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295817

Sigma-Aldrich

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

97%

Sinônimo(s):

(R)-(+)-(1,1′-Binaphthalene-2,2′-diyl)bis(diphenylphosphine), (R)-(+)-BINAP

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About This Item

Fórmula linear:
[(C6H5)2PC10H6-]2
Número CAS:
76189-55-4
Peso molecular:
622.67
Número MDL:
MFCD00010805
Código UNSPSC:
12352005
ID de substância PubChem:
24857814
NACRES:
NA.22

Ensaio

97%

forma

solid

atividade óptica

[α]19/D +233°, c = 0.3 in toluene

pureza óptica

ee: 99% (HPLC)

pf

239-241 °C (lit.)

cadeia de caracteres 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

chave InChI

MUALRAIOVNYAIW-UHFFFAOYSA-N

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Descrição geral

(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.

Aplicação

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.

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

Eyeshields, Gloves, type N95 (US)

Certificados de análise (COA)

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Journal of Organometallic Chemistry, 692, 550-550 (2007)
Masanori Kawasaki et al.
Journal of the American Chemical Society, 128(51), 16482-16483 (2006-12-21)
This communication describes studies in which an azo hetero-Diels-Alder adduct was furnished in high regio- and enantioselectivity using azopyridine as a reagent and silver as a catalyst. The obtained hetero-Diels-Alder adduct was easily converted to the corresponding chiral 1,4-diamino alcohol.
Tetrahedron, 50, 335-335 (1994)
Sci. Synth., 1, 113-264 (2002)
(R)-& (S)-2, 2?-Bis (diphenylphosphino)-1, 1?-binaphthyl
Kitamura M, et al.
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2001)
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Artigos

BINAP/SEGPHOS® Ligands and Complexes

We present an article concerning BINAP/SEGPHOS® Ligands and Complexes.

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