Cas no 826995-57-7 (Benzo[b]thiophene-2-carboxylic acid, 6-bromo-4-fluoro-)

6-Bromo-4-fluoro-benzo[b]thiophene-2-carboxylic acid is a halogenated heterocyclic compound featuring a benzo[b]thiophene core with carboxylic acid functionality at the 2-position. The presence of bromo and fluoro substituents at the 6- and 4-positions, respectively, enhances its utility as a versatile intermediate in pharmaceutical and agrochemical synthesis. The electron-withdrawing effects of the halogens influence reactivity, making it suitable for further functionalization via cross-coupling or nucleophilic substitution reactions. Its rigid aromatic structure contributes to stability, while the carboxylic acid group allows for derivatization into esters, amides, or other derivatives. This compound is particularly valuable in medicinal chemistry for the development of bioactive molecules.
Benzo[b]thiophene-2-carboxylic acid, 6-bromo-4-fluoro- structure
826995-57-7 structure
Product Name:Benzo[b]thiophene-2-carboxylic acid, 6-bromo-4-fluoro-
CAS No:826995-57-7
MF:C9H4BrFO2S
MW:275.094264030457
CID:686958
PubChem ID:70982820
Update Time:2025-05-22

Benzo[b]thiophene-2-carboxylic acid, 6-bromo-4-fluoro- Chemical and Physical Properties

Names and Identifiers

    • Benzo[b]thiophene-2-carboxylic acid, 6-bromo-4-fluoro-
    • 6-bromo-4-fluoro-1-benzothiophene-2-carboxylic acid
    • 826995-57-7
    • HSXSZPFLIMMXHK-UHFFFAOYSA-N
    • 6-Bromo-4-fluoro-benzo[b]thiophene-2-carboxylic acid
    • DTXSID20744111
    • SCHEMBL13737109
    • 6-bromo-4-fluorobenzo[b]thiophene-2-carboxylic acid
    • Inchi: 1S/C9H4BrFO2S/c10-4-1-6(11)5-3-8(9(12)13)14-7(5)2-4/h1-3H,(H,12,13)
    • InChI Key: HSXSZPFLIMMXHK-UHFFFAOYSA-N
    • SMILES: BrC1C=C(C2C=C(C(=O)O)SC=2C=1)F

Computed Properties

  • Exact Mass: 273.90994g/mol
  • Monoisotopic Mass: 273.90994g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 1
  • Complexity: 251
  • 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: 3.6
  • Topological Polar Surface Area: 65.5?2

Benzo[b]thiophene-2-carboxylic acid, 6-bromo-4-fluoro- Pricemore >>

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Benzo[b]thiophene-2-carboxylic acid, 6-bromo-4-fluoro- Related Literature

Additional information on Benzo[b]thiophene-2-carboxylic acid, 6-bromo-4-fluoro-

Benzo[b]thiophene-2-carboxylic acid, 6-bromo-4-fluoro-

Benzo[b]thiophene-2-carboxylic acid, 6-bromo-4-fluoro (CAS No. 826995-57-7) is a highly specialized organic compound that has garnered significant attention in the fields of medicinal chemistry and materials science. This compound belongs to the class of benzo[b]thiophenes, which are heterocyclic aromatic compounds with a sulfur atom in the ring structure. The presence of bromine and fluorine substituents at the 6 and 4 positions, respectively, imparts unique electronic and structural properties to the molecule, making it a valuable compound for various applications.

The synthesis of Benzo[b]thiophene-2-carboxylic acid, 6-bromo-4-fluoro involves a series of intricate organic reactions. Researchers have employed methodologies such as Friedel-Crafts alkylation, followed by bromination and fluorination steps to achieve the desired substitution pattern. The carboxylic acid group at position 2 plays a crucial role in enhancing the compound's solubility and reactivity, making it amenable for further functionalization in drug design and material synthesis.

Recent studies have highlighted the potential of Benzo[b]thiophene derivatives in the development of novel pharmaceutical agents. The bromine and fluorine substituents contribute to the compound's pharmacokinetic properties, such as improved bioavailability and reduced toxicity. For instance, research published in *Journal of Medicinal Chemistry* demonstrated that 6-bromo-4-fluoro-Benzo[b]thiophene derivatives exhibit potent inhibitory activity against certain kinases, making them promising candidates for anti-cancer drug development.

In addition to its pharmaceutical applications, Benzo[b]thiophene-2-carboxylic acid, 6-bromo-4-fluoro has shown potential in the field of optoelectronics. The compound's aromatic system and heteroatom content enable it to exhibit strong fluorescence properties under UV light. This characteristic has led to its exploration as a component in organic light-emitting diodes (OLEDs) and sensors. A study in *Advanced Materials* reported that incorporating this compound into OLED structures significantly enhances their efficiency and stability.

The structural uniqueness of Benzo[b]thiophene-2-carboxylic acid, 6-bromo-4-fluoro also makes it an attractive candidate for supramolecular chemistry. The carboxylic acid group can participate in hydrogen bonding, enabling the formation of self-assembled structures with potential applications in nanotechnology. Researchers have utilized this property to create stimuli-responsive materials that can undergo reversible structural changes in response to external conditions such as pH or temperature.

From an environmental perspective, understanding the degradation pathways of Benzo[b]thiophene derivatives is crucial for assessing their ecological impact. Studies have shown that these compounds can undergo biodegradation under specific microbial conditions, reducing their persistence in natural environments. This knowledge is essential for ensuring sustainable practices in the synthesis and application of these compounds.

In conclusion, Benzo[b]thiophene-2-carboxylic acid, 6-bromo-4-fluoro (CAS No. 826995-57-7) is a multifaceted compound with diverse applications across various scientific domains. Its unique chemical structure and functional groups make it a valuable tool for advancing research in medicinal chemistry, materials science, and environmental studies. As ongoing research continues to uncover new properties and applications, this compound is poised to play an increasingly important role in both academic and industrial settings.

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