Cas no 66033-75-8 (7-Bromo-3-methylbenzo[d]isoxazole)

7-Bromo-3-methylbenzo[d]isoxazole is a halogenated heterocyclic compound featuring a bromine substituent at the 7-position and a methyl group at the 3-position of the benzo[d]isoxazole core. This structure imparts reactivity suitable for further functionalization, making it a valuable intermediate in pharmaceutical and agrochemical synthesis. The bromine atom enhances its utility in cross-coupling reactions, such as Suzuki or Buchwald-Hartwig couplings, enabling the construction of complex molecular frameworks. Its stability under standard conditions and well-defined reactivity profile ensure consistent performance in synthetic applications. The compound is typically handled under inert conditions to preserve its integrity for use in advanced organic transformations.
7-Bromo-3-methylbenzo[d]isoxazole structure
66033-75-8 structure
Product Name:7-Bromo-3-methylbenzo[d]isoxazole
CAS No:66033-75-8
MF:C8H6BrNO
MW:212.043341159821
MDL:MFCD25978058
CID:3168570
PubChem ID:12411329
Update Time:2025-10-22

7-Bromo-3-methylbenzo[d]isoxazole Chemical and Physical Properties

Names and Identifiers

    • SCHEMBL20870710
    • CS-0106925
    • 7-Bromo-3-methyl-1,2-benzisoxazole
    • BS-17866
    • 7-bromo-3-methyl-1,2-benzoxazole
    • SY263395
    • AKOS022976488
    • 7-Bromo-3-methylbenzo[d]isoxazole
    • MFCD25978058
    • AC8269
    • 66033-75-8
    • MDL: MFCD25978058
    • Inchi: 1S/C8H6BrNO/c1-5-6-3-2-4-7(9)8(6)11-10-5/h2-4H,1H3
    • InChI Key: QHSMWCXTVHKPSV-UHFFFAOYSA-N
    • SMILES: BrC1=CC=CC2C(C)=NOC=21

Computed Properties

  • Exact Mass: 210.96328g/mol
  • Monoisotopic Mass: 210.96328g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 0
  • Complexity: 153
  • 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: 2.8
  • Topological Polar Surface Area: 26?2

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Additional information on 7-Bromo-3-methylbenzo[d]isoxazole

Comprehensive Overview of 7-Bromo-3-methylbenzo[d]isoxazole (CAS No. 66033-75-8): Properties, Applications, and Research Insights

7-Bromo-3-methylbenzo[d]isoxazole (CAS No. 66033-75-8) is a heterocyclic organic compound featuring a benzo[d]isoxazole core substituted with a bromine atom at the 7-position and a methyl group at the 3-position. This structurally unique molecule has garnered significant attention in pharmaceutical and agrochemical research due to its potential as a versatile building block. The 7-bromo substitution enhances reactivity in cross-coupling reactions, while the 3-methyl group contributes to steric and electronic modulation, making it valuable for drug discovery pipelines.

Recent studies highlight the growing demand for functionalized isoxazole derivatives, driven by their prevalence in bioactive molecules. Researchers frequently search for "7-Bromo-3-methylbenzo[d]isoxazole synthesis" or "CAS 66033-75-8 applications," reflecting interest in its role in designing kinase inhibitors and antimicrobial agents. The compound's molecular weight (212.04 g/mol) and lipophilicity (LogP ~2.3) align with Lipinski's rule, underscoring its drug-like properties. Analytical data from HPLC and NMR studies confirm high purity (>98%), critical for reproducible results in medicinal chemistry.

In material science, 66033-75-8 serves as a precursor for organic electronic materials, particularly in developing OLED emitters and photovoltaic sensitizers. Its π-conjugated system enables tunable optoelectronic properties, addressing trending searches like "isoxazole-based semiconductors." Environmental considerations are also prominent, with "green synthesis of brominated isoxazoles" emerging as a keyphrase, reflecting industry shifts toward sustainable methodologies.

Regulatory-compliant handling of 7-Bromo-3-methylbenzo[d]isoxazole requires attention to standard laboratory protocols. While not classified as hazardous under major chemical inventories, proper PPE (gloves, goggles) is recommended during manipulation. Storage at 2-8°C under inert atmosphere ensures stability, as indicated by accelerated degradation studies. Patent analyses reveal increasing use in bioconjugation techniques, particularly for proteolysis-targeting chimeras (PROTACs) – a hot topic in targeted protein degradation therapeutics.

The future outlook for CAS 66033-75-8 remains robust, with expanding applications in catalysis and bioconjugate chemistry. Emerging research explores its utility in click chemistry modifications and fluorescent probes, responding to frequent queries about "multifunctional isoxazole scaffolds." Continuous innovation in microwave-assisted synthesis and flow chemistry approaches further enhances its accessibility for high-throughput screening programs.

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