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ChemicalBook >  Product Catalog >  Chemical Reagents >  Organic reagents >  The polycyclic compound >  (S)-(-)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL

(S)-(-)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL

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(S)-(-)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL Basic information

Product Name:
(S)-(-)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL
Synonyms:
  • (S)-TOL-BINAP
  • (R)-TOL-BINAP
  • (S)-(-)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL
  • (R)-(+)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)1,1-BINAPHTHYL
  • (S)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-&
  • (S)-(-)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl, 98+%
  • (S)-(-)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl,98%(S)-Tol-BINAP
  • (S)-(-)-2,2''-BIS(DI-P-TOLYLPHOSPHINO)-1,1''-BINAPHTHYL (S)-TOL-BINAP
CAS:
100165-88-6
MF:
C48H40P2
MW:
678.78
EINECS:
1312995-182-4
Product Categories:
  • BINAP Series
  • Chiral Phosphine
Mol File:
100165-88-6.mol
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(S)-(-)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL Chemical Properties

Melting point:
252-256 °C
alpha 
-160° (c 0.5, C6H6)
Boiling point:
754.4±60.0 °C(Predicted)
storage temp. 
Inert atmosphere,Room Temperature
form 
Powder
color 
White
optical activity
[α]20/D -156°, c = 0.5 in benzene
Water Solubility 
Insoluble in water.
InChIKey
IOPQYDKQISFMJI-UHFFFAOYSA-N
CAS DataBase Reference
100165-88-6(CAS DataBase Reference)
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Safety Information

Risk Statements 
36/37/38
Safety Statements 
26-36/37/39
WGK Germany 
3
TSCA 
No
HS Code 
29333990

MSDS

  • Language:English Provider:ACROS
  • Language:English Provider:ALFA
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(S)-(-)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL 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 iridium-catalyzed enantioselective C-H bond activation of 2-(alkylamino)-pyridine with alkenes.
  10. Iridium-catalyzed regio-, diastereo-, and enantioselective tert-(hydroxyl)-prenylation of alcohols.
  11. Rhodium-catalyzed cross cyclotrimerization.



Chemical Properties

White powder

Uses

(S)-(-)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl is chiral ligand widely used in asymmetric synthesis. It also used as excellent catalysts for asymmetric hydrogenation of alkenes and some cyclic anhydrides. BINAP is used in organic synthesis for enantioselective transformations catalyzed by its complexes of ruthenium, rhodium, and palladium

Uses

(S)-T-BINAP reacts with silver nitrate to form (S)-Tol-BINAP·AgNO3, which can catalyze the enantioselective allylation reaction of aldehydes to form enantiopure secondary alcohols. It may be used as a chiral ligand in the palladium catalyzed asymmetric double carbohydroamination of iodoarenes to form α-aminoamides. It can also catalyze the asymmetric N-allylation reaction of ortho-tert-butylanilide derivatives with diallyl carbonate to form chiral N-allyl ortho-tert-butylanilides.

(S)-(-)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYLSupplier

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(S)-(-)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL(100165-88-6)Related Product Information