5-Iodo-1H-indazole-3-carbonitrile (CAS No. 885278-27-3): A Versatile Building Block in Modern Organic Synthesis
In the realm of heterocyclic chemistry, 5-Iodo-1H-indazole-3-carbonitrile (CAS 885278-27-3) has emerged as a pivotal intermediate for pharmaceutical and materials science applications. This iodo-substituted indazole derivative combines the reactivity of an aryl iodide with the structural diversity of the indazole-carbonitrile scaffold, making it a sought-after compound in cross-coupling reactions and medicinal chemistry design. Its molecular formula C8H4IN3 and precise MW 285.04 g/mol underscore its role in targeted molecular transformations.
The growing interest in 5-Iodo-1H-indazole-3-carbonitrile aligns with trends in fragment-based drug discovery (FBDD), where researchers frequently search for "indazole derivatives as kinase inhibitors" or "iodo-indazole coupling partners." The compound's 3-carbonitrile group enables hydrogen bond interactions critical for protein binding, while the 5-iodo position facilitates palladium-catalyzed reactions – a technique dominating recent publications on click chemistry and DNA-encoded libraries.
From a synthetic perspective, 885278-27-3 serves as a linchpin for constructing polycyclic aromatic systems, addressing frequent search queries like "indazole C-H activation methods" or "cyano-group transformations." Laboratories leverage its X-ray crystallography-friendly structure (as evidenced by Cambridge Structural Database entries) to study molecular stacking interactions – a hot topic in organic electronics research. The compound's stability under microwave-assisted synthesis conditions further enhances its utility in high-throughput workflows.
Recent patent analyses reveal that 5-Iodo-1H-indazole-3-carbonitrile derivatives appear in claims related to JAK/STAT signaling modulators and allosteric GPCR binders, reflecting industry demand for novel scaffold hopping strategies. Its logP ~2.1 (predicted) and moderate solubility profile make it particularly valuable for lead optimization studies, as confirmed by its inclusion in several commercial fragment libraries.
Quality control protocols for CAS 885278-27-3 typically involve HPLC purity verification (>98%) and 19F NMR tracking for fluorinated analogs – techniques frequently discussed in forums about "heterocycle characterization challenges." Storage recommendations (-20°C under inert atmosphere) align with best practices for air-sensitive intermediates, a concern regularly raised in process chemistry communities.
The environmental fate of iodo-indazole derivatives has gained attention following EPA studies on persistent organic pollutants. However, 5-Iodo-1H-indazole-3-carbonitrile's biodegradation potential (predicted QSAR models) positions it favorably compared to heavier halogenated compounds – a distinction important for researchers evaluating "green chemistry metrics" in synthetic routes.
In material science applications, the compound's π-conjugated system and halogen bonding capability have inspired investigations into organic semiconductors and supramolecular assemblies. These developments respond to growing searches for "indazole-based OLED materials" and "non-covalent synthesis templates," particularly in Asian research circles where small-molecule electronics represent a national priority.
As the pharmaceutical industry shifts toward targeted protein degradation strategies, the indazole-3-carbonitrile core in 885278-27-3 shows promise for designing PROTAC linkers – a connection evident in recent conference abstracts discussing "E3 ligase-recruiting fragments." This application potential has driven custom synthesis requests for deuterated versions (D-5-Iodo-1H-indazole-3-carbonitrile) to support ADME studies.
The compound's commercial availability through catalog suppliers (typically 1g to 100g scale) meets demand from academic groups exploring "diversity-oriented synthesis" and industrial teams pursuing "parallel medicinal chemistry." Pricing trends indicate steady demand, with bulk purchases (>50g) showing 12% annual growth – data points often requested in market analysis reports on high-value intermediates.
Looking ahead, the unique properties of 5-Iodo-1H-indazole-3-carbonitrile position it to address emerging challenges in covalent inhibitor design (through selective iodo-alkyne couplings) and bioorthogonal chemistry. These directions align with white papers forecasting growth in next-generation warhead development, ensuring this versatile building block will remain relevant across multiple scientific disciplines.
