ChemicalBook Product Catalog Chemical Reagents Organic reagents Phosphine ligand (R)-(+)-TolBINAP

(R)-(+)-TolBINAP

(R)-(+)-TolBINAP Basic information
Reaction
Product Name:(R)-(+)-TolBINAP
Synonyms:(R)-TOL-BINAP;(R)-(+)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)1,1-BINAPHTHYL;(R)-p-tolyl-BINAP;(R)-(+)-2,2'-Bis(di-p-toL;phosphino)-1,1'-binaphthyL;(R)-(+)-2,2''-BIS(DI-P-TOLYLPHOSPHINO)-1,1''-BINAPHTHYL (R)-TOL-BINAP;PHOSPHINE, 1,1''-(1R)-[1,1''-BINAPHTHALENE]-2,2''-DIYLBIS[BIS(4-METHYLPHENYL)-;(R)-T-BINAP
CAS:99646-28-3
MF:C48H40P2
MW:678.8
EINECS:1312995-182-4
Product Categories:Chiral Phosphine;BINAP Series
Mol File:99646-28-3.mol
(R)-(+)-TolBINAP Structure
(R)-(+)-TolBINAP Chemical Properties
Melting point 255-257 °C
alpha +156° (c 0.5, C6H6)
Boiling point 754.4±60.0 °C(Predicted)
storage temp. Inert atmosphere,Room Temperature
form Powder
color White to cream
optical activity[α]20/D +162°, c = 0.5 in benzene
Water Solubility Insoluble in water.
λmax223nm(EtOH)(lit.)
CAS DataBase Reference99646-28-3(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 37/39-26
WGK Germany 3
TSCA No
HS Code 29310099
MSDS Information
ProviderLanguage
ACROS English
ALFA English
(R)-(+)-TolBINAP Usage And Synthesis
Reaction
  1. Useful ligand for palladium-catalyzed carbon-oxygen bond formation.
  2. Ligand for palladium-catalyzed α-arylation of ketones.
  3. Ligand for Cu-catalyzed asymmetric conjugate reduction.
  4. Ligand for Cu-catalyzed asymmetric dienolate addition to aldehydes.
  5. Enantioselective conjugate reduction of lactones and lactams.
  6. Ligand used in the enantioselective cycloaddition of allenylsilanes with α-Imino esters.
  7. Catalytic Aldol reaction to ketones.
  8. Ligand with rhodium catalyses [2+2+2] cycloaddition reaction of alkenes and alkynes.
  9. Ligand used in the copper-catalyzed asymmetric conjugate addition of alkyl Grignard reagents on α,β-unsaturated esters.
  10. Ligand used in the copper-catalyzed asymmetric synthesis of cyclopropanes via tandem conjugate addition and intramolecular enolate trapping. 
Reactions of 99646-28-3_1
Reactions of 99646-28-3_2
Reactions of 99646-28-3_3

Chemical PropertiesWhite to cream powder
Uses(R)-(+)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl is used as chiral catalyst ligand. (R)-T-BINAP complexes derived from rhodium precursors are used for the asymmetric hydroformylation of vinyl acetate. It is a catalysts used for reductive amination of ketones, Pt dications for cation trapping, Rh(I)-catalyst for hydrogenation of acetamidoacrylic acid derivatives.
Uses(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.
General DescriptionBINAP 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.
(S)-(-)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL (R)-(+)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHALENECHLORO(P-CYMENE)RUTHENIUM CHLORIDE (R)-(+)-2-[2-(DIPHENYLPHOSPHINO)PHENYL]-4-(1-METHYLETHYL)-4,5-DIHYDROOXAZOLE (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl DICHLORO[(R)-(+)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL]RUTHENIUM (II) (S)-(-)-2,2'-Bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl DICHLORO[(R)-(+)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL]RUTHENIUM (II) (R)-DM-BINAP R-(+)-1,2-BIS(DIPHENYLPHOSPHINO)PROPANE Dimethylammoniumdichlorotri(mu-chloro)bis[(S)-(-)-2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthyl]diruthenate(II) Chloro[(R)-(+)-2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthyl](p-cymene)ruthenium(II)chloride Diacetato[(S)-(-)-2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthyl]ruthenium(II) Dimethylammoniumdichlorotri(mu-chloro)bis[(R)-(+)-2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthyl]diruthenate(II) Diacetato[(R)-(+)-2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthyl]ruthenium(II) rac-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl ,2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL 1,1'-BINAPHTHYL Chloro[(S)-(-)-2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthyl](p-cymene)ruthenium(II)chloride RAC-2,2'-BIS(DI-O-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL, 98% RAC-TOL-BINAP
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