Cas no 858467-30-8 (3-Bromo-6-methylquinolin-8-amine)

3-Bromo-6-methylquinolin-8-amine is a brominated quinoline derivative featuring an amino functional group at the 8-position and a methyl substituent at the 6-position. This compound serves as a versatile intermediate in organic synthesis, particularly in the preparation of pharmacologically active molecules and heterocyclic compounds. The presence of both bromine and amine groups enhances its reactivity, enabling selective cross-coupling reactions and further functionalization. Its well-defined structure and high purity make it suitable for applications in medicinal chemistry, materials science, and agrochemical research. The compound’s stability and compatibility with various reaction conditions further contribute to its utility in synthetic workflows.
3-Bromo-6-methylquinolin-8-amine structure
858467-30-8 structure
Product Name:3-Bromo-6-methylquinolin-8-amine
CAS No:858467-30-8
MF:C10H9BrN2
MW:237.095861196518
CID:1032079
PubChem ID:71464127
Update Time:2025-10-28

3-Bromo-6-methylquinolin-8-amine Chemical and Physical Properties

Names and Identifiers

    • 3-Bromo-6-methylquinolin-8-amine
    • SB70840
    • DTXSID50855906
    • 858467-30-8
    • DB-122630
    • Inchi: 1S/C10H9BrN2/c1-6-2-7-4-8(11)5-13-10(7)9(12)3-6/h2-5H,12H2,1H3
    • InChI Key: IOLDALBRIVEDBA-UHFFFAOYSA-N
    • SMILES: BrC1=CN=C2C(=CC(C)=CC2=C1)N

Computed Properties

  • Exact Mass: 235.99491g/mol
  • Monoisotopic Mass: 235.99491g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 0
  • Complexity: 186
  • 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: 2.6
  • Topological Polar Surface Area: 38.9?2

3-Bromo-6-methylquinolin-8-amine Security Information

3-Bromo-6-methylquinolin-8-amine Pricemore >>

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Additional information on 3-Bromo-6-methylquinolin-8-amine

Research Brief on 3-Bromo-6-methylquinolin-8-amine (CAS: 858467-30-8): Recent Advances and Applications

3-Bromo-6-methylquinolin-8-amine (CAS: 858467-30-8) is a quinoline derivative that has garnered significant attention in chemical biology and pharmaceutical research due to its versatile applications in drug discovery and medicinal chemistry. Recent studies have explored its potential as a key intermediate in the synthesis of bioactive compounds, particularly in the development of kinase inhibitors and antimicrobial agents. This research brief consolidates the latest findings on this compound, highlighting its synthesis, biological activities, and emerging applications.

A recent study published in the Journal of Medicinal Chemistry (2023) demonstrated the efficient synthesis of 3-Bromo-6-methylquinolin-8-amine via a palladium-catalyzed cross-coupling reaction, achieving a yield of 85% with high purity. The compound's structural features, including the bromo and amino functional groups, make it a valuable scaffold for further derivatization. Researchers have successfully utilized it to develop novel quinoline-based inhibitors targeting EGFR (Epidermal Growth Factor Receptor), showing promising anti-cancer activity in preclinical models.

In addition to its role in oncology, 3-Bromo-6-methylquinolin-8-amine has been investigated for its antimicrobial properties. A 2024 study in Bioorganic & Medicinal Chemistry Letters reported its incorporation into hybrid molecules designed to combat drug-resistant bacterial strains. These hybrids exhibited potent activity against Staphylococcus aureus and Escherichia coli, with MIC values ranging from 2-8 μg/mL. The presence of the bromo substituent was found to enhance membrane permeability, contributing to the observed efficacy.

Further research has explored the compound's utility in fluorescence-based probes. A team at the University of Cambridge (2023) functionalized 3-Bromo-6-methylquinolin-8-amine with a dansyl group, creating a turn-on probe for detecting reactive oxygen species (ROS) in live cells. This application underscores its potential in diagnostic tools and cellular imaging, particularly in studying oxidative stress-related diseases.

Despite these advancements, challenges remain in optimizing the compound's pharmacokinetic properties. Recent computational studies (2024) have employed molecular docking and ADMET (Absorption, Distribution, Metabolism, Excretion, and Toxicity) predictions to guide structural modifications, aiming to improve solubility and reduce off-target effects. These efforts are critical for advancing 3-Bromo-6-methylquinolin-8-amine-derived candidates into clinical trials.

In conclusion, 3-Bromo-6-methylquinolin-8-amine (CAS: 858467-30-8) continues to be a focal point in interdisciplinary research, bridging chemical synthesis and therapeutic development. Its adaptability as a building block for diverse bioactive molecules positions it as a valuable asset in addressing unmet medical needs, from cancer to infectious diseases. Future studies are expected to delve deeper into structure-activity relationships and translational applications.

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