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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Benzopyrazoles Indazoles

Comprehensive Guide to 1-(1H-indazol-5-yl)ethan-1-one (CAS No. 1001906-63-3): Properties, Applications, and Research Insights

1-(1H-indazol-5-yl)ethan-1-one, with the CAS number 1001906-63-3, is a specialized organic compound gaining attention in pharmaceutical and biochemical research. This heterocyclic ketone features an indazole core linked to an acetyl group, making it a valuable intermediate for drug discovery and material science. Its molecular structure (C₉H₈N₂O) offers unique reactivity, particularly in kinase inhibitor synthesis and cancer therapeutics.

Recent studies highlight its role in modulating protein-protein interactions, a hot topic in targeted therapy development. Researchers are exploring its potential in JAK-STAT signaling pathway inhibition, aligning with the growing demand for precision medicine solutions. The compound's logP value (~1.8) suggests moderate lipophilicity, optimizing cell membrane permeability—a critical factor discussed in ADMET optimization forums.

Synthetic routes to 1-(1H-indazol-5-yl)ethan-1-one typically involve Friedel-Crafts acylation of protected indazole derivatives. Advanced purification techniques like preparative HPLC ensure >98% purity for research applications. Analytical characterization via LC-MS and NMR spectroscopy confirms structural integrity, addressing quality concerns frequently raised in research chemical communities.

In material science, this compound serves as a precursor for photoactive polymers, coinciding with interest in organic electronics. Its electron-withdrawing properties enhance charge transport in OLED materials, as evidenced by recent patent filings. Such applications respond to the surge in searches for sustainable semiconductor alternatives.

Safety data sheets emphasize standard laboratory precautions for handling. The compound's stability under nitrogen atmosphere makes it suitable for high-throughput screening workflows. Storage recommendations (-20°C in amber vials) reflect best practices for light-sensitive compounds, a common query among laboratory technicians.

Market analysis shows growing demand for 1-(1H-indazol-5-yl)ethan-1-one from contract research organizations (CROs), particularly for fragment-based drug design projects. Suppliers now offer custom isotope-labeled versions (e.g., ¹³C, ²H) to support metabolic pathway studies, addressing the need for tracer compounds in pharmacokinetic research.

Ongoing clinical trials investigating indazole-derived therapeutics have increased citations of this compound in medicinal chemistry literature. Its structural similarity to approved BTK inhibitors makes it a benchmark in computer-aided drug design (CADD) tutorials, frequently searched by computational chemists.

Environmental fate studies indicate 1-(1H-indazol-5-yl)ethan-1-one undergoes biodegradation via soil microbiota within 28 days (OECD 301B), relevant to green chemistry discussions. This data supports its selection for benign-by-design pharmaceutical development, aligning with EPA's sustainable chemistry initiatives.

For analytical method development, researchers recommend reverse-phase chromatography (C18 column, 30% acetonitrile/water) with UV detection at 254 nm. These protocols address common challenges in heterocyclic compound analysis discussed in chromatography forums.

The compound's crystallographic data (CCDC deposition numbers available) facilitates molecular docking studies, particularly for allosteric binding site exploration—a trending topic in drug repurposing research. Its torsion angles provide valuable parameters for conformational analysis software validation.

• 189559-85-1(1-(1H-indazol-6-yl)ethan-1-one)
• 253801-04-6(1H-Indazole-5-carbaldehyde)
• 403660-48-0(2,2,2-Trifluoro-1-(1H-Indazol-5-Yl)Ethanone)
• 669050-69-5(1H-Indazole-6-carbaldehyde)
• 185955-92-4(1-(4-cinnolinyl)-Ethanone)
• 1159511-21-3(1-(1H-indazol-4-yl)ethan-1-one)
• 1159511-24-6(1-(1-methylindazol-5-yl)ethanone)
• 1159511-22-4(1-(1H-indazol-7-yl)ethan-1-one)
• 932368-54-2(cinnoline-6-carbaldehyde)
• 669050-70-8(1H-Indazole-4-carbaldehyde)