295825

(S)-(−)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene

97%

• Synonym(s): (S)-(−)-(1,1′-Binaphthalene-2,2′-diyl)bis(diphenylphosphine), (S)-(−)-BINAP
• Linear Formula: [(C₆H₅)₂PC₁₀H₆-]₂
• CAS Number: 76189-56-5
• Molecular Weight: 622.67
• Beilstein: 5321443
• MDL number: MFCD00010805
• PubChem Substance ID: 24857815
• NACRES: NA.22

Properties

• Assay: 97%
• form: solid
• optical activity: [α]19/D −233°, c = 0.3 in toluene
• optical purity: ee: 99% (HPLC)
• mp: 238-240 °C (lit.)
• 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

Application

2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl and its rhodium and ruthenium derivatives are highly selective homogeneous catalysts used for the reduction of aryl ketones, β-keto esters, and α-amino ketones. They have also been used for asymmetric hydrogenation and hydroformylation of olefins, asymmetric Heck reactions, and asymmetric isomerizations of allyls.
Ligand used in a palladium-catalyzed, asymmetric, tandem Heck reaction-carbanion capture process leading to a synthesis of a tricyclic sesquiterpene. Also used in a ruthenium-catalyzed asymmetric hydrogenation of α,β-unsaturated acids.

Reactant involved in:

• Enantioselective and diastereoselective unpoled carbonyl allylation
• Syntehsis of organophophine oxides as anittumor agents
• SN2 halogenation of hydroxy groups
• Synthesis of BINAP complexes
• Studies of conformational flexibility of BINAP chelates

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