Merck
All Photos(2)

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:
5321443
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

form

solid

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

Looking for similar products? Visit Product Comparison Guide

Related Categories

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

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

Susana Aguilar et al.
PloS one, 4(11), e8013-e8013 (2009-12-04)
Many common diseases of the gas exchange surface of the lung have no specific treatment but cause serious morbidity and mortality. Idiopathic Pulmonary Fibrosis (IPF) is characterized by alveolar epithelial cell injury, interstitial inflammation, fibroblast proliferation and collagen accumulation within
Leslie Ann So Alfaro et al.
Stem cells (Dayton, Ohio), 29(12), 2030-2041 (2011-10-15)
Expression of the cell surface sialomucin CD34 is common to many adult stem cell types, including muscle satellite cells. However, no clear stem cell or regeneration-related phenotype has ever been reported in mice lacking CD34, and its function on these
Synlett, 3053-3053 (2006)
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

Articles

BINAP/SEGPHOS® Ligands and Complexes

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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service