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2-(Di-tert-butylphosphino)biphenyl

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2-(Di-tert-butylphosphino)biphenyl Basic information

Product Name:
2-(Di-tert-butylphosphino)biphenyl
Synonyms:
  • (2-biphenyl)di-tert-butylphosphine
  • (2-BIPHENYLYL)DI-TERT-BUTYLPHOSPHINE
  • 2-(DI-TERT-BUTYLPHOSPHINO)BIPHENYL
  • 2-(DI-T-BUTYLPHOSPHINO)BIPHENYL
  • BIPHENYL-2-YL-DI-TERT-BUTYL-PHOSPHANE
  • 2-(Di-t-butylphosphino)biphenyl,99%JohnPhos
  • 2-(Di-t-butylphosphine) biphenyl
  • PHOSPHINE, [1,1''-BIPHENYL]-2-YLBIS(1,1-DIMETHYLETHYL)-
CAS:
224311-51-7
MF:
C20H27P
MW:
298.4
EINECS:
607-074-9
Product Categories:
  • Achiral Phosphine
  • Aryl Phosphine
  • Buchwald Ligands Series
  • Buchwald Ligands&Precatalysts
  • organophosphine ligand
  • Ligand
  • Benzene derivatives
  • Phosphines
  • Phosphine Ligands
  • Synthetic Organic Chemistry
Mol File:
224311-51-7.mol
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2-(Di-tert-butylphosphino)biphenyl Chemical Properties

Melting point:
86-88 °C (lit.)
Boiling point:
405.5±24.0 °C(Predicted)
Density 
1 g/cm3
storage temp. 
Inert atmosphere,Room Temperature
solubility 
Chloroform (Slightly), Dichloromethane (Slightly), DMSO (Slightly, Heated, Sonicated)
form 
Crystals or Crystalline Powder
color 
White
Water Solubility 
Insoluble
BRN 
8322131
Stability:
Air Sensitive
InChI
InChI=1S/C20H27P/c1-19(2,3)21(20(4,5)6)18-15-11-10-14-17(18)16-12-8-7-9-13-16/h7-15H,1-6H3
InChIKey
CNXMDTWQWLGCPE-UHFFFAOYSA-N
SMILES
P(C1=CC=CC=C1C1=CC=CC=C1)(C(C)(C)C)C(C)(C)C
CAS DataBase Reference
224311-51-7(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xn
Risk Statements 
36/37/38-22
Safety Statements 
36/37/39-26-22
WGK Germany 
3
F 
10-23
TSCA 
No
HazardClass 
AIR SENSITIVE
HS Code 
29029090

MSDS

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2-(Di-tert-butylphosphino)biphenyl Usage And Synthesis

Reactions

  1. Ligand used in the palladium-catalyzed synthesis of aromatic amines from aryl chlorides, bromides and triflates.
  2. Ligand employed in a very active and general catalyst for Suzuki coupling reactions using aryl chlorides, bromides and triflates.
  3. Ligand used in palladium-catalyzed synthesis of oxindoles from α-chloroacetanilides.
  4. Effective ligand used in palladium-catalyzed arylation of thiazoles.
  5. Used in the formation of 2-benzylindolines via sequential palladium-catalyzed N-arylation/cyclization/C-arylation.
  6. Selective in the palladium-catalyzed arylation of silyl enol ethers formed from copper-catalyzed reduction of enones.

Chemical Properties

white to light yellow crystal powde

Uses

suzuki reaction

Uses

2-(Di-tert-butylphosphino)biphenyl (also known as JohnPhos) is a Buchwald ligand that is highly efficient in palladium-catalyzed reactions.

General Description

JohnPhos is a Buchwald′s sterically bulky biaryl phosphine ligand. It is a reactive dialkylbiaryl phosphine ligand which catalyzes the carbon-nitrogen bond-forming reactions. Coordination chemistry of gold catalysts bearing JohnPhos as ligand has been investigated by NMR spectroscopy.

reaction suitability

reaction type: Cross Couplings
reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction
reagent type: ligand
reaction type: C-X Bond Formation
reagent type: ligand
reaction type: Heck Reaction
reagent type: ligand
reaction type: Suzuki-Miyaura Coupling

Synthesis

13716-10-4

2052-07-5

224311-51-7

Grignard reagent was prepared by adding 40 g of 2-bromobiphenyl, 5 g of magnesium shavings and 400 ml of anhydrous THF to a 1 L three-necked flask under nitrogen protection and refluxed for 2 hours. After the reaction mixture was cooled to room temperature, 2 g of tetrakis (triphenylphosphine) palladium was added and stirred for 30 minutes. Subsequently, 33 g of di-tert-butylphosphonium chloride was slowly added dropwise at room temperature and the reaction mixture was refluxed for 2 hours after completion of the dropwise addition. Upon completion of the reaction, the mixture was quenched by slow dropwise addition to 200 mL of saturated aqueous ammonium chloride solution under cooling in an ice water bath. The organic phase was separated, dissolved and crystallized by adding methanol, and filtered to give 49 g of white solid 2-(di-tert-butylphosphino)biphenyl in 95.7% yield.

References

[1] Patent: CN105859774, 2016, A. Location in patent: Paragraph 0062; 0063; 0064; 0065; 0066; 0067; 0068; 0069
[2] Journal of the American Chemical Society, 1999, vol. 121, # 41, p. 9550 - 9561
[3] Journal of the American Chemical Society, 1999, vol. 121, # 18, p. 4369 - 4378

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