295817

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

97%

• Sinonimo/i: (R)-(+)-BINAP
• Formula condensata: [(C₆H₅)₂PC₁₀H₆-]₂
• Numero CAS: 76189-55-4
• Peso molecolare: 622.67
• Numero MDL: MFCD00010805
• Codice UNSPSC: 12352005
• ID PubChem: 24857814
• NACRES: NA.22

Proprietà

• Livello qualitativo: 100
• Saggio: 97%
• Forma fisica: solid
• Attività ottica: [α]19/D +233°, c = 0.3 in toluene
• Purezza ottica: ee: 99% (HPLC)
• Punto di fusione: 239-241 °C (lit.)
• Gruppo funzionale: phosphine
• Stringa SMILE: 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; MUALRAIOVNYAIW-UHFFFAOYSA-N

Descrizione

Descrizione generale

(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.

Applicazioni

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.

Informazioni sulla sicurezza

• Codice della classe di stoccaggio: 11 - Combustible Solids
• Classe di pericolosità dell'acqua (WGK): WGK 3
• Punto d’infiammabilità (°F): Not applicable
• Punto d’infiammabilità (°C): Not applicable
• Dispositivi di protezione individuale: Eyeshields, Gloves, type N95 (US)