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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Diazanaphthalenes Quinazolines
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Diazanaphthalenes Benzodiazines Quinazolines

Comprehensive Overview of 8-bromo-6-fluoro-1,2-dihydroquinazolin-2-one (CAS No. 953039-62-8)

8-bromo-6-fluoro-1,2-dihydroquinazolin-2-one (CAS No. 953039-62-8) is a heterocyclic organic compound with significant potential in pharmaceutical and agrochemical research. This compound belongs to the quinazolinone family, a class of nitrogen-containing heterocycles known for their diverse biological activities. Researchers are increasingly interested in this molecule due to its unique structural features, including the presence of both bromine and fluorine substituents, which enhance its reactivity and potential applications in drug discovery.

The growing interest in fluorinated quinazolinones like this compound stems from their improved pharmacokinetic properties compared to non-fluorinated analogs. Fluorination often increases metabolic stability, membrane permeability, and bioavailability - key factors driving pharmaceutical development. Recent studies suggest that 8-bromo-6-fluoro-1,2-dihydroquinazolin-2-one may serve as a valuable building block for designing novel kinase inhibitors, given the importance of quinazolinone scaffolds in targeted cancer therapies.

From a synthetic chemistry perspective, the presence of both bromo and fluoro groups in CAS 953039-62-8 offers multiple sites for further functionalization through cross-coupling reactions or nucleophilic substitutions. This versatility makes it particularly attractive for medicinal chemists working on structure-activity relationship (SAR) studies. The compound's molecular weight (242.03 g/mol) and moderate lipophilicity suggest good potential for drug-like properties.

Recent advancements in heterocyclic chemistry have highlighted the importance of halogenated quinazolinones in developing new antimicrobial agents. With increasing antibiotic resistance becoming a global health concern, researchers are exploring novel scaffolds like 8-bromo-6-fluoro-1,2-dihydroquinazolin-2-one for their potential antibacterial and antifungal properties. Preliminary computational studies indicate possible interactions with bacterial DNA gyrase, though experimental validation is ongoing.

The compound's crystalline nature and well-defined melting point (reported between 210-215°C) make it suitable for X-ray crystallographic studies, providing valuable structural insights for rational drug design. Analytical techniques such as HPLC, NMR, and mass spectrometry have been successfully employed to characterize CAS 953039-62-8, with purity typically exceeding 95% in commercially available samples.

In material science applications, fluorinated quinazolinone derivatives have shown promise as organic semiconductors and fluorescent probes. The electron-withdrawing effects of both bromine and fluorine in 8-bromo-6-fluoro-1,2-dihydroquinazolin-2-one may contribute to interesting photophysical properties worth exploring for optoelectronic applications. Researchers are particularly interested in how these substituents affect the compound's HOMO-LUMO gap and charge transport characteristics.

Storage and handling recommendations for 953039-62-8 typically suggest protection from light and moisture at room temperature. While not classified as highly hazardous, standard laboratory precautions should be followed when working with this compound, including the use of appropriate personal protective equipment. The compound's stability under various pH conditions makes it suitable for diverse experimental setups.

The global market for specialty chemicals like 8-bromo-6-fluoro-1,2-dihydroquinazolin-2-one continues to expand, driven by increasing R&D investments in pharmaceutical and agricultural sectors. Several contract research organizations now include this compound in their screening libraries, recognizing its potential as a privileged structure in medicinal chemistry. Current pricing reflects its status as a research-grade chemical with limited large-scale production.

Future research directions for CAS 953039-62-8 may explore its potential in combination therapies or as a precursor for radiopharmaceuticals, given the utility of bromine in radiohalogenation. The compound's structural features also make it a candidate for fragment-based drug discovery approaches. As synthetic methodologies continue to advance, particularly in C-H functionalization and cross-coupling chemistry, new derivatives of this scaffold will likely emerge with enhanced biological activities.

For researchers considering 8-bromo-6-fluoro-1,2-dihydroquinazolin-2-one in their work, thorough literature review of related quinazolinone derivatives is recommended. Patent databases reveal growing interest in this chemical space, particularly for applications in oncology and CNS disorders. The compound's synthetic accessibility and derivatization potential position it as an important tool for academic and industrial research programs exploring new therapeutic avenues.

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