Chemicals, Inc. New Products Introduced Since Chemiker Vol

Chemicals, Inc. New Products Introduced Since Chemiker Vol. XXV, No. 2 an employee-owned company

metals · inorganics · organometallics · catalysts · ligands · custom synthesis · cGMP facilities · nanomaterials

ALUMINUM (Compounds) $ Price 13-2528 gamma-Alumina, 1/16" spheres [1344-28-1] 500g 92.00 Al O ; FW: 101.96; white spheres 2kg 276.00 2 3 98-4007 25g 2040.00 Trimethylaluminum, elec. gr. (99.999+%-Al) PURATREM, 98-1955, contained in 50 ml electropolished Swagelok® cylinder (96-1077) for CVD/ALD [75-24-1] HAZ (CH3)3Al; FW: 72.09; colorless liq.; m.p. 15.4°; b.p. 20°/8mm; f.p. -1°F; d. 0.752 (20°) moisture sensitive, pyrophoric 98-4008 Trimethylaluminum, elec. gr. (99.999+%-Al) PURATREM, 98-1955, contained in 50 ml 25g 1640.00

Swagelok® cylinder for CVD/ALD [75-24-1] HAZ (CH3)3Al; FW: 72.09; colorless liq.; m.p. 15.4°; b.p. 20°/8 mm; f.p. -1°F; d. 0.752 (20°) moisture sensitive, pyrophoric

ANTIMONY (Compounds) $ Price 51-2400 Antimony(V) sulfide, min. 98% [1315-04-4] 50g 28.00 Sb S ; FW: 403.82; yellow-orange solid 250g 56.00 2 5 51-1430 Antimony(III) telluride (99.96%-Sb) [1327-50-0] 1g 20.00 Sb Te ; FW: 626.32; black pwdr. 5g 80.00 2 3 51-5025 Tris(trimethylsilyl)antimony, 99% [7029-27-8] 100mg 68.00 [(CH ) Si] Sb; FW: 341.33; colorless to yellow liq. 500mg 272.00 3 3 3 amp air sensitive, pyrophoric HAZ NO UPS

BISMUTH (Compounds) $ Price 83-4075 Bismuth(III) telluride (99.99%-Bi) [1304-82-1] 5g 45.00 Bi Te ; FW: 800.76; black pwdr. 25g 198.00 2 3 CARBON (Compounds) $ Price

06-1037 2-Methyl-3-[polyisobutyl(12)]propanol H3C CH3 H3C H 1g 24.00 (50% in heptane/polyisobutylene) 5g 88.00

amp FW: 747; colorless liq. H OH HAZ 12

06-1045 2-Methyl-3-[polyisobutyl(12)]propyl bromide H3C CH3 H3C H 1g 38.00 (50% in heptane/polyisobutylene) 5g 152.00 H Br FW: 1035; pale yellow liq. amp 16 HAZ

06-1055 4-[Polyisobutyl(18)]-2-(t-butyl)phenol H3CCH3 H3CCH3 1g 24.00 (50% in heptane/polyisobutylene) 5g 88.00 H amp FW: 1160; yellow liq. HAZ 17 OH

O 06-1032 5-[Polyisobutyl(18)]-2-hydroxybenzaldehyde H3C CH3 H3C CH3 1g 38.00 (50% in heptane/polyisobutylene) 5g 152.00 H C FW: 1132; yellow liq. H amp 17 HAZ

06-1035 5-[Polyisobutyl(18)]-2-hydroxy-3-(t-butyl)benzaldehyde H3C CH3H3C CH3 O 1g 38.00 (50% in heptane/polyisobutylene) 5g 152.00 H C FW: 1188.00; yellow liq. H amp 17 HAZ OH

C(CH3)3

Visit www.strem.com for new product announcements. 7 Mulliken Way, Newburyport, MA 01950-4098 Tel.: (978) 499-1600 ● Fax: (978) 465-3104 ● Toll Free: (800) 647-8736 ● Fax: (800) 517-8736 Email: [email protected] ● [email protected] ● [email protected] ● [email protected] ● (All other inquiries) [email protected] NpsinceChem25_Vol2_030812

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CARBON (Compounds) $ Price

06-1048 4-[Polyisobutyl(18)]phenol H3C CH3 H3C CH3 1g 24.00 (50% in heptane/polyisobutylene) 5g 88.00 H amp FW: 1104; pale yellow liq. 17 HAZ

CHROMIUM (Compounds) $ Price 24-0185 Chromium arsenide (99%-Cr) [12254-85-2] 5g 90.00 Cr Ad; FW: 178.98; black pwdr. 25g 360.00 2 HAZ

CERIUM (Compounds) $ Price 58-5845 Cerium nitride (99.9%-Ce) [25764-08-3] 250mg 52.00 CeN; FW: 154.12; -60 mesh pwdr. 1g 156.00

COBALT (Compounds) $ Price 27-1965 N,N',N",N"'-(Tetrafluorodiborato)bis[µ-(2,3-butanedionedioximato)]cobalt(II) F F 100mg 68.00 [26220-72-4] B 500mg 272.00 O O C8H12B2CoF4N4O4; FW: 384.75; brown solid Technical Note: H3C NNCH3 C C 1. Effective catalyst for high conversion, chain transfer polymerization of methyl Co methacrylate. C C H C N N CH 3 3 References: O O 1. Macromolecular Engineering, 2011, 5(9-10), 404. B F F 2. Polymer Chemistry, 2011, 2, 815. 3. J. Applied Polymer Science, 2004, 91, 1375.

