Chloroacetates

Chloroacetates are a class of organic compounds that are esters or salts of chloroacetic acid. Chloroacetic acid, also known as monochloroacetic acid, has the chemical formula ClCH2COOH. When it forms esters, a hydrogen atom of the carboxyl group is replaced by an alkyl or aryl group, such as in methyl chloroacetate (ClCH2COOCH3) or ethyl chloroacetate (ClCH2COOCH2CH3). When it forms salts, the hydrogen atom is replaced by a metal cation, for example, sodium chloroacetate (ClCH2COONa).

These compounds are often colorless liquids or solids and are characterized by the presence of a chlorine atom attached to the carbon adjacent to the carbonyl group. This arrangement makes the alpha-carbon electrophilic, facilitating nucleophilic substitution reactions. Chloroacetates are generally soluble in organic solvents and, depending on the specific compound and counterion, can have varying degrees of water solubility.

Chloroacetates find application in various chemical syntheses. They are used as intermediates in the production of pharmaceuticals, dyes, and pesticides. For instance, they can be employed in the synthesis of glycine or other amino acids through reaction with ammonia. Their reactivity also makes them useful in the formation of carboxymethyl cellulose. However, due to the toxicity and irritant nature of chloroacetic acid and some of its derivatives, careful handling and appropriate safety measures are necessary during their use and production.