179477

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53292 4-(trans-3-Methoxy-3-oxo-1-propen-1-yl)benzeneboronic 250mg acid, 97% 1g [Methyl 4-boronocinnamate]

[380430-58-0], C10H11BO4, F.W. 206.00, White solid, m.p. 234-240ø, MDL MFCD02179476

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53291 4-Methoxy-3-(1-piperidinylsulfonyl)benzeneboronic acid, 250mg 95% 1g

[874219-18-8], C12H18BNO5S, F.W. 299.15, White solid, m.p. 157-159ø, MDL MFCD08235037

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53055 4-(3-Methoxypropylcarbamoyl)benzeneboronic acid, 250mg 98% 1g [4-(3-Methoxypropylaminocarbamoyl)phenylboronic acid]

[913835-85-5], C11H16BNO4, F.W. 237.06, White solid, m.p. 130-133ø, MDL MFCD09027225

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Bulk and Specialty Sizes Available 65 Arylboronic Acids Stock # Description Standard Selling Sizes H52997 4-Methoxy-3-(1-pyrrolidinylsulfonyl)benzeneboronic acid, 250mg 95% 1g

[874219-52-0], C11H16BNO5S, F.W. 285.12, White solid, MDL MFCD08235070

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52932 2-Methoxy-5-(trifluoromethyl)benzeneboronic acid, 98% 250mg

[240139-82-6], C8H8BF3O3, F.W. 219.95, White solid, m.p. 144-148ø, 1g MDL MFCD04039222

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52847 3-Methoxy-5-(trifluoromethyl)benzeneboronic acid, 98% 250mg

[871332-97-7], C8H8BF3O3, F.W. 219.95, White solid, m.p. 159-162ø, 1g MDL MFCD08056362

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27062 4-Methoxy-2-(trifluoromethyl)benzeneboronic acid 1g [4-Methoxy-2-(trifluoromethyl)phenylboronic acid] 5g

[313546-16-6], C8H8BF3O3, F.W. 219.95, Solid, m.p. 168-172ø, MDL MFCD03095346

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52660 4-Methoxy-3-(trifluoromethyl)benzeneboronic acid, 98% 250mg

[149507-36-8], C8H8BF3O3, F.W. 219.95, Pale brown solid, 1g m.p. 198-202ø, MDL MFCD07363790 Acids H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B23154 2-Methylbenzeneboronic acid, 98% 1g [2-Methylphenylboronic acid, o-Tolylboronic acid] 5g

[16419-60-6], C7H9BO2, F.W. 135.96, White to cream cryst powder, m.p. ca 25g 162-164ø, RTECS ED7777777, BRN 2935796, MDL MFCD00093526

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Arylboronic Conditions for ligand-free Suzuki cross-coupling of arylboronic acids with aryl iodides, catalyzed by Palladium(II) acetate, 10516, p. 143, to give unsymmetrical biphenyls in high yield, are described: Org. Synth., 75, 61 (1997). See Appendix 5. B23025 3-Methylbenzeneboronic acid, 97% 1g [3-Methylphenylboronic acid, m-Tolylboronic acid] 5g

[17933-03-8], C7H9BO2, F.W. 135.96, White to cream cryst powder, 25g m.p. ca 160-162ø, Application(s): Suzuki coupling reactions, RTECS ED7788888, BRN 2935968, MDL MFCD00040198

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a A13347 4-Methylbenzeneboronic acid, 98% 1g [4-Methylphenylboronic acid, p-Tolylboronic acid] 5g

[5720-05-8], C7H9BO2, F.W. 135.96, White to cream powder, 25g m.p. 246-254ø, RTECS XS7400000, BRN 2935970, MDL MFCD00039138

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a GC reagent for diols: J. Chromat., 158, 33 (1978); 186, 307 (1979). For general chemistry of boronic acids, see Appendix 5. H52508 4-[2-(Methylcarbamothioyl)hydrazinocarbonyl- 250mg ]benzeneboronic acid, 98% 1g [4-[2-(Methylaminothiocarbonyl)hydrazinecarbonyl]phenyl- boronic acid]

[957060-78-5], C9H12BN3O3S, F.W. 253.08, White solid, m.p. 170-171ø, MDL MFCD09027245

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53141 3-(Methylcarbamoyl)benzeneboronic acid, 98% 250mg [3-(Methylaminocarbonyl)phenylboronic acid] 1g

[832695-88-2], C8H10BNO3, F.W. 178.98, White solid, m.p. 114-124ø, MDL MFCD04038918

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53090 4-(Methylcarbamoyl)benzeneboronic acid, 98% 250mg [4-(Methylaminocarbonyl)phenylboronic acid] 1g

[121177-82-0], C8H10BNO3, F.W. 178.98, White solid, m.p. 200-220ø, MDL MFCD03788427

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53260 3-(Methylcarbamoyl)-5-nitrobenzeneboronic acid, 98% 250mg [3-(Methylaminocarbonyl)-5-nitrophenylboronic acid] 1g

[871332-77-3], C8H9BN2O5, F.W. 223.98, White solid, m.p. 219-222ø, MDL MFCD07783869

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

66 www.alfa.com Arylboronic Acids Stock # Description Standard Selling Sizes H26923 2-(2-Methyl-1,3-dioxolan-2-yl)benzeneboronic acid, 95% 250mg [2-Boronoacetophenone ethylene acetal, 2-(2-Methyl-1,3-dioxolan-2-yl)phenyl- 1g boronic acid]

[243140-14-9], C10H13BO4, F.W. 208.02, White powder, m.p. 109-112ø, MDL MFCD04973737

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53286 3-(2-Methyl-1,3-dioxolan-2-yl)benzeneboronic acid, 97% 250mg [3-Boronoacetophenone ethylene acetal] 1g

[850568-50-2], C10H13BO4, F.W. 208.02, White to off-white solid, m.p. 100-104ø, MDL MFCD04973736

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B24217 3,4-(Methylenedioxy)benzeneboronic acid, 98% 1g [1,3-Benzodioxole-5-boronic acid, 3,4-(Methylenedioxy)phenylboronic 5g acid] 25g

[94839-07-3], C7H7BO4, F.W. 165.94, White to pale brown powder, m.p. 239-243ø, BRN 5523347, MDL MFCD01009695

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Suzuki coupling (Appendix 5) with 1-amino-2-bromonaphthalene derivatives has been used in a versatile synthesis of benzo[c]phenanthridine alkaloids: J. Chem. Soc., Perkin 1, 1647 (1996). Arylboronic H52699 4-[Methyl(4-methoxybenzyl)sulfamoyl- 250mg ]benzeneboronic acid, 96% 1g [4-[Methyl(4-methoxybenzyl)aminosulfonyl]phenylboronic acid]

[913835-54-8], C15H18BNO5S, F.W. 335.18, White solid, m.p. 137-139ø, MDL MFCD08689488 Acids H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53182 2-Methyl-5-(4-morpholinylsulfonyl)benzeneboronic acid, 250mg 98% 1g

[871329-74-7], C11H16BNO5S, F.W. 285.12, Off-white solid, m.p. 136-140ø, MDL MFCD07363761

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52998 4-Methylnaphthalene-1-boronic acid, 96% 1g

[103986-53-4], C11H11BO2, F.W. 186.02, White to cream solid, 5g m.p. 239-240ø, MDL MFCD01632204

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H53160 2-Methyl-5-nitrobenzeneboronic acid, 96% 250mg

[100960-11-0], C7H8BNO4, F.W. 180.96, White to cream solid, 1g m.p. 62-66ø, MDL MFCD00757435

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53181 4-Methyl-2-nitrobenzeneboronic acid, 95% 250mg

[143697-03-4], C7H8BNO4, F.W. 180.96, Yellow solid, m.p. 240-244ø, MDL MFCD06659821

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L17052 4-Methyl-3-nitrobenzeneboronic acid, 98% 1g [4-Methyl-3-nitrophenylboronic acid, 3-Nitro-p-tolylboronic acid] 5g

[80500-27-2], C7H8BNO4, F.W. 180.96, m.p. ca 250ø, BRN 3279018, MDL MFCD00191550

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52505 3-(5-Methyl-1,3,4-oxadiazol-2-yl)benzeneboronic acid, 97% 250mg [2-(3-Boronophenyl)-5-methyl-1,3,4-oxadiazole]

[913836-04-1], C9H9BN2O3, F.W. 203.99, White solid, m.p. 160-162ø, MDL MFCD08689540

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52658 4-(5-Methyl-1,3,4-oxadiazol-2-yl)benzeneboronic acid, 98% 250mg [2-(4-Boronophenyl)-5-methyl-1,3,4-oxadiazole]

[913835-70-8], C9H9BN2O3, F.W. 203.99, Yellow solid, m.p. 188-190ø, MDL MFCD08436062

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53008 3-(4-Methyl-1-piperazinylcarbonyl)benzeneboronic acid 250mg hydrochloride, 98% 1g

[957060-92-3], C12H17BN2O3ùHCl, F.W. 284.55, White solid, MDL MFCD09027254

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Bulk and Specialty Sizes Available 67 Arylboronic Acids Stock # Description Standard Selling Sizes H53296 4-(4-Methyl-1-piperazinylcarbonyl)benzeneboronic acid 250mg hydrochloride, 95% 1g

[913835-43-5], C12H17BN2O3ùHCl, F.W. 284.55, White solid, m.p. 187-189ø, MDL MFCD09027217

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53040 3-(4-Methyl-1-piperidinylcarbonyl)benzeneboronic acid, 250mg 95% 1g

[850567-30-5], C13H18BNO3, F.W. 247.10, White solid, m.p. 158-162ø, MDL MFCD04115704

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53366 4-(4-Methyl-1-piperidinylcarbonyl)benzeneboronic acid, 250mg 95% 1g

[850568-21-7], C13H18BNO3, F.W. 247.10, Pale brown solid, m.p. 134-137ø, Y, MDL MFCD04115676

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53119 2-Methyl-5-(-1-piperidinylsulfonyl)benzeneboronic acid, 98% 250mg

[871333-00-5], C12H18BNO4S, F.W. 283.15, White solid, 1g m.p. 132-136ø, MDL MFCD08056364

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53018 5-Methyl-4-propoxy-1,3-phenylenebisboronic acid, 96% 250mg

[850568-70-6], C10H16B2O5, F.W. 237.85, White solid, m.p. >300ø,

Acids MDL MFCD06659835

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52881 2-Methyl-5-(-1-pyrrolidinylsulfonyl)benzeneboronic acid, 98% 250mg

[871333-01-6], C11H16BNO4S, F.W. 269.12, White solid, 1g m.p. 126-128ø, MDL MFCD08056365

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Arylboronic H53163 3-Methylsulfamoylbenzeneboronic acid, 97% 250mg [3-Methylaminosulfonylphenylboronic acid]

[871329-75-8], C7H10BNO4S, F.W. 215.03, White solid, m.p. 120-124ø, MDL MFCD07363845

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52493 4-Methylsulfamoylbenzeneboronic acid, 97% 250mg [4-Methylaminosulfonylphenylboronic acid] 1g

[226396-31-2], C7H10BNO4S, F.W. 215.03, White solid, m.p. 136-140ø, MDL MFCD06659864

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53209 2-(Methylsulfinyl)benzeneboronic acid, 97% 250mg [2-(Methanesulfinyl)phenylboronic acid, 97%] 1g

[850567-97-4], C7H9BO3S, F.W. 184.02, White solid, m.p. 118-122ø, MDL MFCD03095261

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L17865 4-(Methylsulfinyl)benzeneboronic acid, 98% 100mg [4-(Methanesulfinyl)benzeneboronic acid, 4-(Methylsulfinyl)phenyl- 1g boronic acid]

[166386-48-7], C7H9BO3S, F.W. 184.02, m.p. ca 170ø, MDL MFCD02093071

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53288 2-(Methylsulfonylamino)benzeneboronic acid, 95% 250mg [2-(Methanesulfonylamino)phenylboronic acid] 1g

[756520-78-2], C7H10BNO4S, F.W. 215.03, Off-white solid, m.p. 116-120ø, MDL MFCD02179471

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52895 3-(Methylsulfonylamino)benzeneboronic acid, 97% 1g [3-(Methanesulfonylamino)phenylboronic acid] 5g

[148355-75-3], C7H10BNO4S, F.W. 215.03, Off-white solid, m.p. 90-96ø, MDL MFCD02179478

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53020 4-(Methylsulfonylamino)benzeneboronic acid, 95% 250mg [4-(Methanesulfonylamino)phenylboronic acid] 1g

[380430-57-9], C7H10BNO4S, F.W. 215.03, White solid, m.p. 148-154ø, MDL MFCD02179473

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

68 www.alfa.com Arylboronic Acids Stock # Description Standard Selling Sizes H52705 (3-Methylsulfonylaminomethyl)benzeneboronic acid, 98% 250mg [3-Methanesulfonamidomethylphenylboronic acid] 1g

[850568-39-7], C8H12BNO4S, F.W. 229.06, White solid, m.p. 246-248ø, MDL MFCD06659817

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52676 (4-Methylsulfonylaminomethyl)benzeneboronic acid, 98% 250mg [4-Methanesulfonamidomethylphenylboronic acid] 1g

[850568-38-6], C8H12BNO4S, F.W. 229.06, White solid, m.p. 237-239ø, MDL MFCD06659816

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52445 2-(Methylsulfonyl)benzeneboronic acid, 98% 1g [2-(Methanesulfonyl)phenylboronic acid] 5g

[330804-03-0], C7H9BO4S, F.W. 200.02, White solid, m.p. 78-84ø, MDL MFCD02179472

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52916 3-(Methylsulfonyl)benzeneboronic acid, 98% 1g [3-(Methanesulfonyl)phenylboronic acid] 5g

[373384-18-0], C7H9BO4S, F.W. 200.02, White solid, m.p. 102-110ø, MDL MFCD03092935 Arylboronic

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L17720 4-(Methylsulfonyl)benzeneboronic acid, 98% 250mg [4-(Methanesulfonyl)benzeneboronic acid, 4-(Methylsulfonyl)phenyl- 1g boronic acid] 5g

[149104-88-1], C7H9BO4S, F.W. 200.02, m.p. ca 200ø, MDL MFCD01630820

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Acids L17456 2-(Methylthio)benzeneboronic acid, 98+% 1g [2-(Methylthio)phenylboronic acid, 2-Thioanisoleboronic acid] 5g

[168618-42-6], C7H9BO2S, F.W. 168.02, m.p. ca 160ø, BRN 8309529, MDL MFCD01318165

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L20250 3-(Methylthio)benzeneboronic acid, 97% 250mg [3-(Methylthio)phenylboronic acid, 3-Thioanisoleboronic acid] 1g

[128312-11-8], C7H9BO2S, F.W. 168.02, m.p. 158-161ø, 5g BRN 7020728, MDL MFCD01319105

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B23454 4-(Methylthio)benzeneboronic acid, 97% 1g [4-(Methylthio)phenylboronic acid, 4-Thioanisoleboronic acid] 5g

[98546-51-1], C7H9BO2S, F.W. 168.02, White to cream cryst powder, 25g m.p. ca 208-212ø, BRN 3247219, MDL MFCD00093410

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52995 2-(4-Morpholinylcarbonyl)benzeneboronic acid, 95% 250mg

[874219-17-7], C11H14BNO4, F.W. 235.05, White solid, m.p. 150-152ø, 1g MDL MFCD08235036

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52868 3-(4-Morpholinylcarbonyl)benzeneboronic acid, 98% 250mg

[723281-55-8], C11H14BNO4, F.W. 235.05, White solid, 1g m.p. 124-130ø, MDL MFCD04115687

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53126 4-(4-Morpholinylcarbonyl)benzeneboronic acid, 98% 250mg

[389621-84-5], C11H14BNO4, F.W. 235.05, White solid, 1g m.p. 126-132ø, MDL MFCD03411952

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52480 3-(4-Morpholinylcarbonyl)-5-nitrobenzeneboronic acid, 98% 250mg

[871332-80-8], C11H13BN2O6, F.W. 280.04, White solid, 1g m.p. 167-169ø, MDL MFCD08056359

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H53353 4-[2-(4-Morpholinyl)ethylcarbamoyl]benzeneboronic 250mg acid, 98% 1g

[913835-45-7], C13H19BN2O4, F.W. 278.11, White solid, m.p. 112-114ø, MDL MFCD09027219

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Bulk and Specialty Sizes Available 69 Arylboronic Acids Stock # Description Standard Selling Sizes H52689 3-[2-(4-Morpholinyl)ethylcarbamoyl]benzeneboronic 250mg acid hydrochloride, 98% 1g

[957060-89-8], C13H19BN2O4ùHCl, F.W. 314.58, Pale orange solid, m.p. 190-195ø, MDL MFCD09027255

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53242 3-(4-Morpholinylsulfonyl)benzeneboronic acid, 96% 250mg

[871329-60-1], C10H14BNO5S, F.W. 271.09, Off-white solid, 1g m.p. 144-148ø, MDL MFCD07363748

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52601 4-(4-Morpholinylsulfonyl)benzeneboronic acid, 96% 250mg

[486422-69-9], C10H14BNO5S, F.W. 271.09, White solid, 1g m.p. 134-136ø, MDL MFCD06659844

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B21219 1-Naphthaleneboronic acid, 97% 1g [1-Naphthylboronic acid] 5g

[13922-41-3], C10H9BO2, F.W. 171.99, White to cream cryst powder, 25g m.p. 204-210ø, BRN 2937504, MDL MFCD00019722

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a The Suzuki coupling with a protected L-tyrosine triflate, catalyzed by Tetrakis(triphenyl- phosphine)palladium(0), 10548, p. 145, occurred in high yield without racemization when

anhydrous K2CO3 in toluene was used as the base: J. Org. Chem., 57, 379 (1992). For

Acids Ni-catalyzed coupling with allylamines, see: J. Chem. Soc., Perkin 1, 2083 (1995). See Appendix 5. B24157 2-Naphthaleneboronic acid, 97% 1g [2-Naphthylboronic caid] 5g

[32316-92-0], C10H9BO2, F.W. 171.99, White to plae brown cryst 25g powder, m.p. ca 267ø, BRN 2936449, MDL MFCD00236051

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Arylboronic Fluorescent PET receptor useful in saccharide detection: Tetrahedron Lett., 36, 4825 (1995); Pure Appl. Chem., 68, 2179 (1996). Reagent for selective fluorescence detection of F-: Chem. Commun., 1365 (1998). For boronic acid chemistry, see Appendix 5. H52842 10-(1-Naphthyl)anthracene-9-boronic acid, 97% 250mg

C24H17BO2, F.W. 348.21 1g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H52853 10-(2-Naphthyl)anthracene-9-boronic acid, 97% 250mg

C24H17BO2, F.W. 348.21 1g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H52443 2-(2-Naphthyl)benzeneboronic acid, 95% 1g [2-(2-Naphthyl)phenylboronic acid] 5g

C16H13BO2, F.W. 248.09, Pale brown powder

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H52948 3-(2-Naphthyl)benzeneboronic acid, 98% 1g [3-(2-Naphthyl)phenylboronic acid] 5g

C16H13BO2, F.W. 248.09

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52710 4-(1-Naphthyl)benzeneboronic acid, 97% 250mg [4-(1-Naphthyl)phenylboronic acid] 1g

[870774-25-7], C16H13BO2, F.W. 248.09, MDL MFCD08669639

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H52534 4-(2-Naphthyl)benzeneboronic acid, 97% 250mg [4-(2-Naphthyl)phenylboronic acid] 1g

[918655-03-5], C16H13BO2, F.W. 248.09, MDL MFCD09260454

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

70 www.alfa.com Arylboronic Acids Stock # Description Standard Selling Sizes H53167 4-(1-Naphthyl)naphthalene-1-boronic acid, 98% 250mg

C20H15BO2, F.W. 298.15 1g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H52496 4-(Neopentyloxysulfonyl)benzeneboronic acid, 98% 250mg

[957060-74-1], C11H17BO5S, F.W. 272.12, White solid, m.p. 176-179ø, MDL MFCD09027229

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L17988 2-Nitrobenzeneboronic acid, 96% 1g [2-Nitrophenylboronic acid] 5g

[5570-19-4], C6H6BNO4, F.W. 166.93, m.p. 149-151ø, BRN 3032097, MDL MFCD00161358

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a A13336 3-Nitrobenzeneboronic acid, 98% 1g [3-Nitrophenylboronic acid, 3-Nitrophenylboric acid] 5g Arylboronic [13331-27-6], C6H6BNO4, F.W. 166.93, Pale yellow to pale brown 25g powder, m.p. ca 285ø dec., RTECS CY8980000, BRN 2938638, MDL MFCD00007193, Ì

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Reagent for derivatization of diols and diamines for GC: Chromatographia, 11, 347 (1978). Oxidative conversion of arylboronic acids to phenols with potassium monopersulfate in buffered aqueous acetone (in situ dimethyldioxirane) is exemplified for this compound: Tetrahedron Lett., 36, 5117 (1995). Acids Mild Lewis acid catayst, for example in the selective transesterification of á-keto esters: Synlett, 415 (2006). See also 3,4,5-Trifluorobenzeneboronic acid, L18519, p. 77. For reactions of boronic acids, see Appendix 5. H27767 4-Nitrobenzeneboronic acid, 95% 1g [4-Nitrophenylboronic acid] 5g

[24067-17-2], C6H6BNO4, F.W. 166.93, Pale yellow to pale brown powder, m.p. ca 285ø dec., MDL MFCD00161360

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53248 3-Nitro-5-(1-piperidinylcarbonyl)benzeneboronic acid, 98% 250mg

[871332-78-4], C12H15BN2O5, F.W. 278.07, Cream solid, 1g m.p. 180-184ø, MDL MFCD07783871

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H53148 3-Nitro-5-(1-pyrrolidinylcarbonyl)benzeneboronic acid, 98% 250mg

[871332-81-9], C11H13BN2O5, F.W. 264.04, Off-white solid, 1g m.p. 181-183ø, MDL MFCD07783873

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H52859 trans-3-(2-Nitrovinyl)benzeneboronic acid, 96% 250mg [trans-3-(2-Nitrovinyl)phenylboronic acid] 1g

[850567-99-6], C8H8BNO4, F.W. 192.97, Pale brown, m.p. 232-236ø, MDL MFCD04115658

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L17004 trans-4-(2-Nitrovinyl)benzeneboronic acid, 97% 250mg [4-Borono-trans-á-nitrostyrene, trans-4-(á-Nitrovinyl)phenylboronic 1g acid]

[216394-04-6], C8H8BNO4, F.W. 192.97, Yellow to orange powder, m.p. 289-291ø, BRN 3293756, MDL MFCD01075748

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L17753 4-n-Nonylbenzeneboronic acid, 98+% 1g

[256383-45-6], C15H25BO2, F.W. 248.18, m.p. 82-85ø, 5g BRN 8215118, MDL MFCD02093070

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52653 4-n-Octyloxybenzeneboronic acid, 97% 1g

[121554-09-4], C14H23BO3, F.W. 250.14, White solid, m.p. 88-90ø, 5g MDL MFCD00982004

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Bulk and Specialty Sizes Available 71 Arylboronic Acids Stock # Description Standard Selling Sizes H52625 3-(4-Oxo-1-piperidinylcarbonyl)benzeneboronic acid, 97% 250mg

[850567-32-7], C12H14BNO4, F.W. 247.06, White solid, m.p. 36-40ø, MDL MFCD04115707

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52942 4-(4-Oxo-1-piperidinylcarbonyl)benzeneboronic acid, 95% 250mg

[850568-23-9], C12H14BNO4, F.W. 247.06, White solid, m.p. 156-160ø, MDL MFCD04115679

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52946 4-(5-Oxo-3-pyrazolidinyl)benzeneboronic acid, 96% 250mg [5-(4-Boronophenyl)pyrazolidin-3-one] 1g

[874290-64-9], C9H11BN2O3, F.W. 206.01, White solid, m.p. 187-189ø, MDL MFCD08235074

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53158 4,4'-Oxybis(1,4-phenylene)diboronic acid, 97% 250mg [4-(4-Boronophenoxy)phenylboronic acid]

[19014-29-0], C12H12B2O5, F.W. 257.84, White solid, m.p. >300ø, MDL MFCD00433207

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B22922 2,3,4,5,6-Pentafluorobenzeneboronic acid, 97% 5g [2,3,4,5,6-Pentafluorophenylboronic acid] 25g

Acids [1582-24-7], C6H2BF5O2, F.W. 211.88, White to pale brown cryst powder, 100g m.p. 250-255ø, BRN 3033960, MDL MFCD01074663

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Conditions have been reported for successfully accomplishing the normally difficult Suzuki cross-coupling reactions of this boronic acid with aryl halides: Org. Lett., 7, 4915 (2005). H52615 3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydronaphthalene-2-boronic 250mg

Arylboronic acid, 95%

[169126-64-1], C15H23BO2, F.W. 246.16, White solid, m.p. 198-201ø, MDL MFCD08436043

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L18011 4-n-Pentylbenzeneboronic acid, 97% 250mg [4-n-Amylbenzeneboronic acid, 4-n-Pentylphenylboronic acid] 1g

[121219-12-3], C11H17BO2, F.W. 192.07, m.p. 82-84ø, 5g BRN 4782754, MDL MFCD00995151

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53026 4-n-Pentyloxybenzeneboronic acid, 96% 1g

[146449-90-3], C11H17BO3, F.W. 208.06, White solid, m.p. 98-100ø, 5g MDL MFCD04039035

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52546 Phenanthrene-9-boronic acid, 97% 1g

[68572-87-2], C14H11BO2, F.W. 222.05, White solid, m.p. 254-256ø, 5g MDL MFCD00143524

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H53264 2-Phenoxybenzeneboronic acid, 98% 1g

[108238-09-1], C12H11BO3, F.W. 214.03, White to cream solid, m.p. 96-100ø, 5g MDL MFCD01001592

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H32879 3-Phenoxybenzeneboronic acid, 97+% 250mg [3-Boronodiphenyl ether, 3-Phenoxyphenylboronic acid] 1g

[221006-66-2], C12H11BO3, F.W. 214.03, White powder, m.p. 138-143ø, MDL MFCD07780272

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52950 4-Phenoxybenzeneboronic acid, 98% 1g

[51067-38-0], C12H11BO3, F.W. 214.03, White to off-white solid, 5g m.p. 141-145ø, MDL MFCD00093312

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52612 3-Phenylcarbamoylbenzeneboronic acid, 97% 250mg

[397843-71-9], C13H12BNO3, F.W. 241.05, Off-white solid, 1g m.p. 250-260ø, MDL MFCD04115711

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

72 www.alfa.com Arylboronic Acids Stock # Description Standard Selling Sizes H53159 4-Phenylcarbamoylbenzeneboronic acid, 97% 250mg [N-Phenyl 4-boronobenzamide] 1g

[330793-45-8], C13H12BNO3, F.W. 241.05, Off-white solid, m.p. 210-216ø, MDL MFCD04115683

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52647 3-Phenylcarbamoyl-5-nitrobenzeneboronic acid, 98% 250mg [3-Phenylaminocarbonyl-5-nitrophenylboronic acid] 1g

[871332-91-1], C13H11BN2O5, F.W. 286.05, Pale brown solid, m.p. 205-207ø, MDL MFCD07783883

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52991 4-(2-Phenylethylcarbamoyl)benzeneboronic acid, 98% 250mg [4-(2-Phenylethylaminocarbonyl)phenylboronic acid] 1g

[330793-46-9], C15H16BNO3, F.W. 269.11, White solid, m.p. 195-198ø, MDL MFCD09027209

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52952 3-(1-Piperidinylcarbonyl)benzeneboronic acid, 97% 1g

[850568-34-2], C12H16BNO3, F.W. 233.07, White solid, 5g m.p. 150-154ø, MDL MFCD04115686

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Arylboronic H52459 4-(1-Piperidinylcarbonyl)benzeneboronic acid, 97% 250mg

[389621-83-4], C12H16BNO3, F.W. 233.07, White solid, 1g m.p. 150-154ø, MDL MFCD03411951

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52650 4-[2-(1-Piperidinyl)ethylcarbamoyl]benzeneboronic 250mg

acid hydrochloride, 98% 1g Acids [4-[2-(1-Piperidinyl)ethylaminocarbonyl]phenylboronic acid hydrochloride]

[957060-72-9], C14H21BN2O3ùHCl, F.W. 312.60, White solid, m.p. 160-161ø, MDL MFCD09027221

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52644 3-(1-Piperidinylsulfonyl)benzeneboronic acid, 98% 250mg

[690662-96-5], C11H16BNO4S, F.W. 269.12, White solid, 1g m.p. 166-168ø, MDL MFCD07783850

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53094 4-(1-Piperidinylsulfonyl)benzeneboronic acid, 97% 250mg

[486422-58-6], C11H16BNO4S, F.W. 269.12, White solid, 1g m.p. 268-272ø, MDL MFCD06659850

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53129 4-n-Propoxybenzeneboronic acid, 97% 1g [4-n-Propoxyphenylboronic acid] 5g

[186497-67-6], C9H13BO3, F.W. 180.01, White solid, m.p. 104-110ø, MDL MFCD03427189

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52466 3-(n-Propoxycarbonyl)benzeneboronic acid, 97% 250mg [3-(n-Propoxycarbonyl)phenylboronic acid] 1g

[850568-78-4], C10H13BO4, F.W. 208.02, White solid, m.p. 104-108ø, MDL MFCD06659851

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27938 4-(n-Propoxycarbonyl)benzeneboronic acid, 97% 1g [4-(n-Propoxycarbonyl)phenylboronic acid, n-Propyl 10g 4-boronobenzoate]

[91062-38-3], C10H13BO4, F.W. 208.02, White cryst powder, m.p. 121-123ø, MDL MFCD06659852

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53272 4-n-Propoxy-3-methylbenzeneboronic acid, 97% 250mg [4-n-Propoxy-3-methylphenylboronic acid] 1g

[279262-88-3], C10H15BO3, F.W. 194.04, White solid, m.p. 154-156ø, MDL MFCD06659872

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52884 4-n-Propylbenzeneboronic acid, 98% 1g [4-n-Propylphenylboronic acid] 5g

[134150-01-9], C9H13BO2, F.W. 164.01, White powder, m.p. 106-108ø, MDL MFCD00859261

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Bulk and Specialty Sizes Available 73 Arylboronic Acids Stock # Description Standard Selling Sizes H53344 3-(n-Propylcarbamoyl)benzeneboronic acid, 95% 250mg [3-(n-Propylaminocarbonyl)phenylboronic acid] 1g

[850567-22-5], C10H14BNO3, F.W. 207.04, White solid, m.p. 88-96ø, MDL MFCD04038919

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53238 4-(n-Propylcarbamoyl)benzeneboronic acid, 98% 250mg [4-(n-Propylaminocarbonyl)phenylboronic acid] 1g

[171922-46-6], C10H14BNO3, F.W. 207.04, White solid, m.p. 210-214ø, MDL MFCD06656015

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52708 3-(n-Propylcarbamoyl)-5-nitrobenzeneboronic acid, 98% 250mg [3-(n-Propylaminocarbonyl)-5-nitrophenylboronic acid] 1g

[871332-88-6], C10H13BN2O5, F.W. 252.03, White solid, m.p. 190-192ø, MDL MFCD07783880

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53082 4-(1H-Pyrazol-1-ylsulfonyl)benzeneboronic acid, 98% 250mg

[957061-02-8], C9H9BN2O4S, F.W. 252.05, White solid, m.p. 155-158ø, MDL MFCD09027235

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52843 4-(2-Pyridylcarbamoyl)benzeneboronic acid, 97% 250mg [4-(2-Pyridylaminocarbonyl)phenylboronic acid]

Acids [850568-25-1], C12H11BN2O3, F.W. 242.04, Off-white solid, m.p. 124-128ø, MDL MFCD06659876

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52607 3-(1-Pyrrolidinylcarbonyl)benzeneboronic acid, 97% 250mg [3-Borono-N-(1-pyrrolidinyl)benzamide] 1g

[723281-53-6], C11H14BNO3, F.W. 219.05, White solid, m.p. 113-116ø, MDL MFCD04115685 Arylboronic H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53186 4-(1-Pyrrolidinylcarbonyl)benzeneboronic acid, 96% 1g [4-Borono-N-(1-pyrrolidinyl)benzamide] 5g

[389621-81-2], C11H14BNO3, F.W. 219.05, White solid, m.p. 136-140ø, MDL MFCD03411950

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52876 3-[2-(1-Pyrrolidinyl)ethylcarbamoyl]benzeneboronic 250mg acid hydrochloride, 98% [3-[2-(1-Pyrrolidinyl)ethylaminocarbonyl]phenylboronic acid hydrochloride]

[957061-03-9], C13H19BN2O3ùHCl, F.W. 298.58, Pale pink solid, MDL MFCD09027257

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52882 4-[2-(1-Pyrrolidinyl)ethylcarbamoyl]benzeneboronic 250mg acid hydrochloride, 98% 1g [4-[2-(1-Pyrrolidinyl)ethylaminocarbonyl]phenylboronic acid hydrochloride]

[957060-70-7], C13H19BN2O3ùHCl, F.W. 298.58, White solid, m.p. 78-80ø, MDL MFCD09027222

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52694 2-(1-Pyrrolidinylsulfonyl)benzeneboronic acid, 97% 250mg [2-(1-Pyrrolidinylsulfonyl)phenylboronic acid]

[913835-83-3], C10H14BNO4S, F.W. 255.10, White solid, m.p. 124-126ø, MDL MFCD08689515

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52717 3-(1-Pyrrolidinylsulfonyl)benzeneboronic acid, 97% 250mg [3-(1-Pyrrolidinylsulfonyl)phenylboronic acid] 1g

[871329-61-2], C10H14BNO4S, F.W. 255.10, White solid, m.p. 127-129ø, MDL MFCD07783851

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53321 4-(1-Pyrrolidinylsulfonyl)benzeneboronic acid, 97% 250mg [4-(1-Pyrrolidinylsulfonyl)phenylboronic acid] 1g

[486422-57-5], C10H14BNO4S, F.W. 255.10, White solid, m.p. 275-277ø, MDL MFCD06659847

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

74 www.alfa.com Arylboronic Acids Stock # Description Standard Selling Sizes H52438 4-(1-Pyrrolylsulfonyl)benzeneboronic acid, 98% 250mg

[913835-90-2], C10H10BNO4S, F.W. 251.06, Pale brown solid, m.p. 220-222ø, MDL MFCD08689522

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52628 3-Sulfamoylbenzeneboronic acid, 97% 250mg [3-Boronobenzenesulfonamide]

[850568-74-0], C6H8BNO4S, F.W. 201.00, White solid, m.p. 260-266ø, MDL MFCD06659840

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52928 4-Sulfamoylbenzeneboronic acid, 97% 250mg [4-Boronobenzenesulfonamide] 1g

[613660-87-0], C6H8BNO4S, F.W. 201.00, White solid, m.p. 250-256ø, MDL MFCD06659839

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52894 4-Sulfobenzeneboronic acid, 98% 250mg [4-Boronobenzenesulfonic acid]

[913836-00-7], C6H7BO5S, F.W. 201.99, White solid, m.p. >300ø, MDL MFCD09027231 Arylboronic H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27640 1,1':3',1''-Terphenyl-5'-boronic acid, 95% 250mg [3,5-Diphenylbenzeneboronic acid, (3,5-Diphenylphenyl)boronic acid] 1g

[128388-54-5], C18H15BO2, F.W. 274.13, White powder, 5g m.p. 292-296ø, MDL MFCD09953491

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

L19824 2,3,4,5-Tetrafluorobenzeneboronic acid, 97% 250mg Acids [2,3,4,5-Tetrafluorophenylboronic acid] 1g

[179923-32-1], C6H3BF4O2, F.W. 193.90, White powder, m.p. ca 250-255ø, BRN 8554485, MDL MFCD04039308

H:H315-H319-H335, P:P280g-P305+P351+P338 L19825 2,3,4,6-Tetrafluorobenzeneboronic acid, 98% 250mg [2,3,4,6-Tetrafluorophenylboronic acid] 1g

[511295-00-4], C6H3BF4O2, F.W. 193.90, White crystalline powder, m.p. ca 125-129ø, BRN 9200162, MDL MFCD04039309

H:H315-H319-H335, P:P280g-P305+P351+P338 L19826 2,3,5,6-Tetrafluorobenzeneboronic acid, 99% 1g [2,3,5,6-Tetrafluorophenylboronic acid]

[511295-01-5], C6H3BF4O2, F.W. 193.90, White powder, m.p. ca 140-145ø, BRN 9200167, MDL MFCD04039310

H:H315-H319-H335, P:P280g-P305+P351+P338 H50445 4-(2-Tetrahydropyranyloxy)benzeneboronic acid, 96% 250mg [4-(2-Tetrahydropyranyloxy)phenylboronic acid] 1g

[182281-01-2], C11H15BO4, F.W. 222.05, Tan powder, MDL MFCD02183525

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52537 3-(1H-Tetrazol-5-ylcarbamoyl)benzeneboronic acid 250mg hydrochloride, 97% 1g [3-(1H-Tetrazol-5-ylaminocarbonyl)phenylboronic acid hydrochloride]

[850567-38-3], C8H8BN5O3ùHCl, F.W. 269.45, Off-white solid, m.p. >300ø, MDL MFCD06659888

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53245 4-(1H-Tetrazol-5-ylcarbamoyl)benzeneboronic acid 250mg hydrochloride, 97% 1g [4-(1H-Tetrazol-5-ylaminocarbonyl)phenylboronic acid hydrochloride]

