| Identification | More | [Name]
2-(Di-tert-butylphosphino)biphenyl | [CAS]
224311-51-7 | [Synonyms]
(2-biphenyl)di-tert-butylphosphine
(2-BIPHENYLYL)DI-TERT-BUTYLPHOSPHINE
2-(DI-T-BUTYLPHOSPHINO)BIPHENYL
2-(DI-TERT-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)-
JohnPhos
2-(Di-tert-butylphosphino)-biphenyl, JohnPhos
(2-Biphenylyl)di-tert-butylphosphine, 2-(Di-tert-butylphosphino)biphenyl, JohnPhos | [EINECS(EC#)]
607-074-9 | [Molecular Formula]
C20H27P | [MDL Number]
MFCD01862440 | [Molecular Weight]
298.4 | [MOL File]
224311-51-7.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powde | [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) | [Storage Precautions]
Store under inert gas;Air sensitive |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R22:Harmful if swallowed. | [Safety Statements ]
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S22:Do not breathe dust . | [WGK Germany ]
3
| [F ]
10-23 | [TSCA ]
No | [HazardClass ]
AIR SENSITIVE | [HS Code ]
29029090 |
| Hazard Information | Back Directory | [Chemical Properties]
white to light yellow crystal powde | [Uses]
suzuki reaction | [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]
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 |
| Questions And Answer | Back Directory | [Reactions]
- Ligand used in the palladium-catalyzed synthesis of aromatic amines from aryl chlorides, bromides and triflates.
- Ligand employed in a very active and general catalyst for Suzuki coupling reactions using aryl chlorides, bromides and triflates.
- Ligand used in palladium-catalyzed synthesis of oxindoles from α-chloroacetanilides.
- Effective ligand used in palladium-catalyzed arylation of thiazoles.
- Used in the formation of 2-benzylindolines via sequential palladium-catalyzed N-arylation/cyclization/C-arylation.
- Selective in the palladium-catalyzed arylation of silyl enol ethers formed from copper-catalyzed reduction of enones.
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