Cas no 885520-70-7 (4-Bromo-6-fluoro-1H-indole)

4-Bromo-6-fluoro-1H-indole is a halogenated indole derivative with significant utility in pharmaceutical and agrochemical research. The presence of both bromo and fluoro substituents at the 4- and 6-positions, respectively, enhances its reactivity, making it a versatile intermediate for cross-coupling reactions, such as Suzuki or Buchwald-Hartwig amination. Its indole core structure is pivotal in the synthesis of biologically active compounds, including kinase inhibitors and antimicrobial agents. The compound’s high purity and stability under standard conditions ensure reliable performance in synthetic applications. Its distinct substitution pattern also facilitates regioselective modifications, enabling precise structural diversification in drug discovery and material science.
4-Bromo-6-fluoro-1H-indole structure
4-Bromo-6-fluoro-1H-indole structure
Product Name:4-Bromo-6-fluoro-1H-indole
CAS No:885520-70-7
MF:C8H5BrFN
MW:214.03440451622
MDL:MFCD08272203
CID:829980
PubChem ID:24728173
Update Time:2025-08-05

4-Bromo-6-fluoro-1H-indole Chemical and Physical Properties

Names and Identifiers

    • 4-Bromo-6-fluoro-1H-indole
    • 4-Bromo-6-fluoroindole
    • 1H-INDOLE,4-BROMO-6-FLUORO
    • 4-Bromo-6-fluoro (1H)indazole
    • PubChem23229
    • 4-bromo-6-fluoro-indole
    • DMOWKZSCECYXSE-UHFFFAOYSA-N
    • SB15135
    • SY031157
    • BC004897
    • AK113709
    • AB0049685
    • ST24023393
    • Z5269
    • 4-Bromo-6-fluoro-1H-indole (ACI)
    • MFCD08272203
    • 885520-70-7
    • DB-077956
    • AKOS005259813
    • DTXSID50646235
    • SCHEMBL996179
    • AC-29794
    • CS-W019334
    • DS-6340
    • MDL: MFCD08272203
    • Inchi: 1S/C8H5BrFN/c9-7-3-5(10)4-8-6(7)1-2-11-8/h1-4,11H
    • InChI Key: DMOWKZSCECYXSE-UHFFFAOYSA-N
    • SMILES: FC1C=C2C(C=CN2)=C(Br)C=1

Computed Properties

  • Exact Mass: 212.95894g/mol
  • Monoisotopic Mass: 212.95894g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • 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
  • Topological Polar Surface Area: 15.8
  • XLogP3: 2.8

Experimental Properties

  • Density: 1.750

4-Bromo-6-fluoro-1H-indole Security Information

4-Bromo-6-fluoro-1H-indole Pricemore >>

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Additional information on 4-Bromo-6-fluoro-1H-indole

Professional Introduction to 4-Bromo-6-fluoro-1H-indole (CAS No. 885520-70-7)

4-Bromo-6-fluoro-1H-indole, identified by its CAS number 885520-70-7, is a significant compound in the realm of pharmaceutical chemistry and medicinal research. This heterocyclic aromatic molecule has garnered considerable attention due to its versatile structural framework and potential applications in drug discovery. The presence of both bromine and fluorine substituents on the indole ring imparts unique electronic and steric properties, making it a valuable scaffold for designing novel bioactive molecules.

The indole core is a well-documented motif in medicinal chemistry, renowned for its role in various pharmacological activities. Compounds containing the indole scaffold have been extensively studied for their antimicrobial, anti-inflammatory, and anticancer properties. Among these, 4-Bromo-6-fluoro-1H-indole stands out due to the specific positioning of the bromo and fluoro groups, which can modulate the compound's interaction with biological targets. This strategic placement allows for fine-tuning of pharmacokinetic and pharmacodynamic profiles, enhancing its suitability for therapeutic applications.

In recent years, there has been a surge in research focused on developing small-molecule inhibitors targeting intricate biological pathways. The fluorine atom in 4-Bromo-6-fluoro-1H-indole plays a crucial role in improving metabolic stability and binding affinity to biological receptors. This feature is particularly valuable in the design of kinase inhibitors, where fluorine substitution often enhances potency and selectivity. Furthermore, the bromine moiety can serve as a handle for further chemical modifications, enabling the synthesis of more complex derivatives with tailored biological activities.

One of the most compelling aspects of 4-Bromo-6-fluoro-1H-indole is its potential in oncology research. Indole derivatives have shown promise as inhibitors of various cancer-related enzymes and pathways. For instance, studies have demonstrated that compounds structurally similar to 4-Bromo-6-fluoro-1H-indole can inhibit tyrosine kinases, which are frequently overexpressed in tumors. The combination of bromine and fluorine substituents may enhance the compound's ability to disrupt these signaling pathways, offering a novel approach to cancer therapy.

The synthetic accessibility of 4-Bromo-6-fluoro-1H-indole is another factor contributing to its popularity in research settings. The indole ring can be readily functionalized at various positions using established organic chemistry techniques. This flexibility allows chemists to explore a wide range of structural modifications, facilitating the discovery of lead compounds with optimized pharmacological properties. Additionally, the compound's stability under various conditions makes it suitable for both laboratory-scale synthesis and large-scale production.

The impact of substituent effects on the electronic properties of heterocyclic compounds like 4-Bromo-6-fluoro-1H-indole has been extensively studied. Computational methods such as density functional theory (DFT) have been employed to elucidate how bromine and fluorine influence the molecule's reactivity and binding interactions. These studies have provided valuable insights into designing more effective drug candidates by predicting how different substituents will affect the compound's overall behavior.

In conclusion, 4-Bromo-6-fluoro-1H-indole (CAS No. 885520-70-7) represents a promising scaffold for pharmaceutical development. Its unique structural features, combined with its synthetic versatility, make it an attractive candidate for further exploration in drug discovery. As research continues to uncover new therapeutic targets and mechanisms, compounds like this are likely to play a pivotal role in developing next-generation medications that address unmet medical needs.

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