2007 VOLUME 7 NUMBER 4
Product Directory
Grignard and Organozinc Reagents
RIEKE® HIGHLY REACTIVE METALS
GRIGNARD REAGENTS
ORGANOZINC HALIDES
DIALKYLMAGNESIUM AND DIALKYZINC REAGENTS
2-Pyridylzinc bromide: a shelf-stable 2-pyridyl anion equivalent; an important motif in many pharmacologically active molecules.
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Table of Contents Sigma-Aldrich is committed to providing the most extensive portfolio of high-quality Grignard, organozinc, and other organometallic reagents, and we continually expand our product listing. Within each section of this directory, products are listed by increasing carbon content.
Rieke® Highly Reactive Metals If viewing the electronic version simply select Grignard Reagents a category to jump to that section or activate Alkyl Alkenyl Alkynyl Aryl Heteroaryl your Adobe Bookmarks. You may also search by name, product number, molecular formula, Organozinc Halides or CAS registry number simply by using the Alkyl Alkenyl Aryl Heteroaryl “find” feature in Adobe (Ctrl+F in Windows or Introduction Command+F in a Mac environment). Dialkylmagnesium and Dialkylzinc Reagents
If you are unable to find a reagent for your research “Please Bother Us” at [email protected], or contact your local Sigma-Aldrich office (see back cover).
Foreword Reuben D. Rieke President and CEO, Rieke Metals, Inc. Professor Emeritus, University of Nebraska Lincoln, NE In the last 35 years, considerable research has been done in the area of generating reactive metals that can be used to synthesize novel organometallic reagents. In 1972, we reported a general approach for preparing highly reactive metal powders, relying on the reduction of metal salts with alkali metals in ethereal or hydrocarbon solvents. These useful metal powders were eventually named “Rieke metals” and they have greatly expanded the number of organometallic reagents that can be made. Grignard reagents are some of the most widely employed organometallic reagents and a wealth of information is known about their reactivity. Although the formation of these reagents is commonly thought to be completely general, there are many organic halides that do not react with ordinary magnesium turnings. The use of Rieke® Magnesium dramatically increases the range of Grignard reagents that are possible by allowing reactions at lower temperatures and thus avoiding decomposition and side reactions. Rieke® Magnesium, as well as an abundant portfolio of pre-formed Grignard reagents, are conveniently available through Sigma-Aldrich. Prior to the discovery of Rieke® Zinc, it was not possible to react alkyl, aryl, and vinyl bromides or chlorides directly with zinc metal. The preparation of these reagents was only possible by a metathesis reaction of a zinc halide with an organolithium or Grignard reagent. Unfortunately, this approach was of limited utility since the process was not compatible with many types of functional groups. Rieke® Zinc, on the other hand, will react directly with the bromides or chlorides and will tolerate a variety of sensitive groups such as nitriles, esters, amides, ethers, sulfides, and ketones to give functionalized organozinc reagents. Organozinc reagents are powerful C–C bond-forming tools, participating in Cu(I)-promoted reactions (developed at Rieke Metals, Inc.) or in Pd-catalyzed cross-coupling reactions, i.e. the Negishi coupling. Sigma-Aldrich offers Rieke® Zinc, as well as numerous pre-formed Rieke® organozinc reagents for use in these and other important reactions.
R R O OH ROH R Ar R
X O O R O O2 O RCO H 2 CuX CuX Ar Cl CuX X CO2 Br O O Br X O R'CN R' R' RMgX R' MgX R RZnX R R' R' R O CuX CuX R' SnCl R' Y 3 O X Ar X O R' Sn R R' R R'X 3 [Pd] or R' R" CuX OH
R' R R R Ar R OH RR' R' R" R sigma-aldrich.com 3
Rieke® Highly Reactive Metals
Reactive Rieke® Mg metal R Reactive Rieke® Zn metal R Mg Zn MW: 24.31 Mg* MW: 65.39 Zn* [7439-95-4] [7440-66-6] 2.5 g/dL suspension in tetrahydrofuran: 499579 5 g/dL suspension in tetrahydrofuran: 499552 Rieke Grignard Reagents Reactive Metals Alkyl ® Methylmagnesium chloride solution Isopropylmagnesium chloride 8 tert-Butylmagnesium chloride solution Highly CH ClMg C H ClMg 3 lithium chloride complex solution 4 9 H3C MW: 74.79 H3C MgCl C3H7Cl2LiMg MW: 116.87 H3C MgCl CH3 [676-58-4] MW: 145.24 ·LiCl [677-22-5] H3C H3C MgCl 3.0 M in tetrahydrofuran: 189901, 257095 [807329-97-1] 2.0 M in diethyl ether: 224499 1.0 M in tetrahydrofuran: 656984 1.0 M in tetrahydrofuran: 364649, 364657 Methylmagnesium bromide solution
CH3BrMg Cyclopropylmagnesium 1-Methyl-2-propenylmagnesium MW: 119.24 H3C MgBr bromide solution chloride solution
[75-16-1] C3H5BrMg C H ClMg 4 7 MgCl 1.0 M in butyl ether: 302430 MW: 145.28 MgBr MW: 114.86 [23719-80-4] [21969-32-4] CH3 3.0 M in diethyl ether: 189898, 257087 1.4 M in toluene/tetrahydrofuran 0.5 M in tetrahydrofuran: 526797 0.5 M in tetrahydrofuran: 420042 (75:25): 282235 Allylmagnesium chloride solution 2-Methylallylmagnesium Methylmagnesium iodide solution C3H5ClMg chloride solution MW: 100.83 CH3IMg MgCl C4H7ClMg [2622-05-1] MgCl MW: 166.24 H3C MgI MW: 114.86 CH3 [917-64-6] 2.0 M in tetrahydrofuran: 225908, 256617 [5674-01-1] 3.0 M in diethyl ether: 254363, 257109 0.5 M in tetrahydrofuran: 419532 Allylmagnesium bromide solution C H BrMg Methyl-d3-magnesium iodide solution 3 5 2-Butenylmagnesium chloride solution MW: 145.28 CD3IMg MgBr C4H7ClMg D C MgI [1730-25-2] MW: 114.86 MW: 169.26 3 H3C MgCl [41251-37-0] 1.0 M in diethyl ether: 225754, 256609 [22649-70-3] 1.0 M in diethyl ether: 293091 0.5 M in tetrahydrofuran: 419583 Butylmagnesium chloride solution Ethylmagnesium chloride solution C4H9ClMg 3-Butenylmagnesium bromide solution MW: 116.87 CH3 MgCl C2H5ClMg C4H7BrMg [693-04-9] MW: 159.31 MW: 88.82 H3C MgCl MgBr [2386-64-3] 1.45 M in butyl diglyme: 529923 [7103-09-5] 2.0 M in diethyl ether: 300330 2.0 M in diethyl ether: 224375 0.5 M in tetrahydrofuran: 419591 2.0 M in tetrahydrofuran: 303828 2.0 M in tetrahydrofuran: 291005 (Trimethylsilyl)methylmagnesium Ethylmagnesium bromide solution Isobutylmagnesium chloride solution chloride solution C H ClMg C4H11ClMgSi C2H5BrMg 4 9 CH H C 3 MW: 146.97 3 Si MgCl MW: 133.27 H C MgBr MW: 116.87 MgCl H3C 3 H C CH [925-90-6] [5674-02-2] 3 [13170-43-9] 3 3.0 M in diethyl ether: 189871, 256978 2.0 M in diethyl ether: 225746 1.0 M in diethyl ether: 256021 1.0 M in tert-butyl methyl ether: 345105 2.0 M in tetrahydrofuran: 479683 1.0 M in tetrahydrofuran: 364665, 364673 (1,3-Dioxolan-2-ylmethyl)magnesium Isobutylmagnesium bromide solution bromide solution C H BrMg C4H7BrMgO2 Propylmagnesium chloride solution 4 9 CH O MW: 161.32 3 MW: 191.31 C3H7ClMg MgBr H3C O MgBr H C [926-62-5] [180675-22-3] MW: 102.85 3 MgCl [2234-82-4] 2.0 M in diethyl ether: 338257 0.5 M in tetrahydrofuran: 472611 2.0 M in diethyl ether: 224391 sec-Butylmagnesium chloride solution Pentylmagnesium chloride solution C H ClMg Isopropylmagnesium chloride solution C4H9ClMg 5 11 CH3 MW: 116.87 MW: 130.90 MgCl C3H7ClMg H3C CH3 H3C MgCl [6393-56-2] MW: 102.85 MgCl [15366-08-2] [1068-55-9] H3C 2.0 M in diethyl ether: 224421 2.0 M in tetrahydrofuran: 469033 2.0 M in diethyl ether: 224383, 257028 2.0 M in tetrahydrofuran: 230111, 257036 R: Product of Rieke® Metals, Inc. ®Registered trademark of Rieke Metals, Inc.
