Cas no 67365-46-2 (1,5-Dibromo-2-methyl-3-nitrobenzene)

1,5-Dibromo-2-methyl-3-nitrobenzene is a brominated aromatic compound featuring nitro and methyl functional groups at adjacent positions. Its molecular structure (C7H5Br2NO2) makes it a valuable intermediate in organic synthesis, particularly for constructing complex molecules in pharmaceuticals, agrochemicals, and materials science. The presence of bromine atoms enhances reactivity in cross-coupling reactions, such as Suzuki or Ullmann couplings, while the nitro group offers versatility for further functionalization. The compound’s high purity and stability under standard conditions ensure consistent performance in research and industrial applications. Its well-defined reactivity profile makes it a preferred choice for selective modifications in multi-step synthetic routes.
1,5-Dibromo-2-methyl-3-nitrobenzene structure
67365-46-2 structure
Product Name:1,5-Dibromo-2-methyl-3-nitrobenzene
CAS No:67365-46-2
MF:C7H5Br2NO2
MW:294.928100347519
CID:840367
PubChem ID:23462575
Update Time:2025-06-13

1,5-Dibromo-2-methyl-3-nitrobenzene Chemical and Physical Properties

Names and Identifiers

    • 1,5-Dibromo-2-methyl-3-nitrobenzene
    • 1,5-bis(bromanyl)-2-methyl-3-nitro-benzene
    • SCHEMBL629542
    • A835722
    • AKOS015891567
    • DTXSID60634385
    • 67365-46-2
    • Inchi: 1S/C7H5Br2NO2/c1-4-6(9)2-5(8)3-7(4)10(11)12/h2-3H,1H3
    • InChI Key: HTHSMVZFGLLQAH-UHFFFAOYSA-N
    • SMILES: BrC1=CC(=CC(=C1C)[N+](=O)[O-])Br

Computed Properties

  • Exact Mass: 292.86900
  • Monoisotopic Mass: 292.869
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 0
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 1
  • Complexity: 183
  • 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: 45.8A^2

Experimental Properties

  • PSA: 45.82000
  • LogP: 3.95140

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Additional information on 1,5-Dibromo-2-methyl-3-nitrobenzene

Recent Advances in the Application of 1,5-Dibromo-2-methyl-3-nitrobenzene (CAS: 67365-46-2) in Chemical and Biomedical Research

1,5-Dibromo-2-methyl-3-nitrobenzene (CAS: 67365-46-2) is a halogenated nitroaromatic compound that has garnered significant attention in recent years due to its versatile applications in chemical synthesis and biomedical research. This compound serves as a key intermediate in the synthesis of various pharmaceuticals, agrochemicals, and specialty chemicals. Recent studies have explored its potential in drug discovery, particularly in the development of novel antimicrobial and anticancer agents. The unique structural features of this compound, including the presence of bromine and nitro functional groups, make it a valuable building block for the construction of complex molecular architectures.

In a groundbreaking study published in the Journal of Medicinal Chemistry, researchers demonstrated the utility of 1,5-Dibromo-2-methyl-3-nitrobenzene as a precursor for the synthesis of potent kinase inhibitors. The study highlighted the compound's ability to undergo selective cross-coupling reactions, enabling the efficient construction of diverse heterocyclic scaffolds. These scaffolds were subsequently evaluated for their inhibitory activity against a panel of cancer-related kinases, with several derivatives exhibiting nanomolar potency. The findings underscore the potential of this compound in the design of targeted therapies for oncology applications.

Another notable application of 1,5-Dibromo-2-methyl-3-nitrobenzene was reported in the field of antimicrobial research. A team of scientists from leading pharmaceutical institutions utilized this compound as a starting material for the development of novel antibacterial agents. Through a series of structural modifications, they synthesized a library of derivatives with enhanced activity against multidrug-resistant bacterial strains. The most promising candidates demonstrated broad-spectrum activity, including against methicillin-resistant Staphylococcus aureus (MRSA) and extended-spectrum β-lactamase (ESBL)-producing Enterobacteriaceae. These results were published in the Antimicrobial Agents and Chemotherapy journal, highlighting the compound's potential in addressing the global challenge of antibiotic resistance.

Recent advancements in synthetic methodology have also expanded the utility of 1,5-Dibromo-2-methyl-3-nitrobenzene. A study published in Organic Letters described a novel palladium-catalyzed coupling reaction that enables the selective functionalization of this compound at specific positions. This methodology provides access to previously inaccessible derivatives, opening new avenues for structure-activity relationship studies. The researchers demonstrated the application of this approach in the synthesis of fluorescent probes for biological imaging, showcasing the compound's versatility beyond traditional pharmaceutical applications.

From a safety and regulatory perspective, recent toxicological studies have provided valuable insights into the handling and use of 1,5-Dibromo-2-methyl-3-nitrobenzene. A comprehensive assessment published in Chemical Research in Toxicology evaluated the compound's environmental fate and ecotoxicological profile. The study established guidelines for safe handling procedures and waste management, ensuring compliance with current Good Manufacturing Practice (cGMP) standards. These findings are particularly relevant for industrial-scale applications of the compound in pharmaceutical manufacturing.

Looking ahead, the unique properties of 1,5-Dibromo-2-methyl-3-nitrobenzene continue to inspire innovative applications across multiple disciplines. Current research efforts are exploring its potential in materials science, particularly in the development of organic electronic materials and metal-organic frameworks. Additionally, its role in the synthesis of bioactive natural product analogs represents an exciting frontier in drug discovery. As synthetic methodologies advance and our understanding of structure-activity relationships deepens, this compound is poised to remain a valuable tool in chemical and biomedical research for years to come.

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