693049

(R)-Tol-BINAP

• Synonym(s): (R)-(+)-2,2′-Bis(di-p-tolylphosphino)-1,1′-binaphthyl
• Empirical Formula (Hill Notation): C₄₈H₄₀P₂
• CAS Number: 99646-28-3
• Molecular Weight: 678.78
• MDL number: MFCD01311709
• UNSPSC Code: 12352005
• PubChem Substance ID: 329761557
• NACRES: NA.22

Properties

• form: solid
• 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: ligand; 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

Takasago Ligands and Complexes for Asymmetric Reactions

(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.

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

Legal Information

Sold in collaboration with Takasago for research purposes only.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable