Cas no 1227600-53-4 (6-bromo-1H-indol-7-ol)

6-Bromo-1H-indol-7-ol is a brominated indole derivative with a hydroxyl group at the 7-position, making it a versatile intermediate in organic synthesis and pharmaceutical research. Its key advantages include its role as a building block for the preparation of biologically active compounds, particularly in the development of indole-based pharmaceuticals and agrochemicals. The bromine substituent enhances reactivity for further functionalization, while the hydroxyl group provides a site for derivatization or conjugation. This compound is valued for its structural specificity, which facilitates targeted modifications in medicinal chemistry applications. High-purity grades ensure consistent performance in research and industrial processes.
6-bromo-1H-indol-7-ol structure
6-bromo-1H-indol-7-ol structure
Product Name:6-bromo-1H-indol-7-ol
CAS No:1227600-53-4
MF:C8H6BrNO
MW:212.043341159821
CID:2618230
PubChem ID:71819678
Update Time:2025-11-02

6-bromo-1H-indol-7-ol Chemical and Physical Properties

Names and Identifiers

    • 6-bromo-1H-indol-7-ol
    • DTXSID50858593
    • 1227600-53-4
    • SB15152
    • 1H-Indol-7-ol, 6-broMo-
    • Inchi: 1S/C8H6BrNO/c9-6-2-1-5-3-4-10-7(5)8(6)11/h1-4,10-11H
    • InChI Key: IODPLXFAXMLBLH-UHFFFAOYSA-N
    • SMILES: BrC1C=CC2C=CNC=2C=1O

Computed Properties

  • Exact Mass: 210.96328Da
  • Monoisotopic Mass: 210.96328Da
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 1
  • 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: 2.4
  • Topological Polar Surface Area: 36?2

6-bromo-1H-indol-7-ol Pricemore >>

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Additional information on 6-bromo-1H-indol-7-ol

Comprehensive Overview of 6-bromo-1H-indol-7-ol (CAS No. 1227600-53-4): Properties, Applications, and Research Insights

6-bromo-1H-indol-7-ol (CAS No. 1227600-53-4) is a halogenated indole derivative that has garnered significant attention in pharmaceutical and biochemical research due to its unique structural features and potential applications. This compound, characterized by a bromine substitution at the 6-position and a hydroxyl group at the 7-position of the indole scaffold, serves as a versatile intermediate in organic synthesis and drug discovery. Its molecular formula, C8H6BrNO, and molecular weight of 212.05 g/mol make it a valuable building block for designing bioactive molecules.

In recent years, the demand for 6-bromo-1H-indol-7-ol has surged, particularly in the context of cancer research and neurodegenerative disease studies. Researchers are exploring its role as a precursor for synthesizing kinase inhibitors and serotonin receptor modulators, aligning with the growing interest in targeted therapies and precision medicine. The compound's ability to interact with biological targets, such as enzymes and receptors, has made it a focal point in high-throughput screening campaigns.

From a chemical perspective, 6-bromo-1H-indol-7-ol exhibits notable reactivity due to the electron-rich nature of the indole ring and the presence of the bromo substituent. This allows for diverse functionalization, including cross-coupling reactions like Suzuki-Miyaura and Buchwald-Hartwig animations, which are critical for constructing complex heterocyclic frameworks. Such transformations are frequently discussed in organic chemistry forums and patent literature, reflecting the compound's relevance in modern synthetic methodologies.

The compound's physicochemical properties, such as its solubility in polar organic solvents (e.g., DMSO, methanol) and melting point range (typically 180–185°C), are frequently queried in chemical databases and supplier catalogs. These parameters are essential for researchers optimizing reaction conditions or formulating drug delivery systems. Additionally, its stability under inert atmospheres and sensitivity to light underscore the importance of proper storage—a topic often highlighted in laboratory safety guidelines.

In the realm of drug discovery, 6-bromo-1H-indol-7-ol has been investigated for its potential to yield analogs with improved pharmacokinetic profiles. For instance, its incorporation into small-molecule libraries has enabled the identification of lead compounds for treating inflammatory disorders and metabolic syndromes. This aligns with the broader trend of repurposing heterocyclic compounds for multifactorial diseases, a hot topic in biomedical research.

Environmental and regulatory considerations also play a role in the compound's utilization. While 6-bromo-1H-indol-7-ol is not classified as hazardous under current guidelines, its handling requires adherence to green chemistry principles, such as waste minimization and solvent recovery. These aspects resonate with the increasing emphasis on sustainable synthesis in academic and industrial settings.

Looking ahead, the trajectory of 6-bromo-1H-indol-7-ol research is likely to intersect with emerging technologies like AI-assisted molecular design and automated synthesis platforms. These advancements could accelerate the development of novel derivatives with enhanced bioactivity, addressing unmet medical needs. As such, this compound remains a cornerstone in the evolving landscape of medicinal chemistry and chemical biology.

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