ROCOCl

ROCOCl is a generic term for alkyl chloroformates, a class of reactive organic compounds with the general formula ROCOCl, where R represents an alkyl group. They are esters of chloroformic acid and are often referred to simply as chloroformates. The key functional group is the chloroformate moiety (Cl-CO-O-R) attached to an alkyl group.

Preparation and sources of ROCOCl typically involve reaction of an alcohol with phosgene or its substitutes. Common routes include combining a primary or secondary alcohol with phosgene (or triphosgene) in the presence of a base, or using alternative chlorinating reagents that form the chloroformate in situ. Methyl chloroformate and ethyl chloroformate are among the most widely used representatives. These compounds are moisture sensitive and must be handled under dry, inert conditions.

Chemical properties and reactivity: alkyl chloroformates are highly reactive acyl chlorides. They readily react with nucleophiles such as alcohols and amines to form carbonates and carbamates, respectively, often with the concomitant release of hydrogen chloride. They can serve as activating agents in esterifications and as reagents for introducing carbonate or carbamate protections. Hydrolysis in the presence of water gives the corresponding alcohol, carbon dioxide, and HCl, underscoring their moisture sensitivity.

Applications and safety: ROCOCl compounds are useful intermediates in organic synthesis, including preparation of carbonate esters, carbamates, and various protective groups. They are corrosive and irritant, requiring appropriate PPE and ventilation. They should be stored under dry, inert atmosphere to minimize hydrolysis and decomposition.

Examples: methyl chloroformate (MeOCOCl), ethyl chloroformate (EtOCOCl).