3-Chloro-5-fluoropyridine-2-carbonitrile
Overview
3-Chloro-5-fluoropyridine-2-carbonitrile is a halogenated pyridine derivative serving as a versatile building block in organic synthesis. Its molecular structure combines electron-withdrawing groups (chloro, fluoro, and cyano) that enable selective functionalization at specific ring positions. The compound is particularly valued in medicinal chemistry for constructing nitrogen-containing heterocycles found in bioactive molecules. As a specialty chemical, it is typically produced through multistep synthesis involving halogenation and cyanation of pyridine precursors. Commercial suppliers usually offer it in research quantities (mg to kg scale) with purity levels ranging from 95% to 99+% for different application requirements.
Physical and Chemical Properties
This compound presents as a crystalline solid with moderate stability under ambient conditions. The presence of both chloro and fluoro substituents on the pyridine ring creates significant electronic effects, making the carbonitrile group highly reactive toward nucleophiles. The fluorine atom at the 5-position enhances the compound's metabolic stability when used in drug development. Key reactivity includes participation in Suzuki-Miyaura couplings, nucleophilic aromatic substitutions, and cyclization reactions. Its solubility profile favors polar aprotic solvents, with limited water compatibility. Thermal analysis shows decomposition before boiling, necessitating careful handling during high-temperature reactions.
Main Applications
In pharmaceutical R&D, this compound serves as a precursor for kinase inhibitors and central nervous system (CNS) drugs, where the pyridine core contributes to target binding affinity. The fluorine atom is often retained in final drug molecules to modulate bioavailability and pharmacokinetics. Agrochemical manufacturers utilize it to develop novel pesticides and herbicides, leveraging its ability to form stable heterocyclic systems. Additional applications include coordination chemistry (as a ligand precursor) and materials science for creating functionalized polymers with specific electronic properties.
Safety and Storage
As a reactive organic compound, proper handling requires nitrile gloves, safety goggles, and respiratory protection when handling powders. The material safety data sheet (MSDS) should be consulted for specific first aid measures, which typically include flushing exposed skin/eyes with water and seeking medical attention for ingestion. Long-term storage recommendations include amber glass containers with PTFE-lined caps under nitrogen atmosphere, ideally at 2-8°C. Incompatibilities include strong oxidizers, acids, and bases that may cause decomposition. Shelf life is typically 24 months when stored properly, with periodic purity checks advised for sensitive applications.
B2B Procurement Guide
When sourcing this chemical for industrial use, prioritize suppliers with ISO 9001 certification and documented quality control processes. Key procurement considerations include batch-to-batch consistency (verified by COA), residual solvent levels, and heavy metal content for pharmaceutical applications. Technical specifications should clearly state analytical methods (e.g., HPLC purity determination) and provide full spectral data (1H NMR, LC-MS) for identity confirmation. For large-scale purchases (>10kg), request process validation data and consider audit visits to evaluate manufacturing facilities. Lead times may vary from 2-8 weeks depending on customization requirements and global supply chain conditions.
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