Diphenylphosphinic Chloride

clear colorless to yellow liquid

Diphenylphosphinic chloride (Ph₂POCl) is widely used as a precursor to synthesize various chiral phosphine bidentate ligands for asymmetric synthesis, in addition to several peptide coupling agents.

Diphenylphosphinic chloride is a reagent that is used in the synthesis of bidentate ligands and peptide coupling agents. It is used as flame retardants. It also act as pharmaceutical adjuvant.

reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling

To an oven-dried 100 mL, a two-necked flask fitted with a reflux condenser was added Et2O (depending on the Grignard reagent solution's concentration) and POCl3. The solution was cooled in an ice-salt mixture, and a Grignard reagent solution in Et2O was slowly added. After stirring with cooling for 30 min, the reaction mixture was brought to rt and stirred for the indicated time. The mixture was then cooled in an ice-salt mixture, and the alcohol and pyridine were slowly added. Stirring with cooling for 5 min was followed by reaction at rt. The reaction was quenched after the indicated time by cooling in an ice-salt mixture and adding sat aq NH4Cl. The crude mixture was then poured into CH2Cl2, washed three times with HCl, dried, filtered, and evaporated to dryness. The excess alcohol was removed using a short-path vacuum distillation apparatus, and the resulting crude product Diphenylphosphinic Chloride was purified by column chromatography.