[850568-31-9], C8H8BN5O3ùHCl, F.W. 269.45, Pale brown solid, m.p. >300ø, MDL MFCD06659882

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52903 4-(3-Thiazolidinylcarbonyl)benzeneboronic acid, 97% 250mg [4-(3-Thiazolidinylcarbonyl)phenylboronic acid] 1g

[850589-33-2], C10H12BNO3S, F.W. 237.08, Off-white solid, m.p. 146-150ø, MDL MFCD04115680

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Bulk and Specialty Sizes Available 75 Arylboronic Acids Stock # Description Standard Selling Sizes H53250 3-(2-Thiazolinylcarbamoyl)benzeneboronic acid, 97% 250mg [3-[(4,5-Dihydrothiazol-2-yl)aminocarbonyl]phenylboronic acid]

[871333-06-1], C10H11BN2O3S, F.W. 250.08, White solid, m.p. 204-240ø, MDL MFCD07363799

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53136 4-(2-Thiazolinylcarbamoyl)benzeneboronic acid, 97% 250mg [4-[(4,5-Dihydrothiazol-2-yl)aminocarbonyl]phenylboronic acid] 1g

[850568-30-8], C10H11BN2O3S, F.W. 250.08, Off-white solid, m.p. 248-252ø, MDL MFCD06659881

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53204 3-(2-Thiazolylcarbamoyl)benzeneboronic acid, 97+% 250mg [3-(2-Thiazolylaminocarbonyl)phenylboronic acid] 1g

[850567-34-9], C10H9BN2O3S, F.W. 248.06, White solid, m.p. 218-222ø, MDL MFCD06659885

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53317 4-(2-Thiazolylcarbamoyl)benzeneboronic acid, 97+% 250mg [4-(2-Thiazolylaminocarbonyl)phenylboronic acid] 1g

[850568-26-2], C10H9BN2O3S, F.W. 248.06, Off-white solid, m.p. 206-210ø, MDL MFCD06659877

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52639 3-(4-Thiomorpholinylcarbonyl)benzeneboronic acid, 98% 250mg

[850567-37-2], C11H14BNO3S, F.W. 251.11, Off-white solid, 1g Acids m.p. 120-126ø, MDL MFCD06659887

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53318 4-(4-Thiomorpholinylcarbonyl)benzeneboronic acid, 97% 250mg

[850568-28-4], C11H14BNO3S, F.W. 251.11, White solid, 1g m.p. 140-142ø, MDL MFCD06659879

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Arylboronic H52907 4-(4-Thiomorpholinylsulfonyl)benzeneboronic acid, 98% 250mg

[871329-69-0], C10H14BNO4S2, F.W. 287.16, White solid, m.p. 276-280ø, MDL MFCD07363757

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52522 3-(1H-1,2,4-Triazol-3-ylcarbamoyl)benzeneboronic acid, 250mg 95% [3-(1H-1,2,4-Triazol-3-ylaminocarbonyl)phenylboronic acid]

[871333-05-0], C9H9BN4O3, F.W. 232.01, White solid, m.p. 230-236ø, MDL MFCD07363798

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53332 4-(4H-1,2,4-Triazol-4-ylcarbamoyl)benzeneboronic acid 250mg hydrochloride, 98% 1g [4-(4H-1,2,4-Triazol-4-ylaminocarbonyl)phenylboronic acid hydrochloride]

[850568-29-5], C9H9BN4O3ùHCl, F.W. 268.47, White solid, m.p. 230-234ø, MDL MFCD06659880

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52751 3-(2,2,2-Trichloroacetamido)benzeneboronic acid, 97% 250mg

[276669-74-0], C8H7BCl3NO3, F.W. 282.32, Off-white solid, 1g m.p. 220-222ø, MDL MFCD08235073

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L17511 2,3,5-Trichlorobenzeneboronic acid, 98% 1g [2,3,5-Trichlorophenylboronic acid] 5g

[212779-19-6], C6H4BCl3O2, F.W. 225.27, m.p. ca 245ø, MDL MFCD01630856

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52491 2,4,6-Trichlorobenzeneboronic acid, 98% 250mg

[73852-18-3], C6H4BCl3O2, F.W. 225.27, White solid, m.p. 162-164ø, 1g MDL MFCD01074621

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53127 3-(2,2,2-Trifluoroacetamido)benzeneboronic acid, 98% 250mg

[88978-20-5], C8H7BF3NO3, F.W. 232.95, Off-white solid, 1g m.p. 290-293ø, MDL MFCD08235083

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

76 www.alfa.com Arylboronic Acids Stock # Description Standard Selling Sizes L19827 2,3,4-Trifluorobenzeneboronic acid, 98% 250mg [2,3,4-Trifluorophenylboronic acid] 1g

[226396-32-3], C6H4BF3O2, F.W. 175.90, m.p. 202-204ø, MDL MFCD01863168

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27858 2,4,5-Trifluorobenzeneboronic acid, 97% 5g [2,4,5-Trifluorophenylboronic acid] 25g

[247564-72-3], C6H4BF3O2, F.W. 175.90, White powder, m.p. 99-101ø, MDL MFCD01863165

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L19402 2,4,6-Trifluorobenzeneboronic acid, 97% 1g [2,4,6-Trifluorophenylboronic acid] 5g

[182482-25-3], C6H4BF3O2, F.W. 175.90, m.p. ca 235ø, BRN 8549766, MDL MFCD01863169

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L18519 3,4,5-Trifluorobenzeneboronic acid, 97% 250mg [3,4,5-Trifluorophenylboronic acid] 1g

[143418-49-9], C6H4BF3O2, F.W. 175.90, m.p. 275-279ø, BRN 7371914, MDL MFCD02093069 Arylboronic

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Extremely active catalyst for the reaction of carboxylic acids with primary and secondary amines to give the corresponding amides in very high yields: J. Org. Chem., 61, 4196 (1996).

Also useful in the one-pot synthesis of acyl azides from carboxylic acids and NaN3: Tetrahedron Lett., 43, 9715 (2002). Mediates the mild, one-pot reduction of carboxylic acids

to alcohols with NaBH4: Tetrahedron Lett., 44, 3427 (2003). For other boronic acid chemistry, see Appendix 5. H52471 2-(2,2,2-Trifluoroethoxy)benzeneboronic acid, 98% 250mg Acids

[957060-90-1], C8H8BF3O3, F.W. 219.95, White solid, m.p. 125-128ø, 1g MDL MFCD09027258

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53137 3-(2,2,2-Trifluoroethoxy)benzeneboronic acid, 97% 250mg

[850593-08-7], C8H8BF3O3, F.W. 219.95, Brown solid, 1g m.p. 126-129ø, MDL MFCD07363846

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52889 4-(2,2,2-Trifluoroethoxy)benzeneboronic acid, 98% 250mg

[886536-37-4], C8H8BF3O3, F.W. 219.95, White solid, m.p. 191-194ø, 1g MDL MFCD09027239

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53307 4-(2,2,2-Trifluoroethylcarbamoyl)benzeneboronic acid, 98% 250mg [4-(2,2,2-Trifluoroethylaminocarbonyl)phenylboronic acid] 1g

[874459-90-2], C9H9BF3NO3, F.W. 246.98, White solid, m.p. 210-212ø, MDL MFCD08235087

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L19774 2-(Trifluoromethoxy)benzeneboronic acid, 98% 250mg [2-(Trifluoromethoxy)phenylboronic acid] 1g

[175676-65-0], C7H6BF3O3, F.W. 205.93, m.p. 118-120ø, BRN 8766167, MDL MFCD01320763

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L19775 3-(Trifluoromethoxy)benzeneboronic acid, 98% 1g [3-(Trifluoromethoxy)phenylboronic acid] 5g

[179113-90-7], C7H6BF3O3, F.W. 205.93, m.p. ca 80ø, BRN 7531456, MDL MFCD01320697

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B23233 4-(Trifluoromethoxy)benzeneboronic acid, 98% 1g [4-(Trifluoromethoxy)phenylboronic acid] 5g

[139301-27-2], C7H6BF3O3, F.W. 205.93, White to cream powder, 25g m.p. ca 120-125ø, BRN 8548201, MDL MFCD01074648

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B24343 2-(Trifluoromethyl)benzeneboronic acid, 97% 1g [2-(Trifluoromethyl)phenylboronic acid] 5g

[1423-27-4], C7H6BF3O2, F.W. 189.93, White to pale brown cryst powder, 25g m.p. 108-110ø, BRN 2974465, MDL MFCD00236059

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Bulk and Specialty Sizes Available 77 Arylboronic Acids Stock # Description Standard Selling Sizes B21661 3-(Trifluoromethyl)benzeneboronic acid, 98% 1g [3-(Trifluoromethyl)phenylboronic acid] 5g

[1423-26-3], C7H6BF3O2, F.W. 189.93, White to pale yellow cryst solid, 25g m.p. 162-166ø, BRN 6084746, MDL MFCD00151854

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B22374 4-(Trifluoromethyl)benzeneboronic acid, 98% 1g [4-(Trifluoromethyl)phenylboronic acid] 5g

[128796-39-4], C7H6BF3O2, F.W. 189.93, White to cream powder or 25g crystals, m.p. 238-242ø, BRN 3544189, MDL MFCD00151855

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a For phosphine-free palladium-catalyzed Suzuki coupling with aryl halides, see: J. Org. Chem., 59, 5034 (1994). H52940 4-[2-(Trifluoromethyl)phenylcarbamoyl]benzeneboronic 250mg acid, 98% 1g [4-(2-Trifluoromethylphenylaminocarbonyl)phenylboronic acid]

[913835-42-4], C14H11BF3NO3, F.W. 309.05, Yellow solid, m.p. 242-245ø, MDL MFCD09027216

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52899 5-Trifluoromethyl-1,3-phenylenediboronic acid, 98% 250mg

[913835-35-5], C7H7B2F3O4, F.W. 233.75, White solid, 1g MDL MFCD08235085

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Acids B22891 2,4,6-Triisopropylbenzeneboronic acid, 98% 1g [2,4,6-Triisopropylphenylboronic acid] 5g

[154549-38-9], C15H25BO2, F.W. 248.16, White to cream powder, 25g m.p. ca 165ø dec., MDL MFCD02683099

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L19838 2,3,4-Trimethoxybenzeneboronic acid, 98% 1g Arylboronic [2,3,4-Trimethoxyphenylboronic acid] 5g

[118062-05-8], C9H13BO5, F.W. 212.01, m.p. 74-79ø, BRN 4185924, MDL MFCD01318183

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53197 2,3,6-Trimethoxybenzeneboronic acid, 95% 250mg

[380430-67-1], C9H13BO5, F.W. 212.01, White solid, m.p. 34-40ø, 1g MDL MFCD03411944

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

L19837 2,4,6-Trimethoxybenzeneboronic acid, 98% 1g [2,4,6-Trimethoxyphenylboronic acid] 5g

[135159-25-0], C9H13BO5, F.W. 212.01, BRN 4315581, MDL MFCD01114642

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L15191 3,4,5-Trimethoxybenzeneboronic acid, 98+% 1g [3,4,5-Trimethoxyphenylboronic acid] 5g

[182163-96-8], C9H13BO5, F.W. 212.01, m.p. ca 245ø, BRN 8205051, MDL MFCD01075676

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27004 2-(2,2,2-Trimethylacetamido)benzeneboronic acid, 95% 250mg [2-Pivalamidophenylboronic acid] 1g

[146140-95-6], C11H16BNO3, F.W. 221.06, White powder, m.p. 268-271ø, MDL MFCD01114645

H:H315-H319-H335, P:P280g-P305+P351+P338 H52761 3-(2,2,2-Trimethylacetamido)benzeneboronic acid, 96% 250mg [4-Pivalamidophenylboronic acid]

[182344-22-5], C11H16BNO3, F.W. 221.06, White solid, m.p. 240-243ø, MDL MFCD08235071

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B24060 2,4,6-Trimethylbenzeneboronic acid, 97% 1g [Mesitylboronic acid, 2,4,6-Trimethylphenylboronic acid] 5g

[5980-97-2], C9H13BO2, F.W. 164.01, White to cream powder, m.p. ca 25g 120-127ø, BRN 2831927, MDL MFCD00236060

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

78 www.alfa.com Arylboronic Esters Stock # Description Standard Selling Sizes L19828 2-Vinylbenzeneboronic acid, 98% 250mg [Styrene-2-boronic acid, 2-Vinylphenylboronic acid] 1g

[15016-42-9], C8H9BO2, F.W. 147.97, m.p. 105-107ø, BRN 3030430, MDL MFCD01074659

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L19829 3-Vinylbenzeneboronic acid, 98% 250mg [Styrene-3-boronic acid, 3-Vinylphenylboronic acid] 1g

[15016-43-0], C8H9BO2, F.W. 147.97, m.p. 127-129ø, BRN 3030426, MDL MFCD01074679

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B23709 4-Vinylbenzeneboronic acid, 97% 1g [Styrene-4-boronic acid, 4-Vinylphenylboronic acid] 5g

[2156-04-9], C8H9BO2, F.W. 147.97, White to pale cream powder, 25g m.p. ca 190ø, BRN 2829387, MDL MFCD00239441

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Arylboronic Stock # Description Standard Selling Sizes H53013 2-Acetamidobenzeneboronic acid pinacol ester, 96% 1g [2-Acetamidophenylboronic acid pinacol ester] 5g

[380430-61-5], C14H20BNO3, F.W. 261.13, Off-white solid, m.p. 172-176ø, MDL MFCD02179480 Esters H53093 3-Aminobenzeneboronic acid neopentyl glycol ester 1g hydrochloride, 95% 5g [3-Aminophenylboronic acid neopentyl glycol ester hydrochloride]

[850567-43-0], C11H16BNO2ùHCl, F.W. 241.52, Grey solid, m.p. 228-230ø, MDL MFCD06659912 L19951 2-Aminobenzeneboronic acid pinacol ester, 97% È 1g [2-Aminophenylboronic acid pinacol ester, 5g 2-(2-Aminophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane]

[191171-55-8], C12H18BNO2, F.W. 219.09, White to brown cryst powder, m.p. 65-70ø, BRN 8548809, MDL MFCD02179448

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H28448 3-Aminobenzeneboronic acid pinacol ester, 97% 1g [3-Aminophenylboronic acid pinacol ester, 5g 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline]

[210907-84-9], C12H18BNO2, F.W. 219.09, White to cream powder, MDL MFCD03453668

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H51666 4-Aminobenzeneboronic acid pinacol ester, 98% 1g [4-Aminophenylboronic acid pinacol ester, 5g 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline]

[214360-73-3], C12H18BNO2, F.W. 219.09, MDL MFCD02093721

H53194 2-Aminobenzeneboronic acid pinacol ester hydrochloride, 96% 250mg [2-Aminophenylboronic acid pinacol ester hydrochloride] 1g [393877-09-3], C12H18BNO2.HCl, F.W. 255.55, White or cream solid, m.p. 161-163ø, MDL MFCD02179449

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H52702 3-Aminobenzeneboronic acid pinacol ester hydrochloride, 250mg 95% 1g [3-Aminophenylboronic acid pinacol ester hydrochloride]

[850567-51-0], C12H18BNO2ùHCl, F.W. 255.55, Gray solid, m.p. 176-182ø, MDL MFCD06659920

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53195 3-Amino-4-chlorobenzeneboronic acid pinacol ester, 95% 250mg [3-Amino-4-chlorophenylboronic acid pinacol ester] 1g

[850567-56-5], C12H17BClNO2, F.W. 253.54, Off-white solid, m.p. 142-144ø, MDL MFCD06659926

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Bulk and Specialty Sizes Available 79 Arylboronic Esters Stock # Description Standard Selling Sizes H52356 4-Amino-2,5-difluorobenzeneboronic acid pinacol ester, 250mg 96% È 1g [2,5-Difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl- amine]

C12H16BF2NO2, F.W. 255.07, Solid H52349 4-Amino-3-fluorobenzeneboronic acid pinacol ester, 96% 250mg È 1g [2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl- 5g amine]

[819058-34-9], C12H17BFNO2, F.W. 237.08, Off-white solid H53220 2-Amino-4-(methoxycarbonyl)benzeneboronic acid 250mg pinacol ester hydrochloride, 95% 1g [Methyl 3-amino-4-boronobenzoate pinacol ester hydrochloride]

[850567-49-6], C14H20BNO4ùHCl, F.W. 313.59, Off-white solid, m.p. 92-94ø, MDL MFCD06659918

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52870 3-Amino-5-(methoxycarbonyl)benzeneboronic acid 250mg pinacol ester hydrochloride, 95% [Methyl 3-Amino-5-boronobenzoate pinacol ester hydrochloride, 3-Amino-5-(methoxycarbonyl)phenylboronic acid pinacol ester hydrochloride]

[850567-50-9], C14H20BNO4ùHCl, F.W. 313.59, Yellow solid,

Esters m.p. 125-127ø, MDL MFCD06659919

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52475 3-(Aminomethyl)benzeneboronic acid pinacol ester 250mg hydrochloride, 96% 1g [3-(Aminomethyl)phenylboronic acid pinacol ester hydrochloride]

[380430-65-9], C13H20BNO2ùHCl, F.W. 269.58, White solid, m.p. 169-171ø, MDL MFCD03410294 Arylboronic H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53263 3-Amino-4-methylbenzeneboronic acid pinacol ester 250mg hydrochloride, 95% 1g [3-Amino-4-methylphenylboronic acid pinacol ester hydrochloride]

[850567-52-1], C13H20BNO2ùHCl, F.W. 269.58, Off-white solid, m.p. 234-238ø, MDL MFCD06659921

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52691 4-(Aminomethyl)benzeneboronic acid pinacol ester 250mg hydrochloride, 95% 1g [4-(Aminomethyl)phenylboronic acid pinacol ester hydrochloride, [4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methylamine hydrochloride]

[850568-55-7], C13H20BNO2ùHCl, F.W. 269.58, White solid, m.p. 228-238ø, MDL MFCD02179455

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52715 3-Amino-5-nitrobenzeneboronic acid pinacol ester, 97% 250mg [3-Amino-5-nitrophenylboronic acid pinacol ester]

[871329-51-0], C12H17BN2O4, F.W. 264.09, MDL MFCD07363740

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H51921 Anthracene-9,10-diboronic acid bis(pinacol) ester, 1g 95% 5g

[863992-56-7], C26H32B2O4, F.W. 430.16, Solid, MDL MFCD16294538

L16187 1,4-Benzenediboronic acid bis(neopentyl 250mg glycol) ester, 99% 1g [1,4-Benzenediboronic acid bis-2,2-dimethyltrimethylene 5g ester, 2,2'-(1,4-Phenylene)- bis(5,5-dimethyl-1,3,2-dioxaborinane)]

[5565-36-6], C16H24B2O4, F.W. 301.99, White to cream cryst powder, m.p. 231-233ø, BRN 2952607, MDL MFCD01075726

80 www.alfa.com Arylboronic Esters Stock # Description Standard Selling Sizes H51707 1,4-Benzenediboronic acid bis(pinacol) ester, 97% 1g [2,2'-(1,4-Phenylene)- 5g bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)]

C18H28B2O4, F.W. 330.03, Pale brown solid, MDL MFCD08276852 H28205 3-(Benzylaminocarbonyl)benzeneboronic acid pinacol 1g ester, 97% 5g [3-(Benzylaminocarbonyl)phenylboronic acid pinacol ester, N-Benzyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- benzamide]

C20H24BNO3, F.W. 337.22, White powder, m.p. 155-158ø, MDL MFCD09266183 H29271 4-(Benzylaminocarbonyl)benzeneboronic acid pinacol 1g ester, 97% 5g [4-(Benzylaminocarbonyl)phenylboronic acid pinacol ester, N-Benzyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- benzamide]

C20H24BNO3, F.W. 337.22, White powder, m.p. 109-113ø, MDL MFCD09266184

H28682 3-Benzylbenzeneboronic acid pinacol ester, 97% 1g Arylboronic [3-Benzylphenylboronic acid pinacol ester, 2-(3-Benzyl- 5g phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane]

C19H23BO2, F.W. 294.20, White cryst powder, m.p. 67-70ø, MDL MFCD09266179

H28156 4-Benzylbenzeneboronic acid pinacol ester, 97% 1g [4-Benzylphenylboronic acid pinacol ester, 2-(4-Benzyl- 5g phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane] Esters

[911708-01-5], C19H23BO2, F.W. 294.20, White powder, m.p. 90-93ø, MDL MFCD09266180

H52630 4-Benzyloxybenzeneboronic acid pinacol ester, 98% 1g [4-Benzyloxyphenylboronic acid pinacol ester] 5g

[754226-40-9], C19H23BO3, F.W. 310.19, White solid, m.p. 88ø, MDL MFCD04974107

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H52282 4-(Benzyloxycarbamoyl)benzeneboronic acid pinacol 1g ester, 95% 5g [N-Benzyloxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- benzamide]

C20H24BNO4, F.W. 353.22, White to pale brown solid H51708 4-Benzyloxy-3-formylbenzeneboronic acid pinacol ester 1g È 5g [2-Benzyloxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- benzaldehyde]

C20H23BO4, F.W. 338.21, Brown solid, MDL MFCD16294499

H52597 4-(3-Benzylureido)benzeneboronic acid pinacol ester, 250mg 97% 1g [4-(3-Benzylureido)phenylboronic acid pinacol ester, 1-Benzyl-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- phenyl]urea]

[874290-98-9], C20H25BN2O3, F.W. 352.24, White solid, m.p. 204-207ø, MDL MFCD08689513

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H32320 Biphenyl-2-boronic acid pinacol ester, 97% 1g

[914675-52-8], C18H21BO2, F.W. 280.17, White crystalline powder, 5g m.p. 76-79ø, MDL MFCD14636459 25g

L17605 Biphenyl-4,4'-diboronic acid 1g bis(neopentyl glycol) ester, 98% 5g [Biphenyl-4,4'-diboronic acid bis-2,2-dimethyl- trimethylene ester]

[5487-93-4], C22H28B2O4, F.W. 378.09, White to pale cream cryst powder, m.p. 242-247ø, BRN 2952067, MDL MFCD01318103

Bulk and Specialty Sizes Available 81 Arylboronic Esters Stock # Description Standard Selling Sizes H51956 Biphenyl-4,4'-diboronic acid bis(pinacol) 1g ester, 95% 5g

[4,4,5,5-Tetramethyl-2-[4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)[4-biphenylyl- ]-1,3,2-dioxaborolane]

[207611-87-8], C24H32B2O4, F.W. 406.14, Solid, MDL MFCD08669545 H51942 4-[Bis(2-methoxyethyl)aminomethyl- 1g ]benzeneboronic acid pinacol ester, 95% 5g

[Bis(2-methoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzylamine]

C19H32BNO4, F.W. 349.28, Pale yellow liquid, MDL MFCD16294545, Note: Product of Advanced Molecular Technologies Pty Ltd. H32745 250mg 1g Esters

(R)-(+)-2,2'-Bis(methoxymethoxy)-1,1'-binaphthyl-3,3'-diboronic acid pinacol ester, 97%

[260442-17-9], C36H44B2O8, F.W. 626.36, Solid, m.p. 193-195ø, MDL MFCD16294496 Arylboronic H32005 250mg 1g

(S)-(-)-2,2'-Bis(methoxymethoxy)-1,1'-binaphthyl-3,3'-diboronic acid pinacol ester, 97%

[260441-99-4], C36H44B2O8, F.W. 626.36, Solid, m.p. 193-195ø, MDL MFCD16294496 H26075 2,4-Bis(trifluoromethyl)benzeneboronic acid pinacol ester, 1g 96%

C14H15BF6O2, F.W. 340.08, Colorless liquid, b.p. 79-81ø/1mm, MDL MFCD09953467

H51709 3-[2-(Boc-amino)acetamido]benzeneboronic 1g acid pinacol ester, 97% 5g [[3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl- carbamoylmethyl]carbamic acid tert-butyl ester]

C19H29BN2O5, F.W. 376.26, White solid, MDL MFCD16294500 H29020 2-(Boc-amino)benzeneboronic acid pinacol ester, 97% 1g [2-(tert-Butoxycarbonylamino)phenylboronic acid pinacol ester, 5g tert-Butyl-N-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl- ]carbamate]

[159624-15-4], C17H26BNO4, F.W. 319.20, Nearly white crystalline powder, m.p. 98-100ø, MDL MFCD03411943 H27026 3-(Boc-amino)benzeneboronic acid pinacol ester, 1g 97% 5g [3-(Boc-amino)phenylboronic acid pinacol ester, tert-Butyl N-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl- ]carbamate]

[330793-09-4], C17H26BNO4, F.W. 319.20, White powder, m.p. 118-120ø, MDL MFCD03789256

82 www.alfa.com Arylboronic Esters Stock # Description Standard Selling Sizes L19653 4-(Boc-amino)benzeneboronic acid pinacol ester, 1g 97% 5g [4-(Boc-amino)phenylboronic acid pinacol ester, 4-(tert-Butoxycarbonylamino)benzeneboronic acid pinacol ester]

[330793-01-6], C17H26BNO4, F.W. 319.21, White to pale brown solid, m.p. 169-170ø, MDL MFCD02179439 H28289 4-(N-Boc-phenylaminomethyl)benzeneboronic acid 1g pinacol ester, 97% 5g [[4-(N-Boc-phenylaminomethyl)phenyl]boronic acid pinacol ester, N-Boc-N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- ]benzyl]aniline]

C24H32BNO4, F.W. 409.33, White powder, MDL MFCD09953500 H29275 3-(4-Boc-1-piperazinylcarbonyl)benzeneboronic 1g acid pinacol ester, 96% 5g [tert-Butyl 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- benzoyl]piperazine-1-carboxylate] Arylboronic C22H33BN2O5, F.W. 416.32, White powder, MDL MFCD09266185 H28905 4-(4-Boc-1-piperazinylcarbonyl)benzeneboronic 1g acid pinacol ester, 97% 5g [tert-Butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- benzoyl]piperazine-1-carboxylate] Esters [864754-13-2], C22H33BN2O5, F.W. 416.32, White powder, MDL MFCD08706021 H51939 3-(4-Boc-1-piperazinylmethyl)benzeneboronic 1g acid pinacol ester, 95% 5g

C22H35BN2O4, F.W. 402.34, Solid, MDL MFCD16294542, Note: Product of Advanced Molecular Technologies Pty Ltd.

H51743 4-(4-Boc-1-piperazinylmethyl)benzeneboronic 1g acid pinacol ester, 95% 5g

C22H35BN2O4, F.W. 402.34, Powder, MDL MFCD16294502

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L17796 3-Bromobenzeneboronic acid N-methyldiethanolamine ester, 1g 98% 5g

[374538-00-8], C11H15BBrNO2, F.W. 283.96, m.p. 128-129ø, MDL MFCD02093962

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L17775 4-Bromobenzeneboronic acid N-methyldiethanolamine ester, 250mg 98% 1g

[133468-58-3], C11H15BBrNO2, F.W. 283.96, White to cream powder, m.p. 146-149ø, BRN 3320262, MDL MFCD02093957

H:H315-H319-H335, P:P280g-P305+P351+P338 Protected boronic acid derivative enabling selective reaction of the bromo substituent with organometallic (e.g. lithium) derivatives: J. Org. Chem., 54, 4734 (1989). L17455 4-Bromobenzeneboronic acid neopentyl glycol ester, 98+% 1g [2-(4-Bromophenyl)-5,5-dimethyl-1,3,2-dioxaborinane] 5g

[183677-71-6], C11H14BBrO2, F.W. 268.95, White solid, m.p. 109-111ø, MDL MFCD01318105 H53246 4-(2-Bromoethoxy)benzeneboronic acid pinacol ester, 250mg 98% 1g [4-(2-Bromoethoxy)phenylboronic acid pinacol ester]

[913836-27-8], C14H20BBrO3, F.W. 327.03, White solid, m.p. 90-92ø, MDL MFCD09027285

H53287 2-(2-Bromoethyl)benzeneboronic acid pinacol ester, 95% 250mg [2-(2-Bromoethyl)phenylboronic acid pinacol ester]

[850567-53-2], C14H20BBrO2, F.W. 311.03, Colorless liquid, MDL MFCD06659922

Bulk and Specialty Sizes Available 83 Arylboronic Esters Stock # Description Standard Selling Sizes H51718 3-Bromo-5-(methoxycarbonyl)benzeneboronic acid 250mg pinacol ester, 97% 1g [Methyl 3-bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- benzoate]

[1025718-78-8], C14H18BBrO4, F.W. 341.01, Off-white crystalline solid, m.p. 98-102ø, MDL MFCD12405334

H53309 2-(Bromomethyl)benzeneboronic acid neopentyl glycol ester, 250mg 95% 1g [2-(Bromomethyl)phenylboronic acid neopentyl glycol ester, 2-(Bromomethyl)phenylboronic acid mono(2,2-dimethylpropyl) ester]

[441011-76-3], C12H16BBrO2, F.W. 282.97, Yellow-orange liquid, MDL MFCD04039022 H52701 3-(Bromomethyl)benzeneboronic acid neopentyl glycol 250mg ester, 95% 1g [3-(Bromomethyl)phenylboronic acid neopentyl glycol ester]

[143805-78-1], C12H16BBrO2, F.W. 282.97, White to off-white solid, m.p. 86-90ø, MDL MFCD04973735 H53217 2-(Bromomethyl)benzeneboronic acid pinacol ester, 98% 250mg [2-(Bromomethyl)phenylboronic acid pinacol ester, 2-[2-(Bromomethyl)- 1g phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane]

[377780-72-8], C13H18BBrO2, F.W. 297.00, White to cream solid,

Esters m.p. 78-80ø, MDL MFCD01632210

L19954 4-(Bromomethyl)benzeneboronic acid pinacol ester, 95% 1g [4-(Bromomethyl)phenylboronic acid pinacol ester, 5g 2-[(4-Bromomethyl)phenyl- ]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane]

[138500-85-3], C13H18BBrO2, F.W. 296.99, White solid,

Arylboronic m.p. 83-85ø, UN3261, BRN 7921808, MDL MFCD02179493 H:H314, P:P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501a H52599 2-Bromomethyl-4-fluorobenzeneboronic acid neopentyl glycol 250mg ester, 95% 1g [2-Bromomethyl-4-fluorophenylboronic acid neopentyl glycol ester]

[673456-16-1], C12H15BBrFO2, F.W. 300.96, White solid, m.p. 32-34ø, MDL MFCD06659913

H53283 2-Bromomethyl-4-fluorobenzeneboronic acid pinacol ester, 250mg 95% 1g [2-Bromomethyl-4-fluorophenylboronic acid pinacol ester]

[850567-57-6], C13H17BBrFO2, F.W. 314.99, White solid, m.p. 47-48ø, MDL MFCD06659927

H51713 3-Bromo-5-(trifluoromethyl)benzeneboronic acid pinacol 250mg ester, 97% 1g [2-[3-Bromo-5-(trifluoromethyl)phenyl- ]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane]

[479411-92-2], C13H15BBrF3O2, F.W. 350.97, White crystalline solid, m.p. 50-52ø, MDL MFCD12405333

H53357 4-(tert-Butoxycarbonyl)benzeneboronic acid pinacol 1g ester, 97% 5g [4-(tert-Butoxycarbonyl)phenylboronic acid pinacol ester, tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- benzoate]

[850568-72-8], C17H25BO4, F.W. 304.19, White solid, m.p. 128-132ø, MDL MFCD03453055 H52957 2-(tert-Butoxycarboxy)benzeneboronic acid pinacol ester, 95% 250mg [2-(tert-Butoxycarboxyphenyl)boronic acid pinacol ester] 1g

[480424-71-3], C17H25BO5, F.W. 320.19, White solid, m.p. 71-73ø, MDL MFCD03453657

84 www.alfa.com Arylboronic Esters Stock # Description Standard Selling Sizes H51693 6-n-Butoxynaphthalene-2-boronic acid pinacol 1g ester, 97% 5g

[2-(6-n-Butoxy-2-naphthyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane]

C20H27BO3, F.W. 326.24, Pale yellow solid, MDL MFCD16294497 H51669 4-(tert-Butylaminomethyl)benzeneboronic acid 1g pinacol ester, 97% 5g [tert-Butyl[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- benzyl]amine]

C17H28BNO2, F.W. 289.22, White solid, MDL MFCD12546203 H51122 4-(tert-Butyliminomethyl)benzeneboronic acid pinacol 1g ester 5g [4-tert-Butyl- 25g iminomethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- benzene]

C17H26BNO2, F.W. 287.20, MDL MFCD11113039 Arylboronic H52718 4-(3-n-Butylureido)benzeneboronic acid pinacol 250mg ester, 97% 1g [4-(3-n-Butylureido)phenylboronic acid pinacol ester,

1-n-Butyl-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]urea] Esters

[850567-59-8], C17H27BN2O3, F.W. 318.22, White solid, m.p. 207-209ø, MDL MFCD07363843 H52645 4-(3-tert-Butylureido)benzeneboronic acid pinacol 250mg ester, 98% 1g [4-(3-tert-Butyllureido)phenylboronic acid pinacol ester,

1-tert-Butyl-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]urea]

[874297-78-6], C17H27BN2O3, F.W. 318.22, White solid, m.p. 220-222ø, MDL MFCD08689518 H52316 4-Carbamoyl-3,5-difluorobenzeneboronic acid pinacol 250mg ester, 96% 1g [2,6-Difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- benzamide]

C13H16BF2NO3, F.W. 283.08, Solid H52332 4-Carbamoyl-3-fluorobenzeneboronic acid pinacol ester, 250mg 96% 1g [2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- benzamide]

C13H17BFNO3, F.W. 265.09, Solid H51948 9-Carbazolylbenzeneboronic acid pinacol ester, 95% 1g [9-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl- 5g ]carbazole]

C24H24BNO2, F.W. 369.27, Solid, MDL MFCD16294549

H52285 4-(9-Carbazolylmethyl)benzeneboronic acid pinacol 1g ester, 95% 5g [9-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl- ]-9H-carbazole]

C25H26BNO2, F.W. 383.30, Pale brown solid

H26825 4-Carboxybenzeneboronic acid pinacol ester, 97% 1g [4-Carboxylphenylboronic acid pinacol ester, 5g 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid]

[180516-87-4], C13H17BO4, F.W. 248.08, White cryst powder, m.p. 227-231ø, MDL MFCD01863710

Bulk and Specialty Sizes Available 85 Arylboronic Esters Stock # Description Standard Selling Sizes H53190 4-Carboxy-3-fluorobenzeneboronic acid pinacol ester, 98% 250mg [4-Carboxy-3-fluorophenylboronic acid pinacol ester, 1g 2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid]

[867256-77-7], C13H16BFO4, F.W. 266.08, White solid, m.p. 289-295ø, MDL MFCD09027284 H52877 3-Carboxy-5-nitrobenzeneboronic acid pinacol ester, 97% 250mg [3-Carboxy-5-nitrophenylboronic acid pinacol ester] 1g

[377780-80-8], C13H16BNO6, F.W. 293.08, White to off-white solid, m.p. 246-250ø, MDL MFCD03411932

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H51919 4'-Chlorobenzanilide-4-boronic acid pinacol 1g ester, 95% 5g

[N-(4-Chlorophenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide]

C19H21BClNO3, F.W. 357.64, White solid, MDL MFCD16294537 H53022 4-Chloro-3-nitrobenzeneboronic acid pinacol ester, 98% 250mg [4-Chloro-3-nitrophenylboronic acid pinacol ester] 1g

[913836-26-7], C12H15BClNO4, F.W. 283.52, Yellow solid, Esters m.p. 56-58ø, MDL MFCD08235086

H51915 4-(4-Chlorophenylethynyl)benzeneboronic acid 1g pinacol ester, 95% 5g [2-[4-(4-Chlorophenylethynyl)phenyl- ]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane] Arylboronic C20H20BClO2, F.W. 338.64, Solid, MDL MFCD16294534 H51712 3-Chloro-5-(trifluoromethyl)benzeneboronic acid pinacol 250mg ester, 97% 1g [2-[3-Chloro-5-(trifluoromethyl)phenyl- ]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane]

[942069-65-0], C13H15BClF3O2, F.W. 306.52, Pale yellow oil, MDL MFCD11856039

H27469 2-Cyanobenzeneboronic acid pinacol ester, 98% 1g [2-Cyanophenylboronic acid pinacol ester, 5g 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile] 25g

[214360-48-2], C13H16BNO2, F.W. 229.08, White to pale yellow powder, m.p. 88-90ø, MDL MFCD04038747

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H28208 4-Cyanobenzeneboronic acid pinacol ester, 97% 1g [4-Cyanophenylboronic acid pinacol ester, 5g 2-(4-Cyanophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane]

[171364-82-2], C13H16BNO2, F.W. 229.08, White powder, MDL MFCD03093897

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52547 2-Cyanobenzeneboronic acid 1,3-propanediol ester 250mg [2-(1,3,2-Dioxaborinan-2-yl)benzonitrile] 1g

[172732-52-4], C10H10BNO2, F.W. 187.00, Off-white solid, m.p. 42-45ø, MDL MFCD04039012

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H51130 4-(2-Cyano-3-ethoxy-3-oxo-1-propen-1-yl)- 1g benzeneboronic acid pinacol ester 5g [Ethyl 25g à-cyano-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- cinnamate]

C18H22BNO4, F.W. 327.18, Colorless to pale yellow solid, MDL MFCD11113044

H:H302, P:P280f

86 www.alfa.com Arylboronic Esters Stock # Description Standard Selling Sizes H53255 2-(Cyanomethyl)benzeneboronic acid pinacol ester, 97% 250mg

