Cas no 1227579-58-9 (4-Fluoro-1H-indol-6-ol)

4-Fluoro-1H-indol-6-ol is a fluorinated indole derivative with a hydroxyl group at the 6-position, offering unique reactivity and structural versatility for synthetic applications. Its fluorine substitution enhances electron-withdrawing properties, influencing binding affinity and metabolic stability in pharmaceutical intermediates. The phenolic hydroxyl group provides a handle for further functionalization, making it valuable in medicinal chemistry for designing bioactive molecules. This compound is particularly useful in the synthesis of fluorinated analogs of indole-based scaffolds, which are prevalent in drug discovery. High purity and well-defined structure ensure reproducibility in research applications. Suitable for use in cross-coupling reactions, heterocyclic synthesis, and as a building block for fluorinated pharmacophores.
4-Fluoro-1H-indol-6-ol structure
4-Fluoro-1H-indol-6-ol structure
Product Name:4-Fluoro-1H-indol-6-ol
CAS No:1227579-58-9
MF:C8H6FNO
MW:151.137745380402
CID:1083793
PubChem ID:73553637
Update Time:2025-06-11

4-Fluoro-1H-indol-6-ol Chemical and Physical Properties

Names and Identifiers

    • 4-Fluoro-1H-indol-6-ol
    • 4-fluoro-6-hydroxyindole
    • 1227579-58-9
    • DB-062089
    • Inchi: 1S/C8H6FNO/c9-7-3-5(11)4-8-6(7)1-2-10-8/h1-4,10-11H
    • InChI Key: XDNSSHHWAHDSEU-UHFFFAOYSA-N
    • SMILES: FC1=CC(=CC2=C1C=CN2)O

Computed Properties

  • Exact Mass: 151.043341977g/mol
  • Monoisotopic Mass: 151.043341977g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • 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: 1.8
  • Topological Polar Surface Area: 36?2

4-Fluoro-1H-indol-6-ol Pricemore >>

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Additional information on 4-Fluoro-1H-indol-6-ol

Recent Advances in the Study of 4-Fluoro-1H-indol-6-ol (CAS: 1227579-58-9): A Comprehensive Research Brief

The compound 4-Fluoro-1H-indol-6-ol (CAS: 1227579-58-9) has garnered significant attention in the field of chemical biology and pharmaceutical research due to its unique structural properties and potential therapeutic applications. This research brief aims to provide an up-to-date overview of the latest findings related to this compound, focusing on its synthesis, biological activity, and potential applications in drug development.

Recent studies have highlighted the role of 4-Fluoro-1H-indol-6-ol as a key intermediate in the synthesis of various bioactive molecules. Its fluorinated indole scaffold is particularly noteworthy, as it enhances the compound's metabolic stability and bioavailability. Researchers have successfully employed this compound in the development of novel kinase inhibitors, which show promise in targeting cancer-related pathways. The incorporation of the fluorine atom at the 4-position of the indole ring has been shown to significantly improve the compound's binding affinity to target proteins.

In a groundbreaking study published in the Journal of Medicinal Chemistry, scientists demonstrated the efficacy of 4-Fluoro-1H-indol-6-ol derivatives in inhibiting aberrant signaling pathways in non-small cell lung cancer (NSCLC) cells. The study utilized a combination of computational modeling and in vitro assays to elucidate the mechanism of action. Results indicated that these derivatives effectively suppressed tumor growth by targeting specific tyrosine kinases, with minimal off-target effects. This finding opens new avenues for the development of targeted therapies for NSCLC and other malignancies.

Another area of active research involves the application of 4-Fluoro-1H-indol-6-ol in neurodegenerative diseases. Preliminary data from a recent preclinical study suggest that this compound may modulate neuroinflammatory responses by inhibiting key enzymes involved in the production of pro-inflammatory cytokines. While further validation is required, these findings underscore the compound's potential as a therapeutic agent for conditions such as Alzheimer's disease and Parkinson's disease.

The synthesis of 4-Fluoro-1H-indol-6-ol has also seen significant advancements. A recent publication in Organic Letters detailed a novel, high-yield synthetic route that employs palladium-catalyzed cross-coupling reactions. This method not only improves the overall efficiency of the synthesis but also reduces the generation of hazardous byproducts, aligning with the principles of green chemistry. Such innovations are critical for scaling up production and facilitating further pharmacological studies.

In conclusion, 4-Fluoro-1H-indol-6-ol (CAS: 1227579-58-9) represents a versatile and promising scaffold in medicinal chemistry. Its applications span from oncology to neuroscience, driven by its favorable pharmacokinetic properties and ease of derivatization. Ongoing research continues to uncover new therapeutic potentials, making this compound a focal point in the quest for innovative treatments. Future studies should focus on optimizing its derivatives for clinical translation and exploring its mechanisms of action in greater detail.

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