2-Chloromethylpyridine

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

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.

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 ]}

References

1. Ash, Mary Lynne; Pews, R. Garth (1981). "The Synthesis of 2-Chloromethylpyridine from 2-Picoline-N-Oxide". Journal of Heterocyclic Chemistry. 18 (5): 939–940. doi:10.1002/jhet.5570180518.
2. Narendar, P.; Gangadasu, B.; Ramesh, Ch.; China Raju, B.; Jayathirtha Rao, V. (2004). "Facile and Selective Synthesis of Chloromethylpyridines and Chloropyridines Using Diphosgene/Triphosgene". Synthetic Communications. 34 (6): 1097–1103. doi:10.1081/SCC-120028642.
3. 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.
4. 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.