[325141-71-7], C14H18BNO2, F.W. 243.11, Colorless liquid, 1g MDL MFCD02179457

H:H302, P:P264-P270-P301+P312-P330-P501a

H52618 3-(Cyanomethyl)benzeneboronic acid pinacol ester, 96% 250mg

[396131-82-1], C14H18BNO2, F.W. 243.11, White solid, 1g m.p. 44-48ø, MDL MFCD02179458

H:H302, P:P264-P270-P301+P312-P330-P501a

L19956 4-(Cyanomethyl)benzeneboronic acid pinacol ester, 95% 1g [4-(Cyanomethyl)phenylboronic acid pinacol cyclic ester, 5g 2-[(4-Cyanomethyl)phenyl- ]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane]

[138500-86-4], C14H18BNO2, F.W. 243.12, White cryst powder, m.p. 74-78ø, MDL MFCD02179459

H:H302, P:P280f H51127 4-(Cyclohexyliminomethyl)benzeneboronic acid 1g Arylboronic pinacol ester 5g [4-Cyclohexyl- 25g iminomethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- benzene]

C19H28BNO2, F.W. 313.24, Colorless to pale yellow solid, MDL MFCD11113042 Esters H53169 3-(Cyclopentylcarbamoyl)benzeneboronic acid 250mg neopentyl glycol ester, 95% 1g

[N-Cyclopentyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide]

[850567-45-2], C17H24BNO3, F.W. 301.19, Off-white solid, m.p. 158-160ø, MDL MFCD06659914 H52269 4-(N-Cyclopentylcarbamoyl)benzeneboronic acid 1g pinacol ester, 95% 5g

[N-Cyclopentyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide]

[933987-10-1], C18H26BNO3, F.W. 315.22, White to off-white solid, MDL MFCD16660857 H53009 4-(3-Cyclopentylureido)benzeneboronic acid 250mg pinacol ester, 95% 1g

[1-Cyclopentyl-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]urea]

[874297-80-0], C18H27BN2O3, F.W. 330.23, White solid, MDL MFCD09027290 H52589 4-(3-Cyclopropylureido)benzeneboronic acid pinacol 250mg ester, 97% 1g

[1-Cyclopropyl-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]urea]

[874297-79-7], C16H23BN2O3, F.W. 302.18, White solid, m.p. 227-229ø, MDL MFCD08689493 H52661 4-(3-Diethylureido)benzeneboronic acid pinacol 250mg ester, 98% 1g

[1,1-Diethyl-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]urea]

[874290-94-5], C17H27BN2O3, F.W. 318.22, White solid, m.p. 184-186ø, MDL MFCD08689494

Bulk and Specialty Sizes Available 87 Arylboronic Esters Stock # Description Standard Selling Sizes L17266 3,5-Difluorobenzeneboronic acid neopentyl glycol ester, 98+% 1g [2-(3,5-Difluorophenyl)-5,5-dimethyl-1,3,2-dioxaborinane] 5g

[216393-57-6], C11H13BF2O2, F.W. 226.03, White to pale yellow solid, m.p. 43-45ø, MDL MFCD01318139

H52270 4-(N-[2-(Dimethylamino)ethyl]carbamoyl)- 1g benzeneboronic acid pinacol ester, 95% 5g [N-[2-(Dimethylamino)ethyl- ]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-y)- benzamide]

[832114-11-1], C17H27BN2O3, F.W. 318.22, White to pale brown solid, MDL MFCD05864307 H51950 9,9-Dimethylfluorene-2-boronic acid pinacol ester, 95% 1g 5g

[2-(9,9-Dimethyl-2-fluorenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane]

[569343-09-5], C21H25BO2, F.W. 320.24, Solid, MDL MFCD08704229 H51954 9,9-Dimethylfluorene-2,7-diboronic acid 1g bis(pinacol) ester, 95% 5g

[325129-69-9], C27H36B2O4, F.W. 446.20, Solid, Esters MDL MFCD08704230

H27949 3-(N,O-Dimethylhydroxylaminocarbonyl)- 1g benzeneboronic acid pinacol ester, 97+% 5g [[3-(N,O-Dimethyl hydroxylaminocarbonyl)phenyl] boronic acid pinacol ester, N,O-Dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- Arylboronic benzohydroxamate]

C15H22BNO4, F.W. 291.16, White powder, m.p. 69-72ø, MDL MFCD09258775 H28341 4-(N,O-Dimethylhydroxylaminocarbonyl)- 1g benzeneboronic acid pinacol ester, 97% 5g [[4-(N,O-Dimethyl hydroxylaminocarbonyl)phenyl] boronic acid pinacol ester, N,O-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- benzohydroxamate]

C15H22BNO4, F.W. 291.16, White powder, m.p. 96-99ø, MDL MFCD09953501 H51124 1g 5g

4-(1,3-Dimethyl-2,4,6-trioxohexahydropyrimidin-5-ylidenemethyl)benzeneboronic acid pinacol ester [1,3-Dimethyl-5-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl- idene]pyrimidine-2,4,6-trione]

C19H23BN2O5, F.W. 370.21, MDL MFCD11113040 H53258 4-(3,3-Dimethylureido)benzeneboronic acid pinacol 250mg ester, 95% 1g

[1,1-Dimethyl-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]urea]

[874290-93-4], C15H23BN2O3, F.W. 290.17, White solid, m.p. 151-155ø, MDL MFCD08689520 H51953 9,9-Di-n-octylfluorene-2-boronic acid pinacol ester, 95% 1g 5g

[2-(9,9-Di-n-octyl-2-fluorenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane]

C35H53BO2, F.W. 516.61, Solid, MDL MFCD16294553

88 www.alfa.com Arylboronic Esters Stock # Description Standard Selling Sizes H51955 9,9-Di-n-octylfluorene-2,7-diboronic acid 1g bis(pinacol) ester, 95% 5g

C41H64B2O4, F.W. 642.58, Solid, MDL MFCD16294554

H51897 Diphenylacetylene-4,4'-diboronic acid 1g bis(pinacol) ester, 95% 5g

[4,4'-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)diphenylacetylene]

[849681-64-7], C26H32B2O4, F.W. 430.16, Solid, MDL MFCD16294524 H51946 4-(Diphenylamino)benzeneboronic acid pinacol ester, 95% 1g [Diphenyl[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl- 5g ]amine]

C24H26BNO2, F.W. 371.29, Solid, MDL MFCD13195770

H52284 4-(Diphenylaminomethyl)benzeneboronic acid pinacol 1g ester, 95% 5g [N,N-Diphenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- benzylamine] Arylboronic

C25H28BNO2, F.W. 385.31, Pale brown solid H30941 2-(Ethoxycarbonyl)benzeneboronic acid pinacol ester, 97% 1g [2-(Ethoxycarbonyl)phenylboronic acid pinacol ester, 5g 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid ethyl ester]

[269409-99-6], C15H21BO4, F.W. 276.14, Yellow cryst powder, m.p. 57-62ø, MDL MFCD03453660 Esters

H52897 2-(Ethoxycarbonyl)benzeneboronic acid 1,3-propanediol ester, 250mg 95% 1g [Ethyl 2-boronobenzoate 1,3-propanediol ester]

[850567-60-1], C12H15BO4, F.W. 234.06, Colorless liquid, MDL MFCD06659932

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H28086 4-(3-Ethoxycarbonyl-1-piperidinylcarbonyl)- 1g benzeneboronic acid pinacol ester, 98% 5g [Ethyl 1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoyl- ]piperidine-3-carboxylate]

[850411-14-2], C21H30BNO5, F.W. 387.28, White powder, MDL MFCD06657751

H52953 4-(3-Ethylureido)benzeneboronic acid pinacol ester, 250mg 98% 1g [1-Ethyl-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- phenyl]urea]

[874291-00-6], C15H23BN2O3, F.W. 290.17, Off-white solid, m.p. 194-196ø, MDL MFCD08689523 H51902 3-Ethynylbenzeneboronic acid pinacol ester, 95% 1g [2-(3-Ethynylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane] 5g

C14H17BO2, F.W. 228.10, Solid, MDL MFCD16294529

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H51745 4-Ethynylbenzeneboronic acid pinacol ester, 95% 1g

[1034287-04-1], C14H17BO2, F.W. 228.10, White to cream solid, 5g MDL MFCD16294504

H51947 Fluorene-2-boronic acid pinacol ester, 95% 1g [2-(2-Fluorenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane] 5g

C19H21BO2, F.W. 292.18, Solid, MDL MFCD16294548

H51951 Fluoren-9-one-2-boronic acid pinacol ester, 95% 1g [2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)fluoren-9-one] 5g

C19H19BO3, F.W. 306.17, Solid, MDL MFCD16294551

Bulk and Specialty Sizes Available 89 Arylboronic Esters Stock # Description Standard Selling Sizes H52310 4-Fluoro-3-formylbenzeneboronic acid pinacol ester, 96% 250mg [2-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde] 1g

C13H16BFO3, F.W. 250.07, Solid

H53014 3-(4-Fluorophenylcarbamoyl)benzeneboronic acid 250mg pinacol ester, 95% 1g

[850567-58-7], C19H21BFNO3, F.W. 341.19, Grey solid, m.p. 166-168ø, MDL MFCD06659930

H52488 2-Formylbenzeneboronic acid neopentyl glycol ester, 95% 250mg [2-Boronobenzaldehyde neopentyl glycol ester, 2-Formylphenylboronic 1g acid neopentyl glycol ester]

[95752-86-6], C12H15BO3, F.W. 218.06, Cream liquid, MDL MFCD04039025

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H28846 2-Formylbenzeneboronic acid pinacol ester, 97% È 1g [2-Formylphenylboronic acid pinacol ester, 5g 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde]

[380151-85-9], C13H17BO3, F.W. 232.08, Colorless to yellow liquid, d. 1.053, Ë 1.514, MDL MFCD07363841

Esters H:H315-H319, P:P280-P305+P351+P338-P302+P352-P321-P362-P332+P313 H28599 3-(Furfurylaminocarbonyl)benzeneboronic acid 1g pinacol ester, 97% 5g [3-(Furfurylaminocarbonyl)phenylboronic acid pinacol ester,

N-Furfuryl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide] Arylboronic C18H22BNO4, F.W. 327.18, White to cream powder, MDL MFCD09266173 H29236 4-(Furfurylaminocarbonyl)benzeneboronic acid 1g pinacol ester, 97% 5g [4-(Furfurylaminocarbonyl)phenylboronic acid pinacol ester,

N-Furfuryl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide]

C18H22BNO4, F.W. 327.18, White to pale cream powder, m.p. 107-111ø, MDL MFCD09266168 H51121 4-(Furfuryliminomethyl)benzeneboronic acid 1g pinacol ester, 97% 5g [1-[(2-Furylmethyl)iminomethyl- 25g ]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene]

C18H22BNO3, F.W. 311.18, Powder, MDL MFCD11113038 H53096 4-(3-Furfurylureido)benzeneboronic acid pinacol 250mg ester, 98% 1g [1-(2-Furyl-

methyl)-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]urea]

[874297-85-5], C18H23BN2O4, F.W. 342.20, White solid, MDL MFCD09027292 H51744 4-(Hexamethyleneiminomethyl)benzeneboronic acid 1g pinacol ester, 95% 5g [4-(1-Azepanylmethyl)benzeneboronic acid pinacol ester, 4-(1-Homopiperidinylmethyl)benzeneboronic acid pinacol ester]

C19H30BNO2, F.W. 315.26, Solid, MDL MFCD16294503

H:H315-H319-H335, P:P280g-P305+P351+P338 H52712 4-(Hydrazinocarbonyl)benzeneboronic acid pinacol ester, 250mg 98% 1g [4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzohydrazide]

[276694-16-7], C13H19BN2O3, F.W. 262.12, White solid, MDL MFCD07783860

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

90 www.alfa.com Arylboronic Esters Stock # Description Standard Selling Sizes H27836 4-Hydroxybenzeneboronic acid pinacol ester, 97% 1g [4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol, 5g 4-Hydroxyphenylboronic acid pinacol ester]

[269409-70-3], C12H17BO3, F.W. 220.07, White to pale brown powder, m.p. 114-117ø, MDL MFCD02093756

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H51941 4-[2-Hydroxyethyl(methyl)amino]benzeneboronic 1g acid pinacol ester, 95% 5g [2-(Methyl[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- benzyl]amino)ethanol]

C16H26BNO3, F.W. 291.20, Solid, MDL MFCD16294544, Note: Product of Advanced Molecular Technologies Pty Ltd. H51126 3-(Hydroxymethyl)benzeneboronic acid pinacol ester 1g [3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl alcohol] 5g

[443776-76-9], C13H19BO3, F.W. 234.10, White solid, 25g MDL MFCD09266196

H51123 4-(Hydroxymethyl)benzeneboronic acid pinacol ester 1g Arylboronic [4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl alcohol] 5g

[302348-51-2], C13H19BO3, F.W. 234.10, MDL MFCD09837617 25g

H51934 4-([2-(Hydroxymethyl)phenyl]dimethylsilyl)- 1g

benzeneboronic acid pinacol ester, 95% 5g Esters [2-(Dimethyl-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- phenyl]silyl)benzyl alcohol]

C21H29BO3Si, F.W. 368.35, Solid, MDL MFCD16294541, Note: Product of Advanced Molecular Technologies Pty Ltd. H51746 4-(3-Hydroxypropylcarbamoyl)benzeneboronic 1g acid pinacol ester, 95% 5g [4-(3-Hydroxy-n-propylaminocarbonyl)phenylboronic acid pinacol ester]

C16H24BNO4, F.W. 305.18, White to pale brown solid, MDL MFCD16294505 H51901 4-(3-Hydroxy-1-propynyl)benzeneboronic acid pinacol 1g ester, 95% 5g [3-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl- ]-2-propyn-1-ol]

C15H19BO3, F.W. 258.12, Solid, MDL MFCD16294528 H28798 4-[Hydroxy(2-thiazolyl)methyl]benzeneboronic acid 1g pinacol ester, 97% 5g

[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-à-(2-thiazolyl)benzyl alcohol, [à-(2-Thiazolyl)-4-(hydroxymethyl)]benzeneboronic acid pinacol ester]

[1073371-73-9], C16H20BNO3S, F.W. 317.21, White powder, m.p. 147-150ø, MDL MFCD09953504 H51671 4-[3-(1-Imidazolyl)propylaminomethyl]benzeneboronic 1g acid pinacol ester 5g [4-[3-(1-Imidazolyl)propylaminomethayl]phenylboronic acid pinacol ester, N-[3-(1-Imidazolyl)propyl)- ]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzylamine]

C19H28BN3O2, F.W. 341.26, Solid, MDL MFCD12546046

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H28115 3-Iodobenzeneboronic acid pinacol ester, 97% ß 1g [3-Iodophenylboronic acid pinacol ester, 5g 2-(3-Iodophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane]

[408492-28-4], C12H16BIO2, F.W. 329.97, White to cream powder, m.p. 70-72ø, MDL MFCD09953498

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Bulk and Specialty Sizes Available 91 Arylboronic Esters Stock # Description Standard Selling Sizes H28190 4-Iodobenzeneboronic acid pinacol ester, 97% ß 1g [4-Iodophenylboronic acid pinacol ester, 5g 2-(4-Iodophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane]

[73852-88-7], C12H16BIO2, F.W. 329.97, White to cream cryst powder, m.p. 102-104ø, MDL MFCD09953499

H52724 4-(3-Isobutylureido)benzeneboronic acid pinacol 250mg ester, 95% 1g

[1-Isobutyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea]

[874291-03-9], C17H27BN2O3, F.W. 318.22, White solid, MDL MFCD09027289 H53044 3-Isocyanatobenzeneboronic acid pinacol ester, 97% 250mg

[787591-43-9], C13H16BNO3, F.W. 245.08, White solid, 1g m.p. 32-36ø, MDL MFCD06659827

H53003 4-Isocyanatobenzeneboronic acid pinacol ester, 95% 250mg

[380430-64-8], C13H16BNO3, F.W. 245.08, Yellow solid, 1g m.p. 162-168ø, MDL MFCD03411942 Esters H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

L17670 3-Isopropylbenzeneboronic acid ethylene glycol ester, 96% 250mg [3-Cumylboronic acid ethylene glycol cyclic ester, [2-(3-Isopropyl)- 1g phenyl]-1,3,2-dioxaborolane]

[374537-96-9], C11H15BO2, F.W. 190.05, Colorless liquid, Arylboronic b.p. 104ø/0.8mm, Ë 1.5140, MDL MFCD02093946 H53146 4-(3-Isopropylureido)benzeneboronic acid pinacol 250mg ester, 98% 1g

[1-Isopropyl-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]urea]

[874291-02-8], C16H25BN2O3, F.W. 304.20, White solid, m.p. 234-236ø, MDL MFCD08689517 H52280 4-(N-Maleimidomethyl)benzeneboronic acid pinacol 1g ester, 95% 5g [N-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl- ]maleimide]

C17H20BNO4, F.W. 313.16, Pale brown solid H52673 2-Methoxybenzeneboronic acid pinacol ester, 97% 1g

[190788-60-4], C13H19BO3, F.W. 234.10, White solid, m.p. 78-80ø, 5g MDL MFCD05863916

H53124 2-Methoxybenzeneboronic acid 1,3-propanediol ester, 97% 250mg

[141522-26-1], C10H13BO3, F.W. 192.02, Off-white solid, m.p. 56-60ø, 1g MDL MFCD06659934

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H51129 3-(4-Methoxybenzylidineamino)benzeneboronic 1g acid pinacol ester 5g [N-(4-Methoxybenzyl- 25g idene)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- aniline]

[380151-91-7], C20H24BNO3, F.W. 337.22, Pale yellow solid, MDL MFCD11113043

92 www.alfa.com Arylboronic Esters Stock # Description Standard Selling Sizes H52887 4-[3-(4-Methoxybenzyl)- 250mg ureido]benzeneboronic acid pinacol ester, 1g 98%

[1-(4-Methoxybenzyl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea]

[874298-21-2], C21H27BN2O4, F.W. 382.27, White solid, MDL MFCD09027293 H51907 4'-Methoxybiphenyl-4-boronic acid pinacol ester, 1g 95% 5g [2-(4'-Methoxy-4-biphenyl- yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 4-(4-Methoxyphenyl)benzeneboronic acid pinacol ester]

C19H23BO3, F.W. 310.20, Solid, MDL MFCD16294530 H28942 4-(Methoxycarbonyl)benzeneboronic acid pinacol ester, 1g 97% 5g [4-(Methoxycarbonyl)phenylboronic acid pinacol ester, 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid Arylboronic methyl ester]

[171364-80-0], C14H19BO4, F.W. 262.11, White cryst powder, m.p. 77-81ø, MDL MFCD02179438 H51916 3'-(Methoxycarbonyl)biphenyl-4-boronic acid 1g pinacol ester, 95% 5g [4'-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)- biphenyl-3-carboxylic acid methyl ester, 4-(3-Methoxycarbonylphenyl)benzeneboronic acid pinacol Esters ester]

C20H23BO4, F.W. 338.21, Solid, MDL MFCD16294535 H53331 4-Methoxycarbonyl-3-chlorobenzeneboronic acid pinacol 250mg ester, 98% 1g [3-Chloro-4-methoxycarbonylphenylboronic acid pinacol ester]

[334018-52-9], C14H18BClO4, F.W. 296.56, Off-white solid, m.p. 48-51ø, MDL MFCD06659928

H51900 4-[4-(Methoxycarbonyl)phenylethynyl- 1g ]benzeneboronic acid pinacol ester, 95% 5g

[4-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenylethynyl]benzoic acid methyl ester]

C22H23BO4, F.W. 362.23, Solid, MDL MFCD16294527 H28340 3-(2-Methoxyethylaminocarbonyl)benzeneboronic 1g acid pinacol ester, 97% 5g [3-(2-Methoxyethylaminocarbonyl)phenylboronic acid pinacol ester,

N-(2-Methoxyethyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide]

C16H24BNO4, F.W. 305.18, White powder, m.p. 93-98ø, MDL MFCD09266187 H27945 4-(2-Methoxyethylaminocarbonyl)benzeneboronic 1g acid pinacol ester, 97% 5g

[N-(2-Methoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide]

C16H24BNO4, F.W. 305.18, White powder, m.p. 73-76ø, MDL MFCD09266188 H53213 4-(3-Methoxy-3-methylureido)benzeneboronic acid 250mg pinacol ester, 98%

[1-Methoxy-1-methyl-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]urea]

[874297-84-4], C15H23BN2O4, F.W. 306.17, White solid, m.p. 167-170ø, MDL MFCD09027291

Bulk and Specialty Sizes Available 93 Arylboronic Esters Stock # Description Standard Selling Sizes H51914 4-(4-Methoxyphenylethynyl)benzeneboronic 1g acid pinacol ester, 95% 5g [2-[4-(4-Methoxyphenylethynyl)phenyl- ]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane]

C21H23BO3, F.W. 334.22, Solid, MDL MFCD16294533 H51116 4-(4-Methoxyphenyliminomethyl)benzeneboronic acid 1g pinacol ester 5g [1-Methoxyphenyl- 25g iminomethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- benzene]

C20H24BNO3, F.W. 337.22, MDL MFCD10567027 L19563 4-Methylbenzeneboronic acid neopentyl glycol ester, 99% 1g [p-Tolylboronic acid neopentyl glycol ester, 5g 2-(p-Tolyl)-5,5-dimethyl-1,3,2-dioxaborinane] 25g

[380481-66-3], C12H17BO2, F.W. 204.08, White cryst powder, m.p. 93-95ø, MDL MFCD03788728 H52720 2-Methylbenzeneboronic acid 1,3-propanediol ester, 95% 1g [o-Tolylboronic acid 1,3-propanediol ester] 5g

[163517-56-4], C10H13BO2, F.W. 176.02, Colorless liquid, 25g MDL MFCD06659935

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Esters H51659 4-(4-Methyl-1-piperazinyl)benzeneboronic acid 1g pinacol ester 5g [1-Methyl-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- phenyl]piperazine]

[747413-21-4], C17H27BN2O2, F.W. 302.22, Solid, MDL MFCD06795650 H29224 3-(4-Methyl-1-piperazinylcarbonyl)benzeneboronic 1g acid pinacol ester, 97% 5g Arylboronic

[1-Methyl-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoyl]piperazine]

[883738-38-3], C18H27BN2O3, F.W. 330.23, White to pale cream powder, m.p. 86-89ø, MDL MFCD05864308

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H28216 4-(4-Methyl-1-piperazinylcarbonyl)benzeneboronic 1g acid pinacol ester, 97% 5g

[1-Methyl-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoyl]piperazine]

[832114-06-4], C18H27BN2O3, F.W. 330.23, White to pale brown powder, m.p. 110-113ø, MDL MFCD05863914

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H28762 3-(4-Methyl-1-piperazinylmethyl)benzeneboronic 1g acid pinacol ester, 97% 5g

[1-Methyl-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]piperazine]

[883738-27-0], C18H29BN2O2, F.W. 316.25, Colorless to pale yellow liquid, MDL MFCD09266181

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H28495 4-(4-Methyl-1-piperazinylmethyl)benzeneboronic 1g acid pinacol ester, 95% 5g

[1-Methyl-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]piperazine]

[938043-30-2], C18H29BN2O2, F.W. 316.25, White to cream cryst solid, m.p. 61-65ø, MDL MFCD09266182

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

94 www.alfa.com Arylboronic Esters Stock # Description Standard Selling Sizes H53024 2-(Methylsulfonylamino)benzeneboronic acid pinacol ester, 98% 1g [2-Mesylaminophenylboronic acid pinacol ester] 5g

[380430-60-4], C13H20BNO4S, F.W. 297.18, White solid, m.p. 130-134ø, MDL MFCD02179479

H:H302, P:P264-P270-P301+P312-P330-P501a

H53000 4-(3-Methylureido)benzeneboronic acid pinacol ester, 250mg 95% 1g [1-Methyl-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- phenyl]urea]

[874290-99-0], C14H21BN2O3, F.W. 276.14, Off-white solid, m.p. 183-187ø, MDL MFCD06795684 H51925 4-(4-Morpholinyl)benzeneboronic acid pinacol ester, 1g 95% 5g [4-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl- ]morpholine]

[568577-88-8], C16H24BNO3, F.W. 289.18, Solid, MDL MFCD04112544 Arylboronic

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53150 4-(4-Morpholinylcarbonylamino)benzeneboronic acid 250mg pinacol ester, 98% 1g [4-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl- ]morpholine-4-carboxamide]

[874290-97-8], C17H25BN2O4, F.W. 332.21, White solid, m.p. 248-250ø, MDL MFCD08689495 Esters

H:H302, P:P264-P270-P301+P312-P330-P501a H51113 3-(4-Morpholinylcarbonyl)benzeneboronic acid pinacol 1g ester 5g [4-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoyl- 25g ]morpholine]

C17H24BNO4, F.W. 317.19, MDL MFCD09266172

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H28484 4-(4-Morpholinylcarbonyl)benzeneboronic acid pinacol 1g ester, 97% 5g [4-(Morpholine-4-carbonyl)phenylboronic acid pinacol ester, 4-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoyl- ]morpholine]

[656239-38-2], C17H24BNO4, F.W. 317.19, Crystalline powder, m.p. 187-193ø, MDL MFCD05863913 H52272 2-(4-Morpholinylmethyl)benzeneboronic acid pinacol ester, 1g 95% 5g [4-[2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]morpholine]

[876316-33-5], C17H26BNO3, F.W. 303.20, White to pale brown solid, MDL MFCD07781208

H28416 3-(4-Morpholinylmethyl)benzeneboronic acid pinacol 1g ester 97% 5g [4-[3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl- ]morpholine]

[364794-80-9], C17H26BNO3, F.W. 303.20, White solid, m.p. 50-53ø, MDL MFCD06797489

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H28034 4-(4-Morpholinylmethyl)benzeneboronic acid pinacol 1g ester, 97% 5g [4-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl- ]morpholine]

[364794-79-6], C17H26BNO3, F.W. 303.20, White powder, m.p. 86-89ø, MDL MFCD04974052

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H30191 3-(4-Morpholinyl)propyl-1-boronic acid pinacol ester, 98% 1g [4-[3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)propyl- 5g ]morpholine]

C13H26BNO3, F.W. 255.17, Pale brown liquid, Ë 1.4585, MDL MFCD12546182

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Bulk and Specialty Sizes Available 95 Arylboronic Esters Stock # Description Standard Selling Sizes L17612 1-Naphthaleneboronic acid neopentyl glycol ester, 98% 1g

[22871-77-8], C15H17BO2, F.W. 240.11, White solid, m.p. 67-69ø, 5g BRN 3053756, MDL MFCD01318167

H52943 2-(1-Naphthyl)benzeneboronic acid pinacol ester, 97% 250mg [2-(1-Naphthyl)phenylboronic acid pinacol ester] 1g

C22H23BO2, F.W. 330.23

L19963 2-Nitrobenzeneboronic acid pinacol ester, 98+% 1g [2-Nitrophenylboronic acid pinacol ester, 5g 2-(2-Nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane]

[190788-59-1], C12H16BNO4, F.W. 249.08, White solid, m.p. 42-44ø, BRN 7708824, MDL MFCD02179447

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52848 4-Nitrobenzeneboronic acid pinacol ester, 98% 1g

[171364-83-3], C12H16BNO4, F.W. 249.08, Colorless or cream 5g Esters solid, m.p. 108-109ø, MDL MFCD02179437

H53360 4-(2-Oxiranylmethoxy)benzeneboronic acid pinacol 250mg ester, 98% [4,4,5,5-Tetramethyl-2-[4-(oxiran-2-ylmethoxy)phenyl- Arylboronic ]-1,3,2-dioxaborolane]

[664991-83-7], C15H21BO4, F.W. 276.14, White solid, m.p. 57-61ø, MDL MFCD09027286

H52286 4-(10-Phenothiazinylmethyl)benzeneboronic acid 1g pinacol ester, 95% 5g [10-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl- ]-10H-phenothiazine]

C25H26BNO2S, F.W. 415.36, Pale brown solid

H52283 4-(Phenoxymethyl)benzeneboronic acid pinacol ester, 1g 95% 5g [4,4,5,5-Tetramethyl-2-[4-(phenoxymethyl)phenyl- ]-1,3,2-dioxaborolane]

C19H23BO3, F.W. 310.20, White to off-white solid H51668 4-(Phenylcarbamoyl)benzeneboronic acid pinacol ester, 1g 97+% 5g [4-(Phenylaminocarbonyl)phenylboronic acid pinacol ester, N-Phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- benzamide]

C19H22BNO3, F.W. 329.19, Solid, MDL MFCD12546047 H28287 3-(Phenylaminomethyl)benzeneboronic acid pinacol 1g ester, 97% 5g [3-(Phenylaminomethyl)phenylboronic acid pinacol ester, N-[3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)]benzyl]aniline]

C19H24BNO2, F.W. 309.21, White cryst powder, m.p. 112-115ø, MDL MFCD09266198 H29086 4-(Phenylaminomethyl)benzeneboronic acid pinacol 1g ester, 97% 5g [4-(Phenylaminomethyl)phenylboronic acid pinacol ester, N-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)]benzyl]aniline]

C19H24BNO2, F.W. 309.21, White powder, m.p. 114-117ø, MDL MFCD06795652 H51668 4-(Phenylcarbamoyl)benzeneboronic acid pinacol ester, 1g 97+% 5g [4-(Phenylaminocarbonyl)phenylboronic acid pinacol ester, N-Phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- benzamide]

C19H22BNO3, F.W. 329.19, Solid, MDL MFCD12546047

96 www.alfa.com Arylboronic Esters Stock # Description Standard Selling Sizes H51699 4-(Phenylethynyl)benzeneboronic acid pinacol 1g ester, 97% 5g [Diphenylacetylene-4-boronic acid pinacol ester, 4,4,5,5-Tetramethyl-2-(4-phenyl- ethynyl)-1,3,2-dioxaborolane]

C20H21BO2, F.W. 304.19, White solid, MDL MFCD16294498 H28531 4-(Phenyliminomethyl)benzeneboronic acid pinacol ester, 1g 97% 5g [4-(Phenyliminomethyl)phenylboronic acid pinacol ester, 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzanil]

C19H22BNO2, F.W. 307.19, Yellow cryst powder, m.p. 96-99ø, MDL MFCD09266199 H51940 3-(4-Phenyl-1-piperazinylmethyl)benzeneboronic 1g acid pinacol ester, 95% 5g

[1-Phenyl-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]piperazine]

C23H31BN2O2, F.W. 378.32, Solid, MDL MFCD16294543, Note: Product of Advanced Arylboronic Molecular Technologies Pty Ltd.

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H51943 4-(4-Phenyl-1-piperazinylmethyl)benzeneboronic 1g acid pinacol ester, 95% 5g Esters

[1-Phenyl-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]piperazine]

C23H31BN2O2, F.W. 378.32, Solid, MDL MFCD16294546, Note: Product of Advanced Molecular Technologies Pty Ltd.

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52273 2-(N-Phthalimidomethyl)benzeneboronic acid pinacol ester, 1g 95% 5g [N-[2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]phthalamide]

[380430-66-0], C21H22BNO44, F.W. 363.22, White to pale brown solid, MDL MFCD02179492

H52267 4-(N-Phthalimidomethyl)benzeneboronic acid 1g pinacol ester, 95% 5g [N-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl- ]phthalimide]

[138500-87-5], C21H22BNO4, F.W. 363.22, White to pale brown solid, MDL MFCD02179489 H51922 4-(1-Piperidinyl)benzeneboronic acid pinacol ester, 95% 1g [1-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl- 5g ]piperidine]

[852227-96-4], C17H26BNO2, F.W. 287.21, Solid, MDL MFCD07368524 H29339 3-(1-Piperidinylcarbonyl)benzeneboronic acid pinacol 1g ester, 97% 5g [1-[3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoyl- ]piperidine]

C18H26BNO3, F.W. 315.21, White powder, MDL MFCD09027084 H51111 4-(1-Piperidinylcarbonyl)benzeneboronic acid pinacol 1g ester 5g [1-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoyl- 25g ]piperidine]

C18H26BNO3, F.W. 315.21, MDL MFCD09027083

Bulk and Specialty Sizes Available 97 Arylboronic Esters Stock # Description Standard Selling Sizes H52458 4-(1-Piperidinylcarbonyloxy)benzeneboronic acid 250mg pinacol ester, 98% 1g [4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl piperidine-1-carboxylate]

[913836-28-9], C18H26BNO4, F.W. 331.22, White solid, m.p. 166-168ø, MDL MFCD09027287

H:H302, P:P264-P270-P301+P312-P330-P501a H51114 4-(1-Piperidinylmethyl)benzeneboronic acid pinacol 1g ester 5g [1-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl- ]piperidine]

C18H28BNO2, F.W. 301.23, MDL MFCD08271932

H51125 4-(Propargylaminocarbonyl)benzeneboronic acid 1g pinacol ester 5g

[N-(1-Propyn-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide]

C16H20BNO3, F.W. 285.15, Off-white crystalline, MDL MFCD11113041

Esters H53215 4-(3-n-Propylureido)benzeneboronic acid pinacol 250mg ester, 98% 1g

[1-n-Propyl-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]urea]

Arylboronic [874291-01-7], C16H25BN2O3, F.W. 304.20, White solid, m.p. 225-228ø, MDL MFCD09027288 H52281 4-(1H-Pyrazol-1-ylmethyl)benzeneboronic acid pinacol 1g ester, 95% 5g [1-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl- ]-1H-pyrazole]

C16H21BN2O2, F.W. 284.16, Pale brown solid H52499 4-(1-Pyrrolidinylcarbonylamino)benzeneboronic acid 250mg pinacol ester, 97% 1g [N-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl- ]pyrrolidine-1-carboxamide]

[874290-95-6], C17H25BN2O3, F.W. 316.21, White solid, m.p. 243-245ø, MDL MFCD08689514

H:H302, P:P264-P270-P301+P312-P330-P501a H28801 3-(1-Pyrrolidinylcarbonyl)benzeneboronic acid pinacol 1g ester, 97% 5g [3-(Pyrrolidine-1-carbonyl)phenylboronic acid pinacol ester, 1-[3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoyl- ]pyrrolidine]

C17H24BNO3, F.W. 301.19, White to cream powder, m.p. 95-99ø, MDL MFCD09027086 H51115 4-(1-Pyrroldinylmethyl)benzeneboronic acid pinacol 1g ester 5g [1-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl- ]pyrrolidine]

C17H26BNO2, F.W. 287.20, MDL MFCD08690299

H51909 4-Succinimidylmethylbenzeneboronic acid pinacol 1g ester, 95% 5g [1-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl- ]pyrrolidine-2,5-dione]

C17H22BNO4, F.W. 315.17, Solid, MDL MFCD16294531 H28130 3-(Tetrahydrofurfurylaminocarbonyl)- 1g benzeneboronic acid pinacol ester, 97% 5g [3-(Tetrahydrofurfurylaminocarbonyl)phenylboronic acid pinacol ester,

N-Tetrahydrofurfuryl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide]

C18H26BNO4, F.W. 331.21, White to pale cream powder, MDL MFCD09266189

98 www.alfa.com Arylboronic Esters Stock # Description Standard Selling Sizes H28810 4-(Tetrahydrofurfurylaminocarbonyl)- 1g benzeneboronic acid pinacol ester, 97% 5g [4-(Tetrahydrofurfurylaminocarbonyl)phenylboronic acid pinacol ester,

N-Tetrahydrofurfuryl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide]

C18H26BNO4, F.W. 331.21, White powder, MDL MFCD09266200 H51923 4-(1,2,3,4-Tetrahydro-2-isoquinolinylmethyl)- 1g benzeneboronic acid pinacol ester, 95% 5g [2-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl- ]-1,2,3,4-tetrahydroisoquinoline]

C22H28BNO2, F.W. 349.28, Solid, MDL MFCD16294539

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53290 3-(2-Tetrahydropyranyloxy)benzeneboronic acid pinacol 250mg ester, 95% 1g [3-(2-Tetrahydro-2H-pyranoxy)phenylboronic acid pinacol ester] Arylboronic [850568-69-3], C17H25BO4, F.W. 304.19, White solid, m.p. 44-48ø, MDL MFCD06659834

H27250 2-(p-Toluenesulfonylamino)benzeneboronic acid pinacol 1g ester, 97% 5g [4-Methyl-N-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl- ]benzenesulfonamide]

[796061-07-9], C19H24BNO4S, F.W. 373.27, White to pale Esters brown powder, m.p. 135-139ø, MDL MFCD05663862

H27236 3-(p-Toluenesulfonylamino)benzeneboronic 1g acid pinacol ester, 97% 5g

[4-Methyl-N-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]benzenesulfonamide]

[796061-08-0], C19H24BNO4S, F.W. 373.27, White to cream powder, m.p. 164-168ø, MDL MFCD05663863 H32372 3-[3-(Trifluoromethyl)benzoylamino]benzene boronic 500mg acid pinacol ester, 95%

C18H15BF3NO3, F.W. 391.20, Pale brown cryst powder

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

L17232 2,4,6-Trimethylbenzeneboronic acid neopentyl glycol 1g ester, 99% 5g [5,5-Dimethyl-2-(2,4,6-trimethylphenyl)-1,3,2-dioxaborinane, Mesityleneboronic acid 2,2-dimethyltrimethylene cyclic ester]