To discuss how our expertise can benefit your next scale-up project or to obtain a quote, contact your local Sigma-Aldrich office or visit www.safcglobal.com Grignard Reagents 4
sigma-aldrich.com bromide solution (1,3-Dioxan-2-ylethyl)magnesium 2.0 Mindiethylether: [ MW: 173.33 0.5 Mintetrahydrofuran: [ MW: 219.36 C [ MW: 128.88 C Cyclohexylmagnesium chloridesolution 2.0 Mindiethylether: C Hexylmagnesium bromide solution 2.0 Mintetrahydrofuran: C Hexylmagnesium chloridesolution 2.0 Mindiethylether: C bromide solution Cyclopentylmagnesium 2.0 Mindiethylether: C chloride solution Cyclopentylmagnesium 1.0 Mindiethylether: C chloride solution 2,2-Dimethylpropylmagnesium 1.0 Mindiethylether: C chloride solution 1,1-Dimethylpropylmagnesium [ MW: 142.91 [ MW: 189.38 [ MW: 144.93 [ MW: 130.90 [ MW: 130.90 0.5 Mintetrahydrofuran: [ MW: 278.55 C (magnesium bromide) solution Pentamethylenebis- 2.0 Mindiethylether: [ MW: 175.35 C Pentylmagnesium bromide solution 480438-44-6 33240-34-5 32916-51-1 931-51-1 3761-92-0 44767-62-6 13132-23-5 28276-08-6 23708-48-7 693-25-4 6 6 6 6 5 5 5 5 5 5 H H H H H H H H H H 11 11 9 13 13 9 11 11 10 11 BrMg ClMg ClMg BrMg ClMg ClMg ClMg Br BrMg BrMgO 2 Mg ] ] ] 2 2 ] ] ] ] ] ] ] 224413 255025 428337 224405 550213 277282 290998 BrMg H H H 3 561657 641626 310018 3 3 H C C C H 3 H O C 3 3 H C C 3 O C , 256692 CH MgBr MgCl MgCl CH MgCl 3 MgCl 3 MgBr MgBr MgBr MgBr MgCl To order: ContactyourlocalSigma-Aldrichoffice (see backcover), R R [ MW: 150.89 [ MW: 203.40 C Heptylmagnesium bromide solution 0.25 Mintetrahydrofuran: [ MW: 164.92 C chloride solution 2-Methylbenzylmagnesium 1.0 Mintetrahydrofuran: [ MW: 164.92 C Phenethylmagnesium chloridesolution 1.0 Mindiethylether: [ MW: 217.43 C bromide solution (2-Ethylhexyl)magnesium 2.0 Mindiethylether: [ MW: 217.43 C Octylmagnesium bromide solution 2.0 Mintetrahydrofuran: [ MW: 172.98 C Octylmagnesium chloridesolution 0.25 Mintetrahydrofuran: [ MW: 168.88 C chloride solution 4-Fluorobenzylmagnesium 0.25 Mindiethylether: C bromide solution 3-Bromobenzylmagnesium 0.25 Mindiethylether: C bromide solution 2-Bromobenzylmagnesium 2.0 Mintetrahydrofuran: 1.0 Mindiethylether: C Benzylmagnesium chloridesolution 1.0 Mindiethylether: [ MW: 274.24 [ MW: 274.24 6921-34-2 13125-66-1 29875-05-6 90878-19-6 90224-21-8 17049-49-9 38841-98-4 1643-73-8 107549-22-4 56812-60-3 8 8 8 7 7 7 7 7 8 8 H H H H H H H H H H or visitwww.sigma-aldrich.com/order. 6 6 7 15 9 9 17 17 17 6 Br Br ClMg ClMg ClMg ClFMg BrMg BrMg BrMg ClMg 2 2 Mg Mg ] ] ] ] ] ] ] ] ] ] H H 630551 436291 302759 550655 H 3 3 H C C 562130 562149 3 3 C C 424684 324566 225916 F 562173 563927 Br CH Br MgCl 3 MgCl MgCl CH MgBr MgBr MgCl MgBr 3 MgBr MgCl MgBr R R R R 0.2 Mintetrahydrofuran: [ MW: 210.94 C chloride solution 3,5-Dimethoxybenzylmagnesium 0.5 Mintetrahydrofuran: [ MW: 194.94 [ MW: 231.46 C chloride solution 3-Methoxybenzylmagnesium 0.25 Mintetrahydrofuran: C chloride solution 2-Methoxybenzylmagnesium 0.5 Mintetrahydrofuran: C chloride solution 4-Methylbenzylmagnesium 0.5 Mintetrahydrofuran: C chloride solution 3-Methylbenzylmagnesium [ MW: 180.91 [ MW: 180.91 [ MW: 164.92 [ MW: 164.92 C chloride solution 4-Methoxyphenethylmagnesium 1.0 Mindiethylether: C Nonylmagnesium bromide solution 1.0 Mindiethylether: C magnesium bromide solution 4-(Trifluoromethoxy)benzyl- 0.25 Mintetrahydrofuran: C chloride solution 4-Methoxybenzylmagnesium 0.25 Mintetrahydrofuran: [ MW: 180.91 MW: 279.34 135808-66-1 211115-05-8 39691-62-8 26905-40-8 480438-46-8 29875-07-8 29875-06-7 38769-92-5 8 8 8 8 9 9 9 8 8 H H H H H H H H H 11 11 19 9 9 9 9 6 9 ClMgO ClMgO ClMg ClMg BrF ClMgO ClMgO ClMgO BrMg 3 MgO 2 ] ] ] ] ] ] ] ] H 3 550663 663832 C H H H F 3 CO 3 3 3 CO 563811 562203 563773 562157 CO CO H 562092 562033 562084 3 C OCH CH OCH 3 3 OCH MgCl MgCl 3 MgCl 3 MgBr MgCl MgCl MgCl MgCl MgBr 8 R R R R R R R 5
Decylmagnesium bromide solution (2-Naphthalenylmethyl)magnesium Pentadecylmagnesium
C10H21BrMg bromide solution bromide solution
MW: 245.48 CH3 MgBr C11H9BrMg C15H31BrMg MgBr [17049-50-2] MW: 245.40 MW: 315.62 H C MgBr 3 1.0 M in diethyl ether: 347108 [127543-80-0] [78887-70-4] 0.25 M in diethyl ether: 663891 0.5 M in diethyl ether: 424056 3,7-Dimethyloctylmagnesium bromide solution Dodecylmagnesium bromide solution Octadecylmagnesium chloride solution
C10H21BrMg C12H25BrMg C18H37ClMg CH3 CH3 H C MgCl MW: 245.48 MW: 273.54 H3C MgBr MW: 313.24 3 [114499-45-5] H3C MgBr [15890-72-9] [116980-66-6] 1.0 M in diethyl ether: 637963 1.0 M in diethyl ether: 339628 0.5 M in tetrahydrofuran: 394262 Grignard Reagents 2-Methyl-2-phenylpropylmagnesium Tetradecylmagnesium chloride solution
chloride solution C14H29ClMg
C10H13ClMg H3C CH3 MW: 257.14 H3C MgCl MW: 192.97 MgCl [110220-87-6] [35293-35-7] 1.0 M in tetrahydrofuran: 337781 0.5 M in diethyl ether: 420204
Alkenyl
Vinylmagnesium chloride solution 1-Propenylmagnesium bromide solution 1-Methyl-1-propenylmagnesium
C2H3ClMg C3H5BrMg bromide solution H3C MW: 86.80 MgCl MW: 145.28 MgBr C4H7BrMg CH3 [3536-96-7] [14092-04-7] MW: 159.31 H C 3 MgBr 1.6 M in tetrahydrofuran: 476552 0.5 M in tetrahydrofuran: 419540 [85676-85-3] 0.5 M in tetrahydrofuran: 419605 Vinylmagnesium bromide solution Isopropenylmagnesium
C2H3BrMg bromide solution 2-Methyl-1-propenylmagnesium
MW: 131.25 MgBr C3H5BrMg bromide solution CH3 [1826-67-1] MW: 145.28 C4H7BrMg MgBr H3C 1.0 M in tetrahydrofuran: 225584, 257257 [13291-18-4] MW: 159.31 MgBr CH3 0.5 M in tetrahydrofuran: 419567 [38614-36-7] 0.5 M in tetrahydrofuran: 419613
Alkynyl
Ethynylmagnesium chloride solution 1-Propynylmagnesium bromide solution Phenylethynylmagnesium
C2HClMg C3H3BrMg bromide solution
MW: 84.79 MgCl MW: 143.26 H3C MgBr C8H5BrMg [65032-27-1] [16466-97-0] MW: 205.33 MgBr 0.5 M in tetrahydrofuran: 346160 0.5 M in tetrahydrofuran: 429007 [6738-06-3] 1.0 M in tetrahydrofuran: 357510 Ethynylmagnesium bromide solution
C2HBrMg MW: 129.24 MgBr [4301-14-8] 0.5 M in tetrahydrofuran: 346152
R: Product of Rieke® Metals, Inc. ®Registered trademark of Rieke Metals, Inc.
