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Comprehensive Overview of 4-fluoro-3-(2-hydroxyphenyl)benzonitrile (CAS No. 1261957-71-4): Properties, Applications, and Research Insights

4-fluoro-3-(2-hydroxyphenyl)benzonitrile (CAS No. 1261957-71-4) is a fluorinated aromatic compound that has garnered significant attention in pharmaceutical and material science research. This specialty chemical combines a hydroxyphenyl moiety with a fluorobenzonitrile group, making it a versatile intermediate for synthesizing advanced bioactive molecules. Its unique structure, featuring both electron-withdrawing (fluorine and nitrile) and electron-donating (hydroxyl) groups, enables diverse reactivity patterns, which are exploited in drug discovery and organic electronics.

Recent studies highlight the growing demand for fluorinated compounds like 4-fluoro-3-(2-hydroxyphenyl)benzonitrile due to their enhanced metabolic stability and membrane permeability—key traits in CNS drug development. Researchers are particularly interested in its potential as a precursor for kinase inhibitors and GPCR modulators, aligning with trends in targeted cancer therapies and neurodegenerative disease research. The compound’s CAS number 1261957-71-4 frequently appears in patent filings, underscoring its industrial relevance.

From a synthetic chemistry perspective, the ortho-hydroxyphenyl group in 4-fluoro-3-(2-hydroxyphenyl)benzonitrile facilitates chelation-assisted reactions, a hotspot in catalysis research. This property is leveraged in C-H activation methodologies, a trending topic in green chemistry circles. Moreover, its nitrile functionality serves as a handle for click chemistry applications, resonating with the rise of bioconjugation techniques in antibody-drug conjugates (ADCs) development.

Environmental and ADME/Tox profiling of 1261957-71-4 reveals favorable lipophilicity (LogP ~2.8) and moderate aqueous solubility, making it suitable for formulation optimization. These characteristics address frequent queries about drug-likeness and lead compound optimization in medicinal chemistry forums. Analytical methods like HPLC and LC-MS are commonly employed for purity assessment (>98%), a critical parameter for GMP-grade production.

In material science, the π-conjugated system of 4-fluoro-3-(2-hydroxyphenyl)benzonitrile shows promise in OLED materials, coinciding with the global push for energy-efficient displays. Its fluorescence properties are being investigated for bioimaging probes, tapping into the booming theranostics market. Such multidisciplinary applications make this compound a recurring subject in SciFinder and Reaxys searches.

Regulatory-wise, CAS 1261957-71-4 is not classified under restricted categories, but proper handling protocols for nitrile-containing compounds are recommended. This aligns with industry concerns about lab safety and chemical storage, frequently searched topics in research compliance databases. Suppliers typically provide SDS documentation detailing stability under standard conditions (2-8°C, inert atmosphere).

The commercial availability of 4-fluoro-3-(2-hydroxyphenyl)benzonitrile through custom synthesis services meets the demand from contract research organizations (CROs). Price benchmarking data indicates cost variations based on scale-up feasibility—a pain point often discussed in process chemistry webinars. Recent flow chemistry approaches have improved its atom economy, addressing sustainability concerns in fine chemical manufacturing.

Future directions for 1261957-71-4 include exploration in proteolysis-targeting chimeras (PROTACs) and covalent inhibitors, two cutting-edge domains in drug discovery. Its structural motifs are being repurposed for metal-organic frameworks (MOFs), reflecting cross-disciplinary innovation. These applications position the compound as a valuable asset in both academic research and industrial R&D pipelines.

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