Diethyl phosphorocyanidate

CAS 2942-58-7, Cat. No EN300-105912

Reagent for synthesis of amides, esters and nitriles

Diethyl Phosphorocyanidate or DEPC is an efficient and useful reagent for amide formation and is applicable to racemization-free peptide synthesis, ester and thioester formation, and conversion of aldoximes to nitriles^[1]. It is a moisture-sensitive pale yellow liquid that is soluble in DMF, THF, Et₂O, and toluene. In the case of amide formation both aromatic and aliphatic acids easily react with aromatic and aliphatic amines. The reaction is rapid, clean, and usually free of contamination from side products. The esterification process with reagent usually gives a lower yield than usual methods (in the case of thioester yields are generally higher), but the advantage of this method is that the reaction proceeds under mild and almost neutral conditions^[1].

Synonyms: diethyl cyanophosphonate; diethylphosphoryl cyanide; diethoxyphosphoryl cyanide; diethyl cyanophosphate; DEPC

Selected publication

1. Diethyl Phosphorocyanidate.

Patel H. H.; Shioiri T. Encyclopedia of Reagents for Organic Synthesis 2006. DOI: 10.1002/047084289X.rd214.pub2