Chloroformates

Chloroformates are a class of organic compounds defined by the general formula ROC(O)Cl, where ‘R’ represents an alkyl or aryl substituent. These compounds are derived from chloroformic acid and are recognized for their significant reactivity, frequently utilized as crucial intermediates in diverse chemical syntheses. Typically colorless to yellowish liquids with a pungent odor. These compounds are highly reactive and degrade in moist air due to hydrolysis.

Chemical Properties

• Reactivity: Chloroformates readily undergo acylation, esterification, and carbamoylation reactions, making them versatile intermediates.
• Hydrolysis: They react with water to form alcohols, carbon dioxide, and hydrochloric acid.
• Volatility: Most chloroformates are volatile and must be handled under dry conditions.

Applications in Chemistry

• Protecting Groups: Chloroformates are widely used to introduce protective groups like Cbz and FMOC in peptide and organic synthesis.
• Chromatography: They serve as derivatization agents, converting polar compounds into less polar, more volatile derivatives for GC-MS analysis.
• Pharmaceuticals and Agrochemicals: Used as building blocks in the synthesis of active ingredients.

Safety and Handling

• Hazardous: Chloroformates are toxic and corrosive. They release phosgene-like fumes upon decomposition.
• Storage: Must be stored in dry, airtight containers away from moisture.
• Protective Equipment: Use gloves, goggles, and fume hoods when handling.

Common Types