ClCH2CH2NH2

2-Chloroethylamine, with the chemical formula ClCH2CH2NH2, is an organochlorine compound and a primary amine. It is a colorless liquid at room temperature. This compound is a bifunctional molecule, possessing both a reactive chlorine atom and a nucleophilic amino group. These functional groups allow it to participate in a variety of chemical reactions, making it a useful intermediate in organic synthesis.

2-Chloroethylamine can be synthesized through several methods, including the reaction of ethanolamine with thionyl chloride or phosphorus pentachloride. Due to the presence of both an electrophilic carbon atom bonded to chlorine and a nucleophilic nitrogen atom, it can undergo intramolecular cyclization to form aziridine, a three-membered ring containing nitrogen. This reaction typically occurs under basic conditions.

The reactivity of 2-chloroethylamine makes it a precursor for the synthesis of various pharmaceuticals, agrochemicals, and other specialty chemicals. Its potential to form covalent bonds with biological molecules also makes it of interest in biochemical research, although its reactivity also implies potential toxicity. Careful handling and appropriate safety precautions are necessary when working with 2-chloroethylamine.