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]
• 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

Properties

• Quality Level: 200
• 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
• 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

Description

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.

Safety Information

• 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