2-Chloromethylpyridine is an organohalide that consists of a pyridine core bearing a chloromethyl group. It is one of three isomeric chloromethylpyridines, along with 3- and 4-chloromethylpyridine. It is an alkylating agent.
It can be prepared by reaction of 2-methylpyridine with chlorine. A more efficient route involves treating 2-picoline-N-oxide with phosphoryl chloride in the presence of triethylamine:
A related method uses triphosgene in place of phosphoryl chloride.
2-Chloromethylpyridine is a precursor to pyridine-containing ligands.
2-Chloromethylpyridine is an analogue of nitrogen mustards, and has been investigated for its mutagenicity.
2-Picolyl chloride has application in the synthesis of the following drugs: