Cas no 1003879-02-4 (2-bromo-1-(4-bromo-3-fluoro-phenyl)ethanone)

2-Bromo-1-(4-bromo-3-fluorophenyl)ethanone is a brominated and fluorinated aromatic ketone with applications in organic synthesis and pharmaceutical intermediates. Its key structural features include a reactive α-bromo ketone moiety and a halogenated phenyl ring, making it a versatile building block for nucleophilic substitution and cross-coupling reactions. The presence of both bromine and fluorine substituents enhances its utility in medicinal chemistry, particularly in the development of bioactive compounds. The compound exhibits high purity and stability under standard storage conditions, ensuring reliable performance in synthetic workflows. Its well-defined reactivity profile allows for precise functionalization, making it valuable for researchers in fine chemical and drug discovery applications.
2-bromo-1-(4-bromo-3-fluoro-phenyl)ethanone structure
1003879-02-4 structure
Product Name:2-bromo-1-(4-bromo-3-fluoro-phenyl)ethanone
CAS No:1003879-02-4
MF:C8H5Br2FO
MW:295.931104421616
MDL:MFCD11847180
CID:822496
PubChem ID:53416614
Update Time:2025-06-15

2-bromo-1-(4-bromo-3-fluoro-phenyl)ethanone Chemical and Physical Properties

Names and Identifiers

    • 2-Bromo-1-(4-bromo-3-fluorophenyl)ethanone
    • 2-bromo-1-(4-bromo-3-fluoro-phenyl)ethanone
    • 2-bromo-1-(4-bromo-3-fluoro-phenyl)-ethanone
    • AK-89891
    • ANW-67172
    • CTK8C1756
    • KB-228549
    • MFCD11847180
    • 1003879-02-4
    • CS-0210947
    • 4-Bromo-3-fluorophenacyl bromide
    • AS-41255
    • DA-48434
    • AKOS016006494
    • 2-Bromo-1-(4-bromo-3-fluorophenyl)-ethanone
    • DTXSID50697202
    • SCHEMBL2953875
    • IELTVOHIKAUZFA-UHFFFAOYSA-N
    • SY354762
    • 2-bromo-1-(4-bromo-3-fluorophenyl)ethan-1-one
    • Ethanone, 2-bromo-1-(4-bromo-3-fluorophenyl)-
    • MDL: MFCD11847180
    • Inchi: 1S/C8H5Br2FO/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-3H,4H2
    • InChI Key: IELTVOHIKAUZFA-UHFFFAOYSA-N
    • SMILES: BrC1C=CC(C(CBr)=O)=CC=1F

Computed Properties

  • Exact Mass: 295.86707g/mol
  • Monoisotopic Mass: 293.86912g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 2
  • 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: 3.2
  • Topological Polar Surface Area: 17.1?2

Experimental Properties

  • Density: 1.914

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Additional information on 2-bromo-1-(4-bromo-3-fluoro-phenyl)ethanone

Research Brief on 2-Bromo-1-(4-bromo-3-fluoro-phenyl)ethanone (CAS: 1003879-02-4): Recent Advances and Applications in Chemical Biology and Medicine

2-Bromo-1-(4-bromo-3-fluoro-phenyl)ethanone (CAS: 1003879-02-4) is a halogenated aromatic ketone that has garnered significant attention in recent years due to its versatile applications in chemical biology and pharmaceutical research. This compound serves as a key intermediate in the synthesis of various bioactive molecules, particularly those targeting kinase inhibition and covalent protein modification. Recent studies have explored its utility in drug discovery, chemical probe development, and material science, highlighting its importance in advancing therapeutic innovations.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the compound's role as a precursor for irreversible kinase inhibitors, showcasing its reactivity with cysteine residues in ATP-binding pockets. The research team utilized 2-bromo-1-(4-bromo-3-fluoro-phenyl)ethanone to develop a series of selective EGFR inhibitors with improved pharmacokinetic properties. The electron-withdrawing effects of the bromo and fluoro substituents were found to enhance the electrophilicity of the carbonyl carbon, facilitating efficient covalent bond formation with target proteins.

In parallel developments, a 2024 ACS Chemical Biology publication reported the use of this compound in creating activity-based protein profiling (ABPP) probes. The researchers capitalized on its dual reactivity - the α-bromo ketone moiety for protein labeling and the aromatic halogens for subsequent click chemistry modifications. This approach enabled comprehensive mapping of cysteine-reactive proteomes in cancer cell lines, revealing several previously uncharacterized drug targets.

The compound's crystallographic characteristics were recently elucidated in a Chemical Communications article (2024), providing crucial structural insights for rational drug design. The crystal structure revealed a planar conformation stabilized by intramolecular halogen interactions between the bromine at position 4 and the fluorine atom, explaining its enhanced stability compared to analogous compounds. These findings have important implications for the development of more stable drug candidates and chemical probes.

From a synthetic chemistry perspective, recent advances in green chemistry have explored more sustainable routes to produce 2-bromo-1-(4-bromo-3-fluoro-phenyl)ethanone. A 2023 Green Chemistry paper described a photocatalytic bromination method that reduces hazardous waste generation by 60% while maintaining high yield (82%) and purity (>98%). This development addresses growing concerns about the environmental impact of halogenated compound synthesis in pharmaceutical manufacturing.

Emerging applications in materials science have also been reported, particularly in the development of organic electronic materials. The compound's strong electron-accepting properties, attributed to its halogen substituents, make it a promising building block for organic semiconductors. A 2024 Advanced Materials study demonstrated its incorporation into donor-acceptor polymers with exceptional charge transport properties, opening new avenues for bioelectronic devices.

In conclusion, 2-bromo-1-(4-bromo-3-fluoro-phenyl)ethanone continues to prove its value as a multifunctional chemical building block in biomedical research. Recent studies have expanded its applications from traditional medicinal chemistry to cutting-edge areas like chemical proteomics and bioelectronics. Future research directions likely include further optimization of its synthetic accessibility, exploration of new biological targets, and development of novel material applications. The compound's unique combination of reactivity and stability positions it as a valuable tool for addressing complex challenges in chemical biology and drug discovery.

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