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Comprehensive Overview of 8-Bromo-7-chloroquinoline (CAS No. 1447606-16-7): Properties, Applications, and Research Insights

8-Bromo-7-chloroquinoline (CAS No. 1447606-16-7) is a halogenated quinoline derivative that has garnered significant attention in pharmaceutical and materials science research. This compound, characterized by its bromine and chlorine substitutions at the 8th and 7th positions of the quinoline ring, exhibits unique electronic and steric properties. Its molecular formula, C₉H₅BrClN, and molecular weight of 242.5 g/mol make it a versatile intermediate in organic synthesis. Researchers frequently explore its reactivity in cross-coupling reactions, catalysis, and drug discovery, aligning with trends in sustainable chemistry and precision medicine.

The structural motif of 8-Bromo-7-chloroquinoline is pivotal in designing heterocyclic compounds, a hotspot in modern medicinal chemistry. Its halogenated quinoline core is often leveraged to develop antimicrobial agents and fluorescence probes, addressing global challenges like antibiotic resistance and diagnostic imaging. Recent studies highlight its role in metal-organic frameworks (MOFs) and photocatalysts, reflecting the growing demand for eco-friendly materials. Users searching for "quinoline derivatives in drug design" or "halogenated heterocycles applications" will find this compound highly relevant.

From a synthetic perspective, 8-Bromo-7-chloroquinoline serves as a precursor for Suzuki-Miyaura couplings and Buchwald-Hartwig aminations, critical for constructing complex molecules. Its electron-withdrawing properties enhance reactivity in nucleophilic substitutions, a feature exploited in high-throughput screening libraries. Analytical techniques like HPLC, NMR, and mass spectrometry confirm its purity (>98%), meeting stringent industry standards. These attributes resonate with queries such as "how to purify halogenated quinolines" or "quinoline-based catalysts," frequently seen in academic forums.

In material science, the compound’s planar aromatic structure facilitates π-π stacking, enabling applications in organic semiconductors and OLEDs. Its thermal stability (decomposition point >250°C) makes it suitable for high-temperature processes. Researchers investigating "quinolines in optoelectronics" or "small molecule semiconductors" will discover its potential in next-gen devices. Additionally, its solubility in polar aprotic solvents (e.g., DMF, DMSO) simplifies formulation for industrial use.

Environmental and safety profiles of 8-Bromo-7-chloroquinoline adhere to REACH and OECD guidelines, with low ecotoxicity data available. Its handling requires standard lab precautions, aligning with searches for "safe handling of halogenated compounds." As the scientific community prioritizes green chemistry, this compound’s role in atom-efficient synthesis and biodegradable materials continues to expand, bridging gaps between academia and industry.

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• 4357-59-9(Acridine, 4-bromo-9-chloro-)
• 16567-11-6(8-Bromo-6-chloroquinoline)
• 1416440-62-4(3-bromo-5-chloro-quinoline)
• 127827-54-7(6-Bromo-7-chloroquinoline)
• 74575-17-0(3-Bromo-4-chloroquinoline)
• 84973-05-7(3-Bromo-7-chloroquinoline)
• 13669-65-3(3-bromo-6-chloro-quinoline)