Chloroformic acid in the context of "Organic compounds"

Organic compounds are a subclass of chemical compounds of carbon. Little consensus exists among chemists on the exact definition of organic compound; the only universally accepted definition is the quasi-tautological "organic compounds are the subject matter of organic chemistry".

Generally, any large chemical compound containing a carbon–hydrogen or carbon–carbon bond is accepted as an organic compound. Thus alkanes (e.g. ethane, CH₃−CH₃) and their derivatives are typically considered organic. For historical and disciplinary reasons, small molecules containing carbon are generally not accepted: cyanide ion (CN), hydrogen cyanide (HCN), chloroformic acid (ClCO₂H), carbon dioxide (CO₂), and carbonate ion (CO2−3) may all be excluded.

Chloroformates are a class of organic compounds with the formula ROC(O)Cl. They are formally esters of chloroformic acid. Most are colorless, volatile liquids that degrade in moist air. A simple example is methyl chloroformate, which is commercially available.

Chloroformates are used as reagents in organic chemistry. For example, benzyl chloroformate is used to introduce the Cbz (carboxybenzyl) protecting group and fluorenylmethyloxycarbonyl chloride is used to introduce the FMOC protecting group. Chloroformates are popular in the field of chromatography as derivatization agents. They convert polar compounds into less polar more volatile derivatives. 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.

Benzyl chloroformate, also known as benzyl chlorocarbonate or Z-chloride, is the benzyl ester of chloroformic acid. It can be also described as the chloride of the benzyloxycarbonyl (Cbz or Z) group. In its pure form it is a water-sensitive oily colorless liquid, although impure samples usually appear yellow. It possesses a characteristic pungent odor and degrades in contact with water.

The compound was first prepared by Leonidas Zervas in the early 1930s who used it for the introduction of the benzyloxycarbonyl protecting group, which became the basis of the Bergmann-Zervas carboxybenzyl method of peptide synthesis he developed with Max Bergmann. This was the first successful method of controlled peptide chemical synthesis and for twenty years it was the dominant procedure used worldwide until the 1950s. To this day, benzyl chloroformate is often used for amine group protection.