295817

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

97%

• Sinônimo(s): (R)-(+)-(1,1′-Binaphthalene-2,2′-diyl)bis(diphenylphosphine), (R)-(+)-BINAP
• Fórmula linear: [(C₆H₅)₂PC₁₀H₆-]₂
• Número CAS: 76189-55-4
• Peso molecular: 622.67
• Número MDL: MFCD00010805
• Código UNSPSC: 12352005
• ID de substância PubChem: 24857814
• NACRES: NA.22

Propriedades

• Nível de qualidade: 100
• Ensaio: 97%
• forma: solid
• atividade óptica: [α]19/D +233°, c = 0.3 in toluene
• pureza óptica: ee: 99% (HPLC)
• pf: 239-241 °C (lit.)
• grupo funcional: phosphine
• cadeia de caracteres SMILES: 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
• chave InChI: MUALRAIOVNYAIW-UHFFFAOYSA-N

Descrição

Descrição geral

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

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

Aplicação

Useful ligand for transition metal catalyzed asymmetric reactions, including hydrogenation and disilylation. 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.
Complex with Ag(I) used to catalyze an asymmetric aldol reaction between alkenyl trichloroacetates and aldehydes. Also used with Ag(I) to catalyze an enantioselective hetero-Diels-Alder reaction of azo compounds.

Informações de segurança

• Código de classe de armazenamento: 11 - Combustible Solids
• Classe de risco de água (WGK): WGK 3
• Ponto de fulgor (°F): Not applicable
• Ponto de fulgor (°C): Not applicable
• Equipamento de proteção individual: Eyeshields, Gloves, type N95 (US)