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693049

(R)-Tol-BINAP

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C48H40P2
CAS Number:
99646-28-3
Molecular Weight:
678.78
NACRES:
NA.22
PubChem Substance ID:
329761557
UNSPSC Code:
12352005
MDL number:
MFCD01311709
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product line

Buchwald Ligand

Quality Segment

100

form

solid

optical activity

[α]20/D +162°, c = 0.5 in benzene

reaction suitability

reaction type: Asymmetric synthesis, 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, reagent type: ligand
reaction type: Noyori Asymmetric Hydrogenation

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

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

Legal Information

Sold in collaboration with Takasago for research purposes only.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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