[214360-78-8], C14H21BO2, F.W. 232.13, White to pale yellow solid, m.p. 46-48ø, BRN 8689636, MDL MFCD01318178 H51697 4-[(Trimethylsilyl)ethynyl]benzeneboronic acid pinacol 1g ester, 97% 5g [4,4,5,5-Tetramethyl-2-(4-trimethylsilylethynyl- phenyl)-1,3,2-dioxaborolane]

C17H25BO2Si, F.W. 300.28, Cream solid, MDL MFCD08706286 H51917 4-(Triphenylphosphoniomethyl)benzeneboronic acid 1g pinacol ester bromide, 95% 5g [4-(4,4,5,5-Tetramethyl-1,3,2-dioxaboratophenyl)methyl triphenylphosphonium bromide]

C31H33BBrO2P, F.W. 559.29, Cream powder, MDL MFCD16294536 H53046 4-Ureidobenzeneboronic acid pinacol ester, 98% 250mg [1-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]urea] 1g

[877134-77-5], C13H19BN2O3, F.W. 262.12, White solid, m.p. 124-128ø, MDL MFCD06795683

Bulk and Specialty Sizes Available 99 Aryltrifluoroborate Salts Stock # Description Standard Selling Sizes H52472 2-Vinylbenzeneboronic acid 1,3-propanediol ester, 95% 250mg [Styrene-2-boronic acid 1,3-propanediol ester]

[850567-61-2], C11H13BO2, F.W. 188.03, Yellow liquid, MDL MFCD06659933

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Stock # Description Standard Selling Sizes H51149 Potassium 4-(anilinomethyl)phenyltrifluoroborate, 97% 1g

C13H12BF3KN, F.W. 289.15, White crystalline solid, 5g MDL MFCD11052774

H:H315-H319-H335, P:P280g-P305+P351+P338 H51887 Potassium 4-(benzylaminocarbonyl)phenyltrifluoroborate, 1g 95% 5g

C14H12BF3KNO, F.W. 317.16, Solid, MDL MFCD16293900

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Salts H52621 Potassium 4-(benzyloxycarbonylamino)phenyl- 1g trifluoroborate, 96% 5g [Potassium 4-(Cbz-amino)phenyltrifluoroborate]

[850623-45-9], C14H12BF3KNO2, F.W. 333.16, Off-white solid, m.p. 250-266ø, MDL MFCD04115743

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52626 Potassium 4-benzyloxy-2-methylphenyltrifluoroborate, 98% 250mg

[850623-43-7], C14H13BF3KO, F.W. 304.16, White solid, m.p. 196-200ø, 1g MDL MFCD04115740

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Aryltrifluoroborate H52686 Potassium 2-benzyloxyphenyltrifluoroborate, 95% 250mg

[850623-44-8], C13H11BF3KO, F.W. 290.13, White solid, m.p. 200-204ø, 1g MDL MFCD04115742

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52544 Potassium 3-benzyloxyphenyltrifluoroborate, 96% 1g

[850623-58-4], C13H11BF3KO, F.W. 290.13, White solid, m.p. 118-122ø, 5g MDL MFCD04115751

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H51894 Potassium 4-(benzyloxy)phenyltrifluoroborate, 95% 1g

[850623-47-1], C13H11BF3KO, F.W. 290.13, Solid, 5g MDL MFCD04115746

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53113 Potassium 3,5-bis(trifluoromethyl)phenytrifluoroborate, 96% 1g

[166328-09-2], C8H3BF9K, F.W. 320.01, Pale brown solid, m.p. >300ø, 5g MDL MFCD03701625

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L17966 Potassium 3-bromophenyltrifluoroborate, 97% 1g [3-Bromobenzenetrifluoroboric acid potassium salt, 3-Bromophenyl- 5g trifluoroboric acid potassium salt]

[374564-34-8], C6H4BBrF3K, F.W. 262.91, m.p. 178-182ø, MDL MFCD02093977

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L17967 Potassium 4-bromophenyltrifluoroborate, 97% 1g [4-Bromobenzenetrifluoroboric acid potassium salt, 4-Bromophenyl- 5g trifluoroboric acid potassium salt]

[374564-35-9], C6H4BBrF3K, F.W. 262.91, m.p. >300ø, BRN 9297533, MDL MFCD02093978

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53092 Potassium 4-n-butoxyphenyltrifluoroborate, 96% 250mg

[850623-61-9], C10H13BF3KO, F.W. 256.12, White solid, 1g m.p. >300ø, MDL MFCD04115755

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52885 Potassium 4-tert-butylphenyltrifluoroborate, 96% 1g

[423118-47-2], C10H13BF3K, F.W. 240.11, White solid, m.p. >300ø, 5g UN3261, MDL MFCD06659940 H:H314, P:P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501a

100 www.alfa.com Aryltrifluoroborate Salts Stock # Description Standard Selling Sizes H52492 Potassium 2-carbamoylphenyltrifluoroborate, 96% 250mg [Potassium 2-aminocarbonylphenyltrifluoroborate] 1g

[850623-70-0], C7H6BF3KNO, F.W. 227.03, White solid, m.p. >300ø, MDL MFCD04115765

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53054 Potassium 4-carbamoylphenyltrifluoroborate, 96% 1g [Potassium 4-aminocarbonylphenyltrifluoroborate] 5g

[850623-63-1], C7H6BF3KNO, F.W. 227.03, White solid, m.p. >300ø, MDL MFCD04115758

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52543 Potassium 3-carboxy-5-nitrophenyltrifluoroborate, 96% 250mg

[850623-76-6], C7H4BF3KNO4, F.W. 273.02, White solid, m.p. >300ø, 1g MDL MFCD04115772

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H51885 Potassium 3-carboxyphenyltrifluoroborate, 95% 1g

[850313-91-6], C7H5BF3KO2, F.W. 228.02, Solid, MDL MFCD07784423 5g Aryltrifluoroborate H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H51888 Potassium 4-carboxyphenyltrifluoroborate, 95% 1g

[850623-38-0], C7H5BF3KO2, F.W. 228.02, Solid, MDL MFCD04115737 5g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53042 Potassium 3-chloro-4-fluorophenyltrifluoroborate, 96% 1g

[850623-59-5], C6H3BClF4K, F.W. 236.44, Off-white solid, m.p. 234-244ø, 5g MDL MFCD04115752

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53144 Potassium 3-chlorophenyltrifluoroborate, 96% 1g

[411206-75-2], C6H4BClF3K, F.W. 218.45, White solid, m.p. 76-80ø, 5g Salts MDL MFCD04115754

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53231 Potassium 4-chlorophenyltrifluoroborate, 96% 1g

[661465-44-7], C6H4BClF3K, F.W. 218.45, White solid, m.p. 293-295ø, 5g MDL MFCD04115770

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52671 Potassium 3-cyanophenyltrifluoroborate, 96% 1g

[850623-46-0], C7H4BF3KN, F.W. 209.02, White solid, m.p. 196-200ø, 5g MDL MFCD04115744

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53187 Potassium 4-cyanophenyltrifluoroborate, 96% 1g

[850623-36-8], C7H4BF3KN, F.W. 209.02, White solid, m.p. >300ø, 5g MDL MFCD04115736

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53083 Potassium 2,4-dichlorophenyltrifluoroborate, 96% 1g

[192863-38-0], C6H3BCl2F3K, F.W. 252.90, White solid, m.p. 98-104ø, 5g MDL MFCD04115745

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53219 Potassium 3,4-dichlorophenyltrifluoroborate, 96% 1g

[850623-68-6], C6H3BCl2F3K, F.W. 252.90, White solid, m.p. 178-180ø, 5g MDL MFCD04115763

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H51892 Potassium 4-(diethylaminocarbonyl)phenyltrifluoroborate, 1g 95% 5g

C11H14BF3KNO, F.W. 283.14, Solid, MDL MFCD16293903

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53048 Potassium 3,5-difluorophenyltrifluoroborate, 96% 1g

[267006-26-8], C6H3BF5K, F.W. 219.99, Off-white solid, m.p. 273-278ø, 5g MDL MFCD06659939

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H51896 Potassium 4-(N,O-dimethylhydroxylaminocarbonyl)phenyl- 1g trifluoroborate, 95% 5g [Weinreb Amide]

C9H10BF3KNO2, F.W. 271.09, Solid, MDL MFCD16294523

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Bulk and Specialty Sizes Available 101 Aryltrifluoroborate Salts Stock # Description Standard Selling Sizes H53274 Potassium 3,5-dinitro-2-methylphenyltrifluoroborate, 96% 250mg

[850623-72-2], C7H5BF3KN2O4, F.W. 288.03, Cream solid, m.p. 206-210ø, 1g MDL MFCD04115767

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52760 Potassium 2-ethoxycarbonylphenyltrifluoroborate, 96% 250mg

[850623-73-3], C9H9BF3KO2, F.W. 256.07, White solid, m.p. 255-259ø, 1g MDL MFCD04115768

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H51882 Potassium 4-ethoxycarbonylphenyltrifluoroborate, 95% 1g

C9H9BF3KO2, F.W. 256.07, Solid, MDL MFCD09800743 5g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53091 Potassium 4-ethoxyphenyltrifluoroborate, 96% 1g

[850623-60-8], C8H9BF3KO, F.W. 228.06, White solid, m.p. 298-304ø, 5g MDL MFCD04115753

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52677 Potassium 4-(ethylthio)phenyltrifluoroborate, 96% 1g

[850623-75-5], C8H9BF3KS, F.W. 244.12, white solid, m.p. >300ø, 5g MDL MFCD04115771 Salts H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53060 Potassium 3-fluoro-4-methoxyphenyltrifluoroborate, 96% 250mg

[850623-62-0], C7H6BF4KO, F.W. 232.03, Off-white solid, 1g m.p. 276-280ø, MDL MFCD04115757

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53086 Potassium 2-fluorophenyltrifluoroborate, 96% 1g

[166328-10-5], C6H4BF4K, F.W. 202.00, White solid, m.p. >300ø, 5g MDL MFCD06659937

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52450 Potassium 3-fluorophenyltrifluoroborate, 96% 1g Aryltrifluoroborate [267006-24-6], C6H4BF4K, F.W. 202.00, Pale brown solid, m.p. >300ø, 5g MDL MFCD06659938

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L17655 Potassium 4-fluorophenyltrifluoroborate, 95% 1g [4-Fluorobenzenetrifluoroboric acid potassium salt, 4-Fluorophenyltrifluoroboric 5g acid potassium salt]

[192863-35-7], C6H4BF4K, F.W. 202.00, White powder, m.p. 290-292ø, BRN 7783544, MDL MFCD01318170

H:H315-H319-H335, P:P280g-P305+P351+P338 L17968 Potassium 2-formylphenyltrifluoroborate, 97% È 1g [2-Formylbenzenetrifluoroboric acid potassium salt, 2-Formylphenyltrifluoroboric acid potassium salt]

[192863-39-1], C7H5BF3KO, F.W. 212.02, BRN 7783590, MDL MFCD02093979

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H28125 Potassium 3-formylphenyltrifluoroborate, 97% È 1g [3-Formylbenzenetrifluoroboric acid potassium salt, 3-Formylphenyl- 5g trifluoroboric acid potassium salt]

[871231-44-6], C7H5BF3KO, F.W. 212.02, White powder, m.p. ca 200ø, MDL MFCD07784378

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L17969 Potassium 4-formylphenyltrifluoroborate, 97% È 1g [4-Formylbenzenetrifluoroboric acid potassium salt, 4-Formylphenyl- 5g trifluoroboric acid potassium salt]

[374564-36-0], C7H5BF3KO, F.W. 212.02, White powder, m.p. >300ø, MDL MFCD02093980

H:H315-H319-H335, P:P280g-P305+P351+P338 H51182 Potassium 3-(furfurylaminocarbonyl)phenyltrifluoroborate 1g

C12H10BF3KNO2, F.W. 307.12, MDL MFCD11977720 5g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H51147 Potassium [4-(furfurylaminocarbonyl)phenyl- 1g ]trifluoroborate 5g

C12H10BF3KNO2, F.W. 307.12, MDL MFCD11977716

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

102 www.alfa.com Aryltrifluoroborate Salts Stock # Description Standard Selling Sizes H53193 Potassium 2-(hydroxymethyl)phenyltrifluoroborate, 96% 1g

[850623-74-4], C7H7BF3KO, F.W. 214.04, Off-white solid, m.p. 300ø, 5g MDL MFCD04115769

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H51883 Potassium 4-hydroxymethylphenyltrifluoroborate, 95% 1g

C7H7BF3KO, F.W. 214.04, Powder, MDL MFCD08276800 5g

H:H315-H319-H335, P:P280g-P305+P351+P338 H29009 Potassium 3-iodophenyltrifluoroborate, 96% ß 1g

C6H4BF3IK, F.W. 309.90, White to cream powder, m.p. 202-204ø, 5g MDL MFCD09800739

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H28758 Potassium 4-iodophenyltrifluoroborate, 96% ß 1g

[912350-00-6], C6H4BF3IK, F.W. 309.90, White to cream powder, 5g m.p. 297-299ø, MDL MFCD09800738

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53161 Potassium 4-isobutylphenyltrifluoroborate, 96% 250mg Aryltrifluoroborate [850623-66-4], C10H13BF3K, F.W. 240.11, White solid, 1g m.p. 290-298ø, MDL MFCD04115761

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52457 Potassium 3-methoxycarbonyl-5-nitrophenyltrifluoroborate, 96% 250mg

[850623-56-2], C8H6BF3KNO4, F.W. 287.04, White solid, m.p. 280-284ø, 1g MDL MFCD04115749

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52588 Potassium 4-(methoxycarbonyl)phenyltrifluoroborate, 96% 1g

[705254-34-8], C8H7BF3KO2, F.W. 242.05, White solid, m.p. >300ø, 5g

MDL MFCD04115741 Salts

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H51183 Potassium [3-(2-methoxyethylaminocarbonyl)phenyl- 1g ]trifluoroborate 5g

C10H12BF3KNO2, F.W. 285.11, MDL MFCD11977721

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H51148 Potassium [4-(2-methoxyethylaminocarbonyl)phenyl- 1g ]trifluoroborate 5g

C10H12BF3KNO2, F.W. 285.11, MDL MFCD11977717

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52927 Potassium 4-methoxy-2-methylphenyltrifluoroborate, 96% 1g

[850623-69-7], C8H9BF3KO, F.W. 228.06, White solid, m.p. 117-120ø, 5g MDL MFCD04115764

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52582 Potassium 2-methoxyphenyltrifluoroborate, 96% 1g

[236388-46-8], C7H7BF3KO, F.W. 214.04, White solid, m.p. 282-286ø, 5g MDL MFCD04115756

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53200 Potassium 3-methoxyphenyltrifluoroborate, 98% 1g

[438553-44-7], C7H7BF3KO, F.W. 214.04, White solid, m.p. 164-168ø, 5g MDL MFCD04039954

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27384 Potassium 4-methoxyphenyltrifluoroborate, 95% 1g

[192863-36-8], C7H7BF3KO, F.W. 214.04, White powder, m.p. >300ø, 5g MDL MFCD04112717

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53253 Potassium 4-methyl-1-naphthalenetrifluoroborate, 96% 1g

[850623-55-1], C11H9BF3K, F.W. 248.10, Off-white solid, m.p. 204-208ø, 5g MDL MFCD04115748

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H53214 Potassium 2-methylphenyltrifluoroborate, 96% 1g [Potassium o-tolyltrifluoroborate] 5g

[274257-34-0], C7H7BF3K, F.W. 198.04, White solid, m.p. 90-94ø, MDL MFCD03790006

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Bulk and Specialty Sizes Available 103 Aryltrifluoroborate Salts Stock # Description Standard Selling Sizes H53279 Potassium 3-methylphenyltrifluoroborate, 96% 1g

[850623-42-6], C7H7BF3K, F.W. 198.04, White solid, m.p. 226-230ø, 5g MDL MFCD04115739

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L17604 Potassium 4-methylphenyltrifluoroborate, 98% 1g [4-Methylphenyltrifluoroboric acid potassium salt, p-Tolyltrifluoroboric acid 5g potassium salt]

[216434-82-1], C7H7BF3K, F.W. 198.04, m.p. >300ø, BRN 8290098, MDL MFCD01318171

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H51889 Potassium 4-(4-methyl-1-piperazinylcarbonyl)phenyl- 1g trifluoroborate, 95% 5g

C12H15BF3KN2O, F.W. 310.17, Solid, MDL MFCD16293901

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H51884 Potassium 4-(1-methy-4-piperazinyl)phenyltrifluoroborate, 1g 95% 5g

C11H15BF3KN2, F.W. 282.16, Solid, MDL MFCD16294522

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53299 Potassium 3-(methylsulfonylamino)phenyltrifluoroborate, 250mg Salts 96% 1g [Potassium 3-(methanesulfonylamino)phenyltrifluoroborate]

[850623-67-5], C7H8BF3KNO2S, F.W. 277.11, Off-white solid, m.p. 180-190ø, MDL MFCD04115762

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52649 Potassium 2-(methylsulfonyl)phenyltrifluoroborate, 96% 250mg [Potassium 2-(methanesulfonyl)phenyltrifluoroborate] 1g

[850623-65-3], C7H7BF3KO2S, F.W. 262.09, White solid, m.p. 78-84ø, MDL MFCD04115760

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Aryltrifluoroborate H53232 Potassium 4-methylsulfonylphenyltrifluoroborate, 96% 1g

[850623-40-4], C7H7BF3KO2S, F.W. 262.09, White solid, m.p. >300ø, 5g MDL MFCD04115738

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52587 Potassium 2-methylthiophenyltrifluoroborate, 96% 1g

[850623-77-7], C7H7BF3KS, F.W. 230.10, White solid, m.p. 274-276ø, 5g MDL MFCD04115773

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52638 Potassium 3-methylthiophenyltrifluoroborate, 96% 250mg

[850623-48-2], C7H7BF3KS, F.W. 230.10, Off-white solid, m.p. 70-78ø, 1g MDL MFCD04115747

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H51142 Potassium 3-(4-morpholinylcarbonyl)phenyltrifluoroborate 1g

C11H12BF3KNO2, F.W. 297.12, MDL MFCD11977713 5g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H51141 Potassium 4-(4-morpholinylcarbonyl)phenyltrifluoroborate 1g

C11H12BF3KNO2, F.W. 297.12, MDL MFCD09800742 5g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H51890 Potassium 4-(4-morpholinylmethyl)phenyltrifluoroborate, 1g 95% 5g

C11H14BF3KNO, F.W. 283.14, Solid, MDL MFCD16293902

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52979 Potassium 1-naphthalenetrifluoroborate, 96% 1g

[166328-07-0], C10H7BF3K, F.W. 234.07, White solid, m.p. 89-91ø, 5g MDL MFCD06659936

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52901 Potassium 2-naphthalenetrifluoroborate, 96% 1g

[668984-08-5], C10H7BF3K, F.W. 234.07, White solid, m.p. >300ø, 5g MDL MFCD06659941

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

104 www.alfa.com Aryltrifluoroborate Salts Stock # Description Standard Selling Sizes H52636 Potassium 2-nitrophenyltrifluoroborate, 96% 250mg

[850623-64-2], C6H4BF3KNO2, F.W. 229.01, Off-white solid, m.p. 216-220ø, 1g MDL MFCD04115759

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H31684 Potassium 3-nitrophenyltrifluoroborate, 95% 1g

[192863-40-4], C6H4BF3KNO2, F.W. 229.01, White to yellow solid

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53208 Potassium 4-nitrophenyltrifluoroborate, 95% 250mg

[850623-71-1], C6H4BF3KNO2, F.W. 229.01, Off-white solid, m.p. 288-290ø, MDL MFCD04115766

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H51184 Potassium 3-(phenylaminocarbonyl)phenyltrifluoroborate 1g

C13H10BF3KNO, F.W. 303.13, MDL MFCD11977722 5g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H51150 Potassium [4-(phenylaminocarbonyl)phenyl]trifluoroborate 1g Aryltrifluoroborate [912350-01-7], C13H10BF3KNO, F.W. 303.13, m.p. >250ø, 5g MDL MFCD11977719

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L17568 Potassium phenyltrifluoroborate, 98% 1g [Benzenetrifluoroboric acid potassium salt, Phenyltrifluoroboric acid potassium 5g salt]

[153766-81-5], C6H5BF3K, F.W. 184.00, m.p. 296-301ø, Fieser 18,301, BRN 7782070, MDL MFCD01318172

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Treatment with TMS chloride in acetonitrile generates the Lewis acid phenylboron difluoride in situ, avoiding the need to handle boron trihalides: J. Org. Chem., 60, 3020 (1995). Salts Aryltrifluoroborate salts are more nucleophilic than the corresponding arylboronic acids and undergo ligand-free Pd-catalyzed cross-coupling reactions with arenediazonium tetrafluoroborates to give good yields of biaryls: Tetrahedron Lett., 38, 4393 (1997); Eur. J. Org. Chem., 1875 (1999). Cross-coupling with aryl or heteroaryl halides and triflates, under ligand-free conditions, has subsequently been reported: Org. Lett., 4, 1867 (2002). Coupling with diaryliodonium salts has also been reported: Synth. Commun., 29, 2457 (1999). The method has been extended to the synthesis of benzophenones by carbonylative cross-coupling in the presence of CO: J. Chem. Res. (Synop.), 400 (1999). In the presence of Dicarbonyl(2,4-pentanedionato)rhodium(I), 39295, p. 140, K aryl- and alkenyltrifluoroborates add to aldehydes and enones to give secondary alcohols and saturated ketones, respectively: Org. Lett., 1, 1683 (1999):

Asymmetric Rh-catalyzed additions to enones in the presence of a chiral BINAP catalyst give the corresponding saturated ketones in high yield and ee: Eur. J. Org. Chem., 3552 (2002). H51181 Potassium [3-(1-piperidinylcarbonyl)phenyl]trifluoroborate 1g

C12H14BF3KNO, F.W. 295.15, MDL MFCD12546202 5g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H51146 Potassium [4-(1-piperidinylcarbonyl)phenyl]trifluoroborate 1g

C12H14BF3KNO, F.W. 295.15, MDL MFCD11977715 5g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H51895 Potassium 4-(1-piperidinylmethyl)phenyltrifluoroborate, 95% 1g

C12H16BF3KN, F.W. 281.17, Solid, MDL MFCD16293905 5g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H51893 Potassium 4-(1-pyrrolidinylcarbonyl)phenyltrifluoroborate, 1g 95% 5g

C11H12BF3KNO, F.W. 281.13, Solid, MDL MFCD16293904

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H51886 Potassium 4-(tetrahydrofurfurylaminocarbonyl)phenyl- 1g trifluoroborate, 95% 5g

C12H14BF3KNO2, F.W. 311.15, White powder, MDL MFCD16294309

H:H315-H319-H335, P:P280g-P305+P351+P338

Bulk and Specialty Sizes Available 105 Heterocyclic Boronic Acids Stock # Description Standard Selling Sizes H53224 Potassium trifluoro(2-fluoro-4-biphenylyl)borate, 96% 1g [Potassium (3-fluoro-4-phenyl)phenyltrifluoroborate] 5g

[850623-57-3], C12H8BF4K, F.W. 278.10, White solid, m.p. 290-294ø, MDL MFCD08235035

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53259 Potassium 4-(trifluoromethyl)phenyltrifluoroborate, 96% 1g

[166328-08-1], C7H4BF6K, F.W. 252.01, Off-white solid, m.p. 280-286ø, 5g MDL MFCD04039955

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Stock # Description Standard Selling Sizes L15221 5-Acetylthiophene-2-boronic acid, 98% 1g

[206551-43-1], C6H7BO3S, F.W. 170.00, m.p. 142-148ø, 5g BRN 8681302, MDL MFCD01075681 25g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B23676 Benzo[b]furan-2-boronic acid, 98% 1g Acids [98437-24-2], C8H7BO3, F.W. 161.95, White to pale brown cryst 5g powder, BRN 1637889, MDL MFCD00236019 25g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53025 Benzo[b]furan-2,5-diboronic acid, 98% 250mg

[913835-69-5], C8H8B2O5, F.W. 205.77, White solid, Boronic m.p. 293-295ø, MDL MFCD08436058

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B22835 Benzo[b]thiophene-2-boronic acid, 98% 1g [Thianaphthene-2-boronic acid] 5g

[98437-23-1], C8H7BO2S, F.W. 178.02, White to cream solid, m.p. ca 25g 255ø, BRN 1637924, MDL MFCD01075674

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Heterocyclic H52846 4-Benzyloxy-1-Boc-indole-2-boronic acid, 98% 250mg [4-Benzyloxy-1-tert-butoxycarbonylindole-2-boronic acid] 1g

[850568-52-4], C20H22BNO5, F.W. 367.21, Off-white solid, m.p. 102-104ø, MDL MFCD04973739

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52540 5-Benzyloxy-1-Boc-indole-2-boronic acid, 98% 250mg [5-Benzyloxy-1-tert-butoxycarbonylindole-2-boronic acid] 1g

[850568-62-6], C20H22BNO5, F.W. 367.21, White solid, m.p. 106-110ø, MDL MFCD06659824

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52980 6-Benzyloxy-1-Boc-indole-2-boronic acid, 98% 250mg [6-Benzyloxy-1-tert-butoxycarbonylindol-2-ylboronic acid] 1g

[850568-66-0], C20H22BNO5, F.W. 367.21, Off-white solid, m.p. 105-106ø, MDL MFCD06659831

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H26978 2-Benzyloxypyridine-3-boronic acid, 95% 250mg

[1072952-41-0], C12H12BNO3, F.W. 229.04, White powder, m.p. 145-147ø, 1g MDL MFCD06798264

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27346 6-Benzyloxypyridine-3-boronic acid, 95% 250mg

[929250-35-1], C12H12BNO3, F.W. 229.04, White powder, 1g m.p. 107-110ø, MDL MFCD06798262

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27160 1-Benzyl-1H-pyrazole-4-boronic acid, 95% 250mg

[852362-22-2], C10H11BN2O2, F.W. 202.02, MDL MFCD04038760 1g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H52851 2,2'-Bithiophene-5-boronic acid, 96% 250mg [5-(2-Thienyl)thiophene-2-boronic acid]

[132898-95-4], C8H7BO2S2, F.W. 210.07, Off-white solid, m.p. 163-165ø, MDL MFCD03086112

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

106 www.alfa.com Heterocyclic Boronic Acids Stock # Description Standard Selling Sizes H32185 1-Boc-5-bromoindole-2-boronic acid, 95% 1g [5-Bromo-1-tert-butoxycarbonyl-1H-indole-2-boronic acid] 5g

[475102-13-7], C13H15BBrNO4, F.W. 339.98, White solid

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52511 1-Boc-5-(tert-butyldimethylsiloxy)indole-2-boronic acid, 250mg 98% 1g [1-Boc-5-TBDMSO-2-indoleboronic acid, 1-tert-Butoxycarbonyl-5-(tert-butyldimethylsilyloxy)indole]

[335649-61-1], C19H30BNO5Si, F.W. 391.35, White solid, m.p. 104-106ø, MDL MFCD08689532

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52954 1-Boc-4-chloroindole-2-boronic acid, 98% 1g [1-tert-Butoxycarbonyl-4-chloroindole-2-boronic acid] 5g

[475102-11-5], C13H15BClNO4, F.W. 295.53, White solid, m.p. 107-110ø, MDL MFCD04114582

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Heterocyclic H53229 1-Boc-6-chloroindole-2-boronic acid, 98% 250mg [1-tert-Butoxycarbonyl-6-chloroindole-2-boronic acid] 1g

[352359-22-9], C13H15BClNO4, F.W. 295.53, White solid, m.p. 110-113ø, MDL MFCD08689539

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52913 1-Boc-5-cyanoindole-2-boronic acid, 95% 250mg

[1-tert-Butoxycarbonyl-5-cyanoindole-2-boronic acid] Boronic

[475102-15-9], C14H15BN2O4, F.W. 286.09, Yellow solid, m.p. 260-270ø, MDL MFCD04114578

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52520 1-Boc-6-cyanoindole-2-boronic acid, 96% 250mg [1-tert-Butoxycarbonyl-6-cyanoindole-2-boronic acid] 1g Acids

[913835-67-3], C14H15BN2O4, F.W. 286.09, Pale brown solid, m.p. 219-221ø, MDL MFCD08436056

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53019 1-Boc-5-fluoroindole-2-boronic acid, 95% 250mg [1-tert-Butoxycarbonyl-5-fluoroindole-2-boronic acid] 1g

[352359-23-0], C13H15BFNO4, F.W. 279.07, Off-white solid, m.p. 130-140ø, MDL MFCD04114581

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L18009 1-Boc-indole-2-boronic acid, 95% 250mg [1-(tert-Butoxycarbonyl)indole-2-boronic acid] 1g

[213318-44-6], C13H16BNO4, F.W. 261.09, White to cream, m.p. ca 5g 85ø dec., BRN 8148683, MDL MFCD02093045

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52654 1-Boc-5-methoxyindole-2-boronic acid, 95% 1g [1-tert-Butoxycarbonyl-5-methoxyindole-2-boronic acid] 5g

[290331-71-4], C14H18BNO5, F.W. 291.11, White to off-white solid, m.p. 105-108ø, MDL MFCD04039006

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52482 1-Boc-6-methoxyindole-2-boronic acid, 98% 250mg [1-tert-Butoxycarbonyl-6-methoxyindole-2-boronic acid] 1g

[850568-65-9], C14H18BNO5, F.W. 291.11, Pale brown solid, m.p. 100-103ø, MDL MFCD06659830

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53063 1-Boc-7-methoxyindole-2-boronic acid, 98% 250mg [1-tert-Butoxycarbonyl-7-methoxyindole-2-boronic acid] 1g

[913835-81-1], C14H18BNO5, F.W. 291.11, Yellow solid, m.p. 100-102ø, MDL MFCD08689542

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52687 1-Boc-5-methylindole-2-boronic acid, 97% 250mg [1-tert-Butoxycarbonyl-5-methylindole-2-boronic acid] 1g

[475102-14-8], C14H18BNO4, F.W. 275.11, White to off-white solid, m.p. 112-116ø, MDL MFCD04114580

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52622 1-Boc-6-methylindole-2-boronic acid, 95% 250mg [1-tert-Butoxycarbonyl-6-methylindole-2-boronic acid] 1g

[850568-51-3], C14H18BNO4, F.W. 275.11, Off-white solid, m.p. 102-104ø, MDL MFCD04973738

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Bulk and Specialty Sizes Available 107 Heterocyclic Boronic Acids Stock # Description Standard Selling Sizes H53078 1-Boc-pyrrole-2-boronic acid, 96% 1g [1-tert-Butoxycarbonylpyrrole-2-boronic acid] 5g

[135884-31-0], C9H14BNO4, F.W. 211.02, Off-white solid, m.p. 105-108ø, MDL MFCD01318939

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H29021 3-Bromo-2-chloropyridine-4-boronic acid, 97% 250mg

C5H4BBrClNO2, F.W. 236.26, White to cream cryst powder, m.p. ca 170ø dec., 1g MDL MFCD08458470 5g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H26966 5-Bromo-2-chloropyridine-3-boronic acid, 95% 250mg

[1072944-19-4], C5H4BBrClNO2, F.W. 236.26, MDL MFCD09037486 1g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53239 5-Bromo-2-chloropyridine-4-boronic acid, 96% 250mg

[871329-63-4], C5H4BBrClNO2, F.W. 236.26, Whilte solid, m.p. 158-160ø, MDL MFCD07783852

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27460 6-Bromo-2,4-dimethylpyridine-3-boronic acid, 95% 250mg

Acids [1072944-23-0], C7H9BBrNO2, F.W. 229.87, White to cream powder, 1g m.p. ca 145ø dec., MDL MFCD09037491

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53310 5-Bromo-2-ethoxypyridine-3-boronic acid, 97% 250mg

Boronic [871332-98-8], C7H9BBrNO3, F.W. 245.87, White solid, m.p. 152-158ø, MDL MFCD07363847

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53047 5-Bromo-2-ethoxypyridine-4-boronic acid, 97% 250mg

[612845-46-2], C7H9BBrNO3, F.W. 245.87, White solid, m.p. 110-114ø, MDL MFCD07783887

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Heterocyclic L19915 5-Bromo-2-fluoropyridine-3-boronic acid, 98% 250mg [5-Bromo-2-fluoro-3-pyridylboronic acid] 1g

[501435-91-2], C5H4BBrFNO2, F.W. 219.81, m.p. >300ø, 5g MDL MFCD04039317

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Multifunctional boronic acid, developed by Sutherland and Gallagher, with potential for substitution at the 2-, 3- or 5-positions, e.g in the synthesis of unsymmetrically 3,5-disubstituted 2-fluoropyridines and 2-pyridones: J. Org. Chem., 68, 3352 (2003). The authors' review on the synthesis and reactivity of halopyridylboronic acids is available from Alfa Aesar on request. H52678 5-Bromo-2-methoxypyridine-3-boronic acid, 97% 250mg

[850864-59-4], C6H7BBrNO3, F.W. 231.84, White solid, m.p. 220-223ø, MDL MFCD04973352

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52945 5-Bromo-2-methoxypyridine-4-boronic acid, 98% 250mg

[957060-94-5], C6H7BBrNO3, F.W. 231.84, White solid, m.p. 130-134ø, 1g MDL MFCD07781223

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27715 6-Bromo-2-methylpyridine-3-boronic acid, 95% 250mg

[1072944-22-9], C6H7BBrNO2, F.W. 215.84, White powder, m.p. ca 1g 170ø dec., MDL MFCD09037490

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27069 6-Bromo-4-methylpyridine-3-boronic acid, 95% 250mg

[1072945-75-5], C6H7BBrNO2, F.W. 215.84, White powder, 1g m.p. 162-165ø, MDL MFCD09037489

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27221 6-Bromo-5-methylpyridine-3-boronic acid, 95% 250mg

[1003043-34-2], C6H7BBrNO2, F.W. 215.84, White to cream powder, 1g MDL MFCD08274468

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27523 2-Bromopyridine-3-boronic acid, 95% 250mg

[452972-08-6], C5H5BBrNO2, F.W. 201.82, Pale pink crystalline powder, 1g MDL MFCD04113805

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

108 www.alfa.com Heterocyclic Boronic Acids Stock # Description Standard Selling Sizes H27599 2-Bromopyridine-4-boronic acid, 95% 250mg

[458532-94-0], C5H5BBrNO2, F.W. 201.82, White powder, 1g MDL MFCD06798244

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L20084 5-Bromopyridine-3-boronic acid, tech. 85% 250mg [3-Bromo-5-pyridylboronic acid] 1g

[452972-09-7], C5H5BBrNO2, F.W. 201.82, m.p. >300ø, BRN 9119873, 5g MDL MFCD02685634

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L20085 6-Bromopyridine-3-boronic acid, 95% 250mg [2-Bromo-5-pyridylboronic acid] 1g

[223463-14-7], C5H5BBrNO2, F.W. 201.82, m.p. ca 165ø dec., 5g BRN 9119918, MDL MFCD03411558

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L20327 2-Bromoquinoline-3-boronic acid, 97% 250mg

[745784-05-8], C9H7BBrNO2, F.W. 251.88, m.p. 144-147ø, 1g Heterocyclic MDL MFCD05664125 5g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53081 5-(tert-Butylcarbamoyl)pyridine-3-boronic acid, 98% 250mg [3-tert-Butyl 5-borononicotinamide] 1g

[913835-99-1], C10H15BN2O3, F.W. 222.05, White solid, m.p. 245-250ø, MDL MFCD08689533

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Boronic H53035 1-(tert-Butyldimethylsilyl)indole-4-boronic acid, 98% 250mg [1-TBDMS-4-indoleboronic acid] 1g

[351457-64-2], C14H22BNO2Si, F.W. 275.23, White solid, m.p. 130-135ø, MDL MFCD08436007

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Acids

H52624 1-(tert-Butyldimethylsilyl)indole-5-boronic acid, 97% 250mg [1-TBDMS-5-indoleboronic acid] 1g

[913835-68-4], C14H22BNO2Si, F.W. 275.23, White solid, m.p. 248-250ø, MDL MFCD03095156

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52633 1-(tert-Butyldimethylsilyl)indole-6-boronic acid, 98% 250mg [1-TBDMS-6-indoleboronic acid] 1g

[913835-60-6], C14H22BNO2Si, F.W. 275.23, White solid, m.p. 217-219ø, MDL MFCD03095157

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53138 2-Carboxypyridine-5-boronic acid, 97% 250mg [5-Boronopicolinic acid]

[913836-11-0], C6H6BNO4, F.W. 166.93, White solid, m.p. >300ø, MDL MFCD09027238

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53202 5-Carboxypyridine-3-boronic acid, 97% 250mg [5-Borononicotinic acid]

[913836-03-0], C6H6BNO4, F.W. 166.93, White solid, m.p. 226-230ø, MDL MFCD02323212

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53210 2-Carboxythiophene-4-boronic acid, 98% 250mg [4-Boronothiophene-2-carboxylic acid]

[913835-91-3], C5H5BO4S, F.W. 171.96, White solid, m.p. 170-172ø, MDL MFCD08689521

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52503 2-Chloro-5-cyanopyridine-3-boronic acid, 96% 250mg

[957060-96-7], C6H4BClN2O2, F.W. 182.37, White solid, m.p. 238-241ø, MDL MFCD09027243

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27781 3-Chloro-2-fluoropyridine-4-boronic acid, 95% 250mg

[1217500-55-4], C5H4BClFNO2, F.W. 175.35, White to cream powder, 1g m.p. 126-130ø, MDL MFCD09037477

