Chemical Identity and Key Properties

Methyl 2-(2,6-dichloro-3-cyanopyridin-4-yl)acetate (Aladdin SKU: M734416) is a pyridine-based heterocyclic compound featuring a 4-position acetic acid methyl ester side chain, a 3-position nitrile group, and chlorine substituents at the 2- and 6-positions of the pyridine ring. Its molecular formula is C₉H₆Cl₂N₂O₂.

The electron-withdrawing nitrile group at C-3 and the two aryl chlorides collectively render the pyridine ring highly electron-deficient, enhancing its reactivity toward nucleophilic aromatic substitution (SNAr). The methylene group between the aromatic ring and the ester is activated by both the ester carbonyl and the electron-poor ring, making it amenable to alkylation, Knoevenagel condensation, and related C–C bond-forming reactions.

These combined features make this compound a highly versatile bifunctional building block for the construction of complex nitrogen-containing heterocycles.

Handling and Safety Guidelines

As with most halogenated nitrile-containing heterocycles, Methyl 2-(2,6-dichloro-3-cyanopyridin-4-yl)acetate should be handled with appropriate personal protective equipment (PPE), including chemical-resistant gloves, safety goggles, and a lab coat. All operations should be conducted in a well-ventilated fume hood.

Avoid inhalation of dust or vapors. The nitrile group can release toxic hydrogen cyanide under strongly acidic or basic conditions or upon combustion; therefore, any heating or acid/base treatment should be performed with heightened caution and appropriate gas absorption systems in place.

In the event of skin contact, wash immediately with soap and water for at least 15 minutes. For eye exposure, rinse thoroughly with water and seek medical attention. Spills should be collected using inert absorbent material and disposed of in accordance with local chemical waste regulations.

Refer to the product's Safety Data Sheet (SDS) for complete hazard information before use.

Storage and Stability

Store Methyl 2-(2,6-dichloro-3-cyanopyridin-4-yl)acetate in a tightly sealed container in a cool, dry, and well-ventilated area, away from moisture, heat sources, and incompatible substances such as strong bases, strong acids, and strong oxidizing agents.

Moisture can promote hydrolysis of the methyl ester and potentially the nitrile group over time; therefore, desiccant-protected storage is recommended. Refrigerated storage (2–8 °C) under an inert atmosphere (argon or nitrogen) is advisable for long-term preservation of reagent quality.

Upon receipt, inspect the material for any color change or caking that may indicate degradation. Always reseal the container promptly after dispensing to minimize exposure to atmospheric moisture and oxygen.

Synthetic Applications and Reactivity

The dual electrophilic chlorine substituents at the 2- and 6-positions of the pyridine ring enable sequential or selective nucleophilic aromatic substitution (SNAr) reactions. The chlorine at C-2 is typically more reactive than that at C-6 due to the activating influence of the adjacent ring nitrogen, allowing for regioselective mono-substitution with amines, thiols, or alkoxides under controlled conditions.

The activated methylene ester functionality at C-4 can participate in base-mediated alkylation reactions, Claisen-type condensations, and Knoevenagel reactions with aldehydes, providing access to a range of functionalized pyridine derivatives.

The nitrile group at C-3 can be further elaborated via hydrolysis to the corresponding carboxylic acid or amide, converted to tetrazoles via [3+2] cycloaddition with azides, or used as a precursor to aminopyridines through partial reduction. These orthogonal reactivities make this compound an enabling scaffold in the synthesis of kinase inhibitors, agrochemical actives, and other biologically relevant small molecules.

Quality, Ordering, and Technical Support

Methyl 2-(2,6-dichloro-3-cyanopyridin-4-yl)acetate is available from Aladdin Scientific under SKU M734416. Customers are encouraged to verify purity specifications and certificate of analysis (CoA) documentation prior to use in critical synthetic steps.

For research procurement, place orders through the Aladdin Scientific website or contact your regional sales representative. Custom quantities, bulk pricing, and bespoke purity grades may be available upon request.

For technical questions regarding reactivity, compatibility, or application-specific guidance, please contact Aladdin Scientific's technical support team. All products are subject to Aladdin's standard quality assurance procedures to ensure batch-to-batch consistency.