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1.1'-Binaphthyl-2.2'-diphemyl phosphine

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1.1'-Binaphthyl-2.2'-diphemyl phosphine Basic information

Product Name:
1.1'-Binaphthyl-2.2'-diphemyl phosphine
Synonyms:
  • BINAP, 1,1'-Binaphthalene-2,2'-diylbis(diphenylphosphane)
  • 2,2'-Bis(diphenylphosphino)-1,1'-dinaphthalene
  • 2,2-Bis-(diphenylphosphino)-1,1-napthalene
  • 2,2'-Bis(diphenylphosphino)-1,1'-binaphthalene 97%
  • 2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl Synonyms (+/-)-BINAP
  • rac-BINAP 97%
  • (+/-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl In stock Factory
  • rac-BINAP / racemic-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl
CAS:
98327-87-8
MF:
C44H32P2
MW:
622.67
EINECS:
619-338-0
Product Categories:
  • Achiral Phosphine
  • Aryl Phosphine
  • -
  • Phosphines
  • API intermediates
  • BINAP Series
Mol File:
98327-87-8.mol
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1.1'-Binaphthyl-2.2'-diphemyl phosphine Chemical Properties

Melting point:
283-286 °C(lit.)
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
InChIKey
MUALRAIOVNYAIW-UHFFFAOYSA-N
CAS DataBase Reference
98327-87-8(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
22-24/25-37/39-26
WGK Germany 
3
8-10-23
TSCA 
No
HS Code 
29319090

MSDS

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1.1'-Binaphthyl-2.2'-diphemyl phosphine Usage And Synthesis

Chemical Properties

1.1'-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.

Reactions

Phosphine 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 Methods

Dissolve 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 phosphineSupplier

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