To discuss how our expertise can benefit your next scale-up project or to obtain a quote, contact your local Sigma-Aldrich office or visit www.safcglobal.com Grignard Reagents 6
sigma-aldrich.com Aryl [ MW: 233.75 [ MW: 233.75 [ MW: 233.75 0.5 Mintetrahydrofuran: [ MW: 250.20 [ MW: 215.76 [ MW: 215.76 C magnesium bromide solution 4-Chloro-3-fluorophenyl- 0.5 Mintetrahydrofuran: C magnesium bromide solution 3-Chloro-5-fluorophenyl- 0.5 Mintetrahydrofuran: C magnesium bromide solution 3-Chloro-4-fluorophenyl- 0.5 Mintetrahydrofuran: bromide solution 3,5-Dichlorophenylmagnesium 0.5 Mintetrahydrofuran: C bromide solution 3,4-Dichlorophenylmagnesium 1.0 Mindiethylether: C bromide solution 4-Chlorophenylmagnesium 0.5 Mintetrahydrofuran: C bromide solution 3-Chlorophenylmagnesium [ MW: 181.31 [ MW: 136.86 C 1.0 Mintetrahydrofuran: 3.0 Mindiethylether: C Phenylmagnesium bromide solution 2.0 Mintetrahydrofuran: C Phenylmagnesium chloridesolution [ MW: 250.20 170793-00-7 480438-50-4 413589-34-1 82297-90-3 873-77-8 36229-42-2 100-58-3 100-59-4 79175-35-2 6 6 6 6 6 6 6 6 6 H H H H H H H H H 3 3 3 3 3 4 4 5 5 BrClFMg BrClFMg BrClFMg BrCl BrCl BrClMg BrClMg BrMg ClMg 2 2 Mg Mg ] ] ] ] ] ] ] ] ] 262188 171565 562254 563390 563676 562289 562270 563722 331376 224448 Cl Cl Cl Cl F F , Cl C C Cl Cl F 257117 l l , 257125 MgBr MgBr MgCl MgBr MgBr MgBr MgBr MgBr MgBr To order: ContactyourlocalSigma-Aldrichoffice (see backcover), R R R R R [ MW: 199.30 [ MW: 199.30 1.0 Mintetrahydrofuran: [ MW: 150.89 C m 2.0 Mindiethylether: [ MW: 195.34 C o 1.0 Mintetrahydrofuran: [ MW: 150.89 C o 0.5 Mindiethylether: [ MW: 271.27 C bromide solution Pentafluorophenylmagnesium 0.3 Mintetrahydrofuran: C bromide solution 3,4,5-Trifluorophenylmagnesium 0.5 Mintetrahydrofuran: C bromide solution 3,5-Difluorophenylmagnesium 0.5 Mintetrahydrofuran: C bromide solution 3,4-Difluorophenylmagnesium 1.0 Mintetrahydrofuran: 2.0 Mindiethylether: C bromide solution 4-Fluorophenylmagnesium 0.5 Mintetrahydrofuran: 1.0 Mintetrahydrofuran: C bromide solution 3-Fluorophenylmagnesium [ MW: 217.29 [ MW: 235.28 [ MW: 217.29 352-13-6 17318-03-5 121905-60-0 932-31-0 33872-80-9 879-05-0 90897-92-0 156006-28-9 62351-47-7 -Tolylmagnesium bromide solution -Tolylmagnesium chloridesolution 7 6 6 6 6 6 6 7 7 -Tolylmagnesium chloridesolution H BrF H H H H H H H or visitwww.sigma-aldrich.com/order. 3 4 4 7 7 7 2 3 BrF BrFMg BrFMg ClMg BrMg ClMg BrF BrF 5 Mg 2 3 2 Mg Mg Mg ] ] ] ] ] ] ] ] ] 298980 442585 245550 405299 360023 561797 561029 561037 328820 561665 550671 F F F F F F F CH F F F F 3 F F MgCl MgBr MgCl CH CH MgBr MgBr MgBr MgBr MgBr 3 3 MgBr F R R R R 1.0 Mintetrahydrofuran: [ MW: 211.34 [ MW: 211.34 magnesium bromide solution 4-Fluoro-2-methylphenyl- 0.5 Mintetrahydrofuran: C magnesium chloridesolution 3-Fluoro-2-methylphenyl- 0.5 Mintetrahydrofuran: C magnesium bromide solution 4-Chloro-2-methylphenyl- 1.0 Mintetrahydrofuran: 0.5 Mindiethylether: C p [ MW: 168.88 [ MW: 229.78 [ MW: 195.34 C bromide solution 3-Methoxyphenylmagnesium 1.0 Mintetrahydrofuran: 1.0 Mindiethylether: C bromide solution 2-Methoxyphenylmagnesium 0.5 Mintetrahydrofuran: C magnesium bromide solution 3-Fluoro-4-methylphenyl- 1.0 Mintetrahydrofuran: C magnesium bromide solution 4-Fluoro-3-methylphenyl- 0.5 Mintetrahydrofuran: C magnesium bromide solution 5-Fluoro-2-methylphenyl- 0.5 Mintetrahydrofuran: C [ MW: 213.33 [ MW: 213.33 [ MW: 213.33 [ MW: 213.33 36282-40-3 16750-63-3 480424-74-6 480438-47-9 4294-57-9 185077-02-5 82297-89-0 186496-59-3 30897-90-6 -Tolylmagnesium bromide solution 7 7 7 7 7 7 7 7 7 H H H H H H H H H 7 7 6 6 7 6 6 6 6 BrMgO BrMgO ClFMg BrClMg BrMg BrFMg BrFMg BrFMg BrFMg ] ] ] ] ] ] ] ] ] 646075 662453 442194 570818 562262 442178 470414 561711 344605 561746 561738 H H Cl 3 3 F C F C F F OCH F CH 3 MgBr OCH MgBr MgCl CH 3 MgBr CH MgBr MgBr MgBr CH CH 3 MgBr MgBr 3 3 3 3 R R R R R 7
4-Methoxyphenylmagnesium 3,4-Dimethylphenylmagnesium 4-(N,N-Dimethyl)aniline- bromide solution chloride solution R magnesium bromide solution R MgCl MgBr C7H7BrMgO MgBr C8H9ClMg C8H10BrMgN MW: 211.34 MW: 164.92 MW: 224.38 H C H C 3 N [13139-86-1] H3CO [102928-12-1] 3 [7353-91-5] CH3 CH3 0.5 M in tetrahydrofuran: 470260 0.5 M in tetrahydrofuran: 562068 0.5 M in tetrahydrofuran: 561061
3,4-(Methylenedioxy)phenyl- 3,5-Dimethylphenylmagnesium 2-Mesitylmagnesium bromide solution CH magnesium bromide solution bromide solution R C9H11BrMg 3 MgBr C7H5BrMgO2 H3C MgBr MW: 223.39 BrMg O C8H9BrMg MW: 225.32 [2633-66-1] MW: 209.37 H3C CH3 [17680-04-5] O [34696-73-6] CH3 1.0 M in diethyl ether: 332402
1.0 M in toluene/tetrahydrofuran 0.5 M in tetrahydrofuran: 562076 1.0 M in tetrahydrofuran: 227234 Grignard Reagents (50:50): 512931 3,5-Bis(trifluoromethyl)phenyl- 4-n-Propylphenylmagnesium 5-Fluoro-2-methoxyphenyl- magnesium bromide solution bromide solution R magnesium bromide solution R F C MgBr C8H3BrF6Mg 3 C9H11BrMg MgBr C7H6BrFMgO F MgBr MW: 317.31 MW: 223.39 MW: 229.33 [112981-69-8] H3C CF [87942-08-3] [188132-02-7] OCH3 3 0.5 M in tetrahydrofuran: 563730 0.5 M in tetrahydrofuran: 561983 0.5 M in tetrahydrofuran: 639052 4-Isopropylphenylmagnesium 3-Fluoro-4-methoxyphenyl- 4-Ethylphenylmagnesium bromide solution R bromide solution R magnesium bromide solution R C H BrMg MgBr MgBr C8H9BrMg 9 11 C7H6BrFMgO MgBr MW: 209.37 MW: 223.39 H3C MW: 229.33 H3C H3CO [22873-28-5] CH3 [112780-67-3] F 0.5 M in tetrahydrofuran: 561754 0.5 M in tetrahydrofuran: 635669 0.5 M in tetrahydrofuran: 563706
