295817

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

97%

• Synonim(y): (R)-(+)-(1,1′-Binaphthalene-2,2′-diyl)bis(diphenylphosphine), (R)-(+)-BINAP
• Wzór liniowy: [(C₆H₅)₂PC₁₀H₆-]₂
• Numer CAS: 76189-55-4
• Masa cząsteczkowa: 622.67
• Numer MDL: MFCD00010805
• Kod UNSPSC: 12352005
• Identyfikator substancji w PubChem: 24857814
• NACRES: NA.22

Właściwości

• Poziom jakości: 100
• Próba: 97%
• Postać: solid
• aktywność optyczna: [α]19/D +233°, c = 0.3 in toluene
• czystość optyczna: ee: 99% (HPLC)
• mp: 239-241 °C (lit.)
• ciąg 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
• Klucz InChI: MUALRAIOVNYAIW-UHFFFAOYSA-N

Opis

Opis ogólny

(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.

Zastosowanie

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.

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Informacja o środkach bezpieczeństwa

• Kod klasy składowania: 11 - Combustible Solids
• Klasa zagrożenia wodnego (WGK): WGK 3
• Temperatura zapłonu (°F): Not applicable
• Temperatura zapłonu (°C): Not applicable
• Środki ochrony indywidualnej: Eyeshields, Gloves, type N95 (US)