Chloroformate

Chloroformates are a class of organic compounds with the formula ROC(O)Cl.

Most are colorless, volatile liquids that degrade in moist air.

Chloroformates are popular in the field of chromatography as derivatization agents.

In this way, chloroformates enable relatively simple transformation of large array of metabolites (aminoacids, amines, carboxylic acids, phenols) for analysis by gas chromatography / mass spectrometry.

Alkyl chloroformate esters degrate to give the alkyl chloride, with retention of configuration: The reaction is proposed to proceed via a substitution nucleophilic internal mechanism.