CAS 564483-18-7 2-Dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl

Synonyms

Dicyclohexyl(2',4',6'-Triisopropylbiphenyl-2-Yl)Phosphine

IUPAC Name

dicyclohexyl-[2-[2,4,6-tri(propan-2-yl)phenyl]phenyl]phosphane

Molecular Weight

476.72

Molecular Formula

C33H49P

Canonical SMILES

CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C;

InChI

UGOMMVLRQDMAQQ-UHFFFAOYSA-N

InChI Key

InChI=1S/C33H49P/c1-23(2)26-21-30(24(3)4)33(31(22-26)25(5)6)29-19-13-14-20-32(29)34(27-15-9-7-10-16-27)28-17-11-8-12-18-28/h13-14,19-25,27-28H,7-12,15-18H2,1-6H3

Boiling Point

569.8±50.0 °C(Predicted)

Melting Point

187-190 °C(lit.)

Purity

98%

Appearance

Solid

Complexity

545

Covalently-Bonded Unit Count

Exact Mass

476.357g/mol

Heavy Atom Count

Isomeric SMILES

CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C

Monoisotopic Mass

476.357g/mol

Rotatable Bond Count

Topological Polar Surface Area

0A^2

UNII

R271FU23T8

Application

2-Dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl serves as an exceptional ligand in a variety of catalytic applications, enhancing efficiency and selectivity. It is particularly notable for its role in Pd-catalyzed processes, such as amination and amidation of aryl sulfonates, the Suzuki-Miyaura coupling reaction, carbonyl enolate coupling, chemoselective amination of aryl chlorides, and borylation for the formation of trifluoroborates. Additionally, it facilitates the synthesis of novel [1,2,4]triazolo[4,3-a]pyrazine derivatives, acting as a regent for potential selective c-met inhibitors with improved pharmacokinetic properties. This ligand is also crucial for processes such as the palladium-catalyzed three-component synthesis of indoles, synthesis of carbazoles, and direct arylation of picoline N-oxide, among others. It is used in Pt-catalyzed regioselective hydrosilylation and silver-catalyzed hydrogenation of aldehydes, as well as in various coupling reactions, emphasizing its versatility and effectiveness in modern chemical synthesis.

January 8, 2025

Superb Ligand for Efficient Catalysis in Research

Used 2-Dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl in Pd-catalyzed amination of aryl sulfonates. Enhanced catalytic efficiency and simplified workflow significantly improved our synthesis of C-met inhibitors. Highly recommend for precision and reliability in research.