295825

Sigma-Aldrich

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

97%

Synonym(s):
(S)-(−)-BINAP, (S)-(−)-(1,1′-Binaphthalene-2,2′-diyl)bis(diphenylphosphine)
Linear Formula:
[(C6H5)2PC10H6-]2
CAS Number:
Molecular Weight:
622.67
Beilstein/REAXYS Number:
5321443
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

assay

97%

optical activity

[α]19/D −233°, c = 0.3 in toluene

optical purity

ee: 99% (HPLC)

mp

238-240 °C (lit.)

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

InChI key

MUALRAIOVNYAIW-UHFFFAOYSA-N

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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

Packaging

250 mg in glass insert
1, 5 g in glass bottle

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Lee, C.W. Alper, H.
The Journal of Organic Chemistry, 60, 499-499 (1995)
David M Tellers et al.
Journal of the American Chemical Society, 128(51), 17063-17073 (2006-12-21)
Ruthenium complexes employing axially chiral ligands were found to be effective asymmetric hydrogenation catalysts for the reduction of alpha,beta-unsaturated ene acid 1-E to give 2, a prostaglandin D2 (PGD2) receptor antagonist. With [(S-BINAP)Ru(p-cymene)Cl2]2 (3, S-BINAP = (S)-(+)-2,2'-bis(diphenylphospino)-1,1'-binapthyl), it was discovered...
Tani, K. et al.
Organic Syntheses, 67, 33-33 (1989)
Inoue, S.-I. et al.
Journal of the American Chemical Society, 112, 4897-4897 (1990)
Kurihara, Y. et al.
Chemical & Pharmaceutical Bulletin, 42, 2357-2357 (1994)
Articles
We present an article concerning BINAP/SEGPHOS® Ligands and Complexes.
Read More

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