70258-18-3

Raw materials And Preparation Products

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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

150807-86-6

70258-18-3

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.

Questions And Answer

• 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 compounds¹, 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].
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• Sources

  1. https://www.alfa.com/en/catalog/L19284/
  2. https://www.trc-canada.com/product-detail/?C364715
  3. www.szqhbio.com/wap_news_detailen/id/1.htm
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