Cas no 933585-42-3 (Ethyl 4-bromo-3-methoxybenzoate)

Ethyl 4-bromo-3-methoxybenzoate is a brominated aromatic ester with the molecular formula C??H??BrO?. This compound serves as a versatile intermediate in organic synthesis, particularly in pharmaceutical and agrochemical applications. Its key functional groups—the bromo and methoxy substituents—enable selective cross-coupling reactions, such as Suzuki or Heck couplings, facilitating the construction of complex molecular frameworks. The ethyl ester moiety enhances solubility in organic solvents, simplifying purification and handling. With a well-defined reactivity profile, it is valued for its stability under standard conditions and compatibility with diverse reaction conditions. Suitable for research and industrial use, it offers reliable performance in fine chemical synthesis.
Ethyl 4-bromo-3-methoxybenzoate structure
933585-42-3 structure
Product Name:Ethyl 4-bromo-3-methoxybenzoate
CAS No:933585-42-3
MF:C10H11BrO3
MW:259.096542596817
MDL:MFCD14698173
CID:1091355
Update Time:2025-10-31

Ethyl 4-bromo-3-methoxybenzoate Chemical and Physical Properties

Names and Identifiers

    • Ethyl 4-bromo-3-methoxybenzoate
    • AS03600
    • AK145208
    • AX8283287
    • Ethyl 4-bromo-3-methoxybenzoate (ACI)
    • MDL: MFCD14698173
    • Inchi: 1S/C10H11BrO3/c1-3-14-10(12)7-4-5-8(11)9(6-7)13-2/h4-6H,3H2,1-2H3
    • InChI Key: SPZBNOLKHLTDCR-UHFFFAOYSA-N
    • SMILES: O=C(C1C=C(OC)C(Br)=CC=1)OCC

Computed Properties

  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 4
  • Complexity: 196
  • Topological Polar Surface Area: 35.5

Ethyl 4-bromo-3-methoxybenzoate Security Information

  • Hazard Statement: H315-H319-H335
  • Storage Condition:Sealed in dry,Room Temperature

Ethyl 4-bromo-3-methoxybenzoate Pricemore >>

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Additional information on Ethyl 4-bromo-3-methoxybenzoate

Recent Advances in the Application of Ethyl 4-bromo-3-methoxybenzoate (CAS: 933585-42-3) in Chemical Biology and Pharmaceutical Research

Ethyl 4-bromo-3-methoxybenzoate (CAS: 933585-42-3) is a key intermediate in the synthesis of various bioactive compounds and pharmaceutical agents. Recent studies have highlighted its significance in medicinal chemistry, particularly in the development of novel therapeutic agents targeting inflammation, cancer, and infectious diseases. This research brief aims to provide an overview of the latest advancements involving this compound, focusing on its synthetic applications, biological activities, and potential therapeutic implications.

In a recent study published in the Journal of Medicinal Chemistry, researchers explored the use of Ethyl 4-bromo-3-methoxybenzoate as a precursor in the synthesis of small-molecule inhibitors targeting the NF-κB signaling pathway. The compound's bromo and methoxy functional groups were found to be critical for the efficient coupling reactions required to generate these inhibitors. The study demonstrated that derivatives of Ethyl 4-bromo-3-methoxybenzoate exhibited potent anti-inflammatory activity in vitro and in vivo, suggesting its potential as a scaffold for developing new anti-inflammatory drugs.

Another significant application of Ethyl 4-bromo-3-methoxybenzoate was reported in a 2023 study in Bioorganic & Medicinal Chemistry Letters. The research team utilized this compound to synthesize a series of benzimidazole derivatives with promising anticancer properties. The derivatives were tested against a panel of cancer cell lines, including breast, lung, and colon cancer, showing selective cytotoxicity and low toxicity to normal cells. The study emphasized the role of the bromo substituent in enhancing the binding affinity of these compounds to their molecular targets, such as tubulin and topoisomerase II.

Furthermore, Ethyl 4-bromo-3-methoxybenzoate has been employed in the development of antimicrobial agents. A recent publication in Antimicrobial Agents and Chemotherapy detailed its use in the synthesis of novel quinolone derivatives. These derivatives exhibited broad-spectrum activity against drug-resistant bacterial strains, including MRSA and ESBL-producing Escherichia coli. The researchers attributed the enhanced antimicrobial activity to the electron-withdrawing effects of the bromo and methoxy groups, which improved the compounds' interaction with bacterial DNA gyrase.

In addition to its therapeutic applications, Ethyl 4-bromo-3-methoxybenzoate has also been investigated for its role in chemical biology. A 2023 study in Chemical Communications described its use as a versatile building block for the synthesis of fluorescent probes. These probes were designed to detect reactive oxygen species (ROS) in live cells, providing valuable tools for studying oxidative stress-related diseases. The study highlighted the compound's stability and reactivity, making it an ideal candidate for probe development.

In conclusion, Ethyl 4-bromo-3-methoxybenzoate (CAS: 933585-42-3) continues to be a valuable compound in chemical biology and pharmaceutical research. Its versatile chemical properties and biological activities make it a promising scaffold for the development of new therapeutic agents and research tools. Future studies are expected to further explore its potential in drug discovery and biomedical applications, particularly in addressing unmet medical needs.

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