Cas no 1000572-63-3 (4-Bromo-2-chloro-5-fluoroaniline)

4-Bromo-2-chloro-5-fluoroaniline is a halogenated aniline derivative with a molecular formula of C?H?BrClFN. This compound serves as a versatile intermediate in organic synthesis, particularly in the pharmaceutical and agrochemical industries, where its unique substitution pattern enables precise functionalization. The presence of bromo, chloro, and fluoro substituents enhances its reactivity in cross-coupling reactions, such as Suzuki or Buchwald-Hartwig couplings, facilitating the construction of complex aromatic systems. Its high purity and stability under standard conditions make it a reliable building block for medicinal chemistry and material science applications. Proper handling is advised due to potential sensitivity to light and moisture.
4-Bromo-2-chloro-5-fluoroaniline structure
1000572-63-3 structure
Product Name:4-Bromo-2-chloro-5-fluoroaniline
CAS No:1000572-63-3
MF:C6H4BrClFN
MW:224.45806312561
MDL:MFCD09878155
CID:3157778
PubChem ID:26599138
Update Time:2025-11-02

4-Bromo-2-chloro-5-fluoroaniline Chemical and Physical Properties

Names and Identifiers

    • 4-Bromo-2-chloro-5-fluoroaniline
    • DB-167205
    • E81876
    • MFCD09878155
    • DTXSID40650245
    • CHEMBL4965817
    • CS-0146362
    • 1000572-63-3
    • SCHEMBL16303511
    • FS-4351
    • EN300-109514
    • AKOS026671372
    • Z1269132427
    • 4-Bromo-2-chloro-5-fluoro-aniline
    • DTXCID70600995
    • AQB57263
    • 840-047-1
    • MDL: MFCD09878155
    • Inchi: 1S/C6H4BrClFN/c7-3-1-4(8)6(10)2-5(3)9/h1-2H,10H2
    • InChI Key: QIXJYJRZGHXOLM-UHFFFAOYSA-N
    • SMILES: BrC1C(=CC(=C(C=1)Cl)N)F

Computed Properties

  • Exact Mass: 222.91997g/mol
  • Monoisotopic Mass: 222.91997g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 0
  • Complexity: 124
  • 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: 2.7
  • Topological Polar Surface Area: 26?2

4-Bromo-2-chloro-5-fluoroaniline Pricemore >>

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Additional information on 4-Bromo-2-chloro-5-fluoroaniline

Recent Advances in the Application of 4-Bromo-2-chloro-5-fluoroaniline (CAS: 1000572-63-3) in Chemical Biology and Pharmaceutical Research

The compound 4-Bromo-2-chloro-5-fluoroaniline (CAS: 1000572-63-3) has recently garnered significant attention in the field of chemical biology and pharmaceutical research due to its versatile applications in drug discovery and development. This aromatic amine derivative serves as a crucial intermediate in the synthesis of various bioactive molecules, particularly those targeting kinase inhibitors and antimicrobial agents. Recent studies have highlighted its role in the development of novel therapeutic candidates, leveraging its unique halogen-substituted aniline structure to enhance binding affinity and selectivity.

One of the most notable advancements involves the use of 4-Bromo-2-chloro-5-fluoroaniline in the synthesis of kinase inhibitors. A 2023 study published in the Journal of Medicinal Chemistry demonstrated its efficacy as a building block for the development of selective JAK2 inhibitors, which are pivotal in treating myeloproliferative neoplasms. The study reported that the bromo and chloro substituents on the aniline ring significantly improved the compound's interaction with the JAK2 binding pocket, leading to enhanced inhibitory activity and reduced off-target effects.

In addition to its role in kinase inhibitor development, 4-Bromo-2-chloro-5-fluoroaniline has also been explored in antimicrobial research. A recent publication in Bioorganic & Medicinal Chemistry Letters detailed its incorporation into novel fluoroquinolone derivatives, which exhibited potent activity against multidrug-resistant bacterial strains. The researchers attributed this activity to the electron-withdrawing effects of the halogen substituents, which optimized the compounds' pharmacokinetic properties and bacterial membrane penetration.

From a synthetic chemistry perspective, advancements in the scalable production of 4-Bromo-2-chloro-5-fluoroaniline have been reported. A 2024 study in Organic Process Research & Development introduced a cost-effective and environmentally friendly catalytic method for its synthesis, utilizing palladium-catalyzed cross-coupling reactions. This method not only improved yield and purity but also reduced the environmental impact associated with traditional halogenation techniques.

Looking ahead, the potential applications of 4-Bromo-2-chloro-5-fluoroaniline are expanding into areas such as fluorescent probes and agrochemicals. Preliminary research suggests that its halogenated structure could be leveraged to design probes for detecting reactive oxygen species in cellular environments, offering new tools for studying oxidative stress-related diseases. Furthermore, its derivatives are being investigated as potential herbicides with improved selectivity and lower toxicity profiles.

In conclusion, 4-Bromo-2-chloro-5-fluoroaniline (CAS: 1000572-63-3) continues to be a valuable scaffold in chemical biology and pharmaceutical research. Its diverse applications, from drug discovery to material science, underscore its importance in advancing both therapeutic and technological innovations. Future research is expected to further explore its potential, particularly in addressing unmet medical needs and sustainable chemical synthesis.

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