CAS 16523-54-9 Chlorodicyclohexylphosphine - Catalysts / Alfa Chemistry

Synonyms

16523-54-9; PCy2Cl; C12H22ClP; TC-164447; Chlorodicyclohexylphosphine; Dicyclohexylphosphine chloride; MB00232; EN300-105513; Chlorodicyclohexyl phosphine; AKJFBIZAEPTXIL-UHFFFAOYSA-N;

IUPAC Name

chloro(dicyclohexyl)phosphane;

Molecular Weight

232.732g/mol

Molecular Formula

C12H22ClP;

Canonical SMILES

C1CCC(CC1)P(C2CCCCC2)Cl;

InChI

InChI=1S/C12H22ClP/c13-14(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h11-12H,1-10H2;

InChI Key

AKJFBIZAEPTXIL-UHFFFAOYSA-N;

Complexity

142

Covalently-Bonded Unit Count

Exact Mass

232.115g/mol

Heavy Atom Count

Monoisotopic Mass

232.115g/mol

Rotatable Bond Count

Topological Polar Surface Area

0A^2

Application

Chlorodicyclohexylphosphine is a clear, colorless liquid primarily utilized as an intermediate in pharmaceutical applications. It plays a significant role in the synthesis of various phosphines, serving as a crucial reactant in the production of complex ligands. For instance, it can be employed in the formation of the 1,2-Bis(dicyclohexylphosphinoxy)ethane ligand through a reaction with ethylene glycol in the presence of triethylamine, following a Michaelis-Arbuzov type rearrangement. Additionally, it is instrumental in synthesizing the 1,1,2,2-tetracyclohexyldiphosphine monosulfide ligand by treatment with LiS. Beyond these, Chlorodicyclohexylphosphine acts as a starting material for creating other ligands, such as dicyclohexylphosphine oxide, phosphino-substituted N-aryl pyrroles, di-tert-butyl((dicyclohexylphosphino)methyl)phosphine, and dicyclohexylcyclopentylphosphine. These ligands are integral components in palladium-catalyzed cross-coupling reactions, highlighting the product's versatility and importance in advanced chemical synthesis.

January 14, 2025

Essential Intermediate for Ligand Synthesis

Chlorodicyclohexylphosphine is invaluable in our lab, synthesizing phosphines for Pd-catalyzed reactions. Its versatility in creating various ligands, like dicyclohexylphosphine oxide, enhances our research outcomes significantly. Highly recommended for smooth, reliable applications.