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693049 Sigma-Aldrich

(R)-Tol-BINAP

Synonym: (R)-(+)-2,2′-Bis(di-p-tolylphosphino)-1,1′-binaphthyl

  • CAS Number 99646-28-3

  • Empirical Formula (Hill Notation) C48H40P2

  • Molecular Weight 678.78

  •  MDL number MFCD01311709

  •  PubChem Substance ID 329761557

  •  NACRES NA.22

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Properties

Related Categories Asymmetric Synthesis, BINAPs, Buchwald Ligands and Complexes, Buchwald and Related Ligands, Catalysis and Inorganic Chemistry,
Quality Level   100
optical activity   [α]20/D +162°, c = 0.5 in benzene
reaction suitability   reaction type: Buchwald-Hartwig Cross Coupling Reaction
  reaction type: Heck Reaction
  reaction type: Hiyama Coupling
  reaction type: Negishi Coupling
  reaction type: Sonogashira Coupling
  reaction type: Stille Coupling
  reaction type: Suzuki-Miyaura Coupling
  reagent type: catalyst
reaction type: Cross Couplings
mp   254-258 °C
functional group   phosphine
SMILES string   Cc1ccc(cc1)P(c2ccc(C)cc2)c3ccc4ccccc4c3-c5c(ccc6ccccc56)P(c7ccc(C)cc7)c8ccc(C)cc8
InChI   1S/C48H40P2/c1-33-13-23-39(24-14-33)49(40-25-15-34(2)16-26-40)45-31-21-37-9-5-7-11-43(37)47(45)48-44-12-8-6-10-38(44)22-32-46(48)50(41-27-17-35(3)18-28-41)42-29-19-36(4)20-30-42/h5-32H,1-4H3
InChI key   IOPQYDKQISFMJI-UHFFFAOYSA-N

Description

General description

BINAP is based on a bis naphthalene backbone with different phosphine derivatives. 2,2′-bis(di-p-tolylphosphino)-1,1′-binaphthyl (p-Tol-BINAP)·AgF complex catalyzed asymmetric Mukaiyama-type aldol reaction is reported.

Application

(R)-T-BINAP complexes derived from rhodium precursors are used for the asymmetric hydroformylation of vinyl acetate. It may be employed as chiral catalyst for allylation of N-tosyl α-imino esters.

Takasago Ligands and Complexes for Asymmetric Reactions

Catalyst involved in studies of the role of excess phosphine ligand in enantioselective conjugate addition of ethylmagnesium bromide and α,β-unsaturated ester

Reactant serving as a precursor for:
• Catalysts used for reductive amination of ketones
• Rh(I)-catalyst for hydrogenation of acetamidoacrylic acid derivatives
• Chiral platinum catalysts for asymmetric Baeyer-Villiger oxidation of cyclic ketones
• CuI-Tol-BINAP catalysts for enantioselective Michael reactions of Grignard reagents to unsaturated esters
• BINAP Pt Dications for cation trapping

Packaging

100, 500 mg in amber glass bottle

Legal Information

Sold in collaboration with Takasago for research purposes only.

Safety & Documentation

Safety Information

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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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

Baeyer-Villiger Oxidation Reaction

The Baeyer–Villiger reaction involves the oxidation of ketones to esters by C-C bond cleavage of the carbonyl group and the introduction of an oxygen atom adjacent to it.1 This reaction can be accomp...
Keywords: Asymmetric synthesis, Catalysis, Oxidations

Takasago Ligands and Complexes for Asymmetric Reactions

The quest to find chiral catalysts capable of achieving high enantiomeric excess for a variety of asymmetric transformations has been an ongoing endeavor for the past 40 years. One of the most releva...
Keywords: Addition reactions, Arylations, Asymmetric synthesis, Catalysis, Hydrogenations, Ligands, transformation

Related Content

Takasago Ligands - Advantages and Applications

Introduction The quest to find chiral catalysts capable of achieving high enantiomeric excess for a variety of asymmetric transformations has been an ongoing endeavor for the past 40 years. One of th...
Keywords: Addition reactions, Arylations, Asymmetric synthesis, Building blocks, Catalysis, Epoxidations, Hydrogenations, Hydrosilylations, Ligands, Sharpless Epoxidation, transformation

Peer-Reviewed Papers
15

References

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