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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Azoles Phenylpyrazoles
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Azoles Pyrazoles Phenylpyrazoles

Comprehensive Overview of 5-bromo-2-(1H-pyrazol-1-yl)aniline (CAS No. 1134997-99-1): Properties, Applications, and Industry Relevance

5-bromo-2-(1H-pyrazol-1-yl)aniline (CAS No. 1134997-99-1) is a specialized heterocyclic compound that has garnered significant attention in pharmaceutical and agrochemical research due to its unique molecular structure. This compound features a pyrazole ring linked to an aniline moiety substituted with a bromine atom, making it a versatile intermediate for synthesizing bioactive molecules. Its CAS number 1134997-99-1 is frequently searched in chemical databases, reflecting its growing importance in drug discovery pipelines.

The structural motif of 5-bromo-2-(1H-pyrazol-1-yl)aniline aligns with current trends in fragment-based drug design, a hot topic in medicinal chemistry. Researchers are particularly interested in how the pyrazole-aniline scaffold can modulate protein-protein interactions, a key focus area for oncology and inflammation targets. The presence of the bromine substituent offers opportunities for further functionalization via cross-coupling reactions, which explains why this compound appears in numerous patent applications for kinase inhibitors.

From a synthetic chemistry perspective, CAS 1134997-99-1 demonstrates excellent stability under standard laboratory conditions, with melting point data showing consistency between 148-152°C. Analytical studies using HPLC and LC-MS confirm high purity (>98%) in commercial samples, addressing a common query among quality control specialists. The compound's solubility profile—moderate in polar aprotic solvents like DMSO but limited in water—makes it particularly suitable for high-throughput screening applications.

Recent publications have highlighted the role of 5-bromo-2-(1H-pyrazol-1-yl)aniline in developing selective JAK2 inhibitors, responding to the pharmaceutical industry's demand for targeted immunomodulators. This connects with frequent search terms like "JAK-STAT pathway modulators" and "small molecule kinase inhibitors." The compound's electron-rich aromatic system facilitates π-stacking interactions crucial for ATP-competitive binding, a mechanism extensively discussed in drug design forums.

Environmental and regulatory aspects of CAS 1134997-99-1 have also become a focus, with researchers evaluating its biodegradation pathways using advanced mass spectrometry techniques. This addresses growing concerns about green chemistry in synthetic workflows. The compound's relatively low ecotoxicity profile (as per OECD 420 guidelines) positions it favorably compared to traditional halogenated intermediates.

In material science applications, the pyrazole-aniline derivative has shown promise as a building block for organic semiconductors, particularly in the development of OLED materials. Its ability to participate in both hydrogen bonding and charge transfer interactions makes it valuable for tuning electronic properties—a subject trending in materials science conferences.

Supply chain data indicates steady growth in demand for 5-bromo-2-(1H-pyrazol-1-yl)aniline, with major manufacturers offering custom synthesis services at various scales. This reflects the compound's transition from research-grade to preclinical development applications. Analytical method development for this compound—particularly chiral separation techniques when used in asymmetric synthesis—remains an active area of method development.

Future research directions for CAS 1134997-99-1 may explore its potential in PROTAC technology, where its dual functionality could enable targeted protein degradation. This aligns with industry searches for "heterobifunctional degraders" and "E3 ligase recruiters." The compound's balanced lipophilicity (LogP ~2.8) and moderate molecular weight (238.08 g/mol) make it particularly suitable for such advanced applications.

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