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(S)-(-)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl

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(S)-(-)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl manufacturers
(S)-(-)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl Basic information
Reaction
Product Name:(S)-(-)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl
Synonyms:(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;(S)-(-)-2,2''-Bis-[bis-(p-tolylphosphino)]-1,1''-binaphthyl;PHOSPHINE, 1,1''-(1S)-[1,1''-BINAPHTHALENE]-2,2''-DIYLBIS[1,1-BIS(4-METHYLPHENYL)-;(S)-T-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
(S)-(-)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl Structure
(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 Rotation[α]20/D -156°, c = 0.5 in benzene
Water Solubility Insoluble in water.
InChIKeyIOPQYDKQISFMJI-UHFFFAOYSA-N
SMILESP(C1C=CC(C)=CC=1)(C1C=CC(C)=CC=1)C1C=CC2=CC=CC=C2C=1C1C2=CC=CC=C2C=CC=1P(C1C=CC(C)=CC=1)C1C=CC(C)=CC=1
CAS DataBase Reference100165-88-6(CAS DataBase Reference)
Safety Information
Risk Statements 36/37/38
Safety Statements 26-36/37/39
WGK Germany 3
TSCA No
HS Code 29333990
Storage Class11 - Combustible Solids
MSDS Information
ProviderLanguage
ACROS English
ALFA English
(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.
Reactions of 100165-88-6_1
Reactions of 100165-88-6_2
Reactions of 100165-88-6_3
Reactions of 100165-88-6_4
Chemical PropertiesWhite powder
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.
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
Tag:(S)-(-)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl(100165-88-6) Related Product Information
(R)-(+)-TolBINAP Bis(diphenylphosphino)methane 1,1'-Binaphthyl (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl Chloro[(S)-(-)-2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthyl](p-cymene)ruthenium(II)chloride (S)-(-)-2,2'-Bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl (S)-(-)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl 2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl Dichloro{(S)-(-)-2,2'-bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl}[(1S,2S)-(-)-1,2-diphenylethylenediamine]ruthenium(II) Dimethylammoniumdichlorotri(mu-chloro)bis[(S)-(-)-2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthyl]diruthenate(II) Diacetato{(S)-(-)-2,2'-bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl}ruthenium(II) Chloro{(R)-(+)-2,2'-bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl}(p-cymene)ruthenium(II)chloride Dichloro{(R)-(+)-2,2'-bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl}[(2R)-(-)-1,1-bis(4-methoxyphenyl)-3-methyl-1,2-butanediamine]ruthenium(II) Dichloro{(S)-(-)-2,2'-bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl}[(2S)-(+)-1,1-bis(4-methoxyphenyl)-3-methyl-1,2-butanediamine]ruthenium(II) Diacetato[(S)-(-)-2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthyl]ruthenium(II) Dichloro{(R)-(+)-2,2'-bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl}[(1R,2R)-(+)-1,2-diphenylethylenediamine]ruthenium(II) Chloro[(R)-(+)-2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthyl](p-cymene)ruthenium(II)chloride Diacetato[(R)-(+)-2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthyl]ruthenium(II)