GALLIUM (Compounds) $ Price 98-4068 Trimethylgallium, 99+%, 31-2000, contained in 50 ml Swagelok® cylinder for CVD/ALD 10g 1055.00 [1445-79-0] 25g 1520.00

HAZ (CH3)3Ga; FW: 114.83; colorless liq.; m.p. -15.8°; b.p. 55.7°; f.p. -1°F; d. 1.151 moisture sensitive, pyrophoric

98-4047 Trimethylgallium, elec. gr. (99.9999%-Ga) PURATREM, 98-2000, contained in 50 ml 10g 2048.00

electropolished Swagelok® cylinder (96-1077) for CVD/ALD [1445-79-0] HAZ (CH3)3Ga; FW: 114.83; colorless liq.; m.p. -15.8°; b.p. 55.7°; f.p. -1°F; d. 1.151 moisture sensitive, pyrophoric

INDIUM (Compounds) $ Price 98-4057 Cyclopentadienylindium (I), elec. gr. (99.99+%-In) PURATREM, 97-3425, contained in 5g 2374.00

50 ml Swagelok® cylinder for CVD/ALD [34822-89-4] HAZ C5H5In; FW: 179.92; off-white xtl.; b.p. subl. 50°/0.01mm air sensitive, heat sensitive, light sensitive 98-4054 Cyclopentadienylindium(I), elec. gr. (99.99+%-In) PURATREM, 97-3425, contained in 5g 2774.00

50 ml electropolished Swagelok® cylinder (96-1077) for CVD/ALD [34822-89-4] HAZ FW: 179.92; b.p. subl. 50°/0.01 mm air sensitive, heat sensitive, light sensitive, (store cold) 98-4056 Trimethylindium, elec. gr. (99.999%-In) PURATREM, 98-2010, contained in 50 ml 25g 3511.00

electropolished Swagelok® cylinder (96-1077) for CVD/ALD [3385-78-2] HAZ (CH3)3In; FW: 159.93; white xtl.; m.p. 88°; f.p. -1°F; d. 1.568 heat sensitive, moisture sensitive, pyrophoric, (store cold)

IRIDIUM (Compounds) $ Price 77-5074 [(R)-(+)-5,5'-Bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole][4-cyano-3- 100mg 86.00 nitrobenzenecarboxylato][1,2,3-η-2-propenylIr(III), min. 98% [1208092-27-6] 500mg 344.00

C49H35IrN2O8P2; yellow pwdr. Note: Manufactured under license of Takasago patent. Technical Note: 1. See 77-5075 (visit www.strem.com).

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IRON (Compounds) $ Price

26-0320 1,1'-Bis[bis(5-methyl-2-furanyl)phosphino]ferrocene, 98% H3C 100mg 30.00 HiersoPHOS-3 [756824-22-3] 500mg 120.00 O C30H28FeO4P2; FW: 570.33; orange xtl. Technical Notes: P O 1. Amination of Allyl Acetates at Low Palladium Loading (0.01-1.0 mol%) and Mild CH3 Temperatures using allyl acetate, cinnamyl acetate, E-hex-2-en-1-yl acetate and CH Fe 3 monoterpenes such as geranyl acetate with primary and secondary acyclic and cyclic O alkyl and aryl amines. P 2. Heck Coupling Reaction of polyfunctionalized aryl halides bearing unprotected hydroxyl groups. O

3. Additional catalyzed reactions include Suzuki and Sonogashira Cross-Couplings of Aryl CH3 Bromides at Ultra-Low Palladium Loading (Ref. 2). 1 R R1 R3 0.01-1 mol% [Pd(allyl)Cl]2 2 OAc + HN 3 4 R HiersoPHOS-3 R2 NR R R4 Tech. Note (1) or or Ref. (1,2) PhMe or THF 5 20 - 80 °C OAc + H2N R NHR

1 R = H, CH3, 2 R = H, Ph, n-Pr, -(CH2)2CH=C(CH3)2 R3 = R4 = Et, i-Pr, n-octyl 3 4 - - - R -R = -(CH2)4 , -(CH2)5 , -[O(CH2)4] 5 4 R = Ph, CH2Ph R 1 mol% [Pd(allyl)Cl] R1 2 R1 R4 HiersoPHOS-3 R5 R2 Br + R5 R2 or I Cs2CO3, DMF 3 Tech. Note (2) 100 °C R R3 Ref. (2,3)

1 4 R = H, OH, OMe or CH2OH R = H, OH or OMe R2 = H, OH, OMe, or OAc R5 = H or OMe R3 = H or OMe

0.001-0.01 mol% [Pd(allyl)Cl]2 HiersoPHOS-3

R Br + (HO) B 2 R K2CO3,xylene 130 °C R = OMe, COMe Tech. Note (3) Ref. (2)

0.0001-0.1 mol% [Pd(allyl)Cl]2 HiersoPHOS-3

R Br + H R' R R'

CuI, K2CO3,DMF 130 °C R = OMe, COMe

References: 1. Adv. Synth. Catal., 2005, 347, 1198. 2. Tetrahedron, 2005, 61, 9759. 3. Tetrahedron, 2012, submitted.

26-0145 Bis(N,N'-di-t-butylacetamidinato)iron (II), min. 98% C(CH3)3 1g 285.00 [635680-56-7] C(CH3)3 5g 1140.00 N C20H42N4Fe; FW: 394.42; off-white to gray xtl.; m.p. 107° N air sensitive H3C C Fe C CH3 Note: Product sold under, use subject to, terms and conditions N N of label license at www.strem.com/harvard2. C(CH3)3 C(CH3)3

98-4038 Bis(N,N'-di-t-butylacetamidinato)iron(II), min. 98%, 26-0145, contained in 50 ml 5g 1715.00 ® Swagelok cylinder for CVD/ALD [635680-56-7] C20H42N4Fe; FW: 394.42; off-white to gray xtl. air sensitive Note: Product sold under, use subject to, terms and conditions of label license at www.strem.com/harvard2.

IRON (Compounds) $ Price 26-0061 (2R,2'R)-(-)-[N,N'-Bis(2-pyridylmethyl]-2,2'-bipyrrolidinebis 100mg 90.00 (acetonitrile)iron(II) hexafluoroantimonate 500mg 360.00

Fe(R,R-PDP) White-Chen Catalyst N [C24H32FeN6](SbF6)2; FW: 931.90; purple pwdr. N air sensitive NCCH3 Fe2+ Note: Patent pending. NCCH N 3 Technical Note: N 1. See 26-0060 (visit www.strem.com).

