295817

(R)-(+)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene

97%

• Synonym(s): (R)-(+)-(1,1′-Binaphthalene-2,2′-diyl)bis(diphenylphosphine), (R)-(+)-BINAP
• Linear Formula: [(C₆H₅)₂PC₁₀H₆-]₂
• CAS Number: 76189-55-4
• Molecular Weight: 622.67
• MDL number: MFCD00010805
• UNSPSC Code: 12352005
• PubChem Substance ID: 24857814
• 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: 239-241 °C (lit.)
• functional group: phosphine
• SMILES string: c1ccc(cc1)P(c2ccccc2)c3ccc4ccccc4c3-c5c(ccc6ccccc56)P(c7ccccc7)c8ccccc8
• 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

(R)-(+)-BINAP is a chiral diphosphine ligand that exhibits high enantioselectivity and reactivity in various organic reactions.[1]

(R)-(+)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene is an axially dissymmetric bis(triaryl)phosphine ligand for asymmetric reactions.[2]

Application

Useful ligand for transition metal catalyzed asymmetric reactions, including hydrogenation[3] and disilylation.[4] 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,[5] β-keto esters,[6] and α-amino ketones.[7] They have also been used for asymmetric hydrogenation[8] and hydroformylation of olefins,[9] asymmetric Heck reactions,[10] and asymmetric isomerizations of allyls.[11][12]
Complex with Ag(I) used to catalyze an asymmetric aldol reaction between alkenyl trichloroacetates and aldehydes.[13] Also used with Ag(I) to catalyze an enantioselective hetero-Diels-Alder reaction of azo compounds.[14]

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)