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2-Diphenylphosphino-2'-(N,N-dimethylamino)biphenyl

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2-Diphenylphosphino-2'-(N,N-dimethylamino)biphenyl Basic information

Product Name:
2-Diphenylphosphino-2'-(N,N-dimethylamino)biphenyl
Synonyms:
  • 2-DIMETHYLAMINO-2'-(DIPHENYLPHOSPHINO)BIPHENYL
  • 2-(DIPHENYLPHOSPHINO)-2'-(N,N-DIMETHYLAMINO)BIPHENYL
  • 2-Diphenylphosphino-2
  • PhDave-Phos 97%
  • PhDavePhos
  • 2-Diphenylphosphino-2'-(N,N-dimethylamino)biphenyl,98%
  • (N,N-DIMETHYLAMINO)BIPHENYL
  • [1,1''-BIPHENYL]-2-AMINE, 2''-(DIPHENYLPHOSPHINO)-N,N-DIMETHYL-
CAS:
240417-00-9
MF:
C26H24NP
MW:
381.45
EINECS:
607-309-5
Product Categories:
  • Achiral Phosphine
  • Aryl Phosphine
  • Buchwald Ligands Series
  • Buchwald Ligands&Precatalysts
  • Biphenyl & Diphenyl ether
  • Phosphines
Mol File:
240417-00-9.mol
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2-Diphenylphosphino-2'-(N,N-dimethylamino)biphenyl Chemical Properties

Melting point:
126-128 °C
Boiling point:
514.6±43.0 °C(Predicted)
storage temp. 
Inert atmosphere,Room Temperature
pka
4.96±0.18(Predicted)
form 
Powder, Crystals, Crystalline Powder and/or Chunks
color 
White to yellow
Water Solubility 
insoluble
InChIKey
JGFXUYLYPITYGR-UHFFFAOYSA-N
CAS DataBase Reference
240417-00-9
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
37/39-26-36/37/39
WGK Germany 
3
TSCA 
No
HazardClass 
IRRITANT
HS Code 
29310099

MSDS

  • Language:English Provider:ACROS
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2-Diphenylphosphino-2'-(N,N-dimethylamino)biphenyl Usage And Synthesis

Reaction

  1. Useful ligand for sterically hindered substrates in the Pd-catalyzed amination reactions of aryl bromides.
  2. Ligand used for the Cu-catalyzed phosphorylation of alcohols.
  3. Ligand for Pd-catalyzed C-H benzylation.
  4. Ligand for palladium-catalyzed [4 + 2] benzannulation reaction.

Chemical Properties

white to yellow powder, crystals, crystalline

Uses

suzuki reaction

reaction suitability

reaction type: Cross Couplings
reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction
reagent type: ligand
reaction type: C-C Bond Formation

Synthesis

119326-02-2

15475-27-1

240417-00-9

The compound (CAS:119326-02-2) (29.6 mg, 0.0510 mmol) was transferred to an argon protected 10 mL Schlenk flask. The flask was evacuated and filled with argon three times to remove air. Subsequently, anhydrous THF (3.0 mL) was added using a syringe under argon atmosphere. A THF solution (0.46 mL, 0.23 mmol) of 0.5 M LiPPh2 was slowly added dropwise under stirring for a controlled time of 5 min. During the reaction, the color of the mixture changed from yellow to dark red and finally to dark yellow. The reaction mixture was stirred under argon protection at room temperature for 18 hours. After completion of the reaction, the solvent was removed using a rotary evaporator. The crude product was dissolved in dichloromethane (0.5 mL) and purified by preparative thin layer chromatography (silica gel, unfolding reagent was benzene:acetone=10:1). The final isolation afforded the target product (S)-2-diphenylphosphino-2'-(N,N-dimethylamino)biphenyl as a light yellow liquid in 46% yield (15.6 mg).

References

[1] Journal of Organometallic Chemistry, 2013, vol. 745-746, p. 356 - 362

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