26-0324 4-(t-Butyl)-1,2-bis(diphenylphosphino)-1'-(di-i-propylphosphino) 100mg 44.00 ferrocene, 98% HiersoPHOS-4 [776315-37-8] 500mg 176.00

C44H49FeP3; FW: 726.63; orange xtl. P Technical Note: P 1. Sonogashira Cross-Coupling of Aryl (phenyl, naphtyl, anthracenyl) Bromides and Corides bearing alkyl, methoxy, halo, keto, and nitrile substitution in para-, meta- (H3C)3C Fe

ortho-position at Ultra-Low Palladium Loading (Ref. 1,2). (H3C)2HC P 1 R 0.0001-0.5 mol% [Pd(allyl)Cl]2 R1 (H3C)2HC HiersoPHOS-4 2 X + H R R2 K2CO3, (CuI) DMF 130 °C Tech. Note (1) X = Br, Cl (Ref. 1-3)

1 R = 4-COMe, 4-CN, 4-F, 2-CF3, 2-Me, 3-Me, 4-OMe, 3-OMe

2 R = Ph, -(CH2)7CH3, -(CH2)2OH

References: 1. Org. Lett., 2004, 6, 3473. 2. Eur. J. Inorg. Chem., 2007, 3767. 3. Organometallics, 2010, 29, 2815. 26-0985 Dichlorophosphinoferrocene, 98% [1291-31-2] Cl 1g 55.00 C H Cl FeP; FW: 286.90; red-brown solid 5g 220.00 10 9 2 P HAZ moisture sensitive Cl Fe

26-3620 Phosphinoferrocene, 98% [83528-85-2] H 1g 46.00 C H FeP; FW: 218.01; red-brown solid 5g 184.00 10 11 P air sensitive H Fe

MANGANESE (Compounds) $ Price 98-4060 Bis(cyclopentadienyl)manganese, 98+%, 25-0200, contained in 50 ml Swagelok® 10g 1060.00 cylinder for CVD/ALD [73138-26-8] 25g 1425.00

HAZ (C5H5)2Mn; FW: 185.13; brown xtl. air sensitive, moisture sensitive 98-4065 Bis(ethylcyclopentadienyl)manganese, min. 98%, 25-0210, contained in 50 ml 10g 1220.00 Swagelok® cylinder for CVD/ALD [101923-26-6] 25g 2105.00

HAZ [(C2H5)C5H4]2Mn; FW: 241.23; dark red liq. air sensitive, moisture sensitive

NANOMATERIALS (Elemental forms) $ Price 14-0650 Silicon powder (nanocrystalline), min. 97% [7440-21-3] 5g 80.00 20-50nm, brown pwdr. 25g 320.00

HAZ

NANO SURFACTANTS (Compounds) $ Price 07-0440 L-Cysteine ethyl ester hydrochloride, 98% [868-59-7] 25g 28.00 HSCH CH(NH )COOC H ∙HCl; FW: 185.67; white solid; m.p. 123-125° 100g 84.00 2 2 2 5 02-5055 N-Dodecyl-N,N-dimethyl-3-ammonio-1-propanesulfonate (Sulfobetaine 12) [14933-08-5] 10g 65.00 CH (CH ) N+(CH ) CH CH CH SO -; FW: 335.55; white pwdr. 50g 260.00 3 2 11 3 2 2 2 2 3 02-5045 Hexadecyltrimethylammonium bromide, 99+% CTAB [57-09-0] 50g 20.00 CH (CH ) (CH ) N+Br-; FW: 364.45; white solid; m.p. 248-251° 250g 80.00 3 2 15 3 3 Visit www.strem.com for new product announcements. 7 Mulliken Way, Newburyport, MA 01950-4098 Tel.: (978) 499-1600 ● Fax: (978) 465-3104 ● Toll Free: (800) 647-8736 ● Fax: (800) 517-8736 Email: [email protected] ● [email protected] ● [email protected] ● [email protected] ● (All other inquiries) [email protected] NpsinceChem25_Vol2_030812

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NANO SURFACTANTS (Compounds) $ Price 06-4010 Oleic acid, 99% [112-80-1] 5g 35.00 CH (CH ) =CH(CH ) COOH; FW: 282.46; liq.; m.p. 13°; b.p. 194-195° (1.2mm); d. 0.89 25g 140.00 3 2 7 2 7 Note: Surfactant for nanomaterial synthesis. 06-5075 Polyethylene glycol dodecyl ether (Brij™ 35) [9002-92-0] 100g 11.00 CH (CH ) CH (OCH CH )nOH (n~23); FW: ~1199.54; liq. 500g 44.00 3 2 10 2 2 2 02-5065 Tetramethylammonium hydroxide pentahydrate, min. 95% [10424-65-4] 10g 18.00 (CH ) N(OH)·5H O; FW: 181.23; white solid 50g 72.00 3 4 2 Note: Surfactant for nanomaterial synthesis. 07-1815 Polyvinylpyrrolidone (average mol. Wt. 10,000) PVP10 [9003-39-8] 50g 24.00 (C H NO)n; liq. 250g 96.00 6 9 O N

H H n 07-1817 Polyvinylpyrrolidone (average mol.wt. 40,000) PVP40 [9003-39-8] 50g 17.00 (C H NO)n; liq. 250g 68.00 6 9 Sodium dioctylsulfosuccinate (AOT), 98% [577-11-7] CH3 11-2750 O 50g 15.00 C20H36NaO7S; FW: 444.56; white pwdr. 250g 60.00

Note: Surfactant for nanomaterial synthesis. O CH3 H3C O O S O O H3C ONa 11-1285 Sodium dodecylsulfate, min. 99.5% [151-21-3] 50g 52.00 CH (CH ) OSO -Na+; FW: 288.38; white solid; m.p. 204-207° 250g 208.00 3 2 11 3 Note: Surfactant for nanomaterial synthesis. Sodium oleate, 99% [143-19-1] 11-1280 - + 5g 30.00 CH3(CH2)7CH=CH(CH2)7COO Na ; FW: 304.44; white pwdr.; m.p. 232-235° 25g 120.00 Note: Surfactant for nanomaterial synthesis.