H:H315-H319-H335, P:P280g-P305+P351+P338

Bulk and Specialty Sizes Available 109 Heterocyclic Boronic Acids Stock # Description Standard Selling Sizes H53341 5-Chloro-2-fluoropyridine-3-boronic acid, 97% 250mg

[937595-70-5], C5H4BClFNO2, F.W. 175.35, White solid, m.p. 125-126ø, 1g MDL MFCD04972408

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H26950 3-Chloro-2-methoxypyridine-4-boronic acid, 95% 250mg

[957060-88-7], C6H7BClNO3, F.W. 187.39, White to pale yellow powder, 1g m.p. ca 140ø dec., MDL MFCD06798255 5g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53222 2-Chloro-4-methylpyridine-5-boronic acid, 98% 250mg

[913836-08-5], C6H7BClNO2, F.W. 171.39, Off-white solid, 1g m.p. 105-107ø, MDL MFCD07368882

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52664 2-Chloro-5-methylpyridine-3-boronic acid, 98% 250mg

[913835-86-6], C6H7BClNO2, F.W. 171.39, Brown solid, m.p. 115-118ø, 1g MDL MFCD04112563

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53165 6-Chloro-2-methylpyridine-3-boronic acid, 98% 250mg

[913836-15-4], C6H7BClNO2, F.W. 171.39, White solid, m.p. 154-156ø, 1g Acids MDL MFCD07368875

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27099 6-Chloro-5-methylpyridine-3-boronic acid, 95% 250mg

[1003043-40-0], C6H7BClNO2, F.W. 171.39, White to cream powder, 1g

Boronic m.p. 180-183ø, MDL MFCD03411564

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L20303 2-Chloropyridine-3-boronic acid, 96% 1g [2-Chloro-3-pyridylboronic acid] 5g

[381248-04-0], C5H5BClNO2, F.W. 157.37, m.p. 160ø, BRN 9119913, MDL MFCD03094997

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Heterocyclic H27357 2-Chloropyridine-4-boronic acid, 95% 1g

[458532-96-2], C5H5BClNO2, F.W. 157.37, White to pale cream powder, 5g m.p. 160-164ø, MDL MFCD03788416

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52864 3-Chloropyridine-4-boronic acid, 96% 250mg

[458532-98-4], C5H5BClNO2, F.W. 157.37, Off-white solid, m.p. 95-97ø, 1g MDL MFCD03425942

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52697 4-Chloropyridine-3-boronic acid, 98% 250mg

[452972-10-0], C5H5BClNO2, F.W. 157.37, MDL MFCD06801679 1g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H52515 5-Chloropyridine-2-boronic acid, 96% 250mg

[652148-91-9], C5H5BClNO2, F.W. 157.37, Off-white solid, 1g MDL MFCD07368862

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27756 5-Chloropyridine-3-boronic acid, 95% 250mg

[872041-85-5], C5H5BClNO2, F.W. 157.37, White to cream powder, 1g MDL MFCD06798243 5g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L20388 6-Chloropyridine-3-boronic acid, 96% 250mg [6-Chloro-3-pyridylboronic acid] 1g

[444120-91-6], C5H5BClNO2, F.W. 157.37, m.p. 154-157ø, 5g BRN 9119810, MDL MFCD03094998

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L20329 2-Chloroquinoline-3-boronic acid, 97% 250mg

[128676-84-6], C9H7BClNO2, F.W. 207.43, White to pale yellow cryst 1g powder, m.p. 144-147ø, MDL MFCD01114675 5g

H:H315-H319-H335, P:P280g-P305+P351+P338 B23193 5-Chlorothiophene-2-boronic acid, 97% 1g [5-Chloro-2-thienylboronic acid] 5g

[162607-18-3], C4H4BClO2S, F.W. 162.40, White to pale green cryst 25g powder, m.p. ca 136-140ø, BRN 8478804, MDL MFCD00236030

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

110 www.alfa.com Heterocyclic Boronic Acids Stock # Description Standard Selling Sizes H53203 5-Cyanoindole-2-boronic acid 250mg

[871329-64-5], C9H7BN2O2, F.W. 185.98, Yellow solid, m.p. 220-226ø, MDL MFCD06798223

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L18523 5-Cyanothiophene-2-boronic acid, 98% 250mg [5-Cyano-2-thienylboronic acid] 1g

[305832-67-1], C5H4BNO2S, F.W. 152.97, White to yellow powder, m.p. 125-128ø, MDL MFCD02094029

H:H302-H315-H319-H335, P:P280h-P305+P351+P338 L19830 Dibenzofuran-4-boronic acid, 98+% 1g

[100124-06-9], C12H9BO3, F.W. 212.01, m.p. 286-291ø, BRN 1645426, 5g MDL MFCD00092336

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L19831 Dibenzothiophene-4-boronic acid, 95% 1g

[108847-20-7], C12H9BO2S, F.W. 228.08, White to pale yellow solid, 5g

m.p. >300ø, BRN 197863, MDL MFCD01318182 Heterocyclic

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27870 2,4-Dibenzyloxypyrimidine-5-boronic acid, 95% 250mg

[70523-24-9], C18H17BN2O4, F.W. 336.15, White powder, m.p. 88-91ø, 1g MDL MFCD01318938

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H27668 2,3-Dichloropyridine-4-boronic acid, 95% 250mg Boronic

[951677-39-7], C5H4BCl2NO2, F.W. 191.81, White powder, m.p. 136-138ø, 1g MDL MFCD04038756

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H27849 2,5-Dichloropyridine-3-boronic acid, 95% 250mg Acids

[536693-97-7], C5H4BCl2NO2, F.W. 191.81, White to cream powder, 1g m.p. 152-155ø, MDL MFCD06659486

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27170 2,5-Dichloropyridine-4-boronic acid, 95% 1g

[847664-64-6], C5H4BCl2NO2, F.W. 191.81, White to cream powder, m.p. ca 5g 150ø dec., MDL MFCD06798254

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27406 2,6-Dichloropyridine-3-boronic acid, 95% 250mg

[148493-34-9], C5H4BCl2NO2, F.W. 191.81, MDL MFCD03094989 1g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H32803 2,5-Dichlorothiophene-3-boronic acid, 95% 250mg

[177735-28-3], C4H3BCl2O2S, F.W. 196.85, White to pale brown cryst 1g powder

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27509 2,6-Difluoropyridine-3-boronic acid, 95% 250mg

[136466-94-9], C5H4BF2NO2, F.W. 158.90, MDL MFCD03788245 1g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52479 2,3-Dihydrobenzo[b]furan-5-boronic acid, 97% 250mg

[227305-69-3], C8H9BO3, F.W. 163.97, White solid, m.p. 200ø, 1g MDL MFCD02681979

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L20389 2,6-Dimethoxypyridine-3-boronic acid, 95% 250mg

[221006-70-8], C7H10BNO4, F.W. 182.97, m.p. 128-130ø, 1g BRN 9391039, MDL MFCD03788239 5g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H26893 3,5-Dimethylisoxazole-4-boronic acid, 97% 1g

[16114-47-9], C5H8BNO3, F.W. 140.93, White to pale cream cryst powder, 5g m.p. 106-108ø, MDL MFCD02677945

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H32543 2,5-Dimethylthiophene-3-boronic acid, 95% 250mg

[162607-23-0], C6H9BO2S, F.W. 156.01, White cryst powder 1g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Bulk and Specialty Sizes Available 111 Heterocyclic Boronic Acids Stock # Description Standard Selling Sizes L20422 2-Ethoxypyridine-3-boronic acid, 98% 250mg

[854373-97-0], C7H10BNO3, F.W. 166.97, MDL MFCD06201036 1g 5g H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L20398 6-Ethoxypyridine-3-boronic acid, 98% 250mg [2-Ethoxy-5-pyridylboronic acid] 1g

[612845-44-0], C7H10BNO3, F.W. 166.97, m.p. 102-104ø, 5g BRN 9388808, MDL MFCD06201032

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27257 6-(4-Fluorophenyl)pyridine-3-boronic acid, 95% 250mg

C11H9BFNO2, F.W. 217.01, White to cream powder, m.p. ca 100ø 1g dec., MDL MFCD09037487

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

L20108 2-Fluoropyridine-3-boronic acid, 97% 1g [2-Fluoro-3-pyridylboronic acid] 5g

[174669-73-9], C5H5BFNO2, F.W. 140.91, m.p. 172ø, BRN 9119935, MDL MFCD03411557

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Acids H27630 2-Fluoropyridine-4-boronic acid, 95% 1g

[401815-98-3], C5H5BFNO2, F.W. 140.91, MDL MFCD04112534 5g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Boronic H53109 3-Fluoropyridine-4-boronic acid, 98% 250mg

[458532-97-3], C5H5BFNO2, F.W. 140.91, White solid, m.p. 237-239ø, 1g MDL MFCD03788558

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52860 5-Fluoropyridine-3-boronic acid, 98% 250mg

[872041-86-6], C5H5BFNO2, F.W. 140.91, White solid, m.p. 233-236ø, 1g MDL MFCD07368243 Heterocyclic H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L20387 6-Fluoropyridine-3-boronic acid, 95% 250mg [6-Fluoro-3-pyridylboronic acid] 1g

[351019-18-6], C5H5BFNO2, F.W. 140.91, m.p. 177-178ø dec., 5g BRN 8974962, MDL MFCD03411559

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L20341 2-Fluoroquinoline-3-boronic acid, 97% 250mg

[745784-10-5], C9H7BFNO2, F.W. 190.97, m.p. 89-94ø, 1g MDL MFCD05664131 5g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L15198 3-Formylfuran-2-boronic acid, 97% È 1g [2-Borono-3-furaldehyde] 5g

[27339-38-4], C5H5BO4, F.W. 139.90, White/pale yellow/pale brown powder, m.p. ca 150ø dec., BRN 1637137, MDL MFCD01075680

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L17920 5-Formylfuran-2-boronic acid, 97% È 1g [5-Borono-2-furaldehyde] 5g

[27329-70-0], C5H5BO4, F.W. 139.90, Brown powder, m.p. ca 140ø dec., BRN 1637050, MDL MFCD01114696

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Bifunctional reagent used in the synthesis of ã -extended heteroarylfuran systems: Org. Biomol. Chem., 1, 1447 (2003). H25947 5-Formyl-4-methylthiophene-2-boronic acid, 97% È 1g [5-Borono-3-methylthiophene-2-carboxaldehyde] 5g

[352530-25-7], C6H7BO3S, F.W. 169.95, White to pink powder, m.p. 118-120ø, MDL MFCD03093890

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

112 www.alfa.com Heterocyclic Boronic Acids Stock # Description Standard Selling Sizes L15195 2-Formylthiophene-3-boronic acid, 97% È 1g [3-Boronothiophene-2-carboxaldehyde] 5g

[4347-31-3], C5H5BO3S, F.W. 155.97, White to pale brown powder, m.p. ca 200ø dec., BRN 4393584, MDL MFCD01075678

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Suzuki coupling (see Appendix 5) with amino bromo- or iodo-pyridine derivatives is accompanied by in situ cyclization to the thieno[2,3-c]-1,7-naphthyridine ring system: J. Heterocycl. Chem., 31, 11 (1994):

H53298 2-Formylthiophene-4-boronic acid, 98% 1g [4-Boronothiophene-2-carboxaldehyde] 5g

[175592-59-3], C5H5BO3S, F.W. 156.96, Off-white solid, m.p. 270-272ø, MDL MFCD03002365

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Heterocyclic L15196 3-Formylthiophene-2-boronic acid, 97% È 1g [2-Boronothiophene-3-carboxaldehyde] 5g

[17303-83-2], C5H5BO3S, F.W. 155.97, White to pale brown powder, m.p. ca 180ø dec., BRN 4387740, MDL MFCD01075679

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H29289 5-Formylthiophene-2-boronic acid, 97% È 1g

[4347-33-5], C5H5BO3S, F.W. 155.97, Cream to orange powder, 5g Boronic m.p. ca 124ø dec., MDL MFCD02093666

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B23842 Furan-2-boronic acid, 97% È 1g [2-Furylboronic acid] 5g Acids [13331-23-2], C4H5BO3, F.W. 111.89, White to cream cryst powder, m.p. ca 25g 120ø dec., BRN 112370, MDL MFCD00799544

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Undergoes an asymmetric boronic acid Mannich reaction with aldehydes in the presence of the chiral template (S)-5-phenylmorpholine-2-one to give substituted furfurylamines with high diastereomeric excess: Chem. Commun., 1953 (1996); J. Chem. Soc., Perkin 1, 2982 (2000):

L19834 Furan-3-boronic acid, 97% 1g [3-Furylboronic acid] 5g

[55552-70-0], C4H5BO3, F.W. 111.89, m.p. 139-144ø, BRN 1635653, MDL MFCD01319007

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53319 2-(Hydroxymethyl)pyridine-5-boronic acid, 97% 250mg

[913835-98-0], C6H8BNO3, F.W. 152.94, White solid, MDL MFCD09027230

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53050 Imidazo[1,2-a]pyridine-6-boronic acid, 98% 250mg [1-Azaindolizine-6-boronic acid]

[913835-63-9], C7H7BN2O2, F.W. 161.95, Brown solid, m.p. 115-117ø, MDL MFCD06739225

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53037 Indole-4-boronic acid, 95% È 250mg [4-Boronoindole] 1g

[220465-43-0], C8H8BNO2, F.W. 160.97, Off-white solid, MDL MFCD03095175

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H27008 Indole-5-boronic acid, 95% È 1g [5-Boronoindole]

[144104-59-6], C8H8BNO2, F.W. 160.97, Solid, m.p. 170-175ø, MDL MFCD01319013

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Bulk and Specialty Sizes Available 113 Heterocyclic Boronic Acids Stock # Description Standard Selling Sizes H53313 Indole-6-boronic acid, 98% È 250mg [6-Boronoindole] 1g

[147621-18-9], C8H8BNO2, F.W. 160.97, White solid, m.p. 177-181ø, MDL MFCD03095176

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53118 4-Isopropylpyrimidine-5-boronic acid, 95% 250mg

[913835-27-5], C7H11BN2O2, F.W. 165.99, White solid, m.p. 104-109ø, MDL MFCD08235084

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L20430 Isoquinoline-4-boronic acid, 97% 250mg

[192182-56-2], C9H8BNO2, F.W. 172.98, White to pink powder, m.p. >270ø, 1g MDL MFCD03412093

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53230 Isoquinoline-5-boronic acid, 97% 250mg

[371766-08-4], C9H8BNO2, F.W. 172.98, Off-white solid, m.p. 204-206ø, 1g MDL MFCD03839356

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52470 Isoquinoline-5-boronic acid hydrochloride, 97% 250mg Acids C9H8BNO2ùHCl, F.W. 209.44, Off-white solid, m.p. 204-206ø, 1g MDL MFCD03839356

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52700 5-(Methoxycarbonyl)pyridine-3-boronic acid, 95% 250mg

Boronic [Methyl 5-Borononicotinate]

[871329-53-2], C7H8BNO4, F.W. 180.95, Pale yellow solid, m.p. 102-108ø, MDL MFCD07363742

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L20094 2-Methoxypyridine-3-boronic acid, 98% 1g [2-Methoxy-3-pyridylboronic acid] 5g

[163105-90-6], C6H8BNO3, F.W. 152.95, m.p. 136-138ø,

Heterocyclic MDL MFCD03411572

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53241 2-Methoxypyridine-4-boronic acid, 97% 250mg

[762262-09-9], C6H8BNO3, F.W. 152.95, White solid, m.p. 65-70ø, MDL MFCD07368877

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L20087 6-Methoxypyridine-3-boronic acid, 95% 250mg [2-Methoxy-5-pyridylboronic acid] 1g

[163105-89-3], C6H8BNO3, F.W. 152.95, m.p. 132-133ø, 5g BRN 9119950, MDL MFCD02093044

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52532 2-Methoxypyridine-5-boronic acid hydrochloride, 96% 250mg

[370864-57-6], C6H8BNO3ùHCl, F.W. 189.41, White to off-white solid, 1g m.p. 156-160ø, MDL MFCD04973740

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53028 1-Methylindole-2-boronic acid, 95% 250mg

[191162-40-0], C9H10BNO2, F.W. 174.99, Pale brown solid, 1g m.p. 108-112ø, MDL MFCD01114668

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H31640 5-Methyl-6-(4-morpholinyl)pyridine-3-boronic acid, 95% 250mg

C10H15BN2O3, F.W. 222.05, White To cream cryst powder

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H52517 5-Methylpyridine-2-boronic acid, 95% 250mg

[372963-49-0], C6H8BNO2, F.W. 136.95, White solid, m.p. 86-90ø, MDL MFCD00674179

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52891 5-Methylpyridine-3-boronic acid, 98% 250mg

[173999-18-3], C6H8BNO2, F.W. 136.95, Pale brown solid, m.p. >300ø, 1g MDL MFCD03428528

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

114 www.alfa.com Heterocyclic Boronic Acids Stock # Description Standard Selling Sizes H53133 5-(Methylsulfonyl)pyridine-3-boronic acid, 98% 250mg

[913836-01-8], C6H8BNO4S, F.W. 201.00, White solid, m.p. 123-125ø, MDL MFCD08689536

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53201 3-Methylthiophene-2-boronic acid, 98% 250mg

[177735-09-0], C5H7BO2S, F.W. 142.01, White solid, m.p. 192-196ø, 1g MDL MFCD00236049

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B23138 5-Methylthiophene-2-boronic acid, 98% 1g

[162607-20-7], C5H7BO2S, F.W. 142.01, White to cream powder, 5g m.p. ca 160ø dec., BRN 7019569, MDL MFCD01318166 25g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27162 2-(Methylthio)pyridine-3-boronic acid, 95% 250mg

[1072944-21-8], C6H8BNO2S, F.W. 169.01, White powder, m.p. ca 100ø 1g dec., MDL MFCD09037488

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Heterocyclic H52463 5-(Methylthio)pyridine-3-boronic acid, 96% 250mg

[477251-98-2], C6H8BNO2S, F.W. 169.01, White solid, m.p. 210-213ø, MDL MFCD08689538

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27873 6-(Methylthio)pyridine-3-boronic acid, 95% 250mg

[321438-86-2], C6H8BNO2S, F.W. 169.01, Nearly white powder, 1g

MDL MFCD03788238 Boronic

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27286 1H-Pyrazole-3-boronic acid hydrate, 95% 1g

[376584-63-3], C3H5BN2O2ùxH2O, F.W. 111.89, White powder, m.p. 85-88ø, 5g MDL MFCD11044442 Acids H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H53314 Pyridine-2-boronic acid, 95% 250mg

[197958-29-5], C5H6BNO2, F.W. 122.92, White solid, m.p. >300ø, 1g MDL MFCD00151844

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L15040 Pyridine-3-boronic acid 1g [3-Pyridylboronic acid] 5g

[1692-25-7], C5H6BNO2, F.W. 122.92, m.p. >300ø, BRN 471943, MDL MFCD00674177

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L15179 Pyridine-4-boronic acid hydrate, ca 10-15% water 1g [4-Pyridylboronic acid] 5g

[1692-15-5], C5H6BNO2ùxH2O, F.W. 122.92(anhy), White to brown powder, m.p. >300ø, BRN 471944, MDL MFCD08061353

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52648 Pyridine-4-boronic acid hydrochloride, 95% 1g

[913835-65-1], C5H6BNO2ùHCl, F.W. 159.38, White solid, m.p. 340ø, 5g MDL MFCD06201888

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H29212 Pyrimidine-5-boronic acid hemihydrate, 97% 1g

[696602-91-2], C4H5BN2O2ù0.5H2O, F.W. 132.91 (123.91anhy), White to cream powder, 10g m.p. >300ø, MDL MFCD03002366

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52984 Pyrimidine-5-boronic acid, 98% 250mg

[109299-78-7], C4H5BN2O2, F.W. 123.91, White solid, m.p. >300C, 1g MDL MFCD03002366

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L20088 Quinoline-3-boronic acid, 95% 250mg

[191162-39-7], C9H8BNO2, F.W. 172.98, m.p. >300ø, BRN 8764547, 1g MDL MFCD02183527 5g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L19639 Quinoline-5-boronic acid, 97% 250mg

[355386-94-6], C9H8BNO2, F.W. 172.98, m.p. 144-148ø, 1g MDL MFCD03095058

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Bulk and Specialty Sizes Available 115 Heterocyclic Boronic Esters Stock # Description Standard Selling Sizes H52867 Quinoline-6-boronic acid, 97% 250mg

[376581-24-7], C9H8BNO2, F.W. 172.98, Off-white solid, m.p. 106-109ø, 1g MDL MFCD03093100

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L19640 Quinoline-8-boronic acid, 99% 250mg

[86-58-8], C9H8BNO2, F.W. 172.98, m.p. >300ø, Merck 14,8069, 1g BRN 147522, MDL MFCD01114698

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H53021 Quinoline-3-boronic acid hydrochloride, 97% 250mg

[850568-71-7], C9H8BNO2ùHCl, F.W. 209.44, White solid, 1g m.p. 190-194ø, MDL MFCD06659836

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H30380 Quinoline-6-boronic acid hydrochloride, 95% 250mg

C9H8BNO2ùHCl, F.W. 209.44, White to pale grey powder, m.p. ca 1g 220ø dec., MDL MFCD11101398

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L19833 Thianthrene-1-boronic acid, tech. 90% 1g

[108847-76-3], C12H9BO2S2, F.W. 260.14, White to cream solid, 5g

Esters m.p. 145-149ø, BRN 225524, MDL MFCD00093039

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B23071 Thiophene-2-boronic acid, 98% 1g [2-Thienylboronic acid] 5g

Boronic [6165-68-0], C4H5BO2S, F.W. 127.96, White to cream powder, 25g m.p. 128-131ø, BRN 112375, MDL MFCD00151850

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Suzuki coupling (see Appendix 5) to a polymer-bound aryl iodide gives the 2-arylthiophene derivative in high yield: J. Org. Chem., 61, 5169 (1996). B23637 Thiophene-3-boronic acid, 98% 1g [3-Thienylboronic acid] 5g

Heterocyclic [6165-69-1], C4H5BO2S, F.W. 127.96, White to pale brown powder, 25g m.p. 164-169ø, BRN 113573, MDL MFCD00151851

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27219 Uracil-5-boronic acid, 95% 250mg [2,4-Dioxo-1,2,3,4-tetrahydro-5-pyrimidinylboronic acid] 1g

[70523-22-7], C4H5BN2O4, F.W. 155.90, m.p. >300ø, MDL MFCD01318983

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Stock # Description Standard Selling Sizes H27685 6-Aminopyridine-3-boronic acid pinacol ester, 97% 1g [2-Amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine] 5g

[827614-64-2], C11H17BN2O2, F.W. 220.08, White to cream powder, m.p. 131-135ø, MDL MFCD05663837

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H50044 7-Azaindole-5-boronic acid pinacol ester È 250mg 1g

[5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine]

[754214-56-7], C13H17BN2O2, F.W. 244.10, Solid, MDL MFCD08060937

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H29358 Benzofurazan-5-boronic acid pinacol ester, 97% 250mg [5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)furazan] 1g

C12H15BN2O3, F.W. 246.07, White to cream powder, m.p. 87-89ø, 5g MDL MFCD09842717

116 www.alfa.com Heterocyclic Boronic Esters Stock # Description Standard Selling Sizes H51876 Benzo[b]thiophene-3-boronic acid pinacol ester, 95% 250mg [2-Benzo[b]thiophen-3-yl-4,4,5,5-tetramethyl-1,3,2-dioxaboro lane, 1g 4,4,5,5-Tetramethyl-2-benzo[b]thiophen-3-yl-1,3,2-dioxaborolane]

[171364-86-6], C14H17BO2S, F.W. 260.16, Solid, MDL MFCD11110552

H27463 6-(Benzylamino)pyridine-3-boronic acid pinacol ester, 250mg 95% 1g [N-Benzyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- pyridin-2-amine]

[1073354-27-4], C18H23BN2O2, F.W. 310.20, White to pale yellow cryst powder, m.p. 135-138ø, MDL MFCD06798270

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H51949 1-Benzyl-7-azaindole-3-boronic acid pinacol ester, 95% 1g 5g Heterocyclic

[1-Benzyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine]

C20H23BN2O2, F.W. 334.22, Solid, MDL MFCD16294550

H51944 9-Benzylcarbazole-3-boronic acid pinacol ester, 95% 1g Boronic [9-Benzyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole] 5g

C25H26BNO2, F.W. 383.30, Solid, MDL MFCD16294547 Esters

H51945 1-Benzylindole-5-boronic acid pinacol ester, 95% 1g [1-Benzyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indole] 5g

C21H24BNO2, F.W. 333.24, Solid, MDL MFCD11894320

H27842 6-[Benzyl(methyl)amino]pyridine-3-boronic acid pinacol 250mg ester, 95% 1g

[N-Benzyl-N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinamine]

[1073354-30-9], C19H25BN2O2, F.W. 324.23, White to pale yellow powder, MDL MFCD06798271

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27292 4-Benzyloxy-2-chloropyrimidine-5-boronic acid pinacol ester, 250mg 95% 1g [4-Benzyloxy-2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- pyrimidine]

[1073354-22-9], C17H20BClN2O3, F.W. 346.62, Cream to brown powder, m.p. 99-101ø, MDL MFCD06798267

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H26928 2-Benzyloxypyridine-3-boronic acid pinacol ester, 95% 250mg [2-Benzyloxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine] 1g

[1073371-81-9], C18H22BNO3, F.W. 311.19, Colorless/pale yellow visc. liquid, MDL MFCD06798265

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H27708 6-Benzyloxypyridine-3-boronic acid pinacol ester, 95% 250mg [2-Benzyloxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 1g pyridine]

[832735-54-3], C18H22BNO3, F.W. 311.19, White cryst powder, m.p. 138-142ø, MDL MFCD06798263

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Bulk and Specialty Sizes Available 117 Heterocyclic Boronic Esters Stock # Description Standard Selling Sizes H27794 6-(4-Benzyl-1-piperazinyl)pyridine-3-boronic acid 250mg pinacol ester, 95% 1g

[1-Benzyl-4-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]piperazine]

[1015242-03-1], C22H30BN3O2, F.W. 379.31, Cream powder, m.p. 128-131ø, MDL MFCD06798275

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H50094 2-(Boc-amino)pyridine-3-boronic acid pinacol ester È 250mg [tert-Butyl [3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl- 1g ]carbamate]

C16H25BN2O4, F.W. 320.20, Solid, MDL MFCD08063072

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H27500 6-(N-Boc-methylamino)-5-methylpyridine-3-boronic 250mg acid pinacol ester, 95% 1g [tert-Butyl Esters

N-methyl-N-[3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]carbamate]

[1032758-82-9], C18H29BN2O4, F.W. 348.25, White to cream powder, m.p. 152-155ø, MDL MFCD09037485 Boronic H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27430 6-(N-Boc-methylamino)pyridine-3-boronic acid pinacol 250mg ester, 95% 1g [tert-Butyl N-methyl-N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- pyridin-2-yl]carbamate]

[1032758-87-4], C17H27BN2O4, F.W. 334.22, Pale cream

Heterocyclic powder, m.p. 112-119ø, MDL MFCD09037484

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H50058 2-(4-Boc-1-piperazinyl)pyridine-3-boronic acid pinacol ester 1g [tert-Butyl 5g 4-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl- ]piperazine-1-carboxylate]

C20H32BN3O4, F.W. 389.31, Solid, MDL MFCD07781131

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H50145 6-(4-Boc-1-piperazinyl)pyridine-3-boronic acid 250mg pinacol ester 1g [tert-Butyl

4-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]piperazine-1-carboxylate]

[496786-98-2], C20H32BN3O4, F.W. 389.31, Solid, MDL MFCD04039875

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H26222 1-Boc-pyrrolidine-3-boronic acid diethanolamine ester, 97% 250mg [1-(tert-Butoxycarbonyl)pyrrolidine-3-boronic acid diethanolamine 1g ester] 5g

C13H25BN2O4, F.W. 284.17, Solid, m.p. 161-164ø, MDL MFCD09953469

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27666 5-Bromo-2-chloropyridine-3-boronic acid pinacol ester, 95% 250mg [5-Bromo-2-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 1g pyridine]

[1073354-79-6], C11H14BBrClNO2, F.W. 318.40, White powder, m.p. 76-82ø, MDL MFCD09037493

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

118 www.alfa.com Heterocyclic Boronic Esters Stock # Description Standard Selling Sizes H27820 5-Bromo-2-fluoropyridine-3-boronic acid pinacol ester, 95% 250mg [5-Bromo-2-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 1g pyridine]

[1073353-50-0], C11H14BBrFNO2, F.W. 301.95, White powder, m.p. 46-49ø, MDL MFCD08689619

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H50064 5-Bromo-2-methoxypyridine-3-boronic acid pinacol ester 250mg [5-Bromo-2-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 1g pyridine]

C12H17BBrNO3, F.W. 313.99, Solid, m.p. 90ø, MDL MFCD07781157

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H27813 2-Bromopyridine-4-boronic acid pinacol ester, 97% 250mg [2-Bromo-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine] 1g

[458532-82-6], C11H15BBrNO2, F.W. 283.96, White to pale pink cryst powder, m.p. 80-83ø, MDL MFCD06798252 Heterocyclic H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H27041 3-Bromopyridine-4-boronic acid pinacol ester, 95% 1g [3-Bromo-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine] 5g

[458532-92-8], C11H15BBrNO2, F.W. 283.96, White to orange powder, m.p. 88-90ø, MDL MFCD06798250 Boronic H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H27245 6-Bromopyridine-2-boronic acid pinacol ester, 95% 250mg

[2-Bromo-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine] 1g Esters

[651358-83-7], C11H15BBrNO2, F.W. 283.96, White powder, m.p. 125-127ø, MDL MFCD06796177

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H50072 2-Bromopyridine-5-boronic acid pinacol ester 1g [2-Bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine] 5g

[214360-62-0], C11H15BBrNO2, F.W. 283.96, Solid, MDL MFCD03412794

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H52314 2-Carbamoylfuran-4-boronic acid pinacol ester, 96% 250mg [4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-carboxamide] 1g

C11H16BNO4, F.W. 237.06, Solid

H52330 5-Carbamoylpyridine-3-boronic acid pinacol ester, 96% 250mg [5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinamide] 1g

[1169402-51-0], C12H17BN2O3, F.W. 248.09, Solid

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H52353 5-Carbamoylthiophene-2-boronic acid pinacol ester, 96% 250mg [5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)- 1g thiophene-2-carboxamide]

C11H16BNO3S, F.W. 253.13, Solid

H27284 2-Chloro-3-cyanopyridine-4-boronic acid pinacol ester, 95% 250mg [2-Chloro-3-cyano-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine] 1g

[878194-94-6], C12H14BClN2O2, F.W. 264.52, Yellow powder, m.p. 100-101ø, MDL MFCD09037479

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Bulk and Specialty Sizes Available 119 Heterocyclic Boronic Esters Stock # Description Standard Selling Sizes H27457 3-Chloro-2-fluoropyridine-4-boronic acid pinacol ester, 95% 250mg [3-Chloro-2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine] 1g

[1073353-71-5], C11H14BClFNO2, F.W. 257.50, Pale yellow powder, m.p. 76-80ø, MDL MFCD09037476

H:H315-H319-H335, P:P280g-P305+P351+P338

H27513 3-Chloro-2-methoxypyridine-4-boronic acid pinacol ester, 95% 250mg [3-Chloro-2-methoxy-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine] 1g

[1073353-73-7], C12H17BClNO3, F.W. 269.53, White powder, m.p. 47-50ø, MDL MFCD06798258

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H31692 2-Chloro-1-methyl-1H-imidazole-5-boronic acid pinacol ester, 250mg 95%

C10H16BClN2O2, F.W. 242.52, White solid

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Esters H27582 6-Chloro-5-methylpyridine-3-boronic acid pinacol ester, 95% 250mg [2-Chloro-3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 1g pyridine]

[1010101-07-1], C12H17BClNO2, F.W. 253.54, White powder, m.p. 90-93ø, MDL MFCD08063084

Boronic H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H50053 2-Chloropyridine-3-boronic acid pinacol ester 1g [2-Chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine] 5g

[452972-11-1], C11H15BClNO2, F.W. 239.51, Solid, MDL MFCD04039873

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Heterocyclic H50070 2-Chloropyridine-4-boronic acid pinacol ester 1g [2-Chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine] 5g

[458532-84-8], C11H15BClNO2, F.W. 239.51, Solid, MDL MFCD04039870

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H27487 3-Chloropyridine-4-boronic acid pinacol ester, 95% 250mg [3-Chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine] 1g

[458532-90-6], C11H15BClNO2, F.W. 239.51, Pale brown powder, m.p. 103-108ø, MDL MFCD06798249

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H27740 4-Chloropyridine-3-boronic acid pinacol ester, 95% 1g [4-Chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine] 5g

[452972-15-5], C11H15BClNO2, F.W. 239.51, Pale cream powder, MDL MFCD06798247

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H27079 5-Chloropyridine-3-boronic acid pinacol ester, 95% 250mg [3-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine] 1g

[865186-94-3], C11H15BClNO2, F.W. 239.51, White powder, m.p. 79-81ø, MDL MFCD06798284

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H27426 6-Chloropyridine-2-boronic acid pinacol ester, tech. 90% 250mg [2-Chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine] 1g

[652148-92-0], C11H15BClNO2, F.W. 239.51, Cream powder, m.p. 107-110ø, MDL MFCD06798259

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

120 www.alfa.com Heterocyclic Boronic Esters Stock # Description Standard Selling Sizes H50071 6-Chloropyridine-3-boronic acid pinacol ester 1g [2-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine] 5g

[444120-94-9], C11H15BClNO2, F.W. 239.51, Solid, MDL MFCD03412793

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H51037 7-Chloroquinoline-4-boronic acid pinacol ester, 96% 1g [7-Chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline] 5g

[871125-83-6], C15H17BClNO2, F.W. 289.56, Pale yellow solid, MDL MFCD07783020

H31951 3-Chlorothiophene-2-boronic acid pinacol ester, 95% 250mg

C10H14BClO2S, F.W. 244.55, White cryst powder

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Heterocyclic

H27332 2-Cyanopyridine-3-boronic acid pinacol ester, 95% 250mg [2-Cyano-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine] 1g

[878194-93-5], C12H15BN2O2, F.W. 230.07, White powder, m.p. 58-61ø, MDL MFCD08458477

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Boronic

H27814 3-Cyanopyridine-4-boronic acid pinacol ester 250mg [3-Cyano-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine] 1g

[878194-92-4], C12H15BN2O2, F.W. 230.07, White to cream powder,

m.p. 97-99ø, MDL MFCD09037481 Esters

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H27216 4-Cyanopyridine-3-boronic acid pinacol ester 250mg [4-Cyano-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine] 1g

[878194-91-3], C12H15BN2O2, F.W. 230.07, Pink powder, m.p. 84-88ø, MDL MFCD08458478

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H27259 6-(Cyclohexylamino)pyridine-3-boronic acid pinacol 250mg ester, 95% 1g

[N-Cyclohexyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinamine]

[1073354-34-3], C17H27BN2O2, F.W. 302.23, White to cream powder, m.p. 120-122ø, MDL MFCD06798277

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27013 6-[Cyclohexyl(methyl)amino]pyridine-3-boronic acid 250mg pinacol ester, 95% 1g

[N-Cyclohexyl-N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinamine]

[1073354-73-0], C18H29BN2O2, F.W. 316.25, White to cream powder, m.p. 107-110ø, MDL MFCD09027071

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H50111 2-Cyclohexyloxypyridine-3-boronic acid pinacol ester 1g [2-Cyclohexyloxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine] 5g

C17H26BNO3, F.W. 303.21, MDL MFCD07781171

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Bulk and Specialty Sizes Available 121 Heterocyclic Boronic Esters Stock # Description Standard Selling Sizes H50110 2-Cyclopentyloxypyridine-3-boronic acid pinacol ester 1g [2-Cyclopentyloxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine] 5g

C16H24BNO3, F.W. 289.19, Liquid, MDL MFCD07781170

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H50139 6-(Cyclopropylmethoxy)pyridine-3-boronic acid pinacol 250mg ester È 1g [2-Cyclopropyl- methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine]

[947191-69-7], C15H22BNO3, F.W. 275.16, Liquid, MDL MFCD07781184

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27616 2,4-Dibenzyloxypyrimidine-5-boronic acid neopentyl 250mg glycol ester, 95% 1g [2,4-Bis(benzyloxy)-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)- pyrimidine]

[1072944-91-2], C23H25BN2O4, F.W. 404.27, White powder, MDL MFCD09037496

Esters H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27498 2,3-Dichloropyridine-4-boronic acid pinacol ester, 95% 250mg [2,3-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine] 1g

[1073353-78-2], C11H14BCl2NO2, F.W. 273.96, White to pale cream powder, m.p. 83-85ø, MDL MFCD06798257 Boronic H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H27432 2,5-Dichloropyridine-3-boronic acid pinacol ester, 94% 250mg [2,5-Dichloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine] 1g

[1073371-98-8], C11H14BCl2NO2, F.W. 273.96, White to yellow cryst powder, m.p. 75-79ø, MDL MFCD08063094 Heterocyclic H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H27699 2,5-Dichloropyridine-4-boronic acid pinacol ester, 95% 250mg [2,5-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine] 1g

[1073353-98-6], C11H14BCl2NO2, F.W. 273.96, White to cream powder, m.p. 83-85ø, MDL MFCD06798256

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H27605 2,6-Dichloropyridine-3-boronic acid pinacol ester, 95% 250mg [2,6-Dichloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine] 1g

