ChemicalBook Product Catalog Chemical Reagents Organic reagents Phosphine ligand (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl

(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl

(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl Basic information
Reaction
Product Name:(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl
Synonyms:(R)-(+)-BINAP, (R)-(+)-1,1'-Binaphthalene-2,2'-diylbis(diphenylphosphane);(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthalene 97%;(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl;R(+)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHALENE;(R)-(+)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL;(R)-(+)-2,2BIS(DIPHENYLPHOSPHINO)-1,1-BINAPHTHYL;(R)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL;(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl,(R)-BINAP
CAS:76189-55-4
MF:C44H32P2
MW:622.69
EINECS:616-304-7
Product Categories:Asymmetric Synthesis;Phosphine Ligands;Synthetic Organic Chemistry;Adamantanes;B (Classes of Boron Compounds);Ligands;N-Heterocyclic Carbene Ligands;Tetrafluoroborates;Peptide;Chiral Compound;Chiral Reagents;chiral;BINAP Series;Chiral Phosphine;Biphenyl derivatives;Aromatics;Catalyst
Mol File:76189-55-4.mol
(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl Structure
(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl Chemical Properties
Melting point 283-286 °C(lit.)
Boiling point 724.3±55.0 °C(Predicted)
alpha 240 º (c=0.3, toluene)
refractive index 235 ° (C=0.3, Toluene)
storage temp. Inert atmosphere,Room Temperature
solubility Benzene (Slightly), Chloroform (Slightly)
form Powder
color White to cream-white
optical activity[α]20/D +222°, c = 0.5% in benzene
Water Solubility insoluble
Sensitive Air Sensitive
Merck 14,1223
BRN 4914063
CAS DataBase Reference76189-55-4(CAS DataBase Reference)
Safety Information
Hazard Codes Xi,Xn
Risk Statements 36/37/38-20/21/22
Safety Statements 22-24/25-37/39-26-36
WGK Germany 3
F 8-10-23
TSCA No
HS Code 29319090
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl Usage And Synthesis
Reaction
  1. (R)-BINAP or (R)-Tol-BINAP can be combined with dichloro(1,5-cyclooctadiene)ruthenium to form precursors to NOYORI CATALYST SYSTEMS. These systems exhibit very high catalytic activity and enantioselectivity in the hydrogenation of a wide range of substrates. NOYORI CATALYST SYSTEMS have been shown to effect highly enantioselective hydrogenation of functionalized ketones where the substituents are dialkylamino, hydroxy, siloxy, carbonyl, ester, amide or thioester.
  2. Useful ligand in asymmetric Heck processes.
  3. Ligand employed in palladium-catalyzed asymmetric arylation of ketones.
  4. Ligand employed in rhodium-catalyzed 1,4-additions to enones.
  5. Ligand employed in palladium-catalyzed hydroamination of styrene derivatives.
  6. Ligand employed in silver-catalyzed asymmetric Sakuri-Hosomi allylation and Mukaiyama aldol reaction.
  7. Ligand employed in rhodium-catalyzed kinetic resolution of enynes.
  8. Ligand employed in asymmetric rhodium-catalyzed hydroboration of cyclopropenes.
  9. Ligand employed in silver-catalyzed a-hydroxylation of stannyl enol ethers.
  10. Ligand employed in palladium-catalyzed synthesis of chiral allenes.
  11. Ligand for palladium-catalyzed enantioselective hetero Michael addition to form b-amino acid derivatives.
  12. Ligand employed in rhodium-catalyzed asymmetric rearrangement of alkynyl alkenyl carbinols.
  13. Ligand employed in rhodium-catalyzed 1,2-addition of aluminium organyl compounds to cyclic enones.
  14. Ligand employed in iridium-catalyzed transfer hydrogenative allylation of benzylic alcohols.
  15. Ligand employed in rhodium-catalyzed asymmetric C-Si bond formation by conjugate silyl transfer using a Si-B linkage.
  16. Ligand employed in the iridium-catalyzed asymmetric cyclopropane-mediated carbonyl allylation of primary alcohols.
  17. Ligand employed in the nickel-catalyzed asymmetric α-arylation of tetralones.
  18. Ligand employed in the copper-catalyzed asymmetric propargylation of ketones.
  19. Ligand employed in the cobalt-catalyzed asymmetric reductive coupling of alkynes with alkenes.
  20. Ligand employed in the rhodium-catalyzed asymmetric 1,4-addition of arylalanes on trisubstituted enones.
  21. Ruthenium-catalyzed asymmetric hydrocyanation of imines.
  22. Palladium-catalyzed asymmetric intermolecular cyclization.
Reactions of 76189-55-4_1
Reactions of 76189-55-4_2
Reactions of 76189-55-4_3
Reactions of 76189-55-4_4
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Reactions of 76189-55-4_6




