295817

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

97%

• Synonyme(s) : (R)-(+)-BINAP
• Formule linéaire : [(C₆H₅)₂PC₁₀H₆-]₂
• Numéro CAS: 76189-55-4
• Poids moléculaire : 622.67
• Numéro MDL: MFCD00010805
• Code UNSPSC : 12352005
• ID de substance PubChem : 24857814
• Nomenclature NACRES : NA.22

Propriétés

• Niveau de qualité: 100
• Pureté: 97%
• Forme: solid
• Activité optique: [α]19/D +233°, c = 0.3 in toluene
• Pureté optique: ee: 99% (HPLC)
• Pf: 239-241 °C (lit.)
• Groupe fonctionnel: phosphine
• Chaîne 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
• Clé InChI: MUALRAIOVNYAIW-UHFFFAOYSA-N

Description

Description générale

(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.

Application

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.

Informations sur la sécurité

• Code de la classe de stockage: 11 - Combustible Solids
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable
• Équipement de protection individuelle: Eyeshields, Gloves, type N95 (US)