[1073371-78-4], C11H14BCl2NO2, F.W. 273.96, White powder, m.p. 51-53ø, MDL MFCD06798261

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H26958 2,4-Dichloropyrimidine-5-boronic acid pinacol ester, 95% 250mg [2,4-Dichloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine] 1g

[1073354-24-1], C10H13BCl2N2O2, F.W. 274.94, Yellow powder, m.p. 50-53ø, MDL MFCD06798268

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H26965 2,6-Difluoropyridine-3-boronic acid pinacol ester, 95% 250mg [2,6-Difluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine] 1g

[1072945-00-6], C11H14BF2NO2, F.W. 241.04, White to cream cryst powder, m.p. 50-53ø, MDL MFCD09037475

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H27282 2,6-Dimethoxypyridine-3-boronic acid pinacol ester, 95% 250mg [2,6-Dimethoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 1g pyridine]

[214360-59-5], C13H20BNO4, F.W. 265.12, White powder, m.p. 39-42ø, MDL MFCD03788240

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

122 www.alfa.com Heterocyclic Boronic Esters Stock # Description Standard Selling Sizes H32159 3,5-Dimethylpyridine-4-boronic acid pinacol ester, 95% 500mg

C13H20BNO2, F.W. 233.12, White to cream powder

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H32726 250mg 1g

3,5-Dimethyl-1-(2-tetrahydropyranyl)-1H-pyrazole-4-boronic acid neopentyl glycol ester, 95%

C15H25BN2O3, F.W. 292.19, White to cream cryst powder H32478 250mg 1g Heterocyclic

3,5-Dimethyl-1-(2-tetrahydropyranyl)-1H-pyrazole-4-boronic acid pinacol ester, 95%

C16H27BN2O3, F.W. 306.22, White to cream cryst powder Boronic H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H51898 1g 5g Esters

2-(1,3-Dimethyl-2,4,6-trioxohexahydropyrimidin-5-ylidenemethyl)- thiophene-5-boronic acid pinacol ester, 95% [1,3-Dimethyl-5-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-thienylmethyl- ene]pyrimidine-2,4,6-trione]

C17H21BN2O5S, F.W. 376.23, Yellow solid, MDL MFCD16294525 H52312 2-(Ethoxycarbonyl)furan-5-boronic acid pinacol ester, 250mg 96% 1g [Ethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- furan-2-carboxylate]

[1073338-92-7], C13H19BO5, F.W. 266.10 H27122 6-(4-Ethoxycarbonyl-1-piperazinyl)- 250mg pyridine-3-boronic acid pinacol ester, 95% 1g

[4-[5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]piperazine-1-carboxylic acid ethyl ester]

[1073354-26-3], C18H28BN3O4, F.W. 361.25, Pale yellow crystalline powder, m.p. 135-139ø, MDL MFCD06798269 H50096 2-Ethoxypyridine-3-boronic acid pinacol ester 1g [2-Ethoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine] 5g

[848243-23-2], C13H20BNO3, F.W. 249.12, Liquid, MDL MFCD07366721

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H50137 6-Ethoxypyridine-3-boronic acid pinacol ester 250mg [2-Ethoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine] 1g

[1072945-01-7], C13H20BNO3, F.W. 249.12, Solid, MDL MFCD07781182

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Bulk and Specialty Sizes Available 123 Heterocyclic Boronic Esters Stock # Description Standard Selling Sizes H27168 6-(4-Fluorophenyl)pyridine-3-boronic acid pinacol ester, 250mg 95% 1g

[2-(4-Fluorophenyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine]

[1073354-81-0], C17H19BFNO2, F.W. 299.15, White powder, MDL MFCD09037494

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27845 2-Fluoropyridine-3-boronic acid pinacol ester, 95% 250mg [2-Fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine] 1g

[452972-14-4], C11H15BFNO2, F.W. 223.06, Pale cream powder, m.p. 42-45ø, MDL MFCD06798245

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H27179 2-Fluoropyridine-4-boronic acid pinacol ester, 95% 1g [2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine] 5g

[458532-86-0], C11H15BFNO2, F.W. 223.06, Pale yellow fused solid,

Esters m.p. 48-52ø, MDL MFCD06798253

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H50069 3-Fluoropyridine-4-boronic acid pinacol ester, 97% 250mg Boronic [3-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine] 1g

[458532-88-2], C11H15BFNO2, F.W. 223.06, White powder, m.p. 125-127ø, MDL MFCD06798251

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

L17779 5-Formyl-4-methylthiophene-2-boronic acid 1,3-propanediol 250mg Heterocyclic ester, 95% È 1g [5-(1,3,2-Dioxaborinan-2-yl)-3-methylthiophene-2-carboxaldehyde, 2-(2-Formyl-3-methylthien-5-yl)-1,3,2-dioxaborinane]

[374537-98-1], C9H11BO3S, F.W. 210.06, m.p. ca 66ø, MDL MFCD02093958 L18366 Furan-2-boronic acid pinacol ester, 98% 1g [2-Furylboronic acid pinacol ester, 5g 2-(2-Furyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane]

[374790-93-9], C10H15BO3, F.W. 194.04, Colorless to yellow liquid, Ë 1.4720, BRN 9045028, MDL MFCD02094008 H51673 6-Hydroxypyridine-3-boronic acid pinacol ester, 97% 250mg [2-Hydroxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine] 1g

C11H16BNO3, F.W. 221.06, Off-white powder, MDL MFCD06795671

H26976 2-Hydroxypyrimidine-5-boronic acid pinacol ester, 95% 250mg [5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-ol] 1g

[1073354-84-3], C10H15BN2O3, F.W. 222.05, White powder, m.p. 201-204ø, MDL MFCD09037497

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H32507 1H-Indazole-4-boronic acid pinacol ester, 95% 250mg [4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole]

[885618-33-7], C13H17BN2O2, F.W. 244.10, Solid, m.p. 139-142ø, MDL MFCD08059267

H52325 Indole-4-boronic acid pinacol ester, 97+% 250mg

[388116-27-6], C14H18BNO2, F.W. 243.11, White solid 1g 5g

124 www.alfa.com Heterocyclic Boronic Esters Stock # Description Standard Selling Sizes H52317 1-Isoindolinone-5-boronic acid pinacol ester, 96% 250mg [1-Oxoisoindoline-5-boronic acid pinacol ester, 1g 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-isoindolinone]

[376584-62-2], C14H18BNO3, F.W. 259.11, Solid

H50097 2-Isopropoxypyridine-3-boronic acid pinacol ester 1g [2-Isopropoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine] 5g

[848243-25-4], C14H22BNO3, F.W. 263.15, Liquid, MDL MFCD07366722

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H50141 6-Isopropoxypyridine-3-boronic acid pinacol ester, 97% 250mg [2-Isopropoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 1g pyridine]

[871839-91-7], C14H22BNO3, F.W. 263.15, White cryst solid, Heterocyclic m.p. 72-75ø, MDL MFCD07368871

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H50060 2-Methoxypyridine-3-boronic acid pinacol ester 250mg [2-Methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine] 1g

[532391-31-4], C12H18BNO3, F.W. 235.09, Powder, MDL MFCD05663507

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Boronic

H27263 6-Methoxypyridine-2-boronic acid pinacol ester, 97% 1g [2-Methoxy-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine] 5g

[1034297-69-2], C12H18BNO3, F.W. 235.09, White solid, 25g

m.p. 68-72ø, MDL MFCD06798266 Esters

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H50136 6-Methoxypyridine-3-boronic acid pinacol ester 250mg [2-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine] 1g

[445264-61-9], C12H18BNO3, F.W. 235.09, Solid, m.p. 47-51ø, MDL MFCD05663858

H:H315-H319-H335, P:P280g-P305+P351+P338

H27434 6-(4-Methylbenzylamino)pyridine-3-boronic 250mg acid pinacol ester, 95% 1g [N-(4-Methyl-

benzyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinamine]

[1073354-32-1], C19H25BN2O2, F.W. 324.23, White to pale cream powder, m.p. 148-153ø, MDL MFCD06798272

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H51952 9-Methylcarbazole-3-boronic acid pinacol ester, 95% 1g [9-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole] 5g

C19H22BNO2, F.W. 307.20, Solid, MDL MFCD16294552

H31282 5-Methylfuran-2-boronic acid pinacol ester, 97% 1g

[338998-93-9], C11H17BO3, F.W. 208.06, Colorless to pale yellow 5g liquid, d. 1.023, MDL MFCD03094689

Bulk and Specialty Sizes Available 125 Heterocyclic Boronic Esters Stock # Description Standard Selling Sizes H27227 5-Methyl-6-(4-morpholinyl)pyridine-3-boronic acid pinacol 250mg ester, 95% 1g

[4-[3-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]morpholine]

[1073372-03-8], C16H25BN2O3, F.W. 304.20, Pale yellow powder, m.p. ca 100-105ø, MDL MFCD09037483

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27703 1-Methyl-1H-pyrazole-5-boronic acid neopentyl glycol ester, 250mg 95% 1g [5-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)-1-methyl-1H-pyrazole]

[1044851-76-4], C9H15BN2O2, F.W. 194.04, White to cream powder, m.p. 72-75ø, MDL MFCD07777079 H53139 1-Methylpyrazole-4-boronic acid pinacol ester, 97% 250mg [1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole] 1g

[761446-44-0], C10H17BN2O2, F.W. 208.07, White to pale yellow crystalline powder, m.p. 59-64ø Esters

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Boronic H27094 1-Methyl-1H-pyrazole-5-boronic acid pinacol ester, 98% 1g [1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole] 250mg

[847818-74-0], C10H17BN2O2, F.W. 208.07, Cream cryst powder, m.p. 58-61ø, MDL MFCD05861380

H27450 2-Methylpyridine-4-boronic acid pinacol ester, 95% 250mg [2-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine] 1g

Heterocyclic [660867-80-1], C12H18BNO2, F.W. 219.09, White to yellow powder, m.p. 66-71ø, MDL MFCD08061590

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H32135 3-Methylpyridine-4-boronic acid pinacol ester, 95% 250mg

C12H18BNO2, F.W. 219.09, White to pale brown powder

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H53305 1-Methylpyrrole-2-boronic acid pinacol ester, 97% 250mg

[850567-47-4], C11H18BNO2, F.W. 207.08, White solid, m.p. 49-50ø, MDL MFCD06659917

H32023 4-Methylthiophene-3-boronic acid pinacol ester, 95% 250mg

[476620-20-9], C11H17BO2S, F.W. 224.13, Grey cryst powder 1g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H27610 2-(Methylthio)pyridine-3-boronic acid pinacol ester, 95% 250mg [2-Methylthio-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine] 1g

[1073354-78-5], C12H18BNO2S, F.W. 251.15, Nearly white powder, m.p. 62-65ø, MDL MFCD09037492

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H27061 6-(Methylthio)pyridine-3-boronic acid pinacol ester, 95% 250mg [2-Methylthio-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine] 1g

[849934-89-0], C12H18BNO2S, F.W. 251.15, White powder, m.p. 165-168ø, MDL MFCD09037495

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

126 www.alfa.com Heterocyclic Boronic Esters Stock # Description Standard Selling Sizes H26971 6-(4-Morpholinylamino)pyridine-3-boronic acid pinacol 250mg ester, 95% 1g

[N-(4-Morpholinyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinamine]

[1073354-38-7], C15H24BN3O3, F.W. 305.19, MDL MFCD06798279

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H28306 5-(4-Morpholinylmethyl)thiophene-2-boronic acid 1g pinacol ester, 97% 5g [4-[5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-thienyl- ]methylmorpholine]

[950603-39-1], C15H24BNO3S, F.W. 309.23, White to cream powder, m.p. 91-94ø, MDL MFCD09266197

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H50143 6-(4-Morpholinyl)pyridine-3-boronic acid pinacol ester 250mg Heterocyclic [4-[5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl- 1g ]morpholine, 6-(4-Morpholino)pyridine-3-boronic acid pinacol ester]

[485799-04-0], C15H23BN2O3, F.W. 290.17, White to cream powder, MDL MFCD04039874

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H51899 2-(Phenyliminomethyl)thiophene-5-boronic acid pinacol 1g Boronic ester, 95% 5g [Phenyl[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-thienyl- methylene]amine]

C17H20BNO2S, F.W. 313.22, Yellow solid, MDL MFCD16294526 Esters H26954 1-Phenylsulfonyl-1H-pyrazole-4-boronic acid pinacol ester, 250mg 95% 1g

[1-Benzenesulfonyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole]

[1073372-04-9], C15H19BN2O4S, F.W. 334.20, White powder, m.p. 125-130ø, MDL MFCD09037504 H31505 1-Phenylsulfonyl-1H-pyrrolo[2,3-b]pyridine-3-boronic acid 250mg pinacol ester, 95% [1-Benzenesulfonyl-1H-pyrrolo[2,3-b]pyridine-3-boronic acid pinacol ester]

[886547-94-0], C19H21BN2O4S, F.W. 384.27, Brown cryst powder

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27822 2-(1-Piperazinyl)pyridine-4-boronic acid pinacol ester, 97% 1g [4-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl- ]piperazine, 2-(1-Piperazino)pyridine-4-boronic acid pinacol ester]

[957198-31-1], C15H24BN3O2, F.W. 289.18, Solid, m.p. 112-116ø, MDL MFCD06795687

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H27222 6-(1-Piperidinylamino)pyridine-3-boronic acid pinacol 250mg ester, 95% 1g

[N-(1-Piperidinyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinamine]

[1073354-35-4], C16H26BN3O2, F.W. 303.22, Solid, MDL MFCD06798278

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H51117 5-(1-Piperidinylmethyl)thiophene-2-boronic acid pinacol 1g ester 5g [5-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-thienyl- ]piperidine]

C16H26BNO2S, F.W. 307.26, MDL MFCD11113036

Bulk and Specialty Sizes Available 127 Heterocyclic Boronic Esters Stock # Description Standard Selling Sizes H50109 2-n-Propoxypyridine-3-boronic acid pinacol ester 1g [2-n-Propoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine] 5g

C14H22BNO3, F.W. 263.15, Liquid, MDL MFCD07781169

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H27619 1H-Pyrazole-3-boronic acid pinacol ester, 95% 1g [3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole] 5g

[844501-71-9], C9H15BN2O2, F.W. 194.04, White powder, m.p. 105-108ø, MDL MFCD07368044

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

L19654 1H-Pyrazole-4-boronic acid pinacol ester, 98% 1g

[269410-08-4], C9H15BN2O2, F.W. 194.04, White to pale brown 5g powder, m.p. 145-149ø, MDL MFCD03453063

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H53067 Pyridine-2-boronic acid dimethyl ester, 95% 250mg

Esters [136805-54-4], C7H10BNO2, F.W. 150.97, White solid, 1g MDL MFCD03412109

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H52513 Pyridine-3-boronic acid pinacol ester, 98% 250mg [3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine] 1g

Boronic [329214-79-1], C11H16BNO2, F.W. 205.07, Pale yellow solid, m.p. 77-80ø, MDL MFCD03084758

L17854 Pyridine-4-boronic acid pinacol ester, 98% 250mg [2-(4-Pyridyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane] 1g

[181219-01-2], C11H16BNO2, F.W. 205.07, m.p. 150-152ø,

Heterocyclic BRN 7919059, MDL MFCD01319051

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a L17010 Pyridine-3-boronic acid 1,3-propanediol ester, 98+% 1g [2-(3-Pyridyl)-1,3,2-dioxaborinane] 5g

[131534-65-1], C8H10BNO2, F.W. 162.98, m.p. 100-104ø, BRN 6138748, MDL MFCD01075749

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H31954 1-(3-Pyridylmethyl)-1H-pyrazole-4-boronic acid pinacol 250mg ester 1g

[3-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-ylmethyl]pyridine]

[864754-21-2], C15H20BN3O2, F.W. 285.16, Orange powder, m.p. 102-106ø H27147 Pyrimidine-5-boronic acid pinacol ester, 95% 250mg [5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine] 1g

[321724-19-0], C10H15BN2O2, F.W. 206.05, Yellow cryst powder, m.p. 60-66ø, MDL MFCD05155223

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H51118 5-(1-Pyrrolidinylmethyl)thiophene-2-boronic acid pinacol 1g ester 5g [5-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-thienyl- ]pyrrolidine]

C15H24BNO2S, F.W. 293.23, MDL MFCD11113037

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27190 2-(1-Pyrrolidinyl)pyridine-3-boronic acid pinacol ester, 95% 250mg [2-(1-Pyrrolidinyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine, 1g 2-(1-Pyrrolidino)pyridine-3-boronic acid pinacol ester]

[1073354-41-2], C15H23BN2O2, F.W. 274.17, White powder, m.p. 76-78ø, MDL MFCD06798280

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

128 www.alfa.com Heterocyclic Boronic Esters Stock # Description Standard Selling Sizes H27341 6-(1-Pyrrolidinyl)pyridine-3-boronic acid pinacol ester, 250mg 95% 1g [6-(1-Pyrrolidino)pyridine-3-boronic acid pinacol ester, 6-(1-Pyrrolidinyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- pyridine]

[933986-97-1], C15H23BN2O2, F.W. 274.17, White to pale cream powder, m.p. 118-121ø, MDL MFCD06798273

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H51698 Quinoline-8-boronic acid pinacol ester, 95% 1g

[190788-62-6], C15H18BNO2, F.W. 255.12, Solid, 5g MDL MFCD05663894

H32369 1-(2-Tetrahydropyranyl)-1H-imidazole-5-boronic acid pinacol 500mg ester, 95%

[1029684-37-4], C14H23BN2O3, F.W. 278.16, White cryst powder, m.p. 129-133ø Heterocyclic

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H27783 1-(2-Tetrahydropyranyl)-1H-pyrazole-4-boronic acid 250mg neopentyl glycol ester, 95% 1g Boronic [4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)-1-(tetrahydropyran-2-yl)-1H-pyrazole]

C13H21BN2O3, F.W. 264.13, White powder, m.p. 84-90ø, MDL MFCD09037503 H27036 1-(2-Tetrahydropyranyl)-1H-pyrazole-5-boronic acid pinacol 250mg ester, 95% 1g Esters

[1-(Tetrahydropyran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole]

[903550-26-5], C14H23BN2O3, F.W. 278.16, White crystalline powder, MDL MFCD09037501 H31355 Tetrahydrothiophene-1,1-dioxide-3-boronic acid diethanolamine 250mg ester, 97% 1g

C8H16BNO4S, F.W. 233.10, Cream powder, m.p. 242-244ø, 5g MDL MFCD12546196

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27211 6-(N,2,2,2-Tetramethylacetamido)-5-methyl- 250mg pyridine-3-boronic acid pinacol ester, 95% 1g [6-(N-Methylpivalamido)-5-methylpyridine-3-boronic acid pinacol ester,

N-[3-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]-N-methyl-2,2-dimethyl- propionamide]

[1073354-77-4], C18H29BN2O3, F.W. 332.25, Nearly white powder, m.p. 134-136ø, MDL MFCD09037482

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H51725 Thiophene-2,5-diboronic acid bis(pinacol) ester, 97% 1g [2,5-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 5g thiophene]

[175361-81-6], C16H26B2O4S, F.W. 336.06, White to off-white crystalline, m.p. 216-220ø, MDL MFCD09800563 H50112 2-(2,2,2-Trifluoroethoxy)pyridine-3-boronic acid pinacol ester 250mg È 1g [3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(2,2,2-trifluoroethoxy)- pyridine]

C13H17BF3NO3, F.W. 303.09, MDL MFCD07781172

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Bulk and Specialty Sizes Available 129 Heterocyclic Trifluoroborate Salts Stock # Description Standard Selling Sizes H50015 2-(2,2,2-Trimethylacetamido)pyridine-3-boronic acid pinacol 250mg ester 1g [N-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]pivalamide]

[532391-30-3], C16H25BN2O3, F.W. 304.20, Solid, m.p. 155ø, MDL MFCD06658997

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H32930 1,3,5-Trimethyl-1H-pyrazole-4-boronic acid pinacol ester, 250mg 95% 1g

[844891-04-9], C12H21BN2O2, F.W. 236.12, Grey cryst powder

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H27043 1-(2-Trimethylsilylethoxy)- 250mg methyl-1H-pyrazole-5-boronic acid pinacol ester, 95% 1g

[5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(2-trimethylsilylethoxymethyl)-1H-pyrazole]

C15H29BN2O3Si, F.W. 324.31, Colorless to pale yellow liquid, MDL MFCD09037502 Salts

Stock # Description Standard Selling Sizes H28304 Potassium benzofurazan-5-trifluoroborate, 95% 1g

C6H3BF3KN2O, F.W. 226.01, Cream powder, MDL MFCD09800741 5g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H32467 Potassium 1-Boc-indole-2-trifluoroborate, 95% 250mg [Potassium 1-(tert-butoxycarbonyl)indole-2-trifluoroborate] 1g

C13H14BF3KNO2, F.W. 323.17, Pale brown solid Trifluoroborate H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H31781 Potassium 2,5-dimethylthiophene-3-trifluoroborate, 95% 250mg

C6H7BF3KS, F.W. 218.09, White powder 1g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H28102 Potassium 5-formylthiophene-2-trifluoroborate, 97% È 1g

[1025113-78-3], C5H3BF3KOS, F.W. 218.05, Pale cream powder, 5g m.p. 245ø dec., MDL MFCD09800740

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H32458 Potassium furan-2-trifluoroborate, 95% 250mg

C4H3BF3OK, F.W. 173.98, White powder 1g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H51151 Potassium 5-methoxypyridine-2-trifluoroborate 1g

C6H6BF3KNO, F.W. 215.02, MDL MFCD09993103 5g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H32128 Potassium pyrazole-5-trifluoroborate, 95% 250mg

C3H3BF3KN2, F.W. 173.98, White powder 1g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H31906 Potassium pyrimidine-5-trifluoroborate, 95% 250mg

C4H3BF3KN2, F.W. 185.99, Pale brown powder 1g

H:H302-H332-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H51891 Potassium quinoline-8-trifluoroborate, 95% 1g

C9H6BF3KN, F.W. 235.06, Solid, MDL MFCD09993448 5g

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

130 www.alfa.com Oxazaborolidine Reagents

Stock # Description Standard Selling Sizes L07705 Borane-dimethyl sulfide complex, 94% È É 25ml [BMS, Borane-methyl sulfide] 100ml

[13292-87-0], C2H9BS, F.W. 75.97, Colorless liquid, m.p. -38ø, b.p. ca 44ø dec., f.p. -1ø(30øF), d. 0.801, Ë 1.4570, Fieser 4,124 10,49 11,69 12,64 14,53 15,44 17,50 18,59 19,44 20,53, UN2924, EINECS 236-313-6, RTECS PV5080000, BRN 3663489, MDL MFCD00013189, Ì

H:H225-H260-H301-H318-H315-H335-EUH014, P:P210-P280-P305+P351+P338-P309+P311-P370+P378i-P402+P404 Stable, convenient reagent for a wide range of reduction and hydroboration reactions. Reviews: Org. Prep. Proced. Int., 13, 225 (1981); Chem. Rev., 76, 773 (1976); A. Pelter et al, Borane Reagents, Academic Press, N.Y. (1988). Carboxylic acids are readily reduced to alcohols: J. Org. Chem., 38, 2786 (1973). Conditions for reduction of amino acids to amino alcohols without racemization are described

for L-valine: Org. Synth. Coll., 7, 530 (1990). Oxazaborolidine By use of refluxing THF as solvent, the reduction can be extended to include esters, primary, secondary and tertiary amides and nitriles: J. Org. Chem., 47, 1389 (1982); Synth. Commun., 21, 1579 (1991). The selectivity of BMS in reducing free acids more rapidly than esters is reversed in the case of monoesters of malonic acids. The borane binds initially to the acid function, but reduces the ester group intramolecularly: Tetrahedron Lett., 30, 6687 (1989): Reagents

For a discussion of the effect of the alkene structure on hydroboration with borane dimethyl sulfide, see: J. Org. Chem., 48, 644 (1983). For cis-anti-Markovnikov hydration of alkenes by

hydroboration with BMS, followed by H2O2 oxidation of the borane, see: J. Org. Chem., 39, 1437 (1974). L13961 Borane-tetrahydrofuran complex, 1M soln. in THF, stab. with 5mmol 25ml NaBH4 È É 100ml

[14044-65-6], C4H11BO, F.W. 85.94, Colorless liquid, f.p. -17ø(1øF), d. 0.898, 500ml Fieser 1,199 5,184 6,161 7,89 11,69 12,65 13,42 14,110 17,101 20,52, UN3148, EINECS 237-881-8, BRN 3668402, MDL MFCD00012429, Ì

H:H225-H260-H319-H335+H336-EUH019, P:P210-P231+P232-P303+P361+P353-P305+P351+P338-P405-P501a Examples of hydroboration reactions: Hydroboration, followed by reaction of the trialkylborane with a diazoketone to give a homologated ketone: Org. Synth. Coll., 6, 919 (1988). In situ generation of "disiamyl" borane from 2-methyl-2-butene, and use of this reagent in selective hydroboration reactions: Org. Synth. Coll., 7, 258 (1990). Preparation of di-3-pinanylborane from (-)-à-pinene, and its use in asymmetric hydroborations, see: Org. Synth. Coll., 7, 339 (1990). For use in the reduction of carboxylic acids to alcohols, see: Org. Synth. Coll., 7, 221 (1990). For other reactions of borane, see Borane-dimethyl sulfide complex, L07705, p. 131. L09218 (R)-(+)-à,à-Diphenylprolinol, 99% 250mg [(R)-(+)-à,à-Diphenyl-2-pyrrolidinemethanol] 1g

[22348-32-9], C17H19NO, F.W. 253.35, m.p. 76-78ø, ¾ +57.5° (c=3 in methanol), Fieser 14,156, BRN 4353363, MDL MFCD00077754

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Chiral precursor for the asymmetric reduction of ketones, see following entry.

Bulk and Specialty Sizes Available 131 Oxazaborolidine Reagents Stock # Description Standard Selling Sizes L09217 (S)-(-)-à,à-Diphenylprolinol, 98% 1g [(S)-(-)-à,à-Diphenyl-2-pyrrolidinemethanol] 5g

[112068-01-6], C17H19NO, F.W. 253.35, m.p. 76-78ø, ¾ -57.5° (c=3 in methanol), Fieser 14,156, BRN 17103, MDL MFCD00075506

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Precursor of Corey, Bakshi and Shibata's oxazaborolidine derivatives (CBS catalysts) for enantioselective reduction of prochiral ketones: J. Am. Chem. Soc., 109, 5551 (1987). Ketones are not reduced rapidly by either borane-THF or the oxazaborolidine alone but together they form a complex which reduces ketones rapidly and stereoselectively, permitting reduction with very high ee in the presence of a catalytic amount of the oxazaborolidine: J. Am. Chem. Soc., 109, 7925 (1987).

For use in conjunction with borane generated in situ using NaBH4 and iodine, see: Tetrahedron, 50, 6411 (1994). For an optimized in situ procedure for generation and use of the oxazaborolidine from BMS, see: Tetrahedron: Asymmetry, 7, 3147 (1996). In a comparison with other oxazaborolidine precursors, diphenylprolinol gave the best results (same ref.). For in situ generation of an asymmetric reduction system using trimethyl borate and BMS, see: Synlett, 273 (1997). For the generation and use of the phenyl oxazaborolidine, using Benzeneboronic acid, A14257, p. 15, see: Tetrahedron Lett., 31, 7415 (1990); 32, 7175 (1991); J. Org. Chem., 57, 7115 (1992). For a detailed comparative study of various alkyl- Reagents and aryl-substituted borolidines, see: J. Org. Chem., 56, 763 (1991). For a process for the in situ formation of butyl oxazaborolidines using 1-Butylboronic acid, A13725, p. 6, see: Tetrahedron Lett., 33, 4141 (1992). For use for the catalytic enantioselective synthesis of chiral monosubstituted oxiranes, see: Tetrahedron Lett., 34, 5227 (1993). For reviews of oxazaborolidines as enantioselective catalysts, see: Angew. Chem. Int. Ed., 31, 729 (1992); 37, 1986 (1998); Tetrahedron: Asymmetry, 3, 1475 (1992). For reviews of the asymmetric reduction of ketones, see: Synthesis, 605 (1992); Chem. Ind. (London), 552 (1994). See also the preformed catalyst (S)-2-Methyl-CBS-oxazaborolidine, L14583, p. 132, and (S)-2-Methyl-CBS-oxazaborolidine monohydrate, L09219, p. 133. Oxazaborolidine L14582 (R)-2-Methyl-CBS-oxazaborolidine, 1M soln. in toluene È É 1ml [(R)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole] 5ml

[112022-83-0], C18H20BNO, F.W. 277.17, f.p. 4ø(39øF), d. 0.925, 25ml Fieser 14,239 16,253 17,242, UN1993, MDL MFCD00078440

H:H224-H304-H361-H373-H332-H315-H336, P:P210-P241-P301+P310-P303+P361+P353-P405-P501a Anhydrous catalyst for CBS reduction reaction. For further information, see (S)-2-Methyl-CBS-oxazaborolidine monohydrate, L09219, p. 133. L09230 (R)-2-Methyl-CBS-oxazaborolidine monohydrate, 94% 250mg [(R)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole] 1g

C18H20BNOùH2O, F.W. 295.19 (277.17anhy), White powder, Fieser 14,239 16,253 17,242, BRN 9059874, MDL MFCD00078440 Air-stable solid prepared by a modification of Corey's procedure, on which his literature results were based. For anhydrous reagent, see (R)-2-Methyl-CBS-oxazaborolidine, L14582, p. 132. Chiral auxiliary for the highly enantioselective reduction of prochiral ketones, see (S)-2-Methyl-CBS-oxazaborolidine monohydrate, L09219, p. 133. L14583 (S)-2-Methyl-CBS-oxazaborolidine, 1M soln. in toluene È É 1ml [(S)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole] 5ml

[112022-81-8], C18H20BNO, F.W. 277.17, f.p. 4ø(39øF), d. 0.925, 25ml Fieser 14,239 16,253 17,242, UN1993, MDL MFCD00078439

H:H224-H304-H361-H373-H332-H315-H336, P:P210-P241-P301+P310-P303+P361+P353-P405-P501a Anhydrous catalyst for 'CBS' reduction reaction. For examples of use in asymmetric reduction of ketones, see: Org. Synth. Coll., 9, 362, 676 (1998). For further information, see (S)-2-Methyl-CBS-oxazaborolidine monohydrate, L09219, p. 133.

132 www.alfa.com Boronation Reagents Stock # Description Standard Selling Sizes L09219 (S)-2-Methyl-CBS-oxazaborolidine monohydrate, 94% 250mg [(S)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole] 1g

[112022-81-8], C18H20BNOùH2O, F.W. 295.19 (277.17anhy), m.p. 115-117ø, Fieser 14,239 16,253 17,242, BRN 8492123, MDL MFCD00078439 Air-stable solid prepared by a modification of Corey's procedure, on which his literature results were based. For anhydrous reagent, see (S)-2-Methyl-CBS-oxazaborolidine, L14583, p. 132. Catalyst for the CBS (Corey, Bakshi, Shibata) reduction of prochiral ketones with borane-THF, with high enantioselectivity (see (S)-(-)-à,à-Diphenylprolinol, L09217, p. 132): J. Am . Chem. Soc., 109, 7925 (1987):

For successful use of this system in a scaled up asymmetric synthesis of the antiarrythmia agent d-Sotalol, see: Org. Process Res. Dev., 1. 176 (1997). For use in enantioselective reduction of ketones containing heteroatoms, see: Tetrahedron Lett., 34, 785 (1993). For the asymmetric reduction of à-ketoimines, see: Tetrahedron Lett., 35, 5551 (1994).

For reviews of oxazaborolidines as enantioselective catalysts, see: Angew. Chem. Int. Ed., Boronation 31, 729 (1992); 37, 1986 (1998); Tetrahedron: Asymmetry, 3, 1475 (1992). For reviews of the asymmetric reduction of ketones, see: Synthesis, 605 (1992); Chem. Ind. (London), 552 (1994). Reagents Stock # Description Standard Selling Sizes L18675 Bis(neopentyl glycolato)diboron, 97% 250mg [5,5,5',5'-Tetramethyl-2,2'-bi-1,3,2-dioxaborinane] 1g

[201733-56-4], C10H20B2O4, F.W. 225.89, m.p. 180-185ø, 5g BRN 8839038, MDL MFCD02093062

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Boronation reagent, cf Bis(pinacolato)diboron, L16088, p. 134, which undergoes Pd-catalyzed coupling with aryl halides to give neopentylato boronic esters, more readily hydrolyzed to boronic acids than the corresponding pinacolato esters: Chem. Abs., 129, 290220 (1998). Found to be much more efficient than bis(pinacolato)diboron for the synthesis of hindered ortho-substituted arylboronic acids: Tetrahedron Lett., 46, 1671 (2005).

Bulk and Specialty Sizes Available 133 Boronation Reagents Stock # Description Standard Selling Sizes L16088 Bis(pinacolato)diboron, 98+% 1g [4,4,4',4',5,5,5',5'-Octamethyl-2,2'-bi-1,3,2-dioxaborolane] 5g

[73183-34-3], C12H24B2O4, F.W. 253.94, m.p. 135-140ø, 25g BRN 7703552, MDL MFCD00799570

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Reagent introduced by Miyaura for the Pd-catalyzed one-step conversion of aryl halides to pinacolato arylboronic esters: J. Org. Chem., 60, 7508 (1995), allowing access to boronic acid derivatives (see Appendix 5) without protection of functionalities such as ester, ketone, cyano or nitro groups:

Microwave irradiation has been found to offer dramatic rate enhancements and improved yields in the synthesis of otherwise difficult electron-rich boronates: Synlett, 1204 (2003). Polymer-supported aryl iodides have been borylated and coupled in situ under Suzuki conditions to give, after deprotection, unsymmetrical biaryls: Tetrahedron Lett., 38, 1197 (1997). For borylation of benzylic halides, see: Chem. Lett., 780 (2002). For a one-pot borylation/ Suzuki coupling procedure, see: J. Org. Chem., 68, 3729 (2003). Aryldiazonium tetrafluoroborates can also be converted to the arylboronic esters in high yield: Tetrahedron Lett., 41, 8683 (2000). The reagent, catalyzed by Pt(0), also converts alkynes to cis(bis-boryl) alkenes: Organometallics, 15, 713 (1996); coupling of these with polymer-supported iodoarenes has been applied to the parallel synthesis of tamoxifen analogue libraries: J. Org. Chem., 62, 7076 (1997). 1,3-Dienes are converted to 1,4-bis-boryl-2-alkenes: Chem. Commun., 2073 (1996), Reagents and also, with Pd(0) catalysis, allylic acetates to allylboronates: Tetrahedron Lett., 37, 6889 (1996). Arenes undergo direct Ir-catalyzed borylation to give good yields of arylboronates: J. Am. Chem. Soc., 124, 390 (2002); see Chloro(1,5-cyclooctadiene)iridium(I) dimer, 12749, p. 138. Electron-deficient olefins, e.g. à,á-enones, undergo Rh-catalyzed 1,4-addition (see Chlorotris(triphenylphosphine)rhodium(I), 10468, p. 139): Tetrahedron Lett., 43, 2323 (2002). Boronation Addition to à,á-enones has also been described, utilizing a CuOTf/ Bu3P catalyst system: Tetrahedron Lett., 41, 6821 (2000). Dramatic rate-enhancements in this type of reaction have reported using the ligand DPEphos (Bis[(2-diphenylphosphino)phenyl] ether, L18481, p. 147): Org. Lett., 8, 4887 (2006). For a brief feature on uses of the reagent in synthesis, see: Synlett, 2442 (2003). H30234 Catecholborane, 50% w/w in toluene (99+% dry wt.) É 25g [1,3,2-Benzodioxaborole] 100g

[274-07-7], C6H5BO2, F.W. 119.92, Colorless liquid, Ë 1.5025, UN2924, MDL MFCD00005846, Ì

H:H224-H314-H361-H373-H336-EUH014, P:P210-P241-P303+P361+P353-P305+P351+P338-P405-P501a L14998 Catecholborane, 97% É 5g [1,3,2-Benzodioxaborole] 25g

[274-07-7], C6H5BO2, F.W. 119.92, Colorless to pale yellow liquid, m.p. 12ø, b.p. 50ø/50mm, f.p. 2ø(35øF), d. 1.125, Fieser 4,69 8,79 9,97 10,79 16,65 17,67 18,85 19,67 20,29 21,90, May form a precipitate, UN2924, EINECS 205-991-5, BRN 972072, MDL MFCD00005846, Ì

H:H225-H314-EUH014, P:P210-P241-P303+P361+P353-P305+P351+P338-P405-P501a Mild, selective hydroborating agent: J. Am. Chem. Soc., 97, 5249 (1975); Tetrahedron, 32, 981 (1976). Use of Rh(I) and Ir(I) catalysis increases stereo- and regioselectivity: J. Am. Chem. Soc., 114, 6671, 6674 (1992). For Rh catalyzed enantioselective hydroboration of alkenylboronic acids, see: Tetrahedron: Asymmetry, 7, 5 (1996). Hydroboration of olefins can be accomplished at room temperature in the presence of N,N-dimethylacetamide: J. Org. Chem., 61, 3224 (1996). For a brief feature on uses of this reagent in Organic synthesis, see: Synlett, 666 (2007). L17278 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 98% É 1g [Isopropyl pinacolyl borate] 5g

[61676-62-8], C9H19BO3, F.W. 186.06, b.p. 73ø/15mm, 25g f.p. 42ø(107øF), d. 0.912, Ë 1.4090, UN1993, BRN 1906370, MDL MFCD00192241

H:H226-H315-H319-H335, P:P210-P241-P303+P361+P353-P305+P351+P338-P405-P501a Selective reagent for preparation of pinacol boronic esters, e.g. for preparation of allenyl or vinyl pinacol boronates from the Grignard or lithium reagents: Liebigs Ann. Chem., 881 (1987); Chem. Ber., 122, 1777 (1989); Tetrahedron Lett., 33, 6941 (1992).