NIOBIUM (Compounds) $ Price 41-0510 Trihydridobis(pentamethylcyclopentadienyl)niobium(V) [93558-77-1] 100mg 125.00 [(CH ) C ] NbH ; FW: 366.38; light-brown pwdr. 500mg 500.00 3 5 5 2 3 HAZ air sensitive

NITROGEN (Compounds) $ Price

07-4042 1,3-Bis{2,3-dimethyl-4-[polyisobutyl CH3 H3C 500mg 38.00

CH CH3 (24)]phenyl}-4,5-dihydroimidazolium H C 3 CH 3 + 3 tetrafluoroborate (50% in hexane/ NN amp 24 - HAZ polyisobutylene) H BF4 H 24 FW: 3059; yellow liq. CH3 H3C

07-4045 1,3-Bis{2,3-dimethyl-4-[polyisobutyl CH3 H3C 500mg 38.00 CH CH 3 (20)]phenyl}imidazolium chloride H C 3 CH 3 + 3 amp (50% in hexane/polyisobutylene) NN 20 HAZ FW: 2557; orange liq. H Cl- H 20 Technical Note: CH3 H3C 1. Ligand used in the preparation of a phase-separable NHC ruthenium complex, useful for ring-closing metathesis.

n NN H Cl H Ru n Y Cl O X X n n Tech. Note (1) heptane <15 min Ref. (1) X = -C(CO Et) -NSO C H CH Y 2 2 2 6 4 3

Reference: 1. Org. Lett., 2009, 11, 665. 07-4050 1,3-Bis{2,6-di-i-propyl-4-[polyisobutyl CH(CH3)2 (H3C)2HC 500mg 60.00

(20)]phenyl}imidazolium chloride CH3 CH3 H3C CH3 (50% in hexane/polyisobutylene) + amp NN FW: 2669; orange liq. 20 HAZ H Cl- H 20 CH(CH3)2 (H3C)2HC

NITROGEN (Compounds) $ Price 07-4050 1,3-Bis{2,6-di-i-propyl-4-[polyisobutyl(20)]phenyl}imidazolium chloride (50% in hexane/polyisobutylene)

amp HAZ (cont.) Technical Note: 1. Ligand used in the preparation of a phase-separable NHC palladium complex, useful for cross-coupling reactions. i Pr Pr i

NN n Tech. Note (1) H nH i Pr Pd i-Pr Ref. (1) Cl Br + HN O NO KOtBu, heptane

Reference: 1. J. Organomet.Chem., 2011, 696, 1272.

CH3 07-0550 2-[2,6-Bis(1-methylethyl)phenyl]-3,3-dimethyl-2- H3C 100mg 58.00 azoniaspiro[4.5]dec -1-ene hydrogen dichloride [1141464-90-5] 500mg 232.00

C23H36N·HCl2; white pwdr. N hygroscopic Note: US Patent Application 11/449,568 and PCT Application US06/22477.

07-0350 2-{[Bis(2-pyridinylmethyl)amino]ethylamino} N H 100mg 70.00 benzenesulfonic acid ZX1 N N 500mg 280.00

C20H22N4O3S; FW: 398.48; yellow solid air sensitive N HO3S

07-0097 (2R,2'R)-(+)-[N,N'-Bis(2-pyridylmethyl]-2,2'-bipyrrolidine tetrahydrochloride, 98% 100mg 74.00 (R,R)-PDP 500mg 296.00

C20H26N4·4HCl; FW: 468.29; white pwdr. air sensitive Note: Patent pending. 07- 0094 (2S,2'S)-(-)-[N,N'-Bis(2-pyridylmethyl]-2,2'-bipyrrolidine tetrahydrochloride, 98% 100mg 74.00 (S,S)-PDP 500mg 296.00

C20H26N4·4HCl; FW: 468.29; white pwdr.; [α]D -94.6° (c 1.0, methanol) air sensitive Note: Patent pending. 07-0311 9-(2-Carboxyphenyl)-2,7-dichloro-4,5-bis[(2- N N 0.5mg 300.00

picolyl)(pyrazin-2-ylmethyl)aminomethyl]-6-hydoxy- 3-xanthanone ZPP1 [1084898-23-6] N N C44H34Cl2N8O5; FW: 825.70; pink pwdr. NN N N HO OO

Cl Cl

CO2H

07-0332 1-(Chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane CH2Cl 5g 26.00 ® bis(tetrafluoroborate), min. 97% SelectFluor [140681-55-6] + 25g 80.00 (C H ClFN )(BF ) ; FW: 354.26; white to off-white pwdr. N 100g 240.00 7 14 2 4 2

moisture sensitive (BF4)2

N + F 07-0445 N,N'-Dimethylethylenediamine, min. 98% [110-70-3] 5g 44.00 CH3NHCH2CH2NHCH3; FW: 86.15; colorless liq.; b.p. 119°; d. 0.819 25g 144.00 100g 488.00 air sensitive

07-0377 N-{3-[(2,6-Dimethylphenyl)amino]-1-methyl-2-buten-1-ylidene}- H3C CH3 250mg 56.00 CH CH 2,6-dimethylbenzenamine, 98% [267431-79-8] 3 3 1g 168.00

N N C21H26N2; FW: 306.45; white solid H

CH3 H3C

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NITROGEN (Compounds) $ Price H CCHH CCH 07-6110 4-[Polyisobutyl(20)]-2,6-dimethylaniline 3 3 3 3 1g 24.00 (50% in heptane/polyisobutylene) 5g 88.00 H CH 3 amp FW: 1243; pale yellow liq. 19 HAZ

NH2

CH3

07-6120 4-[Polyisobutyl(18)]-2,6-(di-i-propyl)aniline H3C CH3 H3C CH3 1g 24.00 (50% in heptane/polyisobutylene) 5g 88.00 H CH(CH3)2 amp FW: 1187; yellow-orange liq. 17 HAZ

NH2

CH(CH3)2

07-6115 4-[Polyisobutyl(12)]-2-ethylaniline H3C CH3 H3C CH3 1g 24.00 (50% in heptane/polyisobutylene) 5g 88.00 H CH2CH3 amp FW: 794; red-orange liq. 11 HAZ

NH2 OXYGEN (Compounds) $ Price 08-2180 DL-α-Tocopherol methoxypolyethylene glycol succinate solution (2 wt% in water) 10ml 21.00 TPGS-750-M 50ml 84.00 colorless liq. Technical Note: 1. Visit www.strem.com.

