Description
2-Chloro-5-chloromethylpyridine is used for the synthesis of various pharmaceutical compounds. It can also be used for the synthesis of new neonicotinoid compounds
1, having insecticidal activity. It is the raw material of pesticide products such as imidacloprid, acetamiprid as well as bactericide and herbicide
2,3.
Structure
2-Chloro-5-(chloromethyl)pyridine, C6H5Cl2N, is almost planar, with an r.m.s. deviation of 0.0146 Å for all atoms except for the 5-choloromethyl Cl atom. The offset Cl atom lies above this plane with a Cl—C—C angle of 111.11 (17)°. In the crystal, molecules are connected via intermolecular C—H⋯N hydrogen bonds, forming dimers. The crystals were obtained by dissolving 2-Chloro-5-(chloromethyl)pyridine (0.2 g, 1.2 mmol) in ethanol (25 ml) and evaporating the solvent slowly at room temperature for about 5 d[1].
Sources
- https://www.alfa.com/en/catalog/L19284/
- https://www.trc-canada.com/product-detail/?C364715
- www.szqhbio.com/wap_news_detailen/id/1.htm
Chemical Properties
beige moist crystals
Uses
2-Chloro-5-(chloromethyl)pyridine is used for the synthesis of various pharmaceutical compounds. It can also be used for the synthesis of new neonicotinoid compounds.
Synthesis
General procedure for the synthesis of 2-chloro-5-chloromethylpyridine from the compound (CAS:150807-86-6): 18 g (0.1 mol) of 2-chloro-2-chloromethyl-4-cyano-butanal was dissolved in 50 ml of toluene, and 33 g (1.1 eq.) of solid phosgene was added to the toluene solution. The reaction mixture was stirred at 50°C for 5 hours. Upon completion of the reaction, the mixture was cooled to facilitate crystallization to afford the acetamiprid intermediate 2-chloro-5-chloromethylpyridine in 97% yield. Subsequently, the acetamiprid prodrug was further synthesized in 95% yield through methylation and esterification reaction steps.
References
[1] Zhi-Qiang Feng. “2-Chloro-5-(chloro-meth-yl)pyridine.” Acta crystallographica. Section E, Structure reports online 67 Pt 2 (2011): o366.