134 www.alfa.com Boronation Reagents Stock # Description Standard Selling Sizes L19056 2-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 97% É 5g [Methyl pinacolyl borate] 25g

[1195-66-0], C7H15BO3, F.W. 158.01, b.p. 120ø/228mm, f.p. 46ø(114øF), d. 0.966, Ë 1.4120, UN1993, BRN 2827758, MDL MFCD03093086

H:H226, P:P210-P241-P280-P240-P303+P361+P353-P501a Boronation reagent; see 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, L17278, p. 134 . L17558 Pinacolborane, 97% È 5g [4,4,5,5-Tetramethyl-1,3,2-dioxaborolane] 25g

[25015-63-8], C6H13BO2, F.W. 127.98, Colorless liquid, b.p. 42-43ø/50mm, f.p. 5ø(41øF), d. 0.882, Ë 1.3970, UN3399, BRN 7802871, MDL MFCD00674030

H:H225-H261, P:P210-P231+P232-P241-P280-P303+P361+P353-P501a Precursor of boronic esters by hydroboration or coupling reactions. Hydroboration of alkynes, in the presence of Rh or Ni catalysts, yields alkenylboronates: Tetrahedron Lett., 37, 3283 (1996). Hydroboration of alkenes in the presence of Chlorotris(triphenylphosphine)- rhodium(I), 10468, p. 139, affords the alkylboronate: Tetrahedron Lett., 37, 3283 (1996); with phosphine-free catalyst Chloro(1,5-cyclooctadiene)rhodium(I) dimer, 10466, p. 138, dehydrogenative borylation predominates to give the alkenylboronate: Tetrahedron Lett., 40, Boronation 213 (1999); Bull. Chem. Soc. Jpn., 75, 825 (2002):

Coupling aryl iodides and bromides, catalyzed by [1,1'-Bis(diphenylphosphino)- ferrocene]palladium(II) chloride, 41225, p. 137, gives the aryl pinacolboronates: J. Org. Chem., Reagents 62, 6458 (1997); 65, 164 (2000). In the presence of triphenylarsine, Pd-catalyzed coupling with alkenyl triflates and iodides affords vinylboronates: Synthesis, 778 (2000). For a brief review of uses of pinacolborane, see: Synlett, 1210 (2000). A19322 Tri-n-butyl borate, 98% É 100ml [Boric acid tri-n-butyl ester, n-Butyl borate] 500ml

[688-74-4], [CH3(CH2)3O]3B, F.W. 230.16, Liquid, m.p. <-70ø, b.p. 230-235ø, 2.5L f.p. 93ø(199øF), d. 0.853, Ë 1.4095, EINECS 211-706-5, RTECS ED4900000, BRN 1703865, MDL MFCD00009434, Ì

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Used in the synthesis of boronic esters from Grignard or lithium reagents: J. Org. Chem ., 49, 5237 (1984). A17592 Triisopropyl borate, 98+% É 100ml [Boric acid triisopropyl ester, Isopropyl borate] 500ml

[5419-55-6], [(CH3)2CHO]3B, F.W. 188.08, Liquid, m.p. -59ø, b.p. 139-141ø, f.p. 17ø(62øF), 2.5L d. 0.815, Ë 1.3760, UN2616, EINECS 226-529-9, RTECS ED5950000, BRN 1701469, MDL MFCD00008872, Ì

H:H225, P:P210-P241-P280-P240-P303+P361+P353-P501a Reagent for preparation of boronates from Grignard or organolithium reagents, often giving higher yields than other trialkyl borates: Organometallics, 2, 1316 (1983); Tetrahedron Lett ., 29, 2631 (1988). B20215 Trimethyl borate, 99% É 250ml [Boric acid trimethyl ester, Methyl borate] 1L

[121-43-7], C3H9BO3, F.W. 103.92, Clear colourless liquid, m.p. -34ø, b.p. 68-69ø, f.p. -8ø(17øF), d. 0.915, Ë 1.3610, Merck 14,9712, Fieser 1,673, UN2416, EINECS 204-468-9, RTECS ED5600000, BRN 1697939, MDL MFCD00008346, Ì

H:H225-H312, P:P210-P261-P262 For an example of the low temperature reaction with Grignard reagents to give boronic acids., see: Org. Synth. Coll., 4, 68 (1963).

Bulk and Specialty Sizes Available 135 Coupling Catalysts

Stock # Description Standard Selling Sizes 10002 Bis(acetonitrile)dichloropalladium(II), Pd 40.5% [cis-Dichlorobis(acetonitrile)palladium(II)]

[14592-56-4], PdCl2(CH3CN)2, F.W. 259.41, Powder, Solubility: Soluble in acetonitrile, acetone, chloroform, Application(s): Olefin isomerization, preparation of acetals and hemiacetal esters, UN3439, EINECS 238-637-3, MDL MFCD00013122

H:H302-H312-H332-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Organic-soluble complex for catalysis of a variety of reactions, with the advantage over trans-Bis(benzonitrile)dichloropalladium(II), 10006, p. 136, that the nitrile by-product, being volatile and water-miscible, is readily removed in the workup. In the presence of triethylamine, ortho-allylanilines undergo cyclization to indoles: J. Am. Chem. Soc., 98, 2674 (1976):

A 6:1 molar ratio of the high-temperature phase-transfer catalyst Tetraphenylphosphonium chloride, A10575, p. ?, and the Pd complex, provides an effective catalyst for the Heck reaction of normally unreactive aryl halides, e.g. chlorobenzene with styrene to give stilbene. The reaction is performed at 140-150o in DMF or NMP in the presence of sodium acetate: Angew. Chem. Int. Ed., 37, 481 (1997). Effective alternative catalyst to trans-Dichlorobis(triphenylphosphine)palladium(II), 10491, p. 142, for the carbonylative cross-coupling of arylboronic acids with aryl iodides to give unsymmetrical benzophenones: Tetrahedron Lett., 34, 7595 (1993); see also Appendix 5. Catalysts Catalyses the cleavage of phenolic TBDMS ethers under mild conditions: Tetrahedron Lett., 37, 153 (1996), and, in the presence of 2-Bromomesitylene, A12277, p. ?, promotes one-pot desilylation-oxidation of aliphatic silyl ethers to aldehydes or ketones: J. Org. Chem., 61, 2918 (1996); cf J. Org. Chem., 48, 1286 (1983). 10006 trans-Bis(benzonitrile)dichloropalladium(II), Pd 27.7% [Dichlorobis(benzonitrile)palladium(II)] Coupling [14220-64-5], PdCl2[(C6H5)(CN)]2, F.W. 383.55, Powder, Solubility: Soluble in acetone, chloroform, UN3439, EINECS 238-085-3, MDL MFCD00013123

H:H301-H311-H330, P:P260-P301+P310-P320-P361-P405-P501a Air-stable, organic-soluble Pd complex, which catalyzes a variety of reactions: Trimerization of alkynes to aromatic compounds: J. Am. Chem. Soc., 84, 2329 (1962); Synthesis, 659 (1986). Review: Acc. Chem. Res., 9, 93 (1976). Cyclopropanation of various allylic alcohols, ethers and amines by diazomethane: Synthesis, 246 (1990). In the presence of a tert-amine, catalyzes the cyclization of 3- and 4-alkynoic acids to unsaturated lactones in high yield: Tetrahedron Lett., 25, 5323 (1984):

Catalyst for the Ag2O promoted Suzuki coupling of arylboronic acids with sensitive halides: Org. Synth., 75, 69 (1997); for reaction scheme, see 4-Methoxybenzeneboronic acid, A14462, p. 63. In combination with N,N-dimethylglycine, forms a highly active phosphine-free catalyst system for the Heck reaction of aryl bromides: Tetrahedron Lett., 39, 8449 (1998). In combination with CuI, terminal alkynes couple with vinyl chlorides to give conjugated enynes in high yield: Tetrahedron Lett., 32, 6109 (1991). This has been exploited in a synthesis of

lipoxin B4: Synlett, 217 (1993), and of (Z)- and (E)-enediynes from the isomeric 1,2-dichloroethylenes: Tetrahedron Lett., 35, 3543 (1994).

In combination with Ti(O-i-Pr)4, promotes the symmetrical coupling of arylsulfonyl chlorides to biaryls: Chem. Lett., 459 (1990). For a brief feature on uses in synthesis, see: Synlett, 1449 (2006). See also Bis(acetonitrile)dichloropalladium(II), 10002, p. 136. 12764 Bis(dibenzylideneacetone)palladium(0) È É

[32005-36-0], C34H28O2Pd, F.W. 575.00, Powder, Packaged under argon, m.p. 135ø dec., Solubility: Slightly soluble in CH2Cl2, CHCl3 and benzene, Application(s): Hydrogenation, isomerization, carbonylation, oxidation, C-C bond formation, MDL MFCD00051942 46000 Bis[di-tert-butyl(4-dimethylaminophenyl)- phosphine]palladium(0), Pd 16.7% È

C32H56P2N2Pd, F.W. 637.18, Crystalline, MDL MFCD15071402

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a 45853 Bis(di-tert-butyl-phenylphosphine)palladium(0), Pd 19.3% È

[52359-17-8], C28H46P2Pd, F.W. 551.04, Crystalline, MDL MFCD15071400

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

136 www.alfa.com Coupling Catalysts Stock # Description Standard Selling Sizes 44829 1,1'-Bis(di-tert-butylphosphino)ferrocene palladium dichloride, Pd 16.3%

[95408-45-0], C26H44Cl2FeP2Pd, F.W. 651.77, Crystalline, packaged under Argon, Application(s): Coupling reactions, Suzuki couplings, MDL MFCD08064219

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a 44980 [1,1'-Bis(diphenylphosphino)ferrocene]palladium(II) bromide, Pd 12.9%

[124268-93-5], C34H28Br2FeP2Pd, F.W. 820.62, Solid, MDL MFCD09953448

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a 44972 [1,1'-Bis(diphenylphosphino)ferrocene]palladium(II) chloride, complex with acetone, Pd 13.0-15.0%

[851232-71-8], C34H28Cl2FeP2Pdù(CH3)2CO, F.W. 787.81, Application(s): Coupling reactions, carbonylation, MDL MFCD00792899

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a 41225 [1,1'-Bis(diphenylphosphino)ferrocene]palladium(II) chloride,

complex with dichloromethane (1:1), Pd 13% Coupling [Dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichlomethane complex]

[95464-05-4], C34H28Cl2FeP2Pd.CH2Cl2, F.W. 816.64, Powder, m.p. 275-280ø, MDL MFCD00792899

H:H351-H302-H332, P:P280h Preferred catalyst for coupling of aryl halides and triflates to give arylamines or aryl ethers. Catalysts For a review, see: Angew. Chem. Int. Ed., 37, 2046 (1998). Catalyst for boronylation reactions with Bis(pinacolato)diboron, L16088, p. 134: J. Org. Chem., 60, 7508 (1995). 39288 Bis(ethylene)(2,4-pentanedionato)rhodium(I), Rh 39.9% min È [(Acetylacetonato)bis(ethylene)rhodium(I)]

[12082-47-2], C9H15O2Rh, F.W. 258.13, Crystalline, Solubility: Soluble in dichloromethane, chloroform, EINECS 235-147-1, MDL MFCD00015354

45913 Bis[1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)- ferrocene]palladium(0), Pd 7.0% È

C96H94FeP2Pd, F.W. 1527.86, Crystalline, MDL MFCD15071401

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

44845 Bis(tri-tert-butylphosphine)palladium(0), Pd 20.9% ß È É

[53199-31-8], Pd[P(C(CH3)3)3]2, F.W. 510.00, Powder, ampouled under argon, Application(s): Coupling reactions, Heck couplings, MDL MFCD03094580, Note: Decomposes in water

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a 45792 Bis(tricyclohexylphosphine)palladium(0), Pd 15.9% È

[33309-88-5], C36H66P2Pd, F.W. 667.29, Crystalline, MDL MFCD01073796

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a 45814 Bis(tri-o-tolylphosphine)palladium(0), Pd 14.9% È

[69861-71-8], C42H42P2Pd, F.W. 715.16, Crystalline, MDL MFCD12911908

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

40524 Carbonyldihydridotris(triphenylphosphine)ruthenium(II), 99% ß É

[25360-32-1], C55H47OP3Ru, F.W. 917.97, Crystalline, m.p. 161-163ø, MDL MFCD00015870

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Bulk and Specialty Sizes Available 137 Coupling Catalysts Stock # Description Standard Selling Sizes 12749 Chloro(1,5-cyclooctadiene)iridium(I) dimer, Ir 57.2% [Bis(1,5-cyclooctadiene)diiridium(I) dichloride]

[12112-67-3], C16H24Cl2Ir2, F.W. 671.71, Solid, m.p. 190ø dec., Solubility: Soluble in chloroform, toluene. Slightly soluble in acetone, alcohol., EINECS 235-170-7, MDL MFCD00012414 Catalyst precursor for asymmetric hydrogenation: Angew. Chem. Int. Ed., 37, 2897 (1998). With catalytic amounts of dppp (1,3-Bis(diphenylphosphino)propane, A12931, p. 148) and

Cs2CO3, a transfer hydrogenation system with 2-propanol as the H source can reduce both olefinic double bonds and carbonyl groups; for à,á-unsaturated ketones, selective reduction to saturated ketones can be achieved: J. Org. Chem., 66, 4710 (2001). In the presence of a phosphite, catalyzes displacements by carbon nucleophiles at the more substituted position in allylic systems: Angew Chem. Int. Ed., 36, 263 (1997); J. Am. Chem. Soc., 120, 8647 (1998). Catalyst for Miyaura and Hartwig's direct boronylation of arenes with Bis(pinacolato)diboron, L16088, p. 134: J. Am. Chem. Soc., 124, 390 (2002):

Effective catalyst for the reaction of alcohols with vinyl acetate to give vinyl ethers: J. Am. Chem. Soc., 124, 1590 (2002). 10466 Chloro(1,5-cyclooctadiene)rhodium(I) dimer È Ê [Bis(1,5-cyclooctadiene)dirhodium(I) dichloride]

[12092-47-6], C16H24Cl2Rh2, F.W. 493.08, Crystalline, m.p. 243ø dec., Solubility: Sparingly soluble in most common solvents, EINECS 235-157-6, MDL MFCD00012415, Note: Slowly decomposes in air, Ì Catalysts

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Homogeneous catalyst and catalyst precursor. For use in the preparation of a chiral BINAP alkene isomerization catalyst, see: Org. Synth. Coll., 8, 183 (1993). Catalyzes the dehydrogenative coupling reaction of styrenes with Pinacolborane, L17558, p. 135 to give the corresponding vinylboronates: Tetrahedron Lett., 40, 2585 (1999);

Coupling Bull. Chem. Soc. Jpn., 75, 825 (2002). The complex has also been found to promote the atmospheric pressure carbonylation of benzylic halides to give good yields of phenylacetic acids: Tetrahedron Lett., 41, 7601 (2000). Miyaura has reported the Rh-catalyzed conjugate addition of arylboronic acids to à,á-unsaturated carbonyl compounds in a single aqueous phase: Chem. Lett., 722 (2001):

138 www.alfa.com Coupling Catalysts Stock # Description Standard Selling Sizes 10468 Chlorotris(triphenylphosphine)rhodium(I), 97% [Wilkinson's catalyst, Tris(triphenylphosphine)rhodium(I) chloride]

[14694-95-2], C54H45ClP3Rh, F.W. 925.23, Micro Crystals, m.p. ca 250ø dec., Merck 14,10047, Solubility: Soluble in most solvents (e.g. benzene, ethanol, chloroform,

dichloromethane) but with phosphine dissociation. Reacts with O2 in solution, EINECS 238-744-5, MDL MFCD00010016, Note: Slowly decomposes in air, Ì Homogeneous hydrogenation catalyst: J. Chem. Soc.(A), 1711 (1966), useful e.g. for the selective reduction of an unhindered alkene, of an unconjugated in the presence of a conjugated alkene: Org. Synth. Coll., 6, 459 (1988), or an alkene in the presence of a nitro group: J. Org. Chem., 67, 3163 (2002). Hydroxyl groups protected as their allyl ethers may be deprotected by isomerization with Wilkinson's Catalyst to the more readily-hydrolyzed 1-propenyl ether: J. Org. Chem., 38, 3224 (1973). Aldehydes undergo decarbonylation with the complex: Tetrahedron Lett., 3969 (1965); J. Am. Chem. Soc., 93, 5465 (1971). The need for stoichiometric amounts of the complex, due to formation of an inactive Rh carbonyl complex, is a serious disadvantage. However, in the presence of Diphenylphosphonic azide, A12124, p. ?, which regenerates the catalyst from the carbonyl complex, decarbonylations can be carried out catalytically at room temperature, providing a much more cost-effective and attractive method for this type of transformation: J. Org. Chem., 57, 5075 (1992). Catalyst for hydrosilylation reactions, e.g. with Triethylsilane, A10320, p. ?, including

à,á-unsaturated ketones to silyl enol ethers, which can be hydrolyzed to saturated ketones: Coupling Organometallics, 1, 1390 (1982), and à,á-unsaturated esters to silyl ketene acetals with high (Z)-selectivity: Synth. Commun., 17, 1 (1989). Used by Grigg for the catalytic [2+2+2] cyclotrimerization of alkynes, providing an efficient route to benzene-fused ring systems. See, e.g.: J. Chem. Soc., Perkin 1, 1357 (1988). For an intermolecular example with reaction scheme, see 1,6-Heptadiyne, A11318, p. ?.

Intramolecular assembly of suitably constructed triynes can also be accomplished to form Catalysts benzene rings: Tetrahedron, 45, 6239 (1989). Also catalyzes the [5+2] cycloaddition of vinylcyclopropanes and alkynes: J. Am. Chem. Soc., 117, 4720 (1995); 120, 1940 (1998). Co-catalyst giving improved results in intramolecular Heck coupling reactions catalyzed by

Pd(OAc)2: J. Org. Chem., 64, 3461 (1999). Electron-deficient olefins undergo Rh-catalyzed 1,4-addition with Bis(pinacolato)diboron, L16088, p. 134, e.g. 2-cyclohexen-1-one to the á-borylcyclohexanone: Tetrahedron Lett., 43, 2323 (2002):

A16203 Copper(II) acetate monohydrate, 98+% 250g [Acetic acid copper(II) salt, Cupric acetate] 1kg

[6046-93-1], Cu(OOCCH3)2ùH2O, F.W. 199.64 (181.63anhy), Powder, m.p. 115ø, d. 1.882, 5kg Merck 14,2624, UN3077, EINECS 205-553-3, RTECS AG3500000, MDL MFCD00149570, Ì

H:H318-H400-H410-H302, P:P280-P273-P305+P351+P338-P310-P301+P312-P501a Used in formation of Cu chelates of á-dicarbonyl compounds as a means of purification, see, e.g.: Org. Synth. Coll., 3, 16, 292, 390 (1955). For use in the Eglinton (modified Glaser) coupling of terminal alkynes, see: Org. Synth. Coll., 5, 517 (1973); for intramolecular example in the synthesis of [18]annulene, see: Org. Synth. Coll., 6, 68 (1988). Useful catalyst for the Michael reaction giving increased yields and absence of side-reactions: Gazz. Chim. Ital., 114, 417 (1984). Promotes Ullmann-type C-O and C-N coupling reactions of arylboronic acids with phenols, amines and various other nitogen derivatives: Tetrahedron Lett., 39, 2933, 2937, 2941, 7979 (1998). Similar coupling reactions with thiols to give thioethers have also been reported: Org. Lett., 2, 2019 (2000). 42057 1,5-Cyclooctadiene(pyridine)(tricyclohexylphosphine)iridium(I) hexafluorophosphate, 99% É [Crabtree's catalyst, (Tricyclohexyphosphine)(1,5-cyclooctadiene)(pyridine)- iridium(I) hexafluorophosphate]

[64536-78-3], C31H50F6IrNP2, F.W. 804.89, Crystalline, m.p. 175ø dec., Fieser 12,151 13,88, Solubility: Slightly soluble in acetone, dichloromethane, ethanol, diethyl ether, MDL MFCD00075097

H:H315-H319, P:P280-P305+P351+P338-P302+P352-P321-P362-P332+P313 Homogeneous catalyst, introduced by Crabtree, which can be used in non-coordinating solvents (e.g. DCM), and is one of the most active catalysts for homogeneous hydrogenation, effective even for tetrasubstituted alkenes: J. Organomet. Chem., 135, 395; 141, 205 (1977); Acc. Chem. Res., 12, 331 (1979). For a brief feature, see: Synlett, 160 (2001). Promotes stereoselective hydrogenations, directed by an adjacent OH: J. Am. Chem. Soc., 105, 1072 (1983), or carboxamide: J. Org. Chem., 50, 5905 (1985) group. For discussion of the influence of these and various other directing groups on the homogeneous hydrogenation of olefinic double bonds, see: J. Org. Chem., 51, 2655 (1986). Has also been applied to the directed hydroboration of alkenes: J. Org. Chem., 55, 5678 (1990); J. Am. Chem. Soc., 113, 4042 (1991).

Bulk and Specialty Sizes Available 139 Coupling Catalysts Stock # Description Standard Selling Sizes L16948 trans-Di-mu-acetatobis[2-(di-o-tolylphosphino)benzyl- 250mg ]dipalladium(II), 94% 1g [Herrmann's Catalyst]

[172418-32-5], C46H46O4P2Pd2, F.W. 937.66, m.p. ca 230ø, Fieser 21,310, MDL MFCD01075746

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a 'Palladacycle' catalyst, developed by W. A. Herrmann et al, which has been reported to surpass all previously known catalysts in the Heck coupling of aryl halides with olefins, with turnover numbers of up to 200,000: Angew. Chem. Int. Ed., 34, 1844 (1995); DE 4,421,730 (1995 to Hoechst A.-G.); Tetrahedron Lett., 37, 6535 (1996). Also highly effective in the Suzuki coupling of arylboronic acids with aryl halides (see Appendix 5), with turnover numbers up to 74,000: Angew. Chem. Int. Ed., 34, 1848 (1995); EP 690,046 (1996 to Hoechst A.-G.). Superior catalyst for anion-accelerated intramolecular coupling of phenols with aryl halides: J. Org. Chem., 62, 2 (1997):

Catalyst for the first reported Pd catalyzed amination of an aryl chloride: Tetrahedron Lett., 38, 2073 (1997). For use in the Heck reaction in quaternary salt ionic liquids, see: J. Organomet. Chem., 572, 141 (1999). For a review of palladacycles as reactive intermediates, see: Chem. Ber./ Recl., 130, 1567 (1997). For a brief review of applications of the catalyst, see: Synlett, 878 (2001).

Catalysts 44446 Dibromobis(tri-tert-butylphosphine)dipalladium(I) È [Palladium(I) tri-tert-butylphosphine bromide dimer]

[185812-86-6], [Pd(C4H9)3PBr]2, F.W. 777.29, Powder, Application(s): Coupling reactions. Will activate aryl chloride and sterically hindered or electron rich aryl/vinyl bromides and iodides. Especially active in difficult aminations, MDL MFCD04114019

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Coupling 44979 Dibromobis(tri-o-tolylphosphine)palladium(II), Pd 12% È É

[24554-43-6], C42H42Br2P2Pd, F.W. 874.98, Solid, MDL MFCD09953447, Note: Slowly decomposes in air and moisture

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

39295 Dicarbonyl(2,4-pentanedionato)rhodium(I), 99% [(Acetylacetonato)dicarbonylrhodium(I), Acetylacetonatorhodium(I) dicarbonyl ]

[14874-82-9], C7H7RhO4, F.W. 258.04, Crystalline, m.p. 144-147ø subl., Fieser 19,119 20,134 21,1, Solubility: Soluble in acetone, UN3466, EINECS 238-947-9, MDL MFCD00009884, Ì

H:H301-H315-H319-H335, P:P301+P310-P305+P351+P338-P302+P352-P321-P405-P501a

Catalyst for hydroformylation of alkenes with CO/H2 at atmospheric pressure to give enals: Angew. Chem. Int. Ed., 34, 1760 (1995). Miyaura has utilized this complex, in combination with a chelating phosphine ligand, for the conjugate addition of arylboronic acids to enones, to give saturated ketones: Organometallics, 16, 4339 (1997). Addition of aryl- and alkenylboronic acids to aldehydes to give secondary alcohols can also be brought about under similar conditions: Angew. Chem. Int. Ed., 37, 3279 (1998):

An extension of these reactions to the addition of potassium alkenyl- and aryltrifluoroborates to aldehydes and enones has also been reported: Org. Lett., 1, 1683 (1999). 45511 Dichlorobis[di-tert-butyl(4-dimethylaminophenyl)- phosphino]palladium(II)

[887919-35-9], C32H56Cl2N2P2Pd, F.W. 708.07, Crystalline, MDL MFCD09265123

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a 44971 Dichloro[bis(1,4-diphenylphosphino)butane]palladium(II), Pd 17.6%

[29964-62-3], C28H28Cl2P2Pd, F.W. 603.80, Lump, MDL MFCD02093437

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

140 www.alfa.com Coupling Catalysts Stock # Description Standard Selling Sizes 18779 Dichloro[bis(1,2-diphenylphosphino)ethane]palladium(II), Pd 18.5%

[19978-61-1], C26H24Cl2P2Pd, F.W. 575.73, Powder, m.p. >360ø, MDL MFCD00015702

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a 44977 Dichloro[bis(diphenylphosphinophenyl)ether]palladium(II), Pd 14.8%

[205319-06-8], C36H28Cl2OP2Pd, F.W. 715.88, MDL MFCD09953446

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

30167 Dichloro[bis(1,3-diphenylphosphino)propane]nickel(II) [1,3-Bis(diphenylphosphino)propane nickel(II) chloride]

[15629-92-2], C27H26Cl2NiP2, F.W. 542.03, Powder, m.p. 213ø dec., MDL MFCD00015318

H:H351-H315-H319-H317-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a 44844 Dichlorobis(tricyclohexylphosphine)palladium(II), Pd 14.4%

[29934-17-6], PdCl2[P(C6H12)3]2, F.W. 744.24, Powder, MDL MFCD00191830

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Coupling Catalyzes the efficient Pd-catalyzed Heck coupling of aryl chlorides with alkenes, in the presence of cesium carbonate; the corresponding triphenylphosphine complex is ineffective: Tetrahedron Lett., 47, 2573 (2006). 13930 Dichlorobis(triphenylphosphine)nickel(II), 98% Ê [Bis(triphenylphosphine)nickel(II) chloride, Bis(triphenylphosphine)dichloronickel(II)]

[14264-16-5], NiCl2[P(C6H5)3]2, F.W. 654.18, Powder, m.p. ca 225ø dec., Fieser 2,110 Catalysts 9,147 14,125 16,118 18,250, Application(s): Catalyst for cross-coupling of Grignard reagents, Hydrosilylations and hydrogenation, polymerizatron, EINECS 238-154-8, RTECS QR6170000, MDL MFCD00009592, Ì

H:H302, P:P264-P270-P301+P312-P330-P501a Catalyzes the coupling of Grignard reagents with allylic alcohols with displacement of the hydroxyl group: J. Chem. Soc., Chem. Commun., 1604 (1968). This alkene synthesis has been extended to enol ethers and methyl aryl ethers: J. Am. Chem. 101, 2246 (1979). The coupling of dithioacetals with Grignard reagents is also useful: Org. Synth. Coll., 9, 727 (1998), and refs therein. Catalyst for cross-coupling of organometallic reagents with aryl bromides: Tetrahedron Lett., 1389 (1977), and aryl tert-butyl sulfones: J. Chem. Soc., Perkin 1, 7 (1995), to give unsymmetrical biaryls. Symmetrical coupling of aryl halides can be effected in high yield with a Ni(0) catalyst generated in situ with Zn and triphenylphosphine in DMF, as a mild alternative to the Ullmann reaction: Tetrahedron Lett., 4089 (1977). For the analogous homocoupling of aryl mesylates, see: J. Org. Chem., 60, 176 (1995). The method has been extended to the formation aryl cyanides, providing an alternative to the classical CuCN route, and of diaryl sulfides: J. Org. Chem., 60, 6895 (1995):

In the presence of Zn and pyridine, catalyzes the conjugate addition of alkyl bromides to à,á-unsaturated ketones, nitriles and esters: Russ. J. Gen. Chem., 65, 444 (1995).

Bulk and Specialty Sizes Available 141 Coupling Catalysts Stock # Description Standard Selling Sizes 10491 trans-Dichlorobis(triphenylphosphine)palladium(II), Pd 14.0% min Ê [Bis(triphenylphosphine)dichloropalladium(II)]

[13965-03-2], C36H30Cl2P2Pd, F.W. 701.91, Crystalline, m.p. ca 310ø dec., Application(s): Hydrogenation, hydrosilation, carbonylation, oxidation, and C-C bond formation, EINECS 237-744-2, MDL MFCD00009593

H:H302-H315-H319, P:P280h-P305+P351+P338 Catalyst for a wide range of coupling reactions: In combination with CuI and an amine, catalyzes the Sonogashira coupling of terminal alkynes with aryl, vinyl, styryl and 2-pyridyl halides: Tetrahedron Lett., 4467 (1975):

An improved procedure uses triethylamine in THF with catalytic amounts of CuI and the complex, avoiding the need for excess of the acetylene, and gives good yields under mild conditions, even with unreactive aryl bromides: J. Org. Chem., 63, 8551 (1998). Catalyst for the Heck reaction (see Palladium(II) acetate, 10516, p. 143). For effect of high pressure in accelerating the reaction, see: Tetrahedron Lett., 36, 5547 (1995). For use as catalyst in the Stille coupling of arylstannanes, see Tri-n-butyltin chloride, A10746, p. ?. For examples of the Stille coupling of arylstannanes with aryl triflates to give unsymmetrical biaryls, see: Org. Synth. Coll., 9, 553 (1998). For reviews, see: Adv. Met.-Org. Chem., 5, 1 (1996); Org. React, 50, 1 (1997). Catalyst for the carbonylation of benzyl halides with CO in an alcohol, in the presence of a base, e.g. 1,8-Bis(dimethylamino)naphthalene, L00313, p. ?, to give arylacetic esters: J. Org. Chem., 40, 532 (1975). Similarly, allylic chlorides are carbonylated to give predominantly á,-unsaturated acids at atmospheric pressure: Chem. Lett., 957 (1988), and bromo alkanols give lactones: J. Am. Chem. Soc., 102, 4193 (1980): Catalysts

Also catalyzes the low-pressure carbonylative cross-coupling of arylboronic acids with iodoarenes to give unsymmetrical biaryl ketones: Tetrahedron Lett., 34, 7595 (1993);

Coupling J. Org. Chem., 63, 4726 (1998). Catalyzes the exclusively cis-addition of Tri-n-butyltin hydride, A13298, p. ?, to alkynes at room temperature, to give vinylstannanes in good yield: J. Org. Chem., 55, 1857 (1990):

Terminal alkynes give a mixture of regioisomers. In combination with acetic anhydride and triphenylphosphine, catalyzes the selective conversion of carboxylic acids to 1-alkenes of one less carbon atom: J. Org. Chem., 58, 29 (1993). 44976 Dichlorobis(tri-o-tolylphosphine)palladium(II), 98% È É

[40691-33-6], C42H42Cl2P2Pd, F.W. 786.08, Powder, MDL MFCD00274659

A12623 Palladium, 5% on carbon, dry 10g [7440-05-3], Pd, Black powder, Merck 14,6989, Fieser 1,778 11,392 13,230 15,245 50g 18,273 19,247 20,280 21,312, UN1325, EINECS 231-115-6, MDL MFCD00011167, Ì

H:H228-H315-H319-H335, P:P210-P241-P305+P351+P338-P302+P352-P405-P501a General-purpose hydrogenation catalyst suitable for a wide variety of applications. For a monograph, see: P. N. Rylander, Hydrogenation Methods, Academic Press, N.Y. (1985). A large number of examples of hydrogenation reactions can be found in Organic Syntheses, although some of the earlier procedures may be somewhat outdated. A selection of rather more recent examples employing palladium on carbon include: Hydrogenation of alkene to alkane: Org. Synth. Coll., 5, 97 (1973). Reduction of nitro to amine: Org. Synth. Coll., 5, 829 (1973). Reductive alkylation of amines: Org. Synth. Coll., 5, 552 (1973). Reduction of azide to amine: Org. Synth. Coll., 5, 586 (1973). High-pressure reduction of furan rings tetrahydrofurans: Org. Synth. Coll., 6, 856 (1988). 38300 Palladium, 5% on activated carbon powder, standard, reduced, nominally 50% water wet Type A102023-5, 900-1100m2/g, MDL MFCD03457879, Note: Sold on a dry weight basis. Unit weight excludes water weight, Ì 38301 Palladium, 5% on activated carbon powder, standard, unreduced, nominally 50% water wet 900-1100m2/g, MDL MFCD03457879, Note: Sold on a dry weight basis. Unit weight excludes water weight, Ì

142 www.alfa.com Coupling Catalysts Stock # Description Standard Selling Sizes A12012 Palladium, 10% on carbon, dry 2g [7440-05-3], Black powder, Merck 14,6989, Fieser 1,778 7,274 9,351 10,299 11,392 10g 13,230 15,245 18,273 21,312, UN1325, EINECS 231-115-6, MDL MFCD00011167, Ì 50g

H:H228, P:P210-P241-P280-P240-P370+P378a Hydrogenation catalyst, which may be preferred where deactivation by the reaction products is possible: Used in low-pressure hydrogenolysis of N-benzylamines: Org. Synth. Coll., 7, 152 (1990). Reduction of oximes to amines: Org. Synth. Coll., 5, 376 (1973). Widely used along with hydrogen donors such as Ammonium formate, A10699, p. ?, Sodium formate, A17813, p. ?, Formic acid, A13285, p. ?, Cyclohexene, A11359, p. ?, or Hydrazine monohydrate, A14005, p. ?, for catalytic transfer hydrogenation reactions. In combination with Sodium borohydride, 13432, p. ?, promotes the reduction of nitro-compounds to amines, where borohydride alone is ineffective: Synthesis, 713 (1987). 38304 Palladium, 10% on activated carbon powder, standard, reduced, nominally 50% water wet 900-1100m2/g, MDL MFCD03457879, Note: Sold on a dry weight basis. Unit weight excludes water weight, Ì 38305 Palladium, 10% on activated carbon powder, standard, unreduced, nominally 50% water wet 2

900-1100m /g, MDL MFCD03457879, Note: Sold on a dry weight basis. Unit weight Coupling excludes water weight, Ì 44111 Palladium anchored homogeneous catalyst, FibreCatÑ 1001 Application(s): Bromo/Iodo coupling, MDL MFCD04040828 44110 Palladium anchored homogeneous catalyst, FibreCatÑ 1007 Orange/brown fibres, Application(s): Chloro coupling, MDL MFCD04040827 Catalysts 44981 Palladium anchored homogeneous catalyst, FibreCatÑ 1026 MDL MFCD06202019 44730 Palladium anchored homogeneous catalyst, FibreCatÑ 1032 È MDL MFCD08064489 10516 Palladium(II) acetate, trimer, Pd 45.9-48.4% [Acetic acid palladium(II) salt, Palladium diacetate]

[3375-31-3], C12H18O12Pd3, F.W. 673.46, Needles, m.p. ca 205ø dec., Merck 14,6991, Solubility: Soluble as monomer in glacial acetic acid or as trimer in benzene, Application(s): Carbonylation, oxidation and C-C bond formation, EINECS 222-164-4, RTECS AJ1900000, MDL MFCD00012453, Ì H:H318, P:P280i-P305+P351+P338-P337+P313 Widely used as catalyst, in the presence of a phosphine ligand and a base, in the Heck (or Mizoroki-Heck) reaction, for coupling of aryl or vinyl halides with alkenes. Reviews: Org. React., 27, 345 (1982); Acc. Chem. Res., 12, 146 (1979); 28, 2 (1995); Angew. Chem. Int. Ed., 33, 2379 (1994); Chem. Rev., 100, 3009 (2000). In many reactions, e.g. the arylation of à,á-unsaturated esters, Tri(o-tolyl)phosphine, A12093, p. 150 is superior to triphenylphosphine: J. Org. Chem., 43, 2952 (1978). For the Heck-type reaction of arenediazonium salts with alkenes, see p-Anisidine, A10946, p. ?. o-Allylic or o-vinylic phenols undergo phosphine-free Pd-catalyzed cross-coupling with vinylic halides and triflates, giving dihydrobenzopyrans and dihydrobenzofurans respectively: Tetrahedron Lett., 39, 237 (1998):

In the presence of TBAB, catalyzes direct homocoupling of aryl halides: Tetrahedron Lett., 39, 2559 (1998). Use in an improved "Wacker" oxidation of terminal alkenes to 2-alkanones, with p-Benzoquinone, A13162, p. ?, as the co-oxidant, gives rates up to 50 times higher than earlier procedures: J. Org. Chem., 55, 2924 (1990). Also catalyzes the allylic acetoxylation of cycloalkenes: Org. Synth. Coll., 8, 137 (1993). For catalysis of the efficient "ligandless" Suzuki cross-coupling of arylboronic acids with aryl iodides, see: J. Org. Chem., 59, 5034 (1994); Org. Synth., 75, 61 (1997). For a brief feature on uses of palladium acetate in synthesis, see: Synlett, 329 (2006).

