Skip to Content
Merck
CN

481084

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]

Sign In to View Organizational & Contract Pricing.

Select a Size

About This Item

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

Key Documents

View All Documentation
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

SMILES string

P(c8ccccc8)(c7ccccc7)c1c(c6c(cc1)cccc6)c2c3c(ccc2P(c5ccccc5)c4ccccc4)cccc3

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

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

Quality Level

200

Related Categories

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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
SHBS4322
SHBS2685
0000287832
0000245206
0000245206

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Tetrahedron Letters, 47, 5079-5079 (2006)
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
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)
View All Related Papers

Articles

AdQPhos and Pd pre catalysts for alpha arylation reaction

Discover AdQPhos and its Pd pre-catalysts for selective α-arylation of diverse nucleophiles under mild aqueous conditions without hazardous solvents.

Related Content

Phosphine Ligand Application Guide

Phosphine Ligand Application Guide

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