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295817 Aldrich

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

97%

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

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Properties

Related Categories Asymmetric Synthesis, BINAPs, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Privileged Ligands and Complexes More...
InChI Key   MUALRAIOVNYAIW-UHFFFAOYSA-N
assay   97%
optical activity   [α]19/D +233°, c = 0.3 in toluene
optical purity   ee: 99% (HPLC)
mp   239-241 °C(lit.)

Description

Packaging

1, 5 g in glass bottle

250 mg in glass insert

Application

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.

General description

(R)-(+)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene is an axially dissymmetric bis(triaryl)phosphine ligand for asymmetric reactions.

Price and Availability

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
3
Protocols & Articles

Articles

Additional Phosphines from Sigma-Aldrich

Sigma-Aldrich offers an extended variety of phosphines utilized in C-C bond forming processes. Recent work reported by Prof. Gregory Fu and coworkers has expanded the utility of trialkylphosphines an...
ChemFiles Volume 4 Article 2
Keywords: C-C bond formation

BINAP/SEGPHOS® Ligands and Complexes

Since the development of BINAP by Noyori 20 years ago, extensive research has been accomplished using this chiral ligand. BINAP proved to be one of the most versatile ligands, catalyzing a wide range...
William Sommer and Daniel Weibel
Aldrich ChemFiles 2008, 8.2, 3.
Keywords: Addition reactions, Aminations, Arylations, Asymmetric synthesis, Building blocks, Catalysis, Cyclizations, Epoxidations, Hydrogenations, Hydrosilylations, Ligands, Reductive aminations, Sharpless Epoxidation, transformation

Peer-Reviewed Papers
15

References

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