Chemical Propertieswhite to light yellow crystal powde
UsesUseful ligand for transition metal catalyzed asymmetric reactions, including hydrogenation and disilylation. 2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl and its rhodium and ruthenium derivatives are highly selective homogeneous catalysts used for the reduction of aryl ketones, β-keto esters, and α-amino ketones. They have also been used for asymmetric hydrogenation and hydroformylation of olefins, asymmetric Heck reactions, and asymmetric isomerizations of allyls.
Complex with Ag(I) used to catalyze an asymmetric aldol reaction between alkenyl trichloroacetates and aldehydes. Also used with Ag(I) to catalyze an enantioselective hetero-Diels-Alder reaction of azo compounds.
UsesChiral ligand for metal mediated asymmetric catalysis.
General Description(R)-(+)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene is an axially dissymmetric bis(triaryl)phosphine ligand for asymmetric reactions.
(R)-(+)-2,2'-BIS[BIS(3,5-DITRIFLUOROMETHYLPHENYL)PHOSPHINO]-1,1'-BINAPHTHYL HYDROXY[(S)-BINAP]RHODIUM(I) DIMER Chloro[(R)-(+)-2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthyl](p-cymene)ruthenium(II)chloride Phenformin hydrochloride BIS((R)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1' -BINAPHTHYL)RHODIUM(I) PERCHLORATE, 96,BIS((R)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1' -BINAPHTHYL)RHODIUM(I) PERCHLORATE, 96% DICHLORO[(S)-2,2'-BIS-(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL]RUTHENIUM(II) HOMOPOLYMER,DICHLORO[(S)-(-)-,2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL]RUTHENIUM (II) Dichloro[(S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl][(1R,2R)-(+)-1,2-diphenylethylenediamine]ruthenium(II) Dichloro[(R)-(+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl][(2R)-(-)-1,1-bis(4-methoxyphenyl)-3-methyl-1,2-butanediam] Dichloro[(r)-(+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl][(1r,2r)-(+)-1,2-diphenylethylenediamine]ruthenium(ii)min [RAC-2,2'-BIS-(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL]-CHLORO-(P-CYMENE)-RUTHENIUMCHLORIDE DICHLORO[(S)-(-)-,2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL]RUTHENIUM (II),DICHLORO[(S)-2,2'-BIS-(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL]RUTHENIUM(II) HOMOPOLYMER Chloro{(R)-(+)-2,2'-bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl}(p-cymene)ruthenium(II)chloride N-(Carboxymethyl)-N-(phosphonomethyl)-glycine Diacetato[(S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl]ruthenium(II) [(R)-(+)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL]PALLADIUM(II) CHLORIDE,[(S)-(+)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL]PALLADIUM(II)CHLORIDE 2,2'-BIS[BIS(3,5-DITRIFLUOROMETHYLPHENYL)PHOSPHINO]-1,1'-BINAPHTHYL 2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL RACEMIC [(S)-(-)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL](1,5-CYCLOOCTADIENE)RHODIUM(I) PERCHLORATE
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