What Is 3-Cyano-4-fluorobenzyl cyanide?

3-Cyano-4-fluorobenzyl cyanide (Aladdin SKU C184935) is an aromatic compound that carries three distinct reactive handles on a single benzene ring: a nitrile group directly attached to the ring at the 3-position (aryl nitrile), a fluorine substituent at the 4-position (aryl fluoride), and a methylene cyanide (–CH₂CN) side chain at the 1-position. This combination of electron-withdrawing groups makes the molecule highly activated toward a range of synthetic transformations.

The molecular framework belongs to the broader class of fluorinated benzonitrile derivatives, which are widely represented in modern drug discovery pipelines because both fluorine and nitrile substituents modulate lipophilicity, metabolic stability, and binding interactions in a predictable manner.

Key Chemical Reactivity and Synthetic Applications

Benzylic nitrile alkylation and condensation: The –CH₂CN group has a moderately acidic benzylic proton (pK_a typically in the range of 20–25 in DMSO for benzyl cyanides), which can be deprotonated by bases such as NaH, LDA, or K₂CO₃ to generate a stabilized carbanion. This carbanion undergoes alkylation with electrophiles, Knoevenagel-type condensations with aldehydes, and Michael additions, providing rapid access to structurally diverse nitrile-containing intermediates.

Nucleophilic aromatic substitution (SNAr): The aryl fluoride at the 4-position is activated toward SNAr by the flanking electron-withdrawing cyano groups. Treatment with amines, alkoxides, or thiolates under mild conditions can displace fluoride to install N-, O-, or S-linked substituents on the ring, enabling rapid library synthesis.

Nitrile group transformations: Both nitrile groups are available for standard nitrile chemistry, including hydrolysis to carboxylic acids or amides, reduction to primary amines, and cycloaddition reactions to form heterocyclic rings such as tetrazoles or imidazoles, all of which are privileged scaffolds in medicinal chemistry.

Handling, Storage, and Safety Considerations

General handling: As with all aromatic nitrile compounds, 3-Cyano-4-fluorobenzyl cyanide should be handled with appropriate personal protective equipment (PPE), including nitrile gloves, safety glasses, and a lab coat. Work should be conducted in a well-ventilated fume hood to minimize inhalation exposure to dust or vapor.

Storage: Store the compound in a tightly sealed container in a cool, dry, and well-ventilated area, away from heat sources, open flames, and incompatible reagents (e.g., strong oxidizers, strong bases). Consult the product Safety Data Sheet (SDS) for specific hazard classifications and first-aid measures before use.

Waste disposal: Dispose of the compound and any contaminated materials in accordance with applicable local, national, and institutional regulations for chemical waste. Do not pour down the drain without verifying regulatory compliance.

Note: Researchers must obtain and review the current SDS for C184935 from Aladdin Scientific prior to use. The information provided here is for general guidance only and does not replace the SDS.

Ordering, Specifications, and Quality

How to order: 3-Cyano-4-fluorobenzyl cyanide is available from Aladdin Scientific under catalog number C184935. Researchers can place orders through the Aladdin Scientific website or contact the sales team for bulk quantity inquiries and custom packaging options.

Purity and specifications: Specific purity grade, available pack sizes, and analytical data (such as HPLC purity, NMR, or melting point) are listed on the product detail page for C184935 on the Aladdin Scientific website. Researchers requiring certificates of analysis (CoA) or additional characterization data should contact Aladdin Scientific customer support.

Quality assurance: Aladdin Scientific applies quality control procedures to its research reagents to support reproducible experimental outcomes. For specification-critical applications, always verify the CoA against experimental requirements before use.