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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Benzopyrazoles Indazoles

Comprehensive Overview of 2-Methylindazole-3-carboxylic Acid (CAS No. 34252-44-3): Properties, Applications, and Industry Insights

2-Methylindazole-3-carboxylic acid (CAS 34252-44-3) is a heterocyclic organic compound gaining significant attention in pharmaceutical and agrochemical research due to its versatile structural framework. As a derivative of indazole, this compound features a methyl group at the 2-position and a carboxylic acid moiety at the 3-position, offering unique reactivity for synthetic modifications. Its molecular formula C₉H₈N₂O₂ and molecular weight of 176.17 g/mol make it a valuable intermediate for designing bioactive molecules.

Recent studies highlight the role of 2-methylindazole-3-carboxylic acid derivatives in modulating enzyme activity, particularly in inflammation and metabolic disorders. Researchers are exploring its potential as a scaffold for kinase inhibitors and GPCR-targeted drugs, aligning with the growing demand for precision medicine. The compound's hydrogen-bonding capacity and planar aromatic system enable specific molecular interactions, making it a hotspot in fragment-based drug discovery (FBDD).

From a synthetic chemistry perspective, CAS 34252-44-3 serves as a precursor for constructing fused heterocycles through cyclization reactions. Its carboxyl group allows for easy derivatization into esters, amides, or acyl halides, while the indazole core participates in electrophilic substitution reactions. This dual functionality addresses the pharmaceutical industry's need for structural diversity in combinatorial libraries.

Environmental and regulatory considerations for 2-methylindazole-3-carboxylic acid synthesis emphasize green chemistry principles. Modern protocols employ catalytic methods over stoichiometric reagents, reducing waste generation. The compound's biodegradability profile and absence of persistent bioaccumulative traits make it compliant with REACH regulations and OECD test guidelines.

Analytical characterization of 34252-44-3 typically involves HPLC-UV (retention time ~5.2 min in C18 columns), LC-MS (m/z 177.1 for [M+H]⁺), and NMR spectroscopy (characteristic signals at δ 2.6 ppm for methyl protons). These techniques ensure batch-to-batch consistency for research applications. Thermal analysis reveals stability up to 220°C, suitable for high-temperature reactions.

Market trends indicate rising demand for indazole-3-carboxylic acid derivatives in Asia-Pacific pharmaceutical hubs, driven by increased R&D investment in small molecule therapeutics. Suppliers are optimizing multi-step synthesis routes to improve yield (>75% purity by HPLC) while maintaining cost competitiveness. The compound's application in fluorescent probes for cellular imaging further expands its commercial potential.

Safety data sheets recommend standard organic lab precautions when handling 2-methylindazole-3-carboxylic acid: use of PPE, adequate ventilation, and avoidance of strong oxidizers. The compound shows low acute toxicity (LD₅₀ >2000 mg/kg orally in rats) but may cause mild irritation upon prolonged exposure. Proper waste disposal through licensed chemical treatment facilities is advised.

Future research directions for CAS 34252-44-3 include exploring its metal-chelating properties for catalytic applications and developing continuous flow synthesis methods to enhance production scalability. Its structural similarity to natural alkaloids also opens possibilities in natural product-inspired drug design.

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