PALLADIUM (Compounds) $ Price

46-0230 N,N'-[Bis(2,6-dimethylphenyl)-1,3-dimethyl-1,3-propanediylidene] H3C CH3 50mg 99.00 (methyl) (triethylphosphine)palladium (II), min. 97% [1224879-40-6] 250mg 396.00

C28H43N2PPd; FW: 545.05; light brown pwdr. CH3 H3C air sensitive N N Pd Technical Notes: CH3 H3C 1. Catalyst used in the general method for the Heck and Buchwald-Hartwig coupling H3C PEt3 reactions of aryl chlorides. 2. Extremely active and general catalyst for the Suzuki coupling reaction of unreactive aryl chlorides.

R' Pd catalyst (1.0 mol%) R'

Tech. Note (1) K3PO4, DMF-H2O Ref. (1) Cl + R R' R' Pd catalyst (0.5 mol%) R H N N t-BuOK, DME R'' R'' R Pd catalyst (0.1 mol%) 50°C Tech. Note (2) Cl + (HO)2B Ref. (2) R1 R2 R1 R2 K3CO3, EtOH-H2O

Ar Pd catalyst (0.15 mol%) 60°C Tech. Note (3) Ar + 2 (HO)2B Ref. (2) Cl Cl K CO , EtOH-H O R 3 3 2 R R R

Cl Tech. Note (4) Ref. (2) Pd catalyst (0.3 mol%) 60°C + 3 (HO)2B Cl Cl R K3CO3, EtOH-H2O

R R

Cl Cl Pd catalyst (0.5 mol%) 80°C Tech. Note (5)

+ 4 (HO)2B Ref. (2) Cl Cl R K3CO3, EtOH-H2O

References: 1. Org. Lett., 2011, 13(20), 5540. R R 2. Org. Lett., 2011, 13(2), 252. Visit www.strem.com for new product announcements. 7 Mulliken Way, Newburyport, MA 01950-4098 Tel.: (978) 499-1600 ● Fax: (978) 465-3104 ● Toll Free: (800) 647-8736 ● Fax: (800) 517-8736 Email: [email protected] ● [email protected] ● [email protected] ● [email protected] ● (All other inquiries) [email protected] NpsinceChem25_Vol2_030812 -8-

PALLADIUM (Compounds) $ Price CH(CH ) (H C) HC 46-0226 [1,3-Bis(2,6-di-i-propylphenyl)-4,5-dihydroimidazol- 3 2 3 2 100mg 33.00 2-ylidene]{2-[(dimethylamino-kN)methyl]phenyl-kC} NN 500mg 132.00

(pyridine)palladium (II) tetrafluoroborate, min. 97% PACC™ CH(CH3)2 (H3C)2HC - H C [C41H55N4Pd]BF4 ; FW: 797.13; pale yellow solid 3 + N Pd N BF - air sensitive H C 4 Note: Sold under license from Kanata for research purposes only. 3 US App. No. 61/324,022. Technical Note: 1. See 46-0224.

46-0224 [1,3-Bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene]{2- CH3 H3C 100mg 33.00 [(dimethylamino-kN)methyl]phenyl-kC}(pyridine)palladium (II) H3C NN CH3 500mg 132.00 tetrafluoroborate, min. 97% PACC™ - CH3 H3C [C35H43N4Pd]BF4 ; FW: 712.97; pale yellow solid H3C + - air sensitive N Pd N BF4 Note: Sold under license from Kanata for research purposes only. H3C US App. No. 61/324,022. Technical Notes: 1. Catalyst used for Suzuki-Miyaura Coupling. 2. Catalyst used for Negishi Coupling. 3. Catalyst used for Heck-Mizoroki Coupling.

Br B(OH)2 TM PACC , Cs2CO3 Solvent + Tech. Note (1) 16 h, 80°C Ref. (1) Br ZnBr

PACCTM, THF + Tech. Note (2) OCH3 2 h, RT Ref. (1)

OCH3 Br

COOR' PACCTM, dioxane + Tech. Note (3) COOR' Ref. (1) 16 h, 100°C R R' Reference: 1. US Patent Application No. 61/324,022. 46-0285 Cyclopentadienyl[(1,2,3-n)-1-phenyl-2-propenyl]palladium(II), 98% 100mg 92.00 [105333-10-6] 500mg 368.00

C14H14Pd; FW: 288.68; purple-red xtl. Pd air sensitive, (store cold) Technical Note: 1. A superior precursor for the preparation of palladium(0)-based cross-coupling and other catalytic reactions. Reference: 1. J. Org. Chem., 2009, 74, 6674.

PHOSPHORUS (Compounds) $ Price 15-6185 Bis(3,5-dimethylphenyl)phosphine, 98% (10wt% in hexane) [71360-06-0] 1g 62.00 [(CH ) C H ] PH; FW: 242.30; colorless liq. 5g 164.00 3 2 6 3 2 amp air sensitive 15-7309 Bis[2-(di-t-butylphosphino)ethyl]amine, min. 97% (10wt% in hexane) [944710-34-3] 5g 87.00 C H NP ; FW: 361.53; colorless liq. 25g 348.00 20 45 2 air sensitive Note: Sold under license from Kanata for research purposes only. WO 2004096735.

