CAS 247940-06-3 2-(Dicyclohexylphosphino)biphenyl

Synonyms

Cyclohexyl JohnPhos

IUPAC Name

dicyclohexyl-(2-phenylphenyl)phosphane

Molecular Weight

350.48

Molecular Formula

C24H31P

Canonical SMILES

C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4;

InChI

LCSNDSFWVKMJCT-UHFFFAOYSA-N

InChI Key

InChI=1S/C24H31P/c1-4-12-20(13-5-1)23-18-10-11-19-24(23)25(21-14-6-2-7-15-21)22-16-8-3-9-17-22/h1,4-5,10-13,18-19,21-22H,2-3,6-9,14-17H2

Boiling Point

499.5±24.0 °C(Predicted)

Melting Point

102-106 °C(lit.)

Purity

98%

Appearance

Solid

Complexity

356

Covalently-Bonded Unit Count

EC Number

480-030-2

Exact Mass

350.216g/mol

Heavy Atom Count

Isomeric SMILES

C1CCC(CC1)P(C2CCCCC2)C3=CC=CC=C3C4=CC=CC=C4

Monoisotopic Mass

350.216g/mol

Rotatable Bond Count

Topological Polar Surface Area

0A^2

Application

2-(Dicyclohexylphosphino)biphenyl serves as a versatile ligand in various palladium-catalyzed reactions, enhancing the reactivity and efficiency of these processes. It is particularly valuable in the synthesis of aromatic amines, utilizing aryl chlorides, bromides, and triflates. In addition to its role in Suzuki coupling reactions, this ligand is effective for the oxidation of alcohols in the presence of chlorobenzenes and the amination with ammonia equivalents. Its utility extends to gold(I)-catalyzed intramolecular [4+2] cycloadditions involving 1,3-enynes and arylalkynes with alkenes, as well as to the borylation and silylation of aryl bromides and chlorides. Developed by the Buchwald group, 2-(Dicyclohexylphosphino)biphenyl, also known as CyJohnPhos, is an air-stable, bulky, and electron-rich monodentate biarylphosphine ligand that significantly boosts the reactivity of palladium catalysis in cross-coupling reactions.

January 18, 2025

Highly Effective Ligand for Catalysis

The 2-(Dicyclohexylphosphino)biphenyl from Alfa Chemistry is superb for Pd-catalyzed reactions. We successfully used it in Suzuki coupling and aromatic amine synthesis, enhancing yields significantly. The crystal powder form was easy to handle in our experiments.