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 is a precursor to pyridine-containing ligands.[1][2]

2-Chloromethylpyridine
Names
Preferred IUPAC name
2-(Chloromethyl)pyridine
Other names
2-Picolinyl chloride; 2-Picolyl chloride
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • InChI=1S/C6H6ClN/c7-5-6-3-1-2-4-8-6/h1-4H,5H2
    Key: NJWIMFZLESWFIM-UHFFFAOYSA-N
  • C1=CC=NC(=C1)CCl
Properties
C6H6ClN
Molar mass 127.57 g·mol−1
Appearance white solid
Melting point 79 °C (174 °F; 352 K)
Hazards
GHS labelling:
GHS05: Corrosive GHS07: Exclamation mark
Danger
H302, H314
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).

Safety

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

References

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  1. ^ Buhaibeh, Ruqaya; Duhayon, Carine; Valyaev, Dmitry A.; Sortais, Jean-Baptiste; Canac, Yves (2021). "Cationic PCP and PCN NHC Core Pincer-Type Mn(I) Complexes: From Synthesis to Catalysis". Organometallics. 40 (2): 231–241. doi:10.1021/acs.organomet.0c00717. S2CID 234156476.
  2. ^ Rapko, B. M.; Duesler, E. N.; Smith, P. H.; Paine, R. T.; Ryan, R. R. (1993). "Chelating Properties of 2-((Diphenylphosphino)methyl)pyridine N,P-dioxide and 2,6-Bis((diphenylphosphino)methyl)pyridine N,P,P'-trioxide Toward f-Element Ions". Inorganic Chemistry. 32 (10): 2164–2174. doi:10.1021/ic00062a047.