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Comprehensive Overview of 4-(4-Iodophenoxy)benzonitrile (CAS No. 856704-55-7): Properties, Applications, and Industry Insights

4-(4-Iodophenoxy)benzonitrile (CAS No. 856704-55-7) is a specialized organic compound gaining attention in pharmaceutical and material science research. This iodinated aromatic nitrile derivative exhibits unique structural features, combining a benzonitrile core with a 4-iodophenoxy substituent. Its molecular formula, C₁₃H₈INO, and precise molecular weight of 297.11 g/mol make it valuable for targeted synthetic applications. Researchers frequently search for "4-(4-Iodophenoxy)benzonitrile synthesis" and "856704-55-7 applications," reflecting growing interest in its utility as a building block for complex molecules.

The compound's physicochemical properties contribute to its versatility. With a melting point range of 120-123°C and moderate solubility in organic solvents like DMSO and dichloromethane, it serves as an excellent intermediate in cross-coupling reactions. Recent publications highlight its role in palladium-catalyzed reactions, addressing common search queries such as "iodoarene coupling partners" and "nitrile-containing intermediates." The electron-withdrawing cyano group enhances reactivity in nucleophilic aromatic substitutions, while the iodo substituent facilitates metal-catalyzed transformations.

In pharmaceutical development, 4-(4-Iodophenoxy)benzonitrile has emerged as a key precursor for kinase inhibitor scaffolds, aligning with trending searches for "cancer drug intermediates" and "targeted therapy compounds." Its structural motif appears in patented compounds investigating tyrosine kinase inhibition, particularly in angiogenesis-related pathways. The compound's aromatic ether linkage provides metabolic stability, a feature frequently queried as "improving drug half-life" in medicinal chemistry forums.

Material scientists value this compound for developing liquid crystal materials and organic semiconductors, responding to industry demands for "advanced electronic materials." The diphenyl ether structure contributes to planar molecular geometry, enhancing charge transport properties in OLED applications. Recent patent analyses reveal its incorporation into electron-transport layers, addressing popular queries about "small molecule organic electronics."

Quality specifications for CAS No. 856704-55-7 typically require ≥97% purity by HPLC, with particular attention to heavy metal content and residual solvents—topics frequently searched alongside "pharmaceutical intermediate standards." Analytical methods include GC-MS characterization and 1H/13C NMR verification, with the aromatic proton signals between 7.0-8.0 ppm serving as diagnostic markers. Storage recommendations suggest protection from light at 2-8°C to maintain stability, addressing practical concerns about "handling sensitive reagents."

The commercial availability of 4-(4-Iodophenoxy)benzonitrile has expanded significantly, with suppliers offering quantities from milligram to kilogram scales. Market trends show increasing demand for "custom synthetic intermediates" and "structure-activity relationship studies," particularly in academic and industrial research settings. Current pricing data indicates this specialty chemical commands premium value compared to simpler halogenated benzonitriles, reflecting its synthetic utility.

Environmental and safety considerations for 856704-55-7 follow standard laboratory protocols for iodoaromatic compounds. While not classified as hazardous under current regulations, proper personal protective equipment (PPE) including nitrile gloves and safety goggles is recommended—information often sought under "chemical handling best practices." The compound's biodegradability profile and ecotoxicological data remain active research areas, particularly regarding "green chemistry alternatives" in synthetic pathways.

Future applications may exploit the compound's potential in PET radiotracer development (addressing searches for "iodine-123/131 labeling") and metal-organic frameworks (MOFs). Its bifunctional reactivity allows simultaneous modification of the iodoarene and nitrile groups, a feature increasingly important for "multicomponent reactions" in drug discovery. Recent conference presentations highlight its use in constructing molecular rotors for sensor applications, demonstrating expanding utility beyond traditional roles.

Comparative analyses with structural analogs like 4-(4-bromophenoxy)benzonitrile reveal distinct advantages in reactivity selectivity and byproduct formation—technical considerations frequently discussed in "halogen exchange chemistry" forums. The iodo derivative generally shows superior performance in Sonogashira couplings and Buchwald-Hartwig aminations, making it preferable for demanding synthetic applications despite higher molecular weight.

Academic laboratories report improved yields (>85%) when employing 4-(4-Iodophenoxy)benzonitrile in Ullmann-type reactions, particularly for constructing diaryl ether pharmacophores. These findings address common experimental challenges noted in "heterocycle synthesis troubleshooting" discussions. The compound's stability under microwave irradiation conditions has also been documented, providing solutions for "accelerated reaction optimization" in high-throughput screening environments.

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• 933672-32-3(5-IODO-2-METHOXYBENZONITRILE)
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