Bulk and Specialty Sizes Available 143 Coupling Catalysts Stock # Description Standard Selling Sizes 11034 Palladium(II) chloride, 99.9% (metals basis), Pd 59.5% min

[7647-10-1], PdCl2, F.W. 177.31, Crystalline, m.p. 675ø dec., Merck 14,6990, Solubility: Soluble in dilute mineral acids, aqueous metal halides, Application(s): Catalyst precursor, EINECS 231-596-2, MDL MFCD00003558, Ì

H:H302-H312-H332-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Terminal olefins can be oxygenated to ketones using a Cu(I) catalyst in the presence of a

catalytic amount of PdCl2 (the Wacker process): Org. Synth. Coll., 7, 137 (1990). For an example in which the product is readily cyclized to give a useful terpenoid synthon, see: Org. Synth. Coll., 8, 208 (1993):

In combination with benzoquinone as reoxidant, N-methylarylamines add to Michael acceptors to give enamines: J. Org. Chem., 46, 2561 (1981). In the presence of triphenylphosphine and MeLi, a Pd(0) species is generated which catalyzes the coupling of organolithium reagents with aryl or vinyl halides. For tabulated results, see: Org. Synth. Coll., 7, 172 (1990):

For use in the microwave accelerated Heck coupling reaction of aryl halides in the ionic liquid 1-n-Butyl-3-methylimidazolium hexafluorophosphate, L19086, p. ?, see: J. Org. Chem., 67, 6243 (2002). 10517 Palladium(II) 2,4-pentanedionate, Pd 34.7% [Palladium(II) acetylacetonate, Bis(acetylacetonato)palladium(II)] Catalysts [14024-61-4], C10H14O4Pd, F.W. 304.92, Powder, m.p. 210ø dec., Solubility: Soluble in benzene and chloroform, Application(s): Carbonylation, oligomerization, EINECS 237-859-8, MDL MFCD00000025, Ì 11886 Sodium tetrachloropalladate(II) hydrate, 99.95% (metals basis), Pd 30% [Sodium chloropalladate(II), Palladium sodium chloride]

[13820-53-6], Cl4Na2PdùxH2O (x÷3), F.W. 294.20(anhy), Crystalline, EINECS 237-502-6, Coupling RTECS RT3480000, MDL MFCD00003487, Ì

H:H302-H319, P:P280f-P305+P351+P338 For use as a catalyst in the carbonylation of allylic halides to give á,-unsaturated esters, see: Chem. Lett., 1873 (1989). In the presence of CsF in aqueous MeOH, catalyzes the cross-coupling of aryl boronates with aryldiazonium salts to give biaryls; no reaction occurs in anhydrous solvents: Tetrahedron Lett., 41, 6271 (2000).

144 www.alfa.com Coupling Catalysts Stock # Description Standard Selling Sizes 10548 Tetrakis(triphenylphosphine)palladium(0), 99.8% (metals basis), Pd 9% min È [Palladium(0) tetrakis(triphenylphosphine)]

[14221-01-3], Pd[P(C6H5)3]4, F.W. 1155.57, Crystalline, m.p. 100-105ø, Solubility: Soluble in benzene, ethanol and chloroform, Application(s): Hydrosilation, isomerization, carbonylation, oxidation, and C-C bond formation, EINECS 238-086-9, BRN 6704828, MDL MFCD00010012, Note: Heat sensitive, Ì

H:H302, P:P264-P270-P301+P312-P330-P501a Homogeneous catalyst for a wide variety of organometallic coupling reactions. Numerous methods have been developed for the synthesis of unsymmetrical biaryls, many of which are catalyzed by this Pd(0) complex. Aryl halides or triflates can be coupled with, e.g. Grignard reagents: Tetrahedron, 42, 2111 (1986), arylzinc halides: Org. Synth. Coll., 8, 430 (1993), organotin reagents (Stille): Angew. Chem. Int. Ed., 25, 508 (1986); J. Am. Chem. Soc., 109, 5478 (1987), or boronic acids (Suzuki-Miyaura): Synth. Commun., 11, 513 (1981); Chem. Rev., 95, 257 (1995); see Benzeneboronic acid, A14257, p. 15, and Appendix 5. Vinyl iodides couple stereoselectively with alkyl, aryl or vinyl Grignards: Tetrahedron Lett., 191 (1978). For stereoselective arylation of a vinylic bromide with an arylzinc chloride in a synthesis of the anti-estrogen agent (Z)-tamoxifen and derivatives, see: J. Org. Chem., 55, 6184 (1990): Coupling

For an example of the coupling of a terminal acetylene with a vinyl bromide by the Sonogashira method using Copper(I) iodide, 11606, p. ?, see: Org. Synth. Coll., 9, 117 (1998). The conversion of aryl halides or triflates to benzonitriles can be much improved by the use

of the catalyst in combination with Zn(CN)2 in DMF or NaCN/CuI (cat) in acetonitrile, giving good yields at lower temperatures than the classical Rosenmund-von Braun method (see Catalysts Copper(I) cyanide, 12135, p. ?): Tetrahedron Lett., 39, 2907 (1998); J. Org. Chem., 63, 8224 (1998). Vinyl bromides or iodides with KCN/18-crown-6 give acrylonitriles in high yield with retention of configuration: Tetrahedron Lett., 4429 (1977). Vinyl triflates with LiCN can also be used: J. Chem. Soc., Chem. Commun., 756 (1989). For a review of palladium- and copper-catalyzed cyanation reactions, see: Eur. J. Inorg. Chem., 3513 (2004). Allylic esters, halides, etc. form organopalladium intermediates equivalent to allyl cations and react with various nucleophiles, e.g. amines: J. Am. Chem. Soc., 98, 8516 (1976); J. Org. Chem., 44, 3451 (1979); Tetrahedron Lett., 24, 2745 (1983); Org. Synth. Coll., 8, 13 (1993). For stereoselective introduction of an amino group using sodium azide, see: J. Org. Chem., 54, 3292 (1989). Catalyst for a variety of carbonylation reactions. Aryl, vinyl, benzylic and allylic halides with

CO (1-3 atm) in the presence of Bu3SnH give aldehydes: J. Am. Chem. Soc., 105, 7175 (1983); 108, 452 (1986). For carbonylative intramolecular cyclization of aminomethyl vinyl triflates to à,á-unsaturated lactams, see: Tetrahedron, 51, 5585 (1995):

Acyl halides can be coupled with organometallic reagents to give ketones, e.g. organozinc halides: Tetrahedron Lett., 24, 5181 (1983); Org. Synth. Coll., 8, 274 (1993), organotin reagents: Org. Synth. Coll., 8, 268 (1993), or arylboronic acids: Tetrahedron Lett., 40, 3109 (1999). 10549 Tetrakis(triphenylphosphine)platinum(0), Pt 15.2% min È [Platinum(0) tetrakis(triphenylphosphine)]

[14221-02-4], Pt[P(C6H5)3]4, F.W. 1244.21, Crystalline Powder, Solubility: Soluble in benzene, Application(s): Hydrosilation and oxidation, EINECS 238-087-4, MDL MFCD00010014, Ì

H:H302, P:P264-P270-P301+P312-P330-P501a Catalyst for the diboronylation of alkynes with Bis(pinacolato)diboron, L16088, p. 134, to give cis-bis-boryl alkenes: Organometallics, 15, 713 (1996), and of 1,3-dienes to give 1,4-bis-boryl-2-alkenes: Chem. Commun., 2073 (1996):

Similarly, allenes are converted to 2,3-bis-borylalkenes: Tetrahedron Lett., 39, 2357 (1998).

Bulk and Specialty Sizes Available 145 Phosphine Ligands Stock # Description Standard Selling Sizes L15980 Tris(dibenzylideneacetone)dipalladium(0) chloroform 250mg adduct, 98% 1g [Dipalladiumtris(dibenzylideneacetone) chloroform adduct]

[52522-40-4], C51H42O3Pd2ùCHCl3, F.W. 1035.12, m.p. 131-135ø, Fieser 11,508 13,9 14,339 15,353 16,372 17,394 19,390 20,420 21,474, MDL MFCD00075479

H:H351-H373-H302, P:P260-P281-P301+P312-P308+P313-P405-P501a Phosphine-free Pd(0) catalyst. Catalyzes the addition of arylboronic acids to aldehydes, affording secondary alcohols. No reaction was observed in the absence of chloroform: Org. Lett., 7, 4153 (2005). 12760 Tris(dibenzylideneacetone)dipalladium(0), Pd 21.5% min È É

[Bis[tris(dibenzylideneacetone)palladium(0)], Pd2(dba)3]

[51364-51-3], C51H42O3Pd2, F.W. 915.74, Powder, m.p. 152-155ø, Fieser 9,46 12,56 14,38 15,33 17,394 18,389 19,388 20,417 21,469, Solubility: Soluble in chlorinated solvents, MDL MFCD00013310 Stable source of phosphine-free Pd(0), useful in a variety of coupling reactions. Literature

references to the use of either "Pd(dba)2" or "Pd2(dba)3" can normally be regarded as interchangeable since the catalyst is of somewhat variable composition depending on the exact method of preparation. For use in the coupling of aryl- or vinyltin reagents with allyl halides, see: J. Am. Chem. Soc., 105, 7173 (1983). For Suzuki coupling of boronic acids with carbapenem triflates, see: Tetrahedron Lett., 34, 3211 (1993). Catalyzes the reduction of terminal allylic acetates or carbonates to 1-alkenes, with virtually

Ligands complete regioselectivity: Synthesis, 623 (1986). In the presence of allyl bromide, catalyzes the coupling of terminal alkynes to symmetrical diynes under phase-transfer conditions. The reaction is thought to involve a ã-allyl Pd intermediate: Tetrahedron, 52, 1337 (1996). In the presence of a chelating phosphine ligand and NaO-t-Bu, bromopyridines can be aminated: J. Org. Chem., 61, 7240 (1996): Phosphine

Catalyst for Stille and Heck coupling reactions in supercritical CO2, in combination with, e.g. Tris[3,5-bis(trifluoromethyl)phenyl]phosphine, L06941, p. ?: Chem. Commun., 1397 (1998). Catalyzes the hydroxycarbonylation of aryl and vinyl halides or triflates by lithium formate, to give carboxylic acids: Org. Lett., 5, 4269 (2003).

Stock # Description Standard Selling Sizes L19759 1,1'-Bis(di-tert-butylphosphino)ferrocene, 98% È 500mg

[84680-95-5], C26H44FeP2, F.W. 474.43, m.p. 73-78ø, 2g MDL MFCD01630818

H27057 1,1'-Bis(diisopropylphosphino)ferrocene, 98% 1g

[97239-80-0], C22H36FeP2, F.W. 418.34, Orange powder, m.p. 50-52ø, 5g f.p. >110ø(230øF), MDL MFCD02684559

H26226 (ñ)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl, 98% 5g [(+/-)-BINAP, (+/-)-(1,1'-Binaphthalene-2,2'-diyl)bis(diphenylphosphine)] 25g

[98327-87-8], C44H32P2, F.W. 622.69, White to pale cream cryst powder, 100g m.p. 281-285ø, Merck 14,1223, BRN 5321443, MDL MFCD00010805

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

146 www.alfa.com Phosphine Ligands Stock # Description Standard Selling Sizes B23785 (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl, 98% È 250mg [(R)-(+)-BINAP] 1g

[76189-55-4], C44H32P2, F.W. 622.69, White to pale cream cryst powder, m.p. 239-241ø, ¾ +230° (c=0.3 in toluene), Merck 14,1223, Fieser 10,36 13,36 14,38 15,34 16,32 17,34 18,39 19,33 20,41 21,53, BRN 4914063, MDL MFCD00010805

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Chiral chelating ligand which is the basis of a number of homogeneous catalysts which promote hydrogenation reactions with very high enantiomeric excesses. Rh complexes catalyze the asymmetric hydrogenation of à-acylaminoacrylic acids: J. Am. Chem. Soc., 102, 7932 (1980), and the isomerization of allylamines to chiral enamines: J. Chem. Soc., Chem. Commun., 600 (1982); Synthesis, 665 (1991). Asymmetric hydrogenation of á-keto esters is achieved with a Ru based catalyst: J. Org. Chem., 57, 6691 (1992). For preparation of a cycloocta-1,5-diene Rh complex and use in enantioselective hydrogenation reaction, see: Org. Synth. Coll., 8, 183 (1993). For a review of the use of Ru BINAP complexes in asymmetric hydrogenation, see: Acta Chem. Scand., 50, 380 (1996). Reviews: BINAP catalysis: Acc. Chem. Res., 23, 345 (1990); binaphthylic derivatives as chiral auxiliaries: Synthesis, 503 (1992); advances in biaryl-type biphosphne ligands: Tetrahedron, 61, 5405 (2005).

B23872 (S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl, 97% È 250mg Phosphine [(S)-(-)-BINAP] 1g

[76189-56-5], C44H32P2, F.W. 622.69, White to pale cream cryst powder, 5g m.p. 239-241ø, ¾ -230° (c=0.3 in toluene), Merck 14,1223, Fieser 10,36 13,36 14,38 15,34 16,32 17,36 18,39 19,33 20,41 21,53, BRN 5321444, MDL MFCD00010805

H:H315-H319-H335, P:P280g-P305+P351+P338 For use in the Ru-catalyzed homogeneous enantioselective reduction of ketones to secondary Ligands alcohols, see: J. Am. Chem. Soc., 117, 2675, 10417 (1995); Org. Synth., 77, 1 (1999). The combination with Tris(dibenzylideneacetone)dipalladium(0), 12760, p. 146, catalyzes the asymmetric arylation of ketone enolates with aryl bromides: J. Am. Chem. Soc., 120, 1918 (1998). See also previous entry. H31306 2,2'-Bis(diphenylphosphino)biphenyl, 98% 250mg [BIPHEP] 1g

[84783-64-2], C36H28P2, F.W. 522.57, White cryst powder, m.p. 211-215ø, 5g MDL MFCD03094574

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a B21122 1,4-Bis(diphenylphosphino)butane, 98% È 1g [Dppb] 5g

[7688-25-7], (C6H5)2P(CH2)4P(C6H5)2, F.W. 426.48, White cryst powder, m.p. 132-136ø, 25g EINECS 231-698-7, BRN 706446, MDL MFCD00003051, Ì

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Chelating ligand.

The PdCl 2 complex catalyzes the Suzuki coupling of heteroaryl chlorides with boronic acids with reported advantages over other catalysts: Tetrahedron Lett ., 32, 2273 (1991); Tetrahedron, 48, 8117 (1992). Component of a chiral Rh-based homogeneous hydrogenation catalyst: Org. Synth. Coll., 8, 16 (1993). B21166 1,1'-Bis(diphenylphosphino)ferrocene, 97% È 1g [Dppf, 1,1'-Ferrocenebis(diphenylphosphine)] 5g

[12150-46-8], C34H28FeP2, F.W. 554.40, Yellow to orange powder, m.p. ca 25g 182ø dec., EINECS 430-420-3, MDL MFCD00001422

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Hindered bidentate ligand used in, for example, the Ni-catalyzed Suzuki-type crossed coupling of arylboronic acids with aryl mesylates to give biaryls: J. Org. Chem., 60, 1060, 1066 (1995), and of thiophenolates with aryl mesylates to give unsymmetrical diaryl sulfides: J. Org. Chem., 60, 6895 (1995). L18481 Bis[(2-diphenylphosphino)phenyl] ether, 98% 1g [DPEphos] 5g

[166330-10-5], C36H28OP2, F.W. 538.57, m.p. 178-181ø, BRN 7729718, MDL MFCD00233863

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Bidentate ligand, investigated in Rh-catalyzed regioselective hydroformylation of olefins: Organometallics, 14, 3081 (1995). Reported by Buchwald to be highly effective in promoting the Pd-catalyzed N-arylation of anilines: Tetrahedron Lett., 39, 5327 (1998).

Bulk and Specialty Sizes Available 147 Phosphine Ligands Stock # Description Standard Selling Sizes A12931 1,3-Bis(diphenylphosphino)propane, 97% È 5g [Dppp] 25g

[6737-42-4], (C6H5)2P(CH2)3P(C6H5)2, F.W. 412.46, White powder, m.p. 58-63ø, 100g EINECS 229-791-2, BRN 2821785, MDL MFCD00003050, Ì

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

Chelating phosphorus ligand which forms a 1:1 complex with NiCl2, which is an efficient catalyst for the coupling of Grignard reagents with aryl, vinylic or heterocyclic halides: Bull. Chem. Soc. Jpn., 49, 1958 (1976); Tetrahedron, 38, 3347 (1982); Synthesis, 386 (1988). Successful Suzuki coupling of arylboronic acids with aryl chlorides bearing electron-withdrawing groups was achieved in the presence of Palladium(II) acetate, 10516, p. 143, and dppp: Tetrahedron Lett., 38, 5575 (1997). H27585 (ñ)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl, 98% 250mg [rac-p-Tol-BINAP] 1g

[153305-67-0], C48H40P2, F.W. 678.79, White cryst powder, 5g m.p. 267-271ø, MDL MFCD01311709

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

42119 (R)-(+)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl, 98% [(R)-Tol-BINAP]

[99646-28-3], C48H40P2, F.W. 678.79, Powder, m.p. 255-257ø, ¾ +156ø(c=0.5 in benzene), Application(s): Chiral catalyst ligand, MDL MFCD00269856

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Ligands 42120 (S)-(-)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl, 98% [(S)-Tol-BINAP]

[100165-88-6], C48H40P2, F.W. 678.79, Powder, m.p. 255-257ø, Application(s): Chiral catalyst ligand, MDL MFCD00269856

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Phosphine H27680 (R)-(+)-2,2'-Bis(di-3,5-xylylphosphino)-1,1'-binaphthyl, 98% 100mg [(R)-Xylyl-BINAP] 500mg

[137219-86-4], C52H48P2, F.W. 734.91, White to pale yellow cryst powder, m.p. 201-203ø, MDL MFCD01630821

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H26970 (S)-(-)-2,2'-Bis(di-3,5-xylylphosphino)-1,1'-binaphthyl, 98% 100mg [(S)-Xylyl-BINAP] 500mg

[135139-00-3], C52H48P2, F.W. 734.91, White to cream cryst powder, m.p. 201-203ø, MDL MFCD01630821

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H27351 (R)-(+)-2,2'-Bis(di-3,5-xylyl- 50mg phosphino)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl È 250mg [(R)-Xylyl-H8-BINAP]

[190003-81-7], C52H56P2, F.W. 742.97, White powder, MDL MFCD06796646

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27209 2-(Di-tert-butylphosphino)-2'-(N,N-dimethylamino)biphenyl, 98% 250mg È 1g

[224311-49-3], C22H32NP, F.W. 341.47, White crystalline powder, m.p. 114-117ø, MDL MFCD03426986

H:H315-H319-H335, P:P280g-P305+P351+P338

H27742 2-(Di-tert-butylphosphino)-2'-methylbiphenyl, 99% È 250mg

[255837-19-5], C21H29P, F.W. 312.43, White crystalline powder, 1g m.p. 90-93ø, MDL MFCD03453047

H:H315-H319-H335, P:P280g-P305+P351+P338

148 www.alfa.com Phosphine Ligands Stock # Description Standard Selling Sizes H27617 2-Dicyclohexylphosphino-2',6'-diisopropoxy-1,1'-biphenyl, 1g 98% È 5g

[787618-22-8], C30H43O2P, F.W. 466.64, White cryst powder, m.p. 123-126ø, MDL MFCD06798294

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a

H27678 2-Dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl, 98% È 1g [DavePhos, 2-Dimethylamino-2'-dicyclohexylphosphinobiphenyl] 5g

[213697-53-1], C26H36NP, F.W. 393.56, White powder, m.p. 121-124ø, 25g MDL MFCD02183572

H:H315-H319-H335, P:P280g-P305+P351+P338

H27647 2-Dicyclohexylphosphino-2'-methylbiphenyl, 98% È 1g

[251320-86-2], C25H33P, F.W. 364.51, White crystalline solid, m.p. 107-110ø, 5g MDL MFCD03094577

H:H315-H319-H335, P:P280g-P305+P351+P338 Phosphine L19477 Diphenylmethylphosphine, polymer-supported, 0.9-1.4 mmol/g 1g on polystyrene 5g [Diphenylmethylphosphine polystyrene, Diphenylphosphine on Merrifield 25g resin] MDL MFCD01866199 Support for rhodium in the reduction of cyclohexene in benzene: J. Am. Chem. Soc., 93, 3062 (1971). For use as a ligand in Suzuki couplings: Tetrahedron Lett., 38, 1793 (1996); 39, 4287 Ligands (1998). 10178 Tri-tert-butylphosphine, 96% È É

[13716-12-6], C12H27P, F.W. 202.32, Solid, m.p. 30ø, b.p. 102-103ø/13mm, f.p. -16ø(-3øF), UN2845, EINECS 237-266-4, MDL MFCD00015006

H:H250-H252-H314, P:P210-P303+P361+P353-P305+P351+P338-P405-P422a-P501a Ligand which has been used in conjunction with Tris(dibenzylideneacetone)dipalladium(0), 12760, p. 146 in promoting Suzuki cross-coupling reactions of arylboronic acids with aryl and vinyl halides under mild conditions. The system is particularly recommended for coupling reactions with normally unreactive aryl chlorides: J. Am. Chem. Soc., 4070 (2000). The same catalyst system has been found to be effective in the room-temperature cyanation of aryl bromides using zinc cyanide: Synlett, 2237 (2003). Efficient catalyst for the trifluoromethylation of aldehydes, ketones, imides and imines with (Trifluoromethyl)trimethylsilane, B20347, p. ?: Synlett, 267 (2006). For a brief feature on uses of the reagent in synthesis, see: Synlett, 709 (2005). L19752 Tri-tert-butylphosphonium tetrafluoroborate, 97% Ê 1g [Fluoroboric acid tri-tert-butylphosphine adduct, Tri-tert-butylphosphine 5g fluoroboric acid adduct]

[131274-22-1], C12H28BF4P, F.W. 290.13, m.p. ca 260ø dec., BRN 8813613, MDL MFCD07189501

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Convenient, air-stable replacement for tri-tert-butylphosphine, e.g. in Suzuki, Heck, Stille and Sonogashira coupling reactions: Org. Lett., 3, 4295 (2001). 30386 Tricyclohexylphosphine, 96% È

[2622-14-2], (C6H11)3P, F.W. 280.42, Crystalline, m.p. 76-78ø, EINECS 220-069-2, MDL MFCD00003853, Ì

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a 41952 Tricyclohexylphosphine, 98% È

[2622-14-2], (C6H11)3P, F.W. 280.42, Crystalline, m.p. 76-78ø, EINECS 220-069-2, MDL MFCD00003853, Ì

H:H302-H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a H27428 Tricyclohexylphosphonium tetrafluoroborate, 99% 1g

[58656-04-5], C18H34P.BF4, F.W. 368.25, White crystalline powder, m.p. 166-170ø, 5g MDL MFCD03840580 25g

H:H315-H319-H335, P:P280g-P305+P351+P338 Air-stable replacement for tricyclohexylphosphine in various Pd-catalyzed coupling reactions. Used in conjunction with Bis(1,5-cyclooctadiene)nickel(0), 39234, p. ? in Ni(0)-catalyzed Suzuki-Miyaura-type coupling of alkenyl phosphates with arylboronic acids and esters to give 1,1-diarylalkenes: Chem. Commun., 4137 (2006). See also Tri-tert-butylphosphonium tetrafluoroborate, L19752, p. 149.

Bulk and Specialty Sizes Available 149 Phosphine Ligands Stock # Description Standard Selling Sizes L13329 Tri(2-furyl)phosphine, 97% 250mg [Tris(2-furyl)phosphine] 1g

[5518-52-5], C12H9O3P, F.W. 232.18, m.p. 59-64ø, b.p. 136ø/4mm, 5g Fieser 15,32, BRN 1577564, MDL MFCD00151857

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Best ligand for Pd-catalyzed coupling of 5-iodouracil and unsaturated tributylstannanes: Synlett, 157 (1991). Large rate enhancements (10 2 -10 3 ) over triphenylphosphine are observed in Pd-catalyzed coupling of olefinic stannanes and electrophiles: J. Am. Chem. Soc ., 113, 9585 (1991).

In a study of Pd-catalyzed coupling reactions in supercritical CO 2, this ligand was among the best tried in both the Stille and Heck reactions, giving much superior results to e.g. triphenyl- or tri(o-tolyl)phosphine: Chem. Commun., 1397 (1998). See also Tris[3,5-bis(trifluoromethyl)phenyl]phosphine, L06941, p. ?. A14089 Triphenylphosphine, flake, 99% 250g [TPP] 1kg

[603-35-0], (C6H5)3P, F.W. 262.29, White to pale cream flakes, m.p. 79-81ø, b.p. 360ø, 5kg f.p. 181ø(358øF), d. 1.200, Merck 14,9743, Solubility: Insoluble in water. Soluble in benzene, acetone, carbon tetrachloride, ether, and glacial acetic acid, Application(s): In the synthesis of organic compounds, phosphonium salts and other phosphorus compounds, and as a polymerization initiator, EINECS 210-036-0, RTECS SZ3500000, BRN 610776, MDL MFCD00003043, Ì

H:H302-H317-H413, P:P261-P280-P302+P352-P321-P301+P312-P501a L02502 Triphenylphosphine, powder, 99% 50g [TPP] 250g Ligands [603-35-0], (C6H5)3P, F.W. 262.29, m.p. 79-81ø, b.p. 360ø, f.p. 181ø(358øF), d. 1.200, 1kg Merck 14,9743, Fieser 1,1238 15,352 16,366 17,389 18,385 19,382 20,411 21,462, EINECS 210-036-0, RTECS SZ3500000, BRN 610776, MDL MFCD00003043, Ì

H:H302-H317-H413, P:P261-P280-P302+P352-P321-P301+P312-P501a Finds widespread use as a complexing agent with transition metals, either in the preparation of stable complexes, or as an additive in metal-promoted reactions. See also Tri(o-tolyl)-

Phosphine phosphine, A12093, p. 150 and Tri(2-furyl)phosphine, L13329, p. 150. Azides can be converted selectively to amines, in the presence of ester, epoxide or nitro groups, by reduction to iminophosphoranes (Staudinger reaction), followed by hydrolysis. For reviews, see: Tetrahedron, 37, 437 (1981); 48, 1353 (1992):

In suitable circumstances, the iminophosphorane may undergo intramolecular aza-Wittig reaction: Tetrahedron, 45, 6375 (1989):

Reviews: Aza-Wittig reaction in heterocyclic synthesis: Org. Prep. Proced. Int., 24, 209 (1992); Iminophosphoranes as building blocks for the preparation of N-containing heterocycles: Synthesis, 1197 (1994). For use in peptide and other coupling reactions, see 2,2'-Dipyridyl disulfide, A11118, p. ?. For use in the Mitsunobu reaction for conversion of alcohols to alkylating agents, see N-Guanylurea sulfate, A19106, p. ?, and Diisopropyl azodicarboxylate, L10386, p. ?. See also 1,2-Bis(diphenylphosphino)ethane, A11419, p. ?. L19478 Triphenylphosphine, polymer-supported, 1.4-2.0 mmol/g on 1g polystyrene 5g MDL MFCD00148025 25g Support for nickel, rhenium and rhodium in hydrogenation: J. Am. Chem. Soc., 97, 1742 (1975); dimerization of alkenes: J. Am. Chem. Soc., 97, 341 (1974) and hydroformylation: J. Am. Chem. Soc., 98 5402 (1976). For the halogenation of carboxylic acid and alkanes in carbon tetrachloride: Synthesis, 1093 (1992). Addition of iodine in DMF esterifies primary and secondary alcohols to their respective formate esters: Med. Res. Rev., 19, 97 (1999). For use in the Mitsunobu reaction: Tetrahedron Lett., 8751 (1998), and the Wittig reaction: J. Org. Chem., 48, 326 (1983); J. Chem. Soc. Perkin 1, 2243 (1998). A12093 Tri(o-tolyl)phosphine, 98+% È 1g [Tris(2-methylphenyl)phosphine, Tris(o-tolyl)phosphine] 5g

[6163-58-2], C21H21P, F.W. 304.37, White cryst powder, m.p. 122-127ø, 25g EINECS 228-193-9, BRN 661212, MDL MFCD00008514, Ì

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Preferred phosphine ligand for use in combination with Pd salts in the Heck-type coupling reactions of vinylic halides. For examples, see Palladium(II) acetate, 10516, p. 143. For a review of the Heck reaction, see: Org. React., 27, 345 (1982). The Pd-catalyzed amination of bromoarenes with 1-Boc-piperazine, L13363, p. ?, in the presence of this ligand, provides a route to arylpiperazines of potential pharmacological interest: Tetrahedron Lett., 39, 2219 (1998).

150 www.alfa.com Non-Phosphine Ligands

Stock # Description Standard Selling Sizes H27150 1,3-Bis(2,6-diisopropylphenyl)imidazolium chloride, 97% 1g Ê 5g

[250285-32-6], C27H37ClN2, F.W. 425.05, White to cream powder, m.p. ca 280ø dec., MDL MFCD02684545

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a In the presence of a base such as KO-t-Bu, generates the imidazol-2-ylidene, an example of an N-heterocyclic carbene (NHC). NHCs are relatively strong bases, and valuable replacements for phosphine ligands in transition metal chemistry. They are relatively stable to dimerization, but sensitive to air and moisture, so are best generated in situ. Review: Angew. Chem. Int. Ed., 36, 2163 (1997). For a review of stable carbenes, see: Chem. Rev., 100, 39 (2000). Used as a phosphine-free ligand in various metal-catalyzed coupling reactions, often with advantageous results in difficult cases. For use in the Pd-catalyzed cross-coupling of aryl Grignards with aryl chlorides (Kumada reaction), see: J. Am. Chem. Soc., 121, 9889 (1999).

For Pd-catalyzed coupling of trimethoxysilanes with electron-deficient aryl chlorides, see: Non-Phosphine Org. Lett., 2, 2053 (2000). Many examples have been recorded of the use of NHC ligands in the Suzuki coupling reaction, for examples utilizing 1,3-bis(2,6-diisopropylphenyl)imiazol-2-ylidene, enabling otherwise difficult coupling reactions of aryl chlorides with aryl and alkyl boronic acids, see: Synlett, 292 (2001) (includes alkylboronic acids: better yields than 1,3-dimesitylimidazol-2-ylidene); Org. Lett., 6, 4435 (2004); Tetrahedron Lett., 45, 3511 (2004). See also 1,3-Dimesitylimidazolium chloride, H27535, p. 152. A14003 1,4-Diazabicyclo[2.2.2]octane, 98% Ê 25g [Dabco®, TEDA] 100g Ligands [280-57-9], C6H12N2, F.W. 112.17, White to cream cryst powder, m.p. 155-160ø, 500g b.p. 174-176ø, f.p. 62ø(143øF), d. 1.140, Merck 14,9669, Fieser 1,1203 7,86 12,155 13,92 15,109 18,120 19,116 20,128 21,157, EINECS 205-999-9, RTECS HM0354200, BRN 103618, MDL MFCD00006689, Ì

H:H318-H302-H335-H315, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a Dabco is a registered trademark of Air Products and Chemicals Inc. Forms crystalline complexes with organolithium compounds: J. Am. Chem. Soc., 87, 3276 (1965), which show enhanced reactivity, e.g. in the high yield à-metallation of thioanisole by n-BuLi: J. Org. Chem., 31, 4097 (1966).

Forms a stable crystalline complex with H2O2, useful as an equivalent to "anhydrous" H2O2: reaction with TMS chloride gives bis(TMS) peroxide, a useful OH+-equivalent, e.g. in the conversion of aryllithiums to phenols: Synthesis, 633 (1986). Catalyzes the addition of aldehydes to Michael acceptors at the à-position (Baylis-Hillman reaction): Helv. Chim. Acta, 63, 413 (1984):

For further illustrative example, see: Org. Synth., 75, 106 (1997). Complete reaction often takes several days at ambient temperature, while heating causes lower yields. However, it is greatly accelerated by microwave irradiation: Synlett, 444 (1994). Superior results with reduced reaction times can be achieved in aqueous medium: J. Org. Chem., 66, 5413 (2001). The use as reaction medium of tetramethylene sulfone: Tetrahedron Lett., 45, 1183 (2004), or PEG-400: Tetrahedron Lett., 45, 5865 (2004) has also been advocated. Lithium perchlorate was found to increase the reaction rate dramatically: Tetrahedron Lett., 40, 1539 (1999), as was a catalytic amount of a metal triflate, particularly La or Sm; conventional Lewis acids were ineffective: J. Org Chem., 63, 7183 (1998). For asymmetric Baylis-Hillman reaction using (1S,2R)-(-)-10,2-Camphorsultam, A15897, p. ?, as chiral auxiliary, see: J. Am. Chem. Soc., 119. 4317 (1997). See also 3-Quinuclidinol, B21503, p. ?. For more recent discussion and comparison of different catalysts, see: J. Org. Chem., 692 (2003). In a reinterpretaion of the mechanism, a hemiacetal interemediate has been proposed: J. Org. Chem., 70, 3980 (2005). For reviews of the Baylis-Hillman reaction, see: Tetrahedron, 44, 4653 (1988); 52, 8001 (1996). Promotes the cleavage of á-keto esters in refluxing xylene directly to ketones, without the need for prior hydrolysis: J. Org. Chem., 39, 1592, 2647 (1974). Similarly, malonic esters can be cleaved to esters of substituted acetic acids: J. Org. Chem., 41, 208 (1976). In conjunction with palladium acetate and PEG-400 provides a reusable catalyst system for the Suzuki-Miyaura cross-coupling reaction of boronic acids: J. Org. Chem., 70, 5409 (2005).

Bulk and Specialty Sizes Available 151 Non-Phosphine Ligands Stock # Description Standard Selling Sizes H27535 1,3-Dimesitylimidazolium chloride, 96% 1g [1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride] 5g

[141556-45-8], C21H25ClN2, F.W. 340.89, Solid, m.p. >300ø, MDL MFCD02684541

H:H315-H319-H335, P:P261-P305+P351+P338-P302+P352-P321-P405-P501a In the presence of a base such as KO-t-Bu, generates the imidazol-2-ylidene, an example of an N-heterocyclic carbene (NHC). NHCs are relatively strong bases, and valuable replacements for phosphine ligands in transition metal chemistry. They are relatively stable to dimerization, but sensitive to air and moisture, so are best generated in situ. Review: Angew. Chem. Int. Ed., 36, 2163 (1997). For a review of stable carbenes, see: Chem. Rev., 100, 39 (2000). Used as a phosphine-free ligand in various metal-catalyzed coupling reactions, often with advantageous results in difficult cases. For use in the Pd-catalyzed cross-coupling of aryl Grignards with aryl chlorides (Kumada reaction), see: J. Am. Chem. Soc., 121, 9889 (1999). Many examples have been recorded of the use of NHC ligands in the Suzuki coupling reaction, for examples utilizing 1,3-dimesitylimidazol-2-ylidene, in the coupling of arylboronic acids with relatively unreactive aryl chlorides, see: J. Org. Chem., 64, 3804 (1999); J. Organomet. Chem., 595, 186 (2000); Tetrahedron Lett., 45, 3511 (2004). Has been found to give superior results to phosphines in the coupling of sulfonyl chlorides with boronic acids: Org. Lett., 6, 95 (2004). The carbene has also been reported to be an excellent nucleophilic catalyst in transesterification reactions, milder, more selective and more active than conventional systems: Org. Lett., 4, 3583, 3587 (2002). See also 1,3-Bis(2,6-diisopropylphenyl)imidazolium chloride, H27150, p. 151. L03616 Triphenylarsine, 98% 5g Ligands [603-32-7], (C6H5)3As, F.W. 306.24, m.p. 60-62ø, b.p. 360ø, f.p. 265ø(509øF), 25g Fieser 10,445 13,137 15,350, UN3465, EINECS 210-032-9, RTECS CH7942500, BRN 1842037, MDL MFCD00002994, Ì

H:H301-H331-H400-H410, P:P261-P301+P310-P321-P304+P340-P405-P501a Can be cleaved to sodium diphenylarsenide by Na metal. A mole of PhNa is also produced,

but can be selectively destroyed by protonation with NH4Br: Chem. Ber., 100, 1230 (1967). For use in the preparation of chelating ligands, see: Synthesis, 350 (1979). Similarly, Li metal gives Li diphenylarsenide: J. Org. Chem., 32, 2627 (1967). For a review of the chemistry of metal arsenides, see: Synthesis, 328 (1974).

Non-Phosphine Preferred to phosphines as a ligand in certain metal-catalyzed coupling reactions, e.g. in the Pd catalyzed Stille coupling of aryl stannanes with aryl halides: Tetrahedron Lett., 36, 2191 (1995), of silylated allylic stannanes with alkyl halides: J. Org. Chem., 60, 4647 (1995), the Pd catalyzed homocoupling of organostannanes: Synth. Commun., 27, 641 (1997), the Pd catalyzed coupling of aryl- or alkynylzinc chlorides with alkenyl halides: Synlett, 344 (1995), or the Suzuki coupling of arylboronic acids with sensitive halides: Org. Synth., 75, 69 (1997).

152 www.alfa.com