15-0577 Bis(3-sulfonatophenyl)(2-trifluoromethylphenyl)phosphine, SO3Na 100mg 62.00 disodium dihydrate, min. 97% o-DANPHOS [1289463-84-8] 500mg 248.00

C19H14F3Na2O6PS2·2H2O; FW: 534.38 (570.41); white pwdr. Note: Sold under license from UAB for research purposes only. CF3 PCT/EP2010/065531. P SO3Na

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PHOSPHORUS (Compounds) $ Price

15-0575 Bis(3-sulfonatophenyl)(4-trifluoromethylphenyl)phosphine disodium SO3Na 100mg 62.00 dihydrate, min. 97% p-DANPHOS [1289463-79-1] 500mg 248.00

C19H12F3Na2O6PS2·2H2O; FW: 534.38 (570.41); white pwdr. Note: Sold under license from UAB for research purposes only. PCT/EP2010/065531. P SO3Na

F C 3

15-1168 2-(Di-t-butylphosphino)-3-methoxy-6-methyl-2'-4'-6'-tri-i-propyl- OCH3 100mg 115.00 1,1'-biphenyl, min. 98% RockPhos [1262046-34-3] 500mg 460.00 C H OP; FW: 468.69; white xtl.; m.p. 129-130° 2g 1380.00 31 49 Technical Note: H3C P(t-butyl)2 1. Ligand used in the palladium-catalyzed C-O bond forming reactions of secondary and primary alcohols with a range of aryl halides. Heterocyclic halides and, for the first time, electron-rich aryl halides can be coupled with secondary alcohols. X O R1 1 HO R [(allyPdCl)2], 1 R + R Cs2CO3, toluene R2 R2 90° C R1 = alkyl R2 = alkyl, H Reference: 1. Angew. Chem. Int. Ed., 2011, 50, 9943. 15-1089 1-(Dicyclohexylphosphino)-2-phenyl-1H-indole, min. 98% 100mg 36.00 NPCy Phendole-Phos [947402-57-5] 500mg 144.00

C26H32NP; FW: 389.51; white to off-white pwdr. N Technical Note: 1. Suzuki-Miyaura Coupling of Aryl and Hetero-aryl Chlorides. P

B(OH)2 0.2-1% Pd-L R' K3PO4 R' + Tech. Note (1) toluene, 100° Ref. (1)

Cl Reference: 1. Org. Lett., 2007, 9, 2795. 15-7253 (R)-1-(Diphenylphosphino)-2-amino-3,3-dimethylbutane, min. 97% 1g 45.00 (10wt% in hexane) 5g 180.00

HAZ C18H24NP; FW: 285.36; colorless liq. air sensitive Ph2P NH2 15-7255 (S)-1-(Diphenylphosphino)-2-amino-3,3-dimethylbutane, min. 97% (10wt% in hexane) 1g 45.00 [286454-86-2] 5g 180.00

HAZ C18H24NP; FW: 285.36; colorless liq. air sensitive 15-7220 (2R,4R)-(+)-2-(Diphenylphosphinomethyl)-4-(dicyclohexylphosphino)- 50mg 83.00 N-(t-butoxycarbonyl)pyrrolidine, min. 97% (R,R-BCPM) [114751-47-2] 250mg 332.00

C34H49NO2P2; FW: 565.71; white pwdr.

air sensitive P

P N C O O

C(CH3)3 15-7224 (2R,4R)-(+)-2-(Diphenylphosphinomethyl)-4-(dicyclohexylphosphino)- 50mg 89.00 N-methyl-1-pyrrolidinecarboxamide, min. 97% (R,R-MCCPM) 250mg 356.00

[122709-72-2] C H N OP ; FW: 522.64; white pwdr. 31 44 2 2 P air sensitive

P N

C H O N

CH3

PHOSPHORUS (Compounds) $ Price 15-7225 (2S,4S)-(-)-2-(Diphenylphosphinomethyl)-4-(dicyclohexylphosphino)- 50mg 129.00 N-methyl-1-pyrrolidinecarboxamide, min. 97% (S,S-MCCPM) 250mg 516.00

[112521-97-8] C31H44N2OP2; FW: 522.64; white pwdr. air sensitive P

P N C H O N

CH3 15-7216 (2R,4R)-(+)-2-(Diphenylphosphinomethyl)-4-(diphenylphosphino)- 100mg 49.00 N-(t-butoxycarbonyl)pyrrolidine, min. 97% (R,R-BPPM) [72598-03-9] 500mg 196.00

C34H49O2P2; FW: 565.71; white pwdr. air sensitive P

P N

C O O

C(CH ) 3 3 15-7217 (2S,4S)-(-)-2-(Diphenylphosphinomethyl)-4-(diphenylphosphino)- 100mg 46.00 N-(t-butoxycarbonyl)pyrrolidine, min. 97% (S,S-BPPM) [61478-28-2] 500mg 184.00

C34H49NO2P; FW: 565.71; white pwdr. air sensitive P

P N

C O O

C(CH ) 3 3 15-7210 (2R,4R)-(+)-2-(Diphenylphosphinomethyl)-4-(diphenylphosphino) 100mg 105.00 pyrrolidine, min. 97% (R,R-PPM) [77450-05-6] 500mg 420.00

C29H29NP2; FW: 453.50; white pwdr.

air sensitive P

P N H 15-7211 (2S,4S)-(-)-2-(Diphenylphosphinomethyl)-4-(diphenylphosphino) 100mg 98.00 pyrrolidine, min. 97% (S,S-PPM) [61478-29-3] 500mg 392.00

C29H29NP2; FW: 453.50; white pwdr.

air sensitive P

P N H

15-3152 4-Diphenylphosphinophenyl{2-methyl-3-[polyisobutyl(21)] H3C CH3 H3C H 1g 38.00 propyl}ether (50% in heptane/polyisobuylene) 5g 152.00 H O amp FW: 1513; colorless liq. 21 HAZ

P(C6H5)2

-11-

PHOSPHORUS (Compounds) $ Price 15-3152 4-Diphenylphosphinophenyl{2-methyl-3-[polyisobutyl(21)]propyl}ether (50% in heptane/polyisobuylene)

(cont.) Technical Note: 1. Recyclable phosphine catalyst for use in allylic aminations.