3,5-Dimethyl-4-methoxyphenyl- 4-Thioanisolemagnesium 4-Methoxy-2-methylphenyl- magnesium bromide solution R magnesium bromide solution R bromide solution R C H BrMgO C H BrMgO H3C MgBr C H BrMgS 8 9 MgBr 9 11 7 7 MgBr MW: 225.37 MW: 239.39 MW: 227.40 H CO H CO CH 3 H CS [148706-30-3] 3 3 [185416-17-5] [18620-04-7] 3 CH3 0.5 M in tetrahydrofuran: 561762 0.5 M in tetrahydrofuran: 562238 0.5 M in tetrahydrofuran: 563781
2,3-Dimethylphenylmagnesium 2,4-Dimethoxyphenylmagnesium 4-tert-Butylphenylmagnesium bromide solution R bromide solution R bromide solution C H BrMgO MgBr C H BrMg MgBr 8 9 2 MgBr C10H13BrMg 8 9 MW: 241.36 MW: 209.37 MW: 237.42 H3C CH H CO OCH 3 [138109-49-6] 3 3 [63488-10-8] H3C [134640-85-0] CH3 CH3 0.5 M in tetrahydrofuran: 562025 0.5 M in tetrahydrofuran: 563757 2.0 M in diethyl ether: 324655
2,5-Dimethoxyphenylmagnesium 2,4-Dimethylphenylmagnesium 1-Naphthylmagnesium bromide solution R bromide solution R bromide solution R C H BrMgO C H BrMg 8 9 2 H3CO MgBr C10H7BrMg MgBr 8 9 MgBr MW: 241.36 MW: 209.37 MW: 231.37 [62890-98-6] OCH3 [703-55-9] [34589-46-3] H3C CH3 0.5 M in tetrahydrofuran: 561819 0.5 M in tetrahydrofuran: 562041 0.25 M slurry in tetrahydrofuran: 561673
3,4-Dimethoxyphenylmagnesium 2,5-Dimethylphenylmagnesium 2-Naphthylmagnesium bromide solution R bromide solution R bromide solution R C H BrMgO MgBr 8 9 2 C10H7BrMg C8H9BrMg MgBr H3C MgBr MW: 241.36 MW: 231.37 MW: 209.37 H3CO [89980-69-8] OCH [21473-01-8] [30897-86-0] CH3 3 0.5 M in tetrahydrofuran: 561975 0.5 M in tetrahydrofuran: 563765 0.5 M in tetrahydrofuran: 562165
2,6-Dimethylphenylmagnesium 3,5-Dimethoxyphenylmagnesium 2-Methyl-1-napthylmagnesium bromide solution chloride solution bromide solution R C H ClMgO H3CO MgCl CH 8 9 2 C11H9BrMg MgBr C8H9BrMg 3 MW: 196.91 CH3 MW: 209.37 MgBr MW: 245.40 [89981-17-9] [21450-64-6] OCH3 [21450-90-8] CH3 1.0 M in tetrahydrofuran: 425508 1.0 M in tetrahydrofuran: 637629 0.25 M in tetrahydrofuran: 563692
R: Product of Rieke® Metals, Inc. ®Registered trademark of Rieke Metals, Inc.
To discuss how our expertise can benefit your next scale-up project or to obtain a quote, contact your local Sigma-Aldrich office or visit www.safcglobal.com Grignard Reagents 8
sigma-aldrich.com magnesium bromide solution 0.25 Mintetrahydrofuran: C magnesium bromide solution [3-(1-Pyrrolidinylmethyl)phenyl]- 0.25 Mintetrahydrofuran: C magnesium bromide solution [2-(1-Pyrrolidinylmethyl)phenyl]- 0.25 Mintetrahydrofuran: C magnesium bromide solution [2-(4-Morpholinylmethyl)phenyl]- 0.25 Mintetrahydrofuran: C magnesium bromide solution [4-(1-Pyrrolidinylmethyl)phenyl]- 0.5 Mintetrahydrofuran: [ MW: 261.40 C bromide solution 6-Methoxy-2-naphthylmagnesium 0.25 Mintetrahydrofuran: [ MW: 245.40 C bromide solution 4-Methyl-1-naphthylmagnesium [ MW: 280.44 [ MW: 264.44 [ MW: 264.44 [ MW: 264.44 0.5 Mintetrahydrofuran: [ MW: 281.43 C 4-(2-Tetrahydro-2 38046-82-1 115913-58-1 480424-77-9 480424-78-0 480424-79-1 480424-80-4 36637-44-2 11 11 11 11 11 11 11 H H H H H H H 14 14 14 14 13 9 9 BrMgO BrMg BrMgNO BrMgN BrMgN BrMgN BrMgO ] ] 2 ] ] ] ] ] H -pyranoxy)phenyl- H 3 CO O 562246 646946 571180 571199 571164 571172 563684 N O MgBr MgBr N MgBr CH N MgBr N 3 MgBr O MgBr MgBr To order: ContactyourlocalSigma-Aldrichoffice (see backcover), R R R R R R R [ MW: 257.41 [ MW: 257.41 [ MW: 280.44 [ MW: 280.44 magnesium bromide solution [3-(4-Morpholinylmethyl)phenyl]- 0.25 Mintetrahydrofuran: [ MW: 278.47 C magnesium bromide solution [2-(1-Piperidinylmethyl)phenyl]- 1.0 Mintetrahydrofuran: [ MW: 296.24 C magnesium chloridesolution 3-[Bis(trimethylsilyl)amino]phenyl- 0.5 Mintetrahydrofuran: [ MW: 273.41 C bromide solution 4-Phenoxyphenylmagnesium 0.5 Mintetrahydrofuran: C bromide solution 4-Biphenylmagnesium 0.5 Mindiethylether: C bromide solution 2-Biphenylmagnesium 0.25 Mintetrahydrofuran: C magnesium bromide solution [4-(4-Morpholinylmethyl)phenyl]- 0.25 Mintetrahydrofuran: C 3315-91-1 82214-69-5 480424-75-7 480424-76-8 480424-81-5 174484-84-5 21473-02-9 12 12 12 12 12 11 11 or visitwww.sigma-aldrich.com/order. H H H H H H H 9 9 14 14 16 22 9 BrMg BrMg BrMgO BrMgNO BrMgNO BrMgN ClMgNSi ] ] ] ] ] ] ] 2 639125 O (H 3 372005 561681 562009 C) 571202 571121 571156 N 3 Si N O MgBr N MgBr MgBr Si(CH O N MgCl 3 MgBr MgBr ) MgBr 3 R R R R R R 0.25 Mintetrahydrofuran: [ MW: 281.43 [ MW: 287.43 [ MW: 278.47 [ MW: 278.47 C bromide solution 3-Benzyloxyphenylmagnesium 1.0 Mintetrahydrofuran: C bromide solution 2-Benzyloxyphenylmagnesium 0.25 Mintetrahydrofuran: C magnesium bromide solution [4-(1-Piperidinylmethyl)phenyl]- 0.25 Mintetrahydrofuran: C magnesium bromide solution [3-(1-Piperidinylmethyl)phenyl]- [ MW: 287.43 [ 287.43 MW: MW: 336.51 C solution methyl)phenylmagnesium bromide 3-(1,4-Dioxa-8-azaspiro[4.5]dec-8-yl- 0.5 Mintetrahydrofuran: C bromide solution 9-Phenanthrylmagnesium 1.0 Mintetrahydrofuran: C bromide solution 4-Benzyloxyphenylmagnesium 1.0 Mintetrahydrofuran: 71112-64-6 36281-96-6 480424-83-7 480424-82-6 120186-59-6 328000-16-4 13 13 12 12 14 14 13 H H H H H H H 11 18 9 11 16 16 11 BrMg BrMgO BrMgNO BrMgO BrMgN BrMgN BrMgO ] ] ] ] ] ] 2 O O 673013 563749 672998 673005 633143 571229 571210 MgBr N O O N MgBr O MgBr MgBr N MgBr MgBr MgBr 8 8 8 R R R R 9
