Cas no 183543-61-5 (3-Bromo-6-chloro-8-nitroquinoline)

3-Bromo-6-chloro-8-nitroquinoline is a halogenated nitroquinoline derivative with significant utility in synthetic organic chemistry and pharmaceutical research. Its distinct substitution pattern—bromo, chloro, and nitro functional groups—enhances its reactivity, making it a versatile intermediate for constructing complex heterocyclic compounds. The electron-withdrawing nitro group facilitates nucleophilic aromatic substitution, while the bromo and chloro substituents offer selective sites for further functionalization via cross-coupling reactions. This compound is particularly valuable in medicinal chemistry for developing bioactive molecules, including potential antimicrobial and anticancer agents. Its high purity and well-defined structure ensure reproducibility in research applications. Proper handling is advised due to its sensitivity to light and moisture.
3-Bromo-6-chloro-8-nitroquinoline structure
183543-61-5 structure
Product Name:3-Bromo-6-chloro-8-nitroquinoline
CAS No:183543-61-5
MF:C9H4BrClN2O2
MW:287.497260093689
MDL:MFCD16658649
CID:1032076
PubChem ID:384158
Update Time:2025-11-02

3-Bromo-6-chloro-8-nitroquinoline Chemical and Physical Properties

Names and Identifiers

    • 3-Bromo-6-chloro-8-nitroquinoline
    • 3-bromo-6-chloro-8-nitro-quinoline
    • 3-Bromo-6-chloro-8-(hydroxy(oxido)amino)quinoline
    • NCI60_026018
    • AMY27067
    • InChI=1/C9H4BrClN2O2/c10-6-1-5-2-7(11)3-8(13(14)15)9(5)12-4-6/h1-4
    • CHEMBL1991016
    • NSC673448
    • SB70803
    • DB-122622
    • 183543-61-5
    • DTXSID50327638
    • NSC-673448
    • MDL: MFCD16658649
    • Inchi: 1S/C9H4BrClN2O2/c10-6-1-5-2-7(11)3-8(13(14)15)9(5)12-4-6/h1-4H
    • InChI Key: COVFYLACFRNJLF-UHFFFAOYSA-N
    • SMILES: BrC1=CN=C2C(=CC(=CC2=C1)Cl)[N+](=O)[O-]

Computed Properties

  • Exact Mass: 285.91447g/mol
  • Monoisotopic Mass: 285.91447g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 15
  • Rotatable Bond Count: 1
  • Complexity: 261
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 3.3
  • Topological Polar Surface Area: 58.7?2

3-Bromo-6-chloro-8-nitroquinoline Pricemore >>

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Additional information on 3-Bromo-6-chloro-8-nitroquinoline

Comprehensive Overview of 3-Bromo-6-chloro-8-nitroquinoline (CAS No. 183543-61-5): Properties, Applications, and Research Insights

3-Bromo-6-chloro-8-nitroquinoline (CAS No. 183543-61-5) is a halogenated nitroquinoline derivative that has garnered significant attention in pharmaceutical and materials science research. This compound, characterized by its bromine, chlorine, and nitro functional groups, exhibits unique electronic and steric properties, making it a valuable intermediate in synthetic chemistry. Researchers and industries are increasingly exploring its potential in drug discovery, agrochemical development, and advanced material synthesis.

The structural features of 3-Bromo-6-chloro-8-nitroquinoline contribute to its reactivity and versatility. The presence of bromine and chlorine atoms enhances its ability to participate in cross-coupling reactions, such as Suzuki-Miyaura or Buchwald-Hartwig reactions, which are pivotal in constructing complex molecular architectures. Meanwhile, the nitro group offers opportunities for reduction or substitution, enabling the synthesis of diverse derivatives. These attributes align with current trends in green chemistry and sustainable synthesis, as researchers seek efficient pathways to minimize waste and energy consumption.

In the pharmaceutical sector, 3-Bromo-6-chloro-8-nitroquinoline is investigated for its potential as a scaffold in antimicrobial and anticancer agents. Recent studies highlight the role of nitroquinolines in targeting bacterial enzymes or disrupting cellular pathways in tumors. This aligns with the growing demand for novel antibiotics amid rising antimicrobial resistance (AMR), a global health priority. Additionally, its application in photoactive materials and organic electronics is under exploration, driven by the surge in interest for flexible electronics and optoelectronic devices.

From a commercial perspective, the compound's synthesis and scalability are critical topics. Manufacturers and suppliers often address queries like "high-purity 3-Bromo-6-chloro-8-nitroquinoline suppliers" or "CAS 183543-61-5 synthesis optimization", reflecting market needs for reliable and cost-effective production methods. Analytical techniques such as HPLC, NMR, and mass spectrometry are essential for quality control, ensuring compliance with regulatory standards for research and industrial use.

Environmental and safety considerations are also paramount. While 3-Bromo-6-chloro-8-nitroquinoline is not classified as hazardous under standard guidelines, proper handling protocols are recommended due to its reactive functional groups. This resonates with the broader scientific community's focus on lab safety and chemical stewardship, particularly in academic and industrial settings.

In summary, 3-Bromo-6-chloro-8-nitroquinoline (CAS No. 183543-61-5) represents a multifaceted compound with expanding applications across disciplines. Its integration into cutting-edge research underscores its importance in addressing contemporary challenges in healthcare, technology, and sustainability. Future studies may further elucidate its mechanistic roles and commercial potential, solidifying its position in the chemical landscape.

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