481084

Sigma-Aldrich

rac-BINAP

97%

Synonym(s):
2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene, (±)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene, [1,1′-Binaphthalene]-2,2′-diylbis[diphenylphosphine], (±)-BINAP
Linear Formula:
[(C6H5)2PC10H6-]2
CAS Number:
Molecular Weight:
622.67
Beilstein/REAXYS Number:
5321443
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

reaction suitability

reagent type: catalyst
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

Looking for similar products? Visit Product Comparison Guide

General description

Racemic version of BINAP.

Packaging

5, 25, 100, 500 g in glass bottle

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 Germany

WGK 3

Flash Point F

Not applicable

Flash Point C

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Organometallics, 23, 3398-3416 (2004)
Tetrahedron Letters, 47, 5079-5079 (2006)
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...
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.
Advanced Synthesis & Catalysis, 345, 15-32 (2003)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service