Chemical Identity and Structure

2-Chloro-3-(trichloromethyl)pyridine (CAS 72589-96-9, molecular formula C₆H₃Cl₄N, MW ≈ 231.90 g/mol) is a polychlorinated pyridine in which a chlorine atom occupies the 2-position of the pyridine ring and a trichloromethyl (–CCl₃) group is attached at the 3-position. The combination of an electron-deficient aromatic ring (due to the ring nitrogen) with two strongly electron-withdrawing chlorine-bearing substituents renders the molecule highly reactive toward nucleophilic aromatic substitution (SNAr) at the 2-position. The trichloromethyl group can additionally undergo hydrolysis or solvolysis under appropriate conditions, opening pathways to carboxylic acid or ester derivatives. These dual electrophilic handles make the compound a versatile building block in heterocyclic chemistry.

Research and Industrial Applications

The principal application of 2-Chloro-3-(trichloromethyl)pyridine is as a synthetic intermediate for the preparation of chloropyridine-based agrochemicals. Structurally related trichloromethylpyridine scaffolds are well-documented precursors to nitrification inhibitors such as nitrapyrin (2-chloro-6-(trichloromethyl)pyridine), and closely related regioisomers serve analogous roles in the synthesis of soil-management agents and pesticide active ingredients. In medicinal chemistry, the electrophilic pyridine core is exploited to introduce the nitrogen heterocycle into drug candidates via SNAr or transition-metal-catalyzed cross-coupling reactions (e.g., Suzuki, Buchwald–Hartwig). The –CCl₃ moiety can also be converted to a trifluoromethyl (–CF₃) group using fluorinating agents, providing access to fluorinated analogues that are prized for metabolic stability in drug design.

Additional applications include use as a starting material or building block for the synthesis of novel insecticides, herbicides, and fungicides where the halogenated pyridine pharmacophore confers biological activity.

Handling, Storage, and Safety Considerations

As a polychlorinated aromatic compound, 2-Chloro-3-(trichloromethyl)pyridine should be handled with appropriate precautions. Standard laboratory personal protective equipment (PPE) — including chemical-resistant gloves, safety goggles, and a laboratory coat — must be worn when handling this material. Work should be performed in a well-ventilated fume hood to prevent inhalation of dust or vapors. The trichloromethyl group is susceptible to hydrolysis upon contact with moisture, potentially releasing hydrogen chloride (HCl); therefore, the compound should be kept in tightly sealed containers and stored in a cool, dry environment away from moisture, strong bases, and oxidizing agents.

Disposal must comply with local, national, and institutional regulations for halogenated organic waste. Researchers should consult the Safety Data Sheet (SDS) provided by Aladdin Scientific (SKU C194777) for complete hazard classification, first-aid measures, and regulatory information before use.

Procurement and Specifications

Aladdin Scientific supplies 2-Chloro-3-(trichloromethyl)pyridine under SKU C194777. Researchers and procurement personnel should contact Aladdin Scientific directly for current availability, pack sizes, purity specifications, and certificate of analysis (CoA). When placing an order, specifying the desired purity grade and quantity ensures the material is appropriate for the intended synthetic or analytical application. Bulk or custom quantities may be available upon request.