Heteroaryl
2-Thienylmagnesium 3-Methyl-2-thienylmagnesium 5-Chloro-2-thienylmagnesium bromide solution bromide solution R bromide solution R
C4H3BrMgS C5H5BrMgS CH3 C4H2BrClMgS MW: 187.34 MW: 201.37 MW: 221.79 S MgBr Cl S MgBr [5713-61-1] [95184-07-9] S MgBr [111762-30-2] 1.0 M in tetrahydrofuran: 550442 0.5 M in tetrahydrofuran: 562211 0.5 M slurry in tetrahydrofuran: 563803
3-Thienylmagnesium iodide solution R
C4H3IMgS MgI MW: 234.34 [172035-86-8] S 0.3 M in tetrahydrofuran: 561630
Organozinc Halides Organozinc Halides Alkyl
Methylzinc chloride solution tert-Butylzinc bromide solution R 1,1-Dimethylpropylzinc
CH3ClZn C4H9BrZn bromide solution R H3C MW: 115.88 H3C ZnCl MW: 202.41 H3C ZnBr C5H11BrZn H3C H3C CH3 [5158-46-3] [7565-59-5] MW: 216.43 H C 3 ZnBr 2.0 M in tetrahydrofuran: 417297 0.5 M in tetrahydrofuran: 497754 [171860-64-3] 0.5 M in tetrahydrofuran: 498904 1-Propylzinc bromide solution R 3-Cyanopropylzinc bromide solution R
C3H7BrZn C4H6BrNZn Cyclopentylzinc bromide solution R MW: 188.38 ZnBr MW: 213.39 H3C NC ZnBr C5H9BrZn [156567-57-6] [135579-85-0] MW: 214.42 ZnBr 0.5 M in tetrahydrofuran: 499374 0.5 M in tetrahydrofuran: 497967 [171860-68-7] 0.5 M in tetrahydrofuran: 498041 2-Propylzinc 8 4-Chlorobutylzinc bromide solution R
bromide solution R C4H8BrClZn 4-Pentenylzinc bromide solution R ZnBr C3H7BrZn MW: 236.85 C5H9BrZn H3C Cl MW: 188.38 ZnBr [155589-48-3] MW: 214.42 ZnBr H C [77047-87-1] 3 0.5 M in tetrahydrofuran: 497770 [308796-04-5] 0.5 M in tetrahydrofuran: 680966 0.5 M in tetrahydrofuran: 499072 Pentylzinc bromide solution R
2-Cyanoethylzinc bromide solution R C5H11BrZn 4-Cyanobutylzinc bromide solution R MW: 216.43 ZnBr C3H4BrNZn H3C C5H8BrNZn ZnBr ZnBr MW: 199.36 NC [308796-10-3] MW: 227.42 NC [312624-26-3] 0.5 M in tetrahydrofuran: 499285 [226570-68-9] 0.5 M in tetrahydrofuran: 497908 0.5 M in tetrahydrofuran: 497894 3-Methylbutylzinc bromide solution R
Butylzinc bromide solution R C5H11BrZn 5-Chloropentylzinc bromide solution R CH3 C4H9BrZn MW: 216.43 C5H10BrClZn H3C ZnBr MW: 202.41 H3C ZnBr [92274-43-6] MW: 250.88 Cl ZnBr [92273-73-9] 0.5 M in tetrahydrofuran: 498890 [312624-21-8] 0.5 M in tetrahydrofuran: 497746 0.5 M in tetrahydrofuran: 497819 1-Ethylpropylzinc bromide solution R Isobutylzinc bromide solution R C H BrZn 2-(1,3-Dioxolan-2-yl)]ethyl]zinc 5 11 H3C C H BrZn MW: 216.43 bromide solution R 4 9 H C H C 3 ZnBr 3 ZnBr MW: 202.41 [308796-09-0] C5H9BrO2Zn CH3 O [126403-67-6] 0.5 M in tetrahydrofuran: 499277 MW: 246.42 O ZnBr 0.5 M in tetrahydrofuran: 498963 [307531-83-5] 1-Methylbutylzinc bromide solution R 0.5 M in tetrahydrofuran: 533688
sec-Butylzinc bromide solution R C5H11BrZn CH3 C4H9BrZn MW: 216.43 CH3 H3C ZnBr MW: 202.41 H C [308796-07-8] 3 ZnBr [171860-66-5] 0.5 M in tetrahydrofuran: 499269 0.5 M in tetrahydrofuran: 497738
R: Product of Rieke® Metals, Inc. ®Registered trademark of Rieke Metals, Inc.
To discuss how our expertise can benefit your next scale-up project or to obtain a quote, contact your local Sigma-Aldrich office or visit www.safcglobal.com Organozinc Halides 10
sigma-aldrich.com C 5-Hexenylzinc bromide solution 0.5 Mintetrahydrofuran: 0.5 Mintetrahydrofuran: C 6-Chlorohexylzinc bromide solution 0.5 Mintetrahydrofuran: C Cyclohexylzinc bromide solution 0.5 Mintetrahydrofuran: C 1-Ethylbutylzinc bromide solution 0.5 Mintetrahydrofuran: oxopropylzinc bromide solution C 1-Methylpentylzinc bromide solution 0.5 Mintetrahydrofuran: C 2-Ethylbutylzinc bromide solution 0.5 Mintetrahydrofuran: C Hexylzinc bromide solution 0.5 Mintetrahydrofuran: C ( oxopropylzinc bromide solution [ MW: 228.45 [ MW: 264.91 [ MW: 228.45 [ MW: 230.46 [ MW: 230.46 [ MW: 230.46 [ MW: 230.46 0.5 Mintetrahydrofuran: C ( 0.5 Mintetrahydrofuran: C bromide solution 3-Ethoxy-3-oxopropylzinc [ MW: 246.42 [ MW: 246.42 [ MW: 246.42 226570-65-6 135579-83-8 7565-57-3 312693-14-4 312693-13-3 312693-02-0 124397-96-2 312693-18-8 352525-75-8 193065-68-8 S R 6 6 6 6 6 6 6 5 5 5 )-(–)-3-Methoxy-2-methyl-3- H H H H H H H H H H )-(+)-3-Methoxy-2-methyl-3- 11 12 13 11 13 13 13 9 9 9 BrO BrO BrO BrZn BrClZn BrZn BrZn BrZn BrZn BrZn 2 2 2 Zn Zn Zn ] ] ] ] ] ] ] ] ] ] Cl H H H H 3 3 2 H H C C C H H 3 497797 498734 498033 498750 498742 498548 498769 498815 499498 498521 3 3 C 3 3 CO CO C C O H O O 3 O C CH ZnBr CH CH CH ZnBr ZnBr 3 ZnBr ZnBr H H 3 3 ZnBr 3 ZnBr ZnBr ZnBr ZnBr To order: ContactyourlocalSigma-Aldrichoffice (see backcover), R R R R R R R R R R [ MW: 244.49 bromide solution 2-(1,3-Dioxan-2-yl)ethylzinc 0.5 Mintetrahydrofuran: [ MW: 255.47 C bromide solution 6-Cyanohexylzinc 0.5 Mintetrahydrofuran: [ MW: 240.46 C bromide solution exo 0.5 Mintetrahydrofuran: [ MW: 242.47 C bromide solution (Cyclohexylmethyl)zinc 0.5 Mintetrahydrofuran: [ MW: 244.49 C 1-Propylbutylzinc bromide solution 0.5 Mintetrahydrofuran: [ MW: 244.49 C 1-Ethylpentylzinc bromide solution 0.5 Mintetrahydrofuran: [ MW: 244.49 C 1-Methylhexylzinc bromide solution 0.5 Mintetrahydrofuran: C Heptylzinc bromide solution 0.5 Mintetrahydrofuran: C 4-Acetoxybutylzinc bromide solution 0.5 Mintetrahydrofuran: C bromide solution 4-Ethoxy-4-oxobutylzinc 0.5 Mintetrahydrofuran: C MW: 260.44 [ MW: 260.44 [ MW: 260.44 7608-06-2 312624-28-5 342029-20-3 135579-86-1 312693-12-2 312693-11-1 312693-10-0 131379-39-0 307531-82-4 7 7 7 7 7 6 6 6 7 7 H H H H H H H H H H or visitwww.sigma-aldrich.com/order. 