Cas no 19230-58-1 (2-Bromo-5-methylpyridine 1-oxide)

2-Bromo-5-methylpyridine 1-oxide is a heterocyclic compound featuring a pyridine core substituted with a bromo group at the 2-position and a methyl group at the 5-position, further oxidized to the N-oxide. This structure enhances its reactivity, making it a valuable intermediate in organic synthesis, particularly in pharmaceutical and agrochemical applications. The presence of both bromine and the N-oxide group allows for selective functionalization, enabling cross-coupling reactions and nucleophilic substitutions. Its stability under standard conditions and well-defined reactivity profile make it a reliable building block for constructing complex molecules. The compound is typically handled under inert conditions to preserve its integrity.
2-Bromo-5-methylpyridine 1-oxide structure
19230-58-1 structure
Product Name:2-Bromo-5-methylpyridine 1-oxide
CAS No:19230-58-1
MF:C6H6BrNO
MW:188.02194070816
MDL:MFCD11052562
CID:1024614
PubChem ID:13178737
Update Time:2025-10-30

2-Bromo-5-methylpyridine 1-oxide Chemical and Physical Properties

Names and Identifiers

    • 2-Bromo-5-methylpyridine 1-oxide
    • 2-bromo-5-methyl-1-oxidopyridin-1-ium
    • 2-bromo-5-methylpyridine-1-oxide
    • 2-bromo-5-methylpyridin-1-ol
    • 2-Bromo-5-methyl-pyridine 1-oxide
    • 2-Bromo-5-methylpyridine N-oxide
    • AGN-PC-00LB19
    • AN-584
    • ANW-53365
    • CTK0E1366
    • Pyridine, 2-bromo-5-methyl-, 1-oxide
    • 2-broMo-5-Methylpyridine-1-o×ide
    • 2-Bromo-5-methylpyridin-1-ium-1-olate
    • SCHEMBL2596867
    • 19230-58-1
    • AKOS006307633
    • 2-Bromo-5-methyl-1-oxo-1lambda~5~-pyridine
    • DB-364851
    • AN-584/43416184
    • DTXSID20524975
    • AS-30684
    • 2-bromo-5-methylpyridine1-oxide
    • SY115512
    • MFCD11052562
    • PJPYKXAQHIYIFY-UHFFFAOYSA-N
    • MDL: MFCD11052562
    • Inchi: 1S/C6H6BrNO/c1-5-2-3-6(7)8(9)4-5/h2-4H,1H3
    • InChI Key: PJPYKXAQHIYIFY-UHFFFAOYSA-N
    • SMILES: BrC1=CC=C(C)C=[N+]1[O-]

Computed Properties

  • Exact Mass: 186.96328
  • Monoisotopic Mass: 186.96328g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 0
  • Heavy Atom Count: 9
  • Rotatable Bond Count: 0
  • Complexity: 99.1
  • 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: 1.2
  • Topological Polar Surface Area: 25.5?2

Experimental Properties

  • PSA: 26.94

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Additional information on 2-Bromo-5-methylpyridine 1-oxide

Recent Advances in the Application of 2-Bromo-5-methylpyridine 1-oxide (CAS: 19230-58-1) in Chemical Biology and Pharmaceutical Research

2-Bromo-5-methylpyridine 1-oxide (CAS: 19230-58-1) is a heterocyclic compound that has garnered significant attention in recent years due to its versatile applications in chemical biology and pharmaceutical research. This compound serves as a crucial intermediate in the synthesis of various bioactive molecules, including potential drug candidates. The unique structural features of 2-Bromo-5-methylpyridine 1-oxide, such as its bromine substituent and N-oxide moiety, make it a valuable building block for the development of novel therapeutic agents. Recent studies have explored its utility in medicinal chemistry, particularly in the design of kinase inhibitors, antimicrobial agents, and anti-inflammatory compounds.

One of the most notable advancements in the application of 2-Bromo-5-methylpyridine 1-oxide is its role in the synthesis of kinase inhibitors. Kinases are key regulators of cellular signaling pathways and are often implicated in diseases such as cancer and autoimmune disorders. Researchers have successfully utilized 2-Bromo-5-methylpyridine 1-oxide as a precursor to develop selective kinase inhibitors with improved potency and reduced off-target effects. For instance, a 2023 study published in the Journal of Medicinal Chemistry demonstrated the compound's efficacy in the synthesis of novel JAK2 inhibitors, which show promise for the treatment of myeloproliferative neoplasms.

In addition to its applications in kinase inhibitor development, 2-Bromo-5-methylpyridine 1-oxide has also been investigated for its antimicrobial properties. A recent study in Bioorganic & Medicinal Chemistry Letters highlighted the compound's potential as a scaffold for designing new antibacterial agents. The study reported that derivatives of 2-Bromo-5-methylpyridine 1-oxide exhibited significant activity against Gram-positive bacteria, including methicillin-resistant Staphylococcus aureus (MRSA). These findings underscore the compound's potential in addressing the growing challenge of antibiotic resistance.

Another area of research where 2-Bromo-5-methylpyridine 1-oxide has shown promise is in the development of anti-inflammatory agents. A 2022 study in the European Journal of Medicinal Chemistry explored the anti-inflammatory effects of 2-Bromo-5-methylpyridine 1-oxide derivatives in vitro and in vivo. The researchers found that certain derivatives effectively inhibited the production of pro-inflammatory cytokines, such as TNF-α and IL-6, suggesting their potential as therapeutic agents for inflammatory diseases like rheumatoid arthritis and inflammatory bowel disease.

Despite these promising developments, challenges remain in the optimization of 2-Bromo-5-methylpyridine 1-oxide-based compounds for clinical use. Issues such as bioavailability, metabolic stability, and toxicity profiles need to be addressed through further research. However, the compound's versatility and the growing body of evidence supporting its applications in drug discovery make it a valuable tool for medicinal chemists. Future studies are expected to explore new synthetic routes and derivatives of 2-Bromo-5-methylpyridine 1-oxide, as well as their potential in targeting other disease pathways.

In conclusion, 2-Bromo-5-methylpyridine 1-oxide (CAS: 19230-58-1) continues to be a focal point in chemical biology and pharmaceutical research. Its applications in the synthesis of kinase inhibitors, antimicrobial agents, and anti-inflammatory compounds highlight its broad utility in drug discovery. As research progresses, this compound is likely to play an increasingly important role in the development of novel therapeutics for a range of diseases.

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