2-Chloromethylpyridine

2-Chloromethylpyridine.svg 100 2-(Chloromethyl)pyridine 2-Picolinyl chloride; 2-Picolyl chloride 4377-33-7 76601 1620152 21875 23393 59YW2EH117 1S/C6H6ClN/c7-5-6-3-1-2-4-8-6/h1-4H,5H2 NJWIMFZLESWFIM-UHFFFAOYSA-N C1=CC=NC(=C1)CCl 6 6 1 1 white solid 79 05 07 Danger 302 314 260 264 270 280 301+312+330 301+330+331 310 363 405 501 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:10.1002/jhet.5570180518 The Synthesis of 2-Chloromethylpyridine from 2-Picoline-N-Oxide 1981 Ash Mary Lynne Pews R. Garth Journal of Heterocyclic Chemistry 18 5 939–940 CH3C5H4NO + POCl3 + Et3N -> ClCH2C5H4N + Et3NH+[PO2Cl2]- (Et = C2H5) A related method uses triphosgene in place of phosphoryl chloride.10.1081/SCC-120028642 Facile and Selective Synthesis of Chloromethylpyridines and Chloropyridines Using Diphosgene/Triphosgene 2004 Narendar P. Gangadasu B. Ramesh Ch. China Raju B. Jayathirtha Rao V. Synthetic Communications 34 6 1097–1103 2-Chloromethylpyridine is a precursor to pyridine-containing ligands.10.1021/acs.organomet.0c00717 Cationic PCP and PCN NHC Core Pincer-Type Mn(I) Complexes: From Synthesis to Catalysis 2021 Buhaibeh Ruqaya Duhayon Carine Valyaev Dmitry A. Sortais Jean-Baptiste Canac Yves Organometallics 40 2 231–241 234156476 https://hal.archives-ouvertes.fr/hal-03128570 10.1021/ic00062a047 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 1993 Rapko B. M. Duesler E. N. Smith P. H. Paine R. T. Ryan R. R. Inorganic Chemistry 32 10 2164–2174 Safety 2-Chloromethylpyridine is an analogue of nitrogen mustards, and has been investigated for its mutagenicity.August 2022 Applications 2-Picolyl chloride has application in the synthesis of the following drugs: AD-35 [1531586-58-9] Capravirine Pifenate [15686-87-0] Pimeprofen [64622-45-3] SDZ NDD 094 [148257-48-1] References Category:Alkylating agents Category:Chloromethyl compounds Category:2-Pyridyl compounds