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295817 Sigma-Aldrich

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

97%

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

  • CAS Number 76189-55-4

  • Linear Formula [(C6H5)2PC10H6-]2

  • Molecular Weight 622.67

  •  MDL number MFCD00010805

  •  PubChem Substance ID 24857814

  •  NACRES NA.22

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Properties

Related Categories Asymmetric Synthesis, BINAPs, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Privileged Ligands and Complexes More...
Quality Level   100
assay   97%
optical activity   [α]19/D +233°, c = 0.3 in toluene
optical purity   ee: 99% (HPLC)
mp   239-241 °C (lit.)
SMILES string   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
InChI key   MUALRAIOVNYAIW-UHFFFAOYSA-N

Description

General description

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

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.

Packaging

1, 5 g in glass bottle

250 mg in glass insert

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

BINAP/SEGPHOS® Ligands and Complexes

Since the development of BINAP by Noyori, extensive research has been accomplished using this chiral ligand. BINAP proved to be one of the most versatile ligands, catalyzing a wide range of reactions...
William Sommer and Daniel Weibel
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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