15 11 11 11 12 11 13 15 15 15 -2-Norbornylzinc -2-Norbornylzinc BrZn BrO BrO BrO BrNZn BrZn BrZn BrZn BrZn BrZn 2 2 2 Zn Zn Zn ] ] ] ] ] ] ] ] ] H H H NC H 3 3 3 C C C H H 3 C 3 497924 499056 498025 498726 498718 498696 533270 630403 498491 533556 3 O C C O O O O O ZnBr ZnBr ZnBr CH ZnBr CH ZnBr CH ZnBr 3 ZnBr ZnBr ZnBr ZnBr 3 3 R R R R R R R R R R [ MW: 315.32 0.5 Mintetrahydrofuran: C 2-Bromobenzylzinc bromide solution 0.5 Mintetrahydrofuran: 0.5 Mintetrahydrofuran: C chloride solution 2-Fluorobenzylzinc 0.5 Mintetrahydrofuran: C Benzylzinc bromide solution 0.5 Mintetrahydrofuran: C bromide solution 5-Acetoxypentylzinc 0.5 Mintetrahydrofuran: C bromide solution 5-Ethoxy-5-oxopentylzinc [ MW: 209.96 [ MW: 236.42 C 4-Chlorobenzylzinc chloridesolution 0.5 Mintetrahydrofuran: C 3-Chlorobenzylzinc chloridesolution 0.5 Mintetrahydrofuran: C chloride solution 2-Chlorobenzylzinc 0.5 Mintetrahydrofuran: C chloride solution 4-Fluorobenzylzinc 0.5 Mintetrahydrofuran: C chloride solution 3-Fluorobenzylzinc [ MW: 209.96 [ MW: 209.96 MW: 274.47 [ MW: 274.47 [ MW: 226.42 [ MW: 226.42 [ MW: 226.42 307496-27-1 312693-05-3 62673-31-8 312693-07-5 312693-06- 265330-98-1 149923-10-4 312624-13-8 312624-11-6 7 7 7 7 7 7 7 7 7 7 H H H H H H H H H H 6 6 6 6 7 13 13 6 6 6 Br Cl Cl ClFZn BrZn Cl ClFZn ClFZn BrO BrO 2 2 2 2 Zn Zn Zn Zn 2 2 Zn Zn ] 4] ] ] ] ] ] ] ] H H 3 3 C C Cl O F 520314 497762 498580 497517 630381 498513 497576 497568 498602 498599 O O Cl F O Br Cl F ZnBr ZnCl ZnBr ZnCl ZnCl ZnCl ZnCl ZnCl ZnBr ZnBr R R R R R R R R R R 11
3-Bromobenzylzinc bromide solution R 3,4-Difluorobenzylzinc 6-Ethoxy-6-oxohexylzinc
C7H6Br2Zn ZnBr bromide solution R bromide solution R MW: 315.32 C H BrF Zn C H BrO Zn 7 5 2 ZnBr 8 15 2 O [307496-31-7] MW: 272.41 MW: 288.50 Br F ZnBr H3C O 0.5 M in tetrahydrofuran: 521655 [307496-34-0] F [312693-01-9] 0.5 M in tetrahydrofuran: 521698 0.5 M in tetrahydrofuran: 498505 4-Bromobenzylzinc chloride solution R
C7H6BrClZn 3,5-Difluorobenzylzinc a-Methylbenzylzinc ZnCl MW: 270.87 chloride solution R bromide solution R Br F CH C7H5ClF2Zn ZnCl C8H9BrZn 3 0.5 M in tetrahydrofuran: 497541 MW: 227.95 MW: 250.45 ZnBr F [85459-20-7] 4-Bromobenzylzinc bromide solution R 0.5 M in tetrahydrofuran: 498440 0.5 M in tetrahydrofuran: 498777
C7H6Br2Zn ZnBr MW: 315.32 3,5-Difluorobenzylzinc 2-Methylbenzylzinc Br [115055-85-1] bromide solution R chloride solution R F Organozinc Halides 0.5 M in tetrahydrofuran: 499463 C7H5BrF2Zn ZnBr C8H9ClZn MW: 272.41 MW: 206.00 ZnCl [308796-30-7] [312693-19-9] CH3 2-Iodobenzylzinc bromide solution R F
C7H6BrIZn 0.5 M in tetrahydrofuran: 499471 0.5 M in tetrahydrofuran: 498866 MW: 362.32 ZnBr [117269-71-3] I 2,6-Dichlorobenzylzinc 3-Methylbenzylzinc 0.5 M in tetrahydrofuran: 635650 chloride solution R chloride solution R Cl C7H5Cl3Zn C8H9ClZn ZnCl MW: 260.86 ZnCl MW: 206.00 3-Iodobenzylzinc bromide solution R [307531-80-2] Cl [312693-20-2] CH3 C7H6BrIZn ZnBr MW: 362.32 0.5 M in tetrahydrofuran: 533351 0.5 M in tetrahydrofuran: 498874
I 0.5 M in tetrahydrofuran: 533297 2-Chloro-6-fluorobenzylzinc 4-Methylbenzylzinc chloride solution R chloride solution R F C7H5Cl2FZn C8H9ClZn 4-Iodobenzylzinc bromide solution R ZnCl MW: 244.41 ZnCl MW: 206.00 C7H6BrIZn ZnBr H3C MW: 362.32 [307531-98-2] Cl [312693-21-3] I 0.5 M in tetrahydrofuran: 535257 0.5 M in tetrahydrofuran: 498882 0.5 M in tetrahydrofuran: 533289 2,3,4,5,6-Pentafluorobenzylzinc 3-(Trifluoromethyl)benzylzinc 2,4-Difluorobenzylzinc chloride solution R chloride solution R F R C7H2ClF5Zn C8H6ClF3Zn ZnCl bromide solution F MW: 281.93 ZnCl MW: 259.97 C7H5BrF2Zn ZnBr [308796-02-3] [480438-42-4] MW: 272.41 F F CF3 [307496-26-0] F F F 0.5 M in tetrahydrofuran: 561045 0.5 M in tetrahydrofuran: 499064 0.5 M in tetrahydrofuran: 520306 2-Methoxybenzylzinc 2,3,4,5,6-Pentafluorobenzylzinc 2,5-Difluorobenzylzinc chloride solution R bromide solution R chloride solution R C8H9ClOZn C H BrF Zn F ZnCl C H ClF Zn 7 2 5 MW: 222.00 7 5 2 F MW: 326.38 F OCH MW: 227.95 ZnCl ZnBr [312693-15-5] 3 [352534-75-9] [312692-89-0] F F F 0.5 M in tetrahydrofuran: 498785 F 0.5 M in tetrahydrofuran: 498092 0.5 M in tetrahydrofuran: 541273 3-Methoxybenzylzinc chloride solution R 2,5-Difluorobenzylzinc 2-Ethylhexylzinc bromide solution R bromide solution R C8H9ClOZn ZnCl C8H17BrZn H3C ZnBr MW: 222.00 C7H5BrF2Zn F MW: 258.51 ZnBr [312693-16-6] OCH MW: 272.41 [312693-03-1] CH3 3 [307496-32-8] F 0.5 M in tetrahydrofuran: 498793 0.5 M in tetrahydrofuran: 498556 0.5 M in tetrahydrofuran: 521663 4-Methoxybenzylzinc 5-Cyano-5-methylhexylzinc chloride solution R 2,6-Difluorobenzylzinc bromide solution R bromide solution R C8H9ClOZn C8H14BrNZn ZnCl F H3C CH3 MW: 222.00 C7H5BrF2Zn MW: 269.50 [312693-17-7] H3CO MW: 272.41 ZnBr [312693-22-4] NC ZnBr [307496-33-9] 0.5 M in tetrahydrofuran: 498807 F 0.5 M in tetrahydrofuran: 498920 0.5 M in tetrahydrofuran: 521671
R: Product of Rieke® Metals, Inc. ®Registered trademark of Rieke Metals, Inc.
