Cas no 505084-54-8 (2-Bromo-3,5-bis(trifluoromethyl)benzoic acid)

2-Bromo-3,5-bis(trifluoromethyl)benzoic acid is a fluorinated aromatic compound featuring a bromine substituent and two trifluoromethyl groups on the benzoic acid scaffold. This structure imparts high electrophilicity and reactivity, making it a valuable intermediate in pharmaceutical and agrochemical synthesis. The presence of trifluoromethyl groups enhances lipophilicity and metabolic stability, while the bromine atom offers a versatile site for further functionalization via cross-coupling reactions. Its robust stability under various reaction conditions and compatibility with organometallic transformations make it particularly useful in constructing complex molecules. This compound is well-suited for applications requiring precise structural modifications in drug discovery and material science.
2-Bromo-3,5-bis(trifluoromethyl)benzoic acid structure
505084-54-8 structure
Product Name:2-Bromo-3,5-bis(trifluoromethyl)benzoic acid
CAS No:505084-54-8
MF:C9H3BrF6O2
MW:337.013343095779
MDL:MFCD13181635
CID:1083485
PubChem ID:73553498
Update Time:2025-06-12

2-Bromo-3,5-bis(trifluoromethyl)benzoic acid Chemical and Physical Properties

Names and Identifiers

    • 2-Bromo-3,5-bis(trifluoromethyl)benzoic acid
    • 505084-54-8
    • DB-364725
    • 2-Bromo-3,5-bis(trifluoromethyl)benzoicacid
    • MFCD13181635
    • E90833
    • AKOS022181334
    • CS-0196041
    • MDL: MFCD13181635
    • Inchi: 1S/C9H3BrF6O2/c10-6-4(7(17)18)1-3(8(11,12)13)2-5(6)9(14,15)16/h1-2H,(H,17,18)
    • InChI Key: QMARPZPREXIREN-UHFFFAOYSA-N
    • SMILES: BrC1=C(C(=O)O)C=C(C(F)(F)F)C=C1C(F)(F)F

Computed Properties

  • Exact Mass: 335.92206g/mol
  • Monoisotopic Mass: 335.92206g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 18
  • Rotatable Bond Count: 3
  • Complexity: 326
  • 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: 3.9
  • Topological Polar Surface Area: 37.3?2

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Additional information on 2-Bromo-3,5-bis(trifluoromethyl)benzoic acid

Recent Advances in the Application of 2-Bromo-3,5-bis(trifluoromethyl)benzoic Acid (CAS: 505084-54-8) in Chemical Biology and Pharmaceutical Research

2-Bromo-3,5-bis(trifluoromethyl)benzoic acid (CAS: 505084-54-8) is a highly versatile chemical intermediate that has garnered significant attention in recent years due to its unique structural and electronic properties. This compound, characterized by the presence of bromine and trifluoromethyl groups on a benzoic acid scaffold, has found extensive applications in medicinal chemistry, agrochemical development, and materials science. Recent studies have highlighted its potential as a key building block in the synthesis of bioactive molecules, particularly in the design of enzyme inhibitors and receptor modulators.

One of the most notable applications of 2-Bromo-3,5-bis(trifluoromethyl)benzoic acid is its role in the development of kinase inhibitors. Kinases are critical targets in cancer therapy, and the trifluoromethyl groups in this compound enhance its binding affinity to ATP-binding sites. A 2023 study published in the Journal of Medicinal Chemistry demonstrated that derivatives of this compound exhibited potent inhibitory activity against EGFR and VEGFR2 kinases, with IC50 values in the low nanomolar range. The study also highlighted the compound's favorable pharmacokinetic properties, making it a promising candidate for further preclinical development.

In addition to its therapeutic potential, 2-Bromo-3,5-bis(trifluoromethyl)benzoic acid has been employed in the synthesis of advanced materials. Researchers have utilized its electron-withdrawing properties to design novel organic semiconductors and liquid crystals. A recent publication in Advanced Materials (2024) described the use of this compound as a precursor for the development of high-performance organic field-effect transistors (OFETs), showcasing its versatility beyond pharmaceutical applications.

The synthetic utility of 2-Bromo-3,5-bis(trifluoromethyl)benzoic acid has also been explored in agrochemical research. Its halogenated and fluorinated motifs are particularly valuable in the design of herbicides and fungicides. A 2023 study in Pest Management Science reported the synthesis of a series of novel fungicides derived from this compound, which exhibited broad-spectrum activity against phytopathogenic fungi while demonstrating low toxicity to non-target organisms.

Despite its promising applications, challenges remain in the large-scale production and purification of 2-Bromo-3,5-bis(trifluoromethyl)benzoic acid. Recent advances in flow chemistry and continuous manufacturing have addressed some of these issues, as reported in Organic Process Research & Development (2024). These technological innovations have significantly improved the yield and purity of the compound, making it more accessible for industrial applications.

Looking ahead, the unique properties of 2-Bromo-3,5-bis(trifluoromethyl)benzoic acid (CAS: 505084-54-8) position it as a valuable tool in drug discovery and materials science. Ongoing research is exploring its potential in targeted drug delivery systems and as a scaffold for the development of covalent inhibitors. As synthetic methodologies continue to evolve, this compound is expected to play an increasingly important role in addressing complex challenges in chemical biology and pharmaceutical development.

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