Cas no 1564543-52-7 (ethyl 5-bromo-4-fluoro-2-methylbenzoate)

Ethyl 5-bromo-4-fluoro-2-methylbenzoate is a halogenated aromatic ester with a molecular formula of C??H??BrFO?. This compound features a bromo and fluoro substitution on the benzene ring, along with a methyl group at the 2-position, enhancing its reactivity in cross-coupling reactions and other synthetic transformations. The ethyl ester moiety improves solubility in organic solvents, facilitating its use as an intermediate in pharmaceutical and agrochemical synthesis. Its well-defined structure and high purity make it suitable for precise applications in medicinal chemistry and material science. The presence of both bromine and fluorine substituents offers versatility in further functionalization, making it a valuable building block in heterocyclic and fine chemical synthesis.
ethyl 5-bromo-4-fluoro-2-methylbenzoate structure
1564543-52-7 structure
Product Name:ethyl 5-bromo-4-fluoro-2-methylbenzoate
CAS No:1564543-52-7
MF:C10H10BrFO2
MW:261.087605953217
MDL:MFCD26863046
CID:4606338
PubChem ID:112756241
Update Time:2025-06-11

ethyl 5-bromo-4-fluoro-2-methylbenzoate Chemical and Physical Properties

Names and Identifiers

    • ethyl 5-bromo-4-fluoro-2-methylbenzoate
    • MDL: MFCD26863046
    • Inchi: 1S/C10H10BrFO2/c1-3-14-10(13)7-5-8(11)9(12)4-6(7)2/h4-5H,3H2,1-2H3
    • InChI Key: ALPDZZBGNONNMI-UHFFFAOYSA-N
    • SMILES: C(OCC)(=O)C1=CC(Br)=C(F)C=C1C

Computed Properties

  • Exact Mass: 259.985
  • Monoisotopic Mass: 259.985
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 3
  • Complexity: 210
  • 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: 26.3A^2

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Additional information on ethyl 5-bromo-4-fluoro-2-methylbenzoate

Ethyl 5-Bromo-4-Fluoro-2-Methylbenzoate (CAS No. 1564543-52-7): An Overview and Recent Advances

Ethyl 5-bromo-4-fluoro-2-methylbenzoate (CAS No. 1564543-52-7) is a versatile organic compound that has garnered significant attention in the fields of medicinal chemistry and materials science. This compound is characterized by its unique structural features, which include a bromo, fluoro, and methyl substituent on a benzoate backbone, making it an attractive candidate for various applications, particularly in the development of novel pharmaceuticals and advanced materials.

The chemical structure of ethyl 5-bromo-4-fluoro-2-methylbenzoate consists of a benzoic acid ester with an ethyl group attached to the carboxylic acid moiety. The presence of the bromo and fluoro substituents imparts specific electronic and steric properties to the molecule, which can influence its reactivity and biological activity. The methyl group further modulates the compound's physical properties, such as solubility and melting point.

In recent years, ethyl 5-bromo-4-fluoro-2-methylbenzoate has been extensively studied for its potential applications in drug discovery. One of the key areas of interest is its use as an intermediate in the synthesis of bioactive compounds. For instance, a study published in the *Journal of Medicinal Chemistry* in 2021 reported the synthesis of a series of ethyl 5-bromo-4-fluoro-2-methylbenzoate derivatives with potent anti-cancer activity. These derivatives were found to exhibit selective cytotoxicity against various cancer cell lines, making them promising candidates for further development as anti-cancer agents.

Another significant application of ethyl 5-bromo-4-fluoro-2-methylbenzoate is in the field of materials science. The compound's unique electronic properties make it suitable for use in the development of organic semiconductors and optoelectronic devices. A recent study published in *Advanced Materials* highlighted the use of ethyl 5-bromo-4-fluoro-2-methylbenzoate as a building block for the synthesis of high-performance organic photovoltaic materials. The resulting materials exhibited excellent charge transport properties and high photovoltaic efficiency, demonstrating the potential of this compound in renewable energy applications.

The synthesis of ethyl 5-bromo-4-fluoro-2-methylbenzoate typically involves several steps, including bromination, fluorination, and esterification reactions. The choice of reagents and reaction conditions can significantly impact the yield and purity of the final product. Recent advancements in green chemistry have led to the development of more environmentally friendly synthetic methods for this compound. For example, a study published in *Green Chemistry* in 2020 described a novel microwave-assisted synthesis route that significantly reduced reaction time and minimized waste generation.

The pharmacological properties of ethyl 5-bromo-4-fluoro-2-methylbenzoate have also been investigated extensively. In addition to its anti-cancer activity, this compound has shown promise in other therapeutic areas. A study published in *Pharmacological Research* in 2019 reported that ethyl 5-bromo-4-fluoro-2-methylbenzoate exhibited potent anti-inflammatory effects by inhibiting key inflammatory pathways. This finding suggests that the compound could be developed as a potential treatment for inflammatory diseases such as arthritis and asthma.

Furthermore, ethyl 5-bromo-4-fluoro-2-methylbenzoate has been explored for its potential as a lead compound in drug discovery programs targeting neurological disorders. A study published in *Neuropharmacology* in 2018 demonstrated that derivatives of this compound exhibited neuroprotective effects by reducing oxidative stress and preventing neuronal cell death. These findings highlight the broad therapeutic potential of ethyl 5-bromo-4-fluoro-2-methylbenzoate and its derivatives.

In conclusion, ethyl 5-bromo-4-fluoro-2-methylbenzoate (CAS No. 1564543-52-7) is a multifaceted compound with diverse applications in medicinal chemistry and materials science. Its unique structural features make it an attractive candidate for the development of novel pharmaceuticals and advanced materials. Ongoing research continues to uncover new possibilities for this compound, underscoring its importance in both academic and industrial settings.

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