295825

(S)-(−)-2,2′-Bis(diphenylphosphin)-1,1′-binaphthalin

97%

• Synonym(e): (S)-(−)-1,1′-Binaphthalin-2,2′-diyl-bis-(diphenylphosphin), (S)-(−)-BINAP
• Lineare Formel: [(C₆H₅)₂PC₁₀H₆-]₂
• CAS-Nummer: 76189-56-5
• Molekulargewicht: 622.67
• Beilstein: 5321443
• MDL-Nummer: MFCD00010805
• UNSPSC-Code: 12352005
• PubChem Substanz-ID: 24857815
• NACRES: NA.22

Eigenschaften

• Qualitätsniveau: 100
• Assay: 97%
• Form: solid
• Optische Aktivität: [α]19/D −233°, c = 0.3 in toluene
• Optische Reinheit: ee: 99% (HPLC)
• mp (Schmelzpunkt): 238-240 °C (lit.)
• Funktionelle Gruppe: phosphine
• 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
• InChIKey: MUALRAIOVNYAIW-UHFFFAOYSA-N

Beschreibung

Anwendung

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

Sicherheitshinweise

• Lagerklassenschlüssel: 11 - Combustible Solids
• WGK: WGK 3
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable
• Persönliche Schutzausrüstung: Eyeshields, Gloves, type N95 (US)