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481084

Sigma-Aldrich

rac-BINAP

97%

Synonym(s):

(±)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene, 2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene, (±)-BINAP, [1,1′-Binaphthalene]-2,2′-diylbis[diphenylphosphine]

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About This Item

Linear Formula:
[(C6H5)2PC10H6-]2
CAS Number:
98327-87-8
Molecular Weight:
622.67
Beilstein:
5321443
MDL number:
MFCD00010805
UNSPSC Code:
12352005
PubChem Substance ID:
24871738
NACRES:
NA.22

Assay

97%

reaction suitability

reaction type: Cross Couplings
reagent type: ligand
reaction type: Acylations
reagent type: ligand
reaction type: Arylations
reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction
reagent type: ligand
reaction type: C-C Bond Formation
reagent type: ligand
reaction type: Decarboxylations
reagent type: ligand
reaction type: Stille Coupling

mp

283-286 °C (lit.)

functional group

phosphine

InChI

1S/C44H32P2/c1-5-19-35(20-6-1)45(36-21-7-2-8-22-36)41-31-29-33-17-13-15-27-39(33)43(41)44-40-28-16-14-18-34(40)30-32-42(44)46(37-23-9-3-10-24-37)38-25-11-4-12-26-38/h1-32H

InChI key

MUALRAIOVNYAIW-UHFFFAOYSA-N

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General description

Racemic version of BINAP.

Application

Ligand employed in a palladium-catalyzed arylamine coupling in the preparation of demethylthiocholchines. Used with Cu (II) to catalyze addition of arylsulfonamides to styrenes and olefins. Amination of terpyridines with Pd catalysis.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Tetrahedron Letters, 47, 5079-5079 (2006)
Advanced Synthesis & Catalysis, 345, 15-32 (2003)
Jason G Taylor et al.
Organic letters, 8(16), 3561-3564 (2006-07-28)
[reaction: see text] Regioselective additions of arylsulfonamides to vinylarenes, norbornene, and cyclohexadiene were achieved using a copper-diphosphine catayst under mild reaction conditions. These processes appear to be ligand-accelerated.
Organometallics, 23, 3398-3416 (2004)
Akira Sakakura et al.
Nature protocols, 2(7), 1746-1751 (2007-07-21)
A protocol for ester condensation between equimolar amounts of carboxylic acids and alcohols catalyzed by bulky diarylammonium pentafluorobenzenesulfonate is described. We also present procedures for the synthesis of N-(2,6-diisopropylphenyl)-N-mesitylammonium pentafluorobenzenesulfonate. The present ester condensation proceeds well under mild conditions even
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