2-Chloromethylpyridine

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.

2-Chloromethylpyridine

Names
Preferred IUPAC name 2-(Chloromethyl)pyridine
Other names 2-Picolinyl chloride; 2-Picolyl chloride
Identifiers
CAS Number	4377-33-7
3D model (JSmol)	Interactive image
ChEBI	CHEBI:76601
ChEMBL	ChEMBL1620152
ChemSpider	21875
PubChem CID	23393
UNII	59YW2EH117
CompTox Dashboard (EPA)	DTXSID2043824
InChI InChI=1S/C6H6ClN/c7-5-6-3-1-2-4-8-6/h1-4H,5H2 Key: NJWIMFZLESWFIM-UHFFFAOYSA-N
SMILES C1=CC=NC(=C1)CCl
Properties
Chemical formula	C6H6ClN
Molar mass	127.57 g·mol−1
Appearance	white solid
Melting point	79 °C (174 °F; 352 K)
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H314
Precautionary statements	P260, P264, P270, P280, P301+P312+P330, P301+P330+P331, P310, P363, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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]

Safety

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