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295825 Sigma-Aldrich

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

97%

Synonym: (S)-(−)-(1,1′-Binaphthalene-2,2′-diyl)bis(diphenylphosphine), (S)-(−)-BINAP

  • CAS Number 76189-56-5

  • Linear Formula [(C6H5)2PC10H6-]2

  • Molecular Weight 622.67

  •  Beilstein/REAXYS Number 5321443

  •  MDL number MFCD00010805

  •  PubChem Substance ID 24857815

  •  NACRES NA.22

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Properties

Related Categories Asymmetric Synthesis, BINAPs, Chemical Synthesis, Chemicals for the synthesis of candidate COVID-19 treatments, Chiral Catalysts, Ligands, and Reagents,
Quality Level   100
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

Description

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

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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