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2-Chloromethylpyridine

Chemical compound From Wikipedia, the free encyclopedia

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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.

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Preparation and reactions

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:[1]

CH3C5H4NO + POCl3 + Et3N → ClCH2C5H4N + Et3NH+[PO2Cl2] (Et = C2H5)

A related method uses triphosgene in place of phosphoryl chloride.[2]

2-Chloromethylpyridine is a precursor to pyridine-containing ligands.[3][4]

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Safety

2-Chloromethylpyridine is an analogue of nitrogen mustards, and has been investigated for its mutagenicity.[citation needed]

References

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