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Comprehensive Overview of Ethyl 5-cyclopropyl-1H-pyrazole-3-carboxylate (CAS No. 133261-06-0)

Ethyl 5-cyclopropyl-1H-pyrazole-3-carboxylate (CAS No. 133261-06-0) is a specialized organic compound that has garnered significant attention in pharmaceutical and agrochemical research. This pyrazole derivative is characterized by its unique molecular structure, featuring a cyclopropyl substituent and an ethyl ester functional group. Its versatility in synthetic chemistry makes it a valuable intermediate for developing novel bioactive molecules.

In recent years, the demand for heterocyclic compounds like Ethyl 5-cyclopropyl-1H-pyrazole-3-carboxylate has surged due to their applications in drug discovery. Researchers are particularly interested in its potential as a scaffold for kinase inhibitors, a hot topic in oncology and inflammation studies. The compound's structural modularity allows for easy derivatization, aligning with the growing trend of fragment-based drug design (FBDD) in modern medicinal chemistry.

The synthesis of CAS No. 133261-06-0 typically involves cyclocondensation reactions of hydrazines with β-keto esters, followed by cyclopropylation steps. This process highlights the compound's relevance in green chemistry discussions, as newer catalytic methods aim to improve atom economy and reduce waste—a key concern for sustainable pharmaceutical manufacturing.

Analytical characterization of Ethyl 5-cyclopropyl-1H-pyrazole-3-carboxylate employs advanced techniques like NMR spectroscopy and high-resolution mass spectrometry (HRMS), addressing the precision requirements of quality control in API production. These methods are frequently searched by analytical chemists optimizing protocols for heteroaromatic compound analysis.

Beyond pharmaceuticals, this pyrazole ester shows promise in material science, particularly in developing organic electronic materials. Its conjugated system and ability to form stable complexes with metals make it interesting for OLED applications—a trending area in display technology research.

Storage and handling of CAS 133261-06-0 require standard laboratory precautions. While not classified as hazardous, proper chemical stability maintenance under inert atmospheres is recommended to preserve its reactivity for downstream transformations—an important consideration for process chemists frequently searching for compound storage best practices.

The global market for fine chemical intermediates like Ethyl 5-cyclopropyl-1H-pyrazole-3-carboxylate continues to expand, driven by increasing R&D investments in targeted therapies. Patent landscapes reveal its incorporation in several PCT applications related to metabolic disease treatments, reflecting industry alignment with current healthcare priorities.

For researchers exploring structure-activity relationships (SAR), this compound offers valuable insights into how steric effects from the cyclopropyl group influence biological activity—a subject of numerous QSAR studies and molecular modeling inquiries in recent literature.

Quality specifications for 133261-06-0 typically include ≥98% purity by HPLC, with strict control of process-related impurities. These standards address the pharmaceutical industry's heightened focus on ICH guidelines for impurities, a frequently searched regulatory topic among quality assurance professionals.

Future research directions may explore the compound's utility in click chemistry applications or as a building block for covalent inhibitors—both trending areas in chemical biology. Its balanced lipophilicity (predicted LogP ~2.1) makes it particularly interesting for CNS drug development, another highly searched therapeutic area.

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