To discuss how our expertise can benefit your next scale-up project or to obtain a quote, contact your local Sigma-Aldrich office or visit www.safcglobal.com Organozinc Halides 12
sigma-aldrich.com Alkenyl [ MW: 250.45 [ MW: 261.43 [ MW: 261.43 [ MW: 248.44 0.5 Mintetrahydrofuran: C Phenethylzinc bromide solution 0.5 Mintetrahydrofuran: C 4-Cyanobenzylzinc bromide solution 0.5 Mintetrahydrofuran: C 3-Cyanobenzylzinc bromide solution [ MW: 261.43 [ MW: 300.90 0.5 Mintetrahydrofuran: C 2-Cyanobenzylzinc bromide solution 0.5 Mintetrahydrofuran: C chloride solution 5-Bromo-2-methoxybenzylzinc 0.5 Mintetrahydrofuran: C 1-Phenylvinylzinc bromide solution 308796-14-7 135579-87-2 117269-72-4 151073-86-8 199465-66-2 352530-35-9 8 8 8 8 8 8 H H H H H H 9 6 6 7 6 8 BrZn BrNZn BrNZn BrZn BrNZn BrClOZn ] ] ] ] ] ] NC Br 499307 517380 517372 499390 520322 533394 CN CN ZnBr OCH ZnBr ZnBr ZnBr ZnCl ZnBr 3 To order: ContactyourlocalSigma-Aldrichoffice (see backcover), R R R R R R [ MW: 236.03 [ MW: 236.03 C 2-Ethoxybenzylzinc chloridesolution 0.5 Mintetrahydrofuran: C chloride solution 3,5-Dimethoxybenzylzinc 0.5 Mintetrahydrofuran: C chloride solution 3,4-Dimethoxybenzylzinc 0.5 Mintetrahydrofuran: C chloride solution 2,5-Dimethoxybenzylzinc 0.5 Mintetrahydrofuran: C 4-Ethoxybenzylzinc chloridesolution 0.5 Mintetrahydrofuran: [ MW: 252.03 [ MW: 252.03 [ MW: 252.03 308796-29-4 308796-28-3 307531-79-9 352530-32-6 352530-33-7 9 9 9 9 9 H H H H H or visitwww.sigma-aldrich.com/order. 11 11 11 11 11 ClO ClO ClOZn ClOZn ClO 2 2 2 Zn Zn Zn ] ] ] ] ] H 3 H H H C 3 3 3 533335 533327 533319 499455 499447 CO CO CO O OCH OCH O ZnCl 3 3 OCH CH ZnCl ZnCl ZnCl 3 ZnCl 3 R R R R R [ MW: 308.57 [ MW: 280.52 [ MW: 280.52 0.5 Mintetrahydrofuran: C bromide solution 3,5-Dimethyl-1-adamantylzinc 0.5 Mintetrahydrofuran: C bromide solution (2-Naphthylmethyl)zinc 0.5 Mintetrahydrofuran: C 2-Adamantylzinc bromide solution 0.5 Mintetrahydrofuran: C 1-Adamantylzinc bromide solution [ MW: 312.52 [ MW: 286.48 0.5 Mintetrahydrofuran: C bromide solution (2-Biphenylylmethyl)zinc 312692-99-2 171860-65-4 312624-15-0 312624-17-2 152329-44-7 12 11 10 10 13 H H H H H 19 9 15 15 11 BrZn BrZn BrZn BrZn BrZn ] ] ] ] ] 498432 499021 497614 497606 497622 H 3 C ZnBr ZnBr ZnBr ZnBr CH ZnBr 3 R R R R R 13
Aryl
Phenylzinc bromide solution R 4-Chloro-3-fluorophenylzinc 3,5-Dichlorophenylzinc C H BrZn R R 6 5 ZnBr iodide solution iodide solution ZnI Cl ZnI MW: 222.40 C6H3ClFIZn C6H3Cl2IZn [38111-44-3] MW: 321.83 MW: 338.29 Cl 0.5 M in tetrahydrofuran: 524719 [312693-42-8] F [312692-86-7] Cl 0.5 M in tetrahydrofuran: 524506 0.5 M in tetrahydrofuran: 498076 Phenylzinc iodide solution R C H IZn 6 5 ZnI 3-Chloro-4-fluorophenylzinc 2-Methylphenylzinc MW: 269.40 iodide solution R iodide solution R [23665-09-0] ZnI C6H3ClFIZn C7H7IZn ZnI MW: 321.83 MW: 283.42 0.5 M in tetrahydrofuran: 499331 F CH3 [312624-19-4] Cl [312693-23-5] 2-Fluorophenylzinc iodide solution R 0.5 M in tetrahydrofuran: 497789 0.5 M in tetrahydrofuran: 498939
C6H4FIZn
ZnI Organozinc Halides MW: 287.39 4-Bromo-2-fluorophenylzinc 3-Methylphenylzinc [186000-41-9] F iodide solution R iodide solution R ZnI 0.5 M in tetrahydrofuran: 533513 C6H3BrFIZn ZnI C7H7IZn MW: 366.28 MW: 283.42 [352530-44-0] Br F [312693-24-6] 3-Fluorophenylzinc iodide solution R CH3 ZnI C6H4FIZn 0.5 M in tetrahydrofuran: 535249 0.5 M in tetrahydrofuran: 498947 MW: 287.39
[307496-28-2] F 4-Bromo-3-fluorophenylzinc 4-Methylphenylzinc 0.5 M in tetrahydrofuran: 520489 iodide solution R iodide solution R ZnI C6H3BrFIZn C7H7IZn ZnI MW: 366.28 MW: 283.42 4-Fluorophenylzinc bromide solution R Br H C [352525-65-6] F [300766-53-4] 3 C6H4BrFZn ZnBr MW: 240.39 0.5 M in tetrahydrofuran: 497630 0.5 M in tetrahydrofuran: 498955 [181705-93-1] F 0.5 M in tetrahydrofuran: 498645 3,5-Difluorophenylzinc 5-Fluoro-2-methylphenylzinc bromide solution R iodide solution R F ZnBr 2-Chlorophenylzinc iodide solution R C6H3BrF2Zn C7H6FIZn F ZnI MW: 258.38 MW: 301.42 C6H4ClIZn ZnI CH3 MW: 303.84 [307531-85-7] F [312693-09-7] [148651-35-8] Cl 0.5 M in tetrahydrofuran: 533726 0.5 M in tetrahydrofuran: 498629 0.5 M in tetrahydrofuran: 499803 2,3-Dichlorophenylzinc 3-Fluoro-4-methylphenylzinc 3-Chlorophenylzinc iodide solution R iodide solution R iodide solution R ZnI ZnI ZnI C6H3Cl2IZn C7H6FIZn C6H4ClIZn MW: 338.29 MW: 301.42 MW: 303.84 Cl H3C [307531-97-1] [312693-08-6] F [186000-42-0] Cl Cl 0.5 M in tetrahydrofuran: 497827 0.5 M in tetrahydrofuran: 535214 0.5 M in tetrahydrofuran: 498610
4-Chlorophenylzinc iodide solution R 2,4-Dichlorophenylzinc 3-Chloro-4-methylphenylzinc iodide solution R iodide solution R C6H4ClIZn ZnI ZnI MW: 303.84 C6H3Cl2IZn ZnI C7H6ClIZn Cl MW: 338.29 MW: 317.87 [151073-70-0] H C [352530-42-8] Cl Cl [352525-66-7] 3 0.5 M in tetrahydrofuran: 497835 Cl 0.5 M in tetrahydrofuran: 535222 0.5 M in tetrahydrofuran: 497800
3-Bromophenylzinc iodide solution R ZnI 2,5-Dichlorophenylzinc 2-Cyanophenylzinc C6H4BrIZn MW: 348.29 iodide solution R bromide solution R C H Cl IZn C H BrNZn [186000-44-2] Br 6 3 2 Cl ZnI 7 4 ZnBr MW: 338.29 MW: 247.41 0.5 M in tetrahydrofuran: 497649 [352530-43-9] Cl [131379-17-4] CN 0.5 M in tetrahydrofuran: 535230 0.5 M in tetrahydrofuran: 520233 4-Bromophenylzinc iodide solution R
C6H4BrIZn ZnI MW: 348.29 3,4-Dichlorophenylzinc 3-Cyanophenylzinc [148651-39-2] Br iodide solution R iodide solution R C H Cl IZn ZnI C H INZn ZnI 0.5 M in tetrahydrofuran: 497657 6 3 2 7 4 MW: 338.29 MW: 294.41 Cl [312692-85-6] Cl [288309-53-5] CN 0.5 M in tetrahydrofuran: 498068 0.5 M in tetrahydrofuran: 497940
R: Product of Rieke® Metals, Inc. ®Registered trademark of Rieke Metals, Inc.
