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1.1'-Binaphthyl-2.2'-diphemyl phosphine

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1.1'-Binaphthyl-2.2'-diphemyl phosphine Basic information
1.1'-Binaphthyl-2.2'-diphemyl phosphine Chemical Properties
  • Melting point:283-286 °C(lit.)
  • Boiling point:724.3±55.0 °C(Predicted)
  • storage temp. Keep in dark place,Inert atmosphere,Room temperature
  • form Powder
  • color White to light beige
  • Water Solubility Soluble in tetrahydrofuran, benzene and dichloromethane. Slightly soluble in ether, methanol and ethanol. Insoluble in water.
  • Sensitive Air Sensitive
  • Merck 14,1223
  • BRN 5321443
  • CAS DataBase Reference98327-87-8(CAS DataBase Reference)
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1.1'-Binaphthyl-2.2'-diphemyl phosphine Usage And Synthesis
  • Chemical Properties1.1'-Binaphthyl-2.2'-diphemyl phosphine is White to light beige powder
  • Uses
    1. racemic-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl ( (+/-)-BINAP ) is an essential role in the organic synthesis of enantioselective transformations catalyzed by the complexes of ruthenium, rhodium and palladium.
    2. It is also employed in palladium-catalyzed arylamine coupling in the preparation of demethylthiocholchines.
    3. used with Cu(II) to catalyze the addition of arylsulfonamides to styrenes and olefins.
  • ReactionsPhosphine Ligand Kit component.
    1. Useful ligand for palladium-catalyzed carbon-nitrogen bond formation.
    2. Useful ligand for rhodium-catalyzed C-C bond formation.
    3. Useful ligand for palladium-catalyzed intramolecular acylation of aryl bromides via C-H activation.
    4. Used in the preparation of Buchwald third generation precatalyst.
    5. Used in methoxy directed Rhodium migration.
    6. Used in Nickel catalyzed C-N cross-coupling reactions.
  • Purification MethodsDissolve the enantiomer in toluene, wash it with 30% aqueous NaOH, three times with H2O, dry (Na2SO4), evaporate to ~15% of its volume and add an equal volume of degassed MeOH. Collect the solid, wash it with MeOH and dry it at 80o/0.005mm for 6hours. Recrystallise it from a 1:1 mixture of toluene/EtOH to optical purity (m 241-242o) [Takaya et al. Org Synth 67 20 1989]. [Noyori & Takaya Acc Chem Res 2 3 345 1990, Kitamura et al. Org Synth 71 1 1993, Takaya et al. Org Synth 72 74 1995, Kitamura et al. J Org Chem 57 4053 1992.]
1.1'-Binaphthyl-2.2'-diphemyl phosphine Preparation Products And Raw materials
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