CAS 224311-51-7 2-(Di-tert-butylphosphino)biphenyl

Synonyms

(2-Biphenylyl)-Di-Tert-Butylphosphine;

IUPAC Name

ditert-butyl-(2-phenylphenyl)phosphane

Molecular Weight

298.40

Molecular Formula

C20H27P

Canonical SMILES

CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)C(C)(C)C;

InChI

CNXMDTWQWLGCPE-UHFFFAOYSA-N

InChI Key

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

Boiling Point

405.5±24.0 °C(Predicted)

Melting Point

86-88 °C (lit.)

Purity

98%

Density

1 g/cm3

Appearance

Solid

Complexity

300

Covalently-Bonded Unit Count

Exact Mass

298.185g/mol

Heavy Atom Count

Isomeric SMILES

CC(C)(C)P(C1=CC=CC=C1C2=CC=CC=C2)C(C)(C)C

Monoisotopic Mass

298.185g/mol

Rotatable Bond Count

Topological Polar Surface Area

0A^2

UNII

5Y743P380H

Application

2-(Di-tert-butylphosphino)biphenyl, commonly known as JohnPhos, serves as a versatile and highly effective ligand in various palladium-catalyzed reactions. This sterically bulky biaryl phosphine ligand is instrumental in facilitating carbon-nitrogen bond formation, as well as in the synthesis of aromatic amines from aryl chlorides, bromides, and triflates. It plays a crucial role in Suzuki coupling reactions, making it an active and general catalyst for such processes involving aryl chlorides, bromides, and triflates. Additionally, JohnPhos is employed in the palladium-catalyzed synthesis of oxindoles from α-chloroacetanilides and in the arylation of thiazoles. This ligand is also effective in forming 2-benzylindolines through a sequential N-arylation/cyclization/C-arylation process and demonstrates selectivity in the arylation of silyl enol ethers produced from copper-catalyzed reduction of enones. Its coordination chemistry, explored through NMR spectroscopy with gold catalysts, further underscores its importance in organometallic chemistry.

February 27, 2025

Efficient and Versatile Catalyst for Research Applications

JohnPhos has been invaluable in our lab for Suzuki coupling reactions, streamlining the synthesis of aromatic amines. Its effectiveness in catalyzing carbon-nitrogen bond formations is impressive. Highly recommend it for reliable and consistent results.