OAc O

O2N CH3 H O n O Tech. Note (1) Ref. (1) O2N P(C6H5)2 + O H C N THF, rt, 3 24h 96% HN O O

O Reference: 1. J. Org. Chem., 2011, 76, 6912. 15-3155 {2-methyl-3-[polyisobutyl(20)]propyl} 1g 38.00 diphenylphosphine (50% in heptane/polyisobutylene) 5g 152.00

amp FW: 1364; colorless liq. H CCHH CH HAZ 3 3 3 H P 20

RUTHENIUM (Compounds) $ Price 44-0074 Carbonylhydrido(tetrahydroborato)[bis(2-diphenylphosphinoethyl)amino] H 250mg 53.00 ruthenium(II), min.98% Ru-MACHO™-BH [1295649-41-0] H Ph 1g 158.00 C29H34BNOP2Ru; FW: 586.41; white to yellow pwdr. N P 5g 632.00 air sensitive Ru Ph Note: Manufactured under license of Takasago patent PCT/JP2010-004301. P CO Ph Technical Note: Ph H 1. Catalyst used for hydrogenation of esters. BH3

Ru-cat. (S/C = 1000) H2 (5 MPa) COOCH3 Ph Ph OH Tech. Note (1) THF, 80°C, 16h Ref. (1) CH3 CH3 yield - 77%, ee (%) <1

NHBoc Ru-cat. (S/C = 1000) NHBoc H2 (5 MPa) OH Tech. Note (1) Ref. (1) COOCH3 THF, 80°C, 16h

yield - 78%, ee (%) <1 Ru-cat. (S/C = 1000) NHBoc NHBoc H2 (5 MPa) COOCH3 Tech. Note (1) THF, 80°C, 16h OH Ref. (1)

yield - 78%, ee (%) <1

NHCbz Ru-cat. (S/C = 1000) NHCbz H2 (5 MPa) OH THF, 80°C, 16h HO O O Tech. Note (1) yield - 88%, ee (%) 2 Ref. (1)

Ru-cat. (S/C = 1000) O COOCH3 H (5 MPa) O 2 OH

THF, 80°C, 16h OH O O COOCH3 Tech. Note (1) Ref. (1) yield - 93%, ee (%) <1

ee (%) = (%ee of substrate) - (%ee of product) Visit www.strem.com for new product announcements. 7 Mulliken Way, Newburyport, MA 01950-4098 Tel.: (978) 499-1600 ● Fax: (978) 465-3104 ● Toll Free: (800) 647-8736 ● Fax: (800) 517-8736 Email: [email protected] ● [email protected] ● [email protected] ● [email protected] ● (All other inquiries) [email protected] NpsinceChem25_Vol2_030812 -12-

RUTHENIUM (Compounds) $ Price 44-0074 Carbonylhydrido(tetrahydroborato)[bis(2-diphenylphosphinoethyl)amino] ™ ruthenium(II), min.98% Ru-MACHO -BH [1295649-41-0] (cont.) Reference: 1. PCT Application No. PCT/JP2010-004301. 44-0218 Chloro{(S)-(-)-2,2'-bis[di(3,5-xylyl)phosphino]-1,1'- 250mg 64.00 binaphthyl}[(2S)-(+)-1-(4-methoxyphenyl)-1’-(4-methoxy- xyl OCH 1g 190.00 xyl Cl H 3 phenyl-kC)-3-methyl-1,2-butanediamine] P 2 5g 759.00 ™ N ruthenium(II) (S)-RUCY -XylBINAP Ru H P N 2 H C71H73ClN2O2P2Ru; FW: 1184.82; xyl yellow to dark brown/green solid xyl CH(CH3)2 air sensitive H3CO Note: Manufactured under license of Takasago patent application no. JP2010-104552. Technical Note: 1. See 44-0217 (visit www.strem.com). 44-0185 N-[(1R,2R)-1,2-Diphenyl-2-(2-(4-methylbenzyloxy)ethylamino)ethyl]-4- 250mg 64.00 ™ methylbenzene sulfonamide(chloro)ruthenium(II) (R,R)-Ts-DENEB 1g 190.00 C H ClN O RuS; FW: 650.19; gray to brown pwdr. 5g 759.00 31 33 2 3 air sensitive CH3 Note: Manufactured under license of Takasago patent application PCT/JP2011/064490 O While supplies last, with any purchase of a Takasago product, O S Ru receive 100mg of 44-0185 at no additional charge. Supplies are limited. N Cl This Bonus Offer is limited to one bonus per customer order. Please add O N 100mg of 44-0185 at the time your order is placed. H Technical Notes: 1. Catalyst used for asymmetric -transfer hydrogenation.

O OH (R,R)-Ru-cat

+ HCO2H/Et3N = 5/2 (2M) R R' 60°C R R'

O O O Cl

HO Tech. Note (1) Ref. (1) (S/C=30,000, 96h) (S/C=1,000, 5h) (S/C=500, 24h) 95% conv. 97% ee >99% conv. 97% ee >99% conv. 95% ee (>95% select.)

O O O CN OH

OMe

(S/C=1,000, 5h) (S/C=1,000, 24h) (S/C=1,000, 5h) >99% conv. 95% ee >99% conv. 93% ee 98% conv. 96% ee 2. Catalyst used for asymmetric H2 – hydrogenation.

