295825

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

97%

• Synonyme(s) : (S)-(−)-(1,1′-Binaphthalene-2,2′-diyl)bis(diphenylphosphine), (S)-(−)-BINAP
• Formule linéaire : [(C₆H₅)₂PC₁₀H₆-]₂
• Numéro CAS: 76189-56-5
• Poids moléculaire : 622.67
• Beilstein: 5321443
• Numéro MDL: MFCD00010805
• Code UNSPSC : 12352005
• ID de substance PubChem : 24857815
• Nomenclature NACRES : NA.22

Propriétés

• Niveau de qualité: 100
• Essai: 97%
• Forme: solid
• Activité optique: [α]19/D −233°, c = 0.3 in toluene
• Pureté optique: ee: 99% (HPLC)
• Pf: 238-240 °C (lit.)
• Groupe fonctionnel: phosphine
• Chaîne SMILES: 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
• Clé InChI: 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

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)