To discuss how our expertise can benefit your next scale-up project or to obtain a quote, contact your local Sigma-Aldrich office or visit www.safcglobal.com Organozinc Halides 14
sigma-aldrich.com [ MW: 297.45 [ MW: 297.45 [ MW: 297.45 [ MW: 268.49 0.5 Mintetrahydrofuran: [ MW: 315.49 [ MW: 299.42 [ MW: 299.42 C iodide solution 2,3-Dimethylphenylzinc 0.5 Mintetrahydrofuran: C iodide solution 4-Ethylphenylzinc 0.5 Mintetrahydrofuran: C iodide solution 2-Ethylphenylzinc 0.5 Mintetrahydrofuran: bromide solution 4-(Methylthio)phenylzinc 0.5 Mintetrahydrofuran: C iodide solution 2-(Methylthio)phenylzinc 0.5 Mintetrahydrofuran: C iodide solution 4-Methoxyphenylzinc 0.5 Mintetrahydrofuran: C iodide solution 3-Methoxyphenylzinc [ MW: 299.42 [ MW: 247.41 C 0.5 Mintetrahydrofuran: C iodide solution 2-Methoxyphenylzinc 0.5 Mintetrahydrofuran: C bromide solution 4-Cyanophenylzinc 312692-94-7 312693-04-2 307496-24-8 308796-24-9 254454-47-2 300825-30-3 282727-20-2 131379-14-1 282727-19-9 8 8 7 7 7 7 7 7 8 H H H H H H H H H 9 9 7 7 7 7 7 4 9 IZn IZn BrSZn ISZn IOZn IOZn IOZn BrNZn IZn ] ] ] ] ] ] ] ] ] H H H 498378 498572 498564 520225 499420 498858 498831 498823 520292 NC 3 3 3 CS C CO H 3 C OCH ZnI OCH SCH ZnI ZnI 3 CH ZnI ZnI CH ZnBr ZnBr 3 3 3 ZnI 3 ZnI To order: ContactyourlocalSigma-Aldrichoffice (see backcover), R R R R R R R R R [ MW: 297.45 [ MW: 297.45 [ MW: 297.45 [ MW: 297.45 iodide solution 2,4-Dimethylphenylzinc 0.5 Mintetrahydrofuran: [ MW: 311.48 C iodide solution 2-Isopropylphenylzinc 0.5 Mintetrahydrofuran: MW: 327.43 C iodide solution 4-Acetoxyphenylzinc 0.5 Mintetrahydrofuran: MW: 327.43 C iodide solution 3-Acetoxyphenylzinc 0.5 Mintetrahydrofuran: MW: 327.43 C iodide solution 2-Acetoxyphenylzinc 0.5 Mintetrahydrofuran: [ MW: 297.45 C iodide solution 3,5-Dimethylphenylzinc 0.5 Mintetrahydrofuran: C iodide solution 3,4-Dimethylphenylzinc 0.5 Mintetrahydrofuran: C iodide solution 2,6-Dimethylphenylzinc 0.5 Mintetrahydrofuran: C iodide solution 2,5-Dimethylphenylzinc 0.5 Mintetrahydrofuran: C 312692-97-0 282727-21-3 312692-96-9 312692-95-8 308796-17-0 312692-98-1 8 8 8 8 8 8 8 9 8 H H H H H H H H H or visitwww.sigma-aldrich.com/order. 9 9 9 9 11 7 7 7 9 IZn IZn IZn IZn IO IO IO IZn IZn 2 2 2 Zn Zn Zn ] ] ] ] ] ] H 499358 630365 630373 630357 498424 498416 498408 498394 498386 H H H H H 3 C 3 3 3 3 3 C C C C C O H CH H H O 3 O 3 3 C C C O 3 CH ZnI O ZnI CH ZnI CH 3 O CH CH ZnI ZnI 3 ZnI ZnI ZnI 3 ZnI 3 3 R R R R R R R R R 0.5 Mintetrahydrofuran: [ MW: 298.49 MW: 345.49 [ MW: 341.46 C bromide solution 4-(Ethoxycarbonyl)phenylzinc 0.5 Mintetrahydrofuran: [ MW: 341.46 C iodide solution 3-(Ethoxycarbonyl)phenylzinc 0.5 Mintetrahydrofuran: C bromide solution 2-(Ethoxycarbonyl)phenylzinc 0.5 Mintetrahydrofuran: C iodide solution 4-Isopropylphenylzinc [ MW: 339.53 [ MW: 311.48 C 4-Biphenylzinc bromide solution 0.5 Mintetrahydrofuran: C 2-Biphenylzinc iodidesolution 0.5 Mintetrahydrofuran: C 4-Pentylphenylzinc iodidesolution 0.5 Mintetrahydrofuran: C 1-Naphthylzinc iodidesolution 0.5 Mintetrahydrofuran: C iodide solution 4-(Ethoxycarbonyl)phenylzinc 0.5 Mintetrahydrofuran: [ MW: 319.46 [ MW: 294.46 [ MW: 294.46 312693-44-0 131379-16-3 282727-18-8 308796-05-6 308796-20-5 46000-10-6 131379-15-2 131379-40-3 9 9 9 9 12 12 11 10 9 H H H H H H H H H 9 9 9 11 9 9 9 BrO IO BrO 15 7 IO BrZn IZn IZn IZn IZn 2 2 Zn Zn 2 2 Zn Zn ] ] ] ] ] ] ] ] H H H 3 3 C 3 C C H 524727 498467 520470 499366 630411 499080 499048 498475 520284 3 O C O O CH O O ZnBr ZnI O O 3 O ZnI ZnI CH CH 3 ZnI ZnBr ZnBr 3 ZnI ZnI R R R R R R R R R 15
Heteroaryl
5-Ethoxycarbonyl-2-furylzinc 5-Bromo-2-thienylzinc 4-Methyl-2-pyridylzinc bromide solution R bromide solution R bromide solution R
C H BrO Zn H C C H Br SZn C H BrNZn CH3 7 7 3 3 O 4 2 2 6 6 MW: 284.42 ZnBr MW: 307.32 MW: 237.41 O Br ZnBr O S [151073-94-8] [308795-93-9] N ZnBr 0.5 M in tetrahydrofuran: 641812 0.5 M in tetrahydrofuran: 497665 0.5 M in tetrahydrofuran: 498998
5-Ethoxycarbonyl-2-furylzinc 5-(1,3-Dioxolan-2-yl)-2- 5-Methyl-2-pyridylzinc chloride solution R thienylzinc bromide solution R bromide solution R C8H9ClO3Zn H C 3 C7H7BrO2SZn C6H6BrNZn O H3C MW: 254.00 ZnCl O O MW: 300.49 ZnBr MW: 237.41 [352530-38-2] O S [307531-84-6] O [257876-05-4] N ZnBr 0.5 M in tetrahydrofuran: 533564 0.5 M in tetrahydrofuran: 533696 0.5 M in tetrahydrofuran: 499005
2-Thienylzinc bromide solution R 5-Ethoxycarbonyl-2- 6-Methyl-2-pyridylzinc C H BrSZn 4 3 thienylzinc bromide solution R bromide solution R MW: 228.43 ZnBr S C7H7BrO2SZn H C C6H6BrNZn [45438-80-0] 3 O
MW: 300.49 MW: 237.41 and Dialkylzinc Reagents Dialkylmagnesium S ZnBr 0.5 M in tetrahydrofuran: 499412 [352530-37-1] O [308795-98-4] H3C N ZnBr 0.5 M in tetrahydrofuran: 533548 0.5 M in tetrahydrofuran: 499013 3-Thienylzinc iodide solution R C H ISZn 4 3 ZnI 2-Thiazolylzinc bromide solution R 6-Methoxy-2-pyridylzinc MW: 275.43 C3H2BrNSZn bromide solution R [172035-85-7] S N MW: 229.41 C H BrNOZn ZnBr 6 6 0.5 M in tetrahydrofuran: 561622 [173382-28-0] S MW: 253.41 H CO N ZnBr 0.5 M in tetrahydrofuran: 499404 [352530-39-3] 3 3-Methyl-2-thienylzinc 0.5 M in tetrahydrofuran: 533718 bromide solution R 2-Pyridylzinc bromide solution R C5H5BrSZn CH3 C5H4BrNZn (2-Chloro-5-pyridyl)methylzinc MW: 242.45 MW: 223.39 ZnBr chloride solution R [312693-45-1] S [218777-23-2] N ZnBr C6H5Cl2NZn ZnCl 0.5 M in tetrahydrofuran: 525111 0.5 M in tetrahydrofuran: 499382 MW: 227.41 [352530-36-0] Cl N 5-Chloro-2-thienylzinc 3-Methyl-2-pyridylzinc 0.5 M in tetrahydrofuran: 533475 bromide solution R bromide solution R C4H2BrClSZn C6H6BrNZn MW: 262.87 CH3 Cl ZnBr MW: 237.41 [312624-22-9] S [308795-91-7] N ZnBr 0.5 M in tetrahydrofuran: 497843 0.5 M in tetrahydrofuran: 498971
Dialkylmagnesium and Dialkylzinc Reagents
Di-n-butylmagnesium solution Diethylzinc solution Dibutylzinc solution
C8H18Mg C4H10Zn C8H18Zn
MW: 138.53 H3C Mg CH3 MW: 123.51 H3C Zn CH3 MW: 179.62 H3C Zn CH3 [1191-47-5] [557-20-0] [1119-90-0] ~0.75 M in diethyl ether: 34765 neat: 256781 ~1 M in heptane: 34905 1.0 M in heptane: 345113 1.0 M in hexanes: 296112 1.0 M in heptane: 406023 Dimethylzinc solution 15 wt. % in toluene: 220809
C2H6Zn MW: 95.46 H3CZnCH3 Diisopropylzinc solution [544-97-8] C6H14Zn H3C CH3 1.0 M in heptane: 417246 MW: 151.57 Zn H C CH 2.0 M in toluene: 364401 [625-81-0] 3 3 1.0 M in toluene: 568112
R: Product of Rieke® Metals, Inc. ®Registered trademark of Rieke Metals, Inc.
To discuss how our expertise can benefit your next scale-up project or to obtain a quote, contact your local Sigma-Aldrich office or visit www.safcglobal.com Sigma-Aldrich Worldwide Locations
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