O OH

H (R,R)-Ru-cat + 2 (3 MPa) R R' MeOH, 60°C R R'

O O Tech. Note (2) OH Ref. (1)

(S/C=1,000, 20h) (S/C=5,000, 18h) >99% conv. 99% ee >99% conv. 93% ee

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RUTHENIUM (Compounds) $ Price 44-0185 N-[(1R,2R)-1,2-Diphenyl-2-(2-(4-methylbenzyloxy)ethylamino)ethyl]-4-methylbenzene sulfonamide(chloro)ruthenium(II) ™ (R,R)-Ts-DENEB (cont.) 3. Catalyst used for dynamic kinetic resolution. O OH (R,R)-Ru-cat Ph + HCO2H/Et3N = 5/2 Ph (2M) Ph DMF, 60°C Ph Tech. Note (3) Ref. (1) O OH (S/C=10,000, 32h) >99% conv. (dl:meso = 97.2:2.8 >99% ee (dl) Reference: 1. J. Am. Chem.Soc., 2011, 133, 14960.

SILICON (Elemental forms) $ Price 14-0655 Silicon powder (amorphous), min. 97% [7440-21-3] 1g 99.00 1-2 micron, brown pwdr. 5g 396.00

HAZ

SILICON (Compounds) $ Price 98-4027 Silicon(IV) chloride, fiber optic grade (99.9999%-Si, 50ppm-Fe) PURATREM, 98-0147, 50g 990.00

contained in a 50 ml electropolished Swagelok® cylinder (96-1077) for CVD/ALD HAZ [10026-04-7] SiCl4; FW: 169.90; colorless liq.; m.p. -70°; b.p. 57.6°; d. 1.483 moisture sensitive 14-7015 Tri-t-butoxysilanol (99.999%-Si) PURATREM [18166-43-3] 5g 55.00 [(CH ) CO] SiOH; FW: 264.43; colorless liq. 25g 220.00 3 3 3 moisture sensitive Note: Product sold under, use subject to, terms and conditions of label license at www.strem.com/harvard1. 98-6025 Tri-t-butoxysilanol (99.999%-Si) PURATREM 14-7015 contained in 50 ml Swagelok® cylinder 25g 1270.00

(96-1070) for CVD/ALD [18166-43-3] [(CH3)3CO]3SiOH; FW: 264.43; colorless liq. moisture sensitive Note: Product sold under, use subject to, terms and conditions of label license at www.strem.com/harvard1. 14-7020 Tri-t-pentoxysilanol (99.999%-Si) PURATREM [17906-35-3] 5g 110.00 [CH CH C(CH ) O] SiOH; FW: 306.51; colorless liq. 25g 440.00 3 2 3 2 3 moisture sensitive Note: Product sold under, use subject to, terms and conditions of label license at www.strem.com/harvard1. 98-6028 Tri-t-pentoxysilanol (99.999%-Si) PURATREM 14-7020 contained in 50 ml Swagelok® 25g 1490.00

cylinder (96-1070) for CVD/ALD [17906-35-3] [CH3CH2C(CH3)2O]3SiOH; FW: 306.51; colorless liq. moisture sensitive Note: Product sold under, use subject to, terms and conditions of label license at www.strem.com/harvard1. 98-4035 Tris(dimethylamino)silane, 99+%, 14-8750, contained in 50 ml Swagelok® cylinder for 25g 754.00

CVD/ALD [15112-89-7] HAZ [(CH3)2N]3SiH; FW: 161.32; colorless to light yellow liq.; b.p. 145-148° (4°/16mm); f.p. 77°F; d. 0.84

TANTALUM (Compounds) $ Price 98-4045 t-Butylimidotris(dimethylamido)tantalum(V), min. 98%, 73-0700, contained in 50 ml 10g 1055.00 Swagelok® cylinder for CVD/ALD [69039-11-8] 25g 1715.00 C10H27N4Ta; FW: 384.30; colorless solid air sensitive, moisture sensitive Note: High temperature Swagelok® cylinder assembly 96-1071 available at extra cost. 73-1080 Tantalum(V) ethoxide (99.9999%-Ta) PURATREM [6074-84-6] 1g 50.00 Ta(OC H ) ; FW: 406.26; yellow liq.; m.p. 21°; b.p. 145°/0.1mm; f.p. 87°F; d. 1.56 5g 150.00 2 5 5 amp moisture sensitive HAZ

TIN (Compounds) $ Price 98-4052 N,N'-Di-t-butyl-2,3-diamidobutanetin(II), 98%, 50-1150, contained in 50 ml Swagelok® 5g 1986.00

cylinder for CVD/ALD [1268357-44-3] C12N26N2Sn; FW: 317.06; white to off-white pwdr. (store cold) Note: ALD Precursor. US Patent Application 61/320,069 filed April 1, 2010. Product sold under, use subject to, terms and conditions of label license at www.strem.com/harvard3.

TUNGSTEN (Compounds) $ Price

74-1830 Tris(2,2-dimethylpropyl)(2,2- (H3C)3CH2C 100mg 41.00 dimethylpropylidyne)tungsten(VI), 98% [68490-69-7] 500mg 164.00 (H3C)3CH2CWC C(CH3)3 C20H42W; FW: 466.39; yellow xtl. air sensitive, (store cold) (H3C)3CH2C

ZINC (Compounds) $ Price 98-4001 Dimethylzinc, 99%, 97-5061, contained in 50 ml Swagelok® cylinder (96-1070) for 25g 1110.00

CVD/ALD [544-97-8] HAZ Zn(CH3)2; FW: 95.44; colorless liq.; m.p. -42°; b.p. 46°; f.p. -1°F; d. 1.386 (20°) moisture sensitive, pyrophoric

98-4002 Dimethylzinc, elec. gr. (99.999%-Zn) PURATREM, 97-5060, contained in 50 ml 10g 1780.00 ® electropolished Swagelok cylinder (96-1077) for CVD/ALD [544-97-8] HAZ Zn(CH3)2; FW: 95.44; colorless liq.; m.p. -42°; b.p. 46°; f.p. -1°F; d. 1.386 (20°) moisture sensitive, pyrophoric