Cas no 503308-97-2 (5-bromo-2,4-dimethyl-3-Thiophenecarboxylic acid)

5-Bromo-2,4-dimethyl-3-thiophenecarboxylic acid is a halogenated thiophene derivative with a carboxylic acid functional group, offering versatile reactivity for synthetic applications. Its bromine substituent enables further functionalization via cross-coupling reactions, while the carboxylic acid group allows for esterification, amidation, or other derivatization pathways. The dimethyl substitution pattern enhances steric and electronic control in subsequent reactions, making it a valuable intermediate in pharmaceutical and agrochemical synthesis. This compound is particularly useful in heterocyclic chemistry for constructing complex thiophene-based scaffolds. Its well-defined structure and high purity ensure consistent performance in research and industrial processes.
5-bromo-2,4-dimethyl-3-Thiophenecarboxylic acid structure
503308-97-2 structure
Product Name:5-bromo-2,4-dimethyl-3-Thiophenecarboxylic acid
CAS No:503308-97-2
MF:C7H7BrO2S
MW:235.098280191422
CID:2135820
PubChem ID:12993675
Update Time:2025-05-26

5-bromo-2,4-dimethyl-3-Thiophenecarboxylic acid Chemical and Physical Properties

Names and Identifiers

    • 5-bromo-2,4-dimethyl-3-Thiophenecarboxylic acid
    • 3-Thiophenecarboxylic acid, 5-bromo-2,4-dimethyl-
    • DB-071168
    • 5-bromo-2,4-dimethylthiophene-3-carboxylic acid
    • EN300-7720062
    • SCHEMBL5727379
    • GISRVMJLLUHBAZ-UHFFFAOYSA-N
    • DTXSID201243673
    • 503308-97-2
    • 5-bromo-2,4-dimethylthiophene-3-carboxylicacid
    • Inchi: 1S/C7H7BrO2S/c1-3-5(7(9)10)4(2)11-6(3)8/h1-2H3,(H,9,10)
    • InChI Key: GISRVMJLLUHBAZ-UHFFFAOYSA-N
    • SMILES: BrC1=C(C)C(C(=O)O)=C(C)S1

Computed Properties

  • Exact Mass: 233.93501g/mol
  • Monoisotopic Mass: 233.93501g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 1
  • Complexity: 174
  • 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: 2.9
  • Topological Polar Surface Area: 65.5?2

5-bromo-2,4-dimethyl-3-Thiophenecarboxylic acid Pricemore >>

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Additional information on 5-bromo-2,4-dimethyl-3-Thiophenecarboxylic acid

Recent Advances in the Application of 5-Bromo-2,4-dimethyl-3-Thiophenecarboxylic Acid (CAS: 503308-97-2) in Chemical Biology and Pharmaceutical Research

5-Bromo-2,4-dimethyl-3-Thiophenecarboxylic acid (CAS: 503308-97-2) is a heterocyclic carboxylic acid derivative that has recently gained significant attention in chemical biology and pharmaceutical research due to its versatile applications in drug discovery and material science. This compound, characterized by its thiophene ring substituted with bromine and methyl groups, serves as a key intermediate in the synthesis of various biologically active molecules. Recent studies have explored its potential as a building block for novel therapeutic agents, particularly in the development of kinase inhibitors and anti-inflammatory drugs.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the utility of 5-bromo-2,4-dimethyl-3-Thiophenecarboxylic acid in the synthesis of selective JAK3 inhibitors. The researchers utilized this compound as a core scaffold to develop potent and selective inhibitors that showed promising results in preclinical models of autoimmune diseases. The bromine substitution at the 5-position was found to be critical for maintaining the compound's binding affinity to the JAK3 kinase domain, while the carboxylic acid group facilitated interactions with key amino acid residues in the active site.

In the field of material science, recent investigations have highlighted the potential of 503308-97-2 as a precursor for organic electronic materials. A 2024 publication in Advanced Materials reported the use of this thiophene derivative in the synthesis of novel semiconducting polymers with improved charge transport properties. The researchers attributed the enhanced performance to the electron-withdrawing nature of the bromine substituent and the steric effects of the methyl groups, which contributed to better molecular packing in the solid state.

Pharmacokinetic studies of derivatives containing the 5-bromo-2,4-dimethyl-3-Thiophenecarboxylic acid moiety have shown interesting metabolic profiles. A recent investigation published in Drug Metabolism and Disposition (2024) revealed that this structural motif can influence both the absorption and distribution characteristics of drug candidates. The carboxylic acid group was found to improve water solubility, while the bromine atom contributed to increased membrane permeability, making it a valuable structural element for optimizing drug-like properties.

The synthetic versatility of 503308-97-2 has been further demonstrated in recent work on antimicrobial agents. Researchers have successfully incorporated this building block into novel quinolone hybrids, showing enhanced activity against drug-resistant bacterial strains. The 2024 study, published in Bioorganic & Medicinal Chemistry Letters, reported that the bromine atom played a crucial role in improving target binding through halogen bonding interactions with bacterial DNA gyrase.

Ongoing research continues to explore new applications of 5-bromo-2,4-dimethyl-3-Thiophenecarboxylic acid in pharmaceutical development. Current investigations include its use in PROTAC (Proteolysis Targeting Chimera) design, where its structural features may contribute to improved linker properties and target engagement. As the understanding of this compound's chemical biology expands, it is expected to play an increasingly important role in the development of next-generation therapeutics and functional materials.

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