Cas no 936249-94-4 (2-Bromo-1-(difluoromethoxy)-4-fluorobenzene)

2-Bromo-1-(difluoromethoxy)-4-fluorobenzene is a fluorinated aromatic compound featuring both bromo and difluoromethoxy substituents, which enhance its reactivity and utility in synthetic chemistry. The presence of bromine at the 2-position makes it a versatile intermediate for cross-coupling reactions, such as Suzuki or Buchwald-Hartwig couplings, while the difluoromethoxy group contributes to its stability and lipophilicity. The additional fluorine at the 4-position further modifies its electronic properties, making it valuable for pharmaceutical and agrochemical applications. This compound is particularly useful in the development of bioactive molecules, where selective functionalization is required. Its well-defined structure ensures consistent performance in complex synthetic pathways.
2-Bromo-1-(difluoromethoxy)-4-fluorobenzene structure
936249-94-4 structure
Product Name:2-Bromo-1-(difluoromethoxy)-4-fluorobenzene
CAS No:936249-94-4
MF:C7H4BrF3O
MW:241.005271911621
MDL:MFCD09935620
CID:875871
PubChem ID:24696917
Update Time:2025-11-02

2-Bromo-1-(difluoromethoxy)-4-fluorobenzene Chemical and Physical Properties

Names and Identifiers

    • 2-bromo-1-(difluoromethoxy)-4-fluorobenzene
    • 2-Bromo-1-difluoromethoxy-4-fluoro-benzene
    • 2-(Difluoromethoxy)-5-fluorobromobenzene
    • TQU0280
    • OQANLAKJTFXSQM-UHFFFAOYSA-N
    • NE17325
    • 3-Bromo-4-(difluoromethoxy)fluorobenzene
    • AK326847
    • 3-bromo-4-(difluoromethoxy)-1-fluorobenzene
    • Z55672060
    • DTXSID70640811
    • A916586
    • MFCD09935620
    • CS-0139188
    • EN300-127078
    • 936249-94-4
    • AKOS000177964
    • PS-11657
    • SCHEMBL1438674
    • SY078423
    • 2-Bromo-1-(difluoromethoxy)-4-fluorobenzene
    • MDL: MFCD09935620
    • Inchi: 1S/C7H4BrF3O/c8-5-3-4(9)1-2-6(5)12-7(10)11/h1-3,7H
    • InChI Key: OQANLAKJTFXSQM-UHFFFAOYSA-N
    • SMILES: BrC1C=C(C=CC=1OC(F)F)F

Computed Properties

  • Exact Mass: 239.94000
  • Monoisotopic Mass: 239.93976g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 2
  • Complexity: 145
  • 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: 3.6
  • Topological Polar Surface Area: 9.2

Experimental Properties

  • PSA: 9.23000
  • LogP: 3.18960

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Additional information on 2-Bromo-1-(difluoromethoxy)-4-fluorobenzene

Recent Advances in the Application of 2-Bromo-1-(difluoromethoxy)-4-fluorobenzene (CAS: 936249-94-4) in Chemical Biology and Pharmaceutical Research

The compound 2-Bromo-1-(difluoromethoxy)-4-fluorobenzene (CAS: 936249-94-4) has recently garnered significant attention in the field of chemical biology and pharmaceutical research due to its unique structural properties and versatile applications. This halogenated aromatic compound, characterized by the presence of bromine, fluorine, and a difluoromethoxy group, serves as a critical intermediate in the synthesis of various bioactive molecules. Recent studies have highlighted its role in the development of novel therapeutic agents, particularly in the areas of oncology, neurology, and infectious diseases.

One of the most notable applications of 2-Bromo-1-(difluoromethoxy)-4-fluorobenzene is its use as a key building block in the synthesis of small-molecule inhibitors targeting protein kinases. A 2023 study published in the Journal of Medicinal Chemistry demonstrated its utility in the development of potent and selective inhibitors for the epidermal growth factor receptor (EGFR), a well-validated target in cancer therapy. The researchers employed a structure-activity relationship (SAR) approach, leveraging the compound's halogenated aromatic core to optimize binding affinity and pharmacokinetic properties. The resulting inhibitors exhibited nanomolar potency against EGFR mutants associated with resistance to first-generation therapies.

In addition to its role in kinase inhibitor development, 2-Bromo-1-(difluoromethoxy)-4-fluorobenzene has been explored as a precursor for radiopharmaceuticals. A recent study in the European Journal of Nuclear Medicine and Molecular Imaging reported its use in the synthesis of fluorine-18 labeled tracers for positron emission tomography (PET) imaging. The difluoromethoxy group, in particular, was found to enhance the metabolic stability of the tracers, improving their in vivo performance. This advancement holds promise for the non-invasive detection and monitoring of neurological disorders such as Alzheimer's disease.

From a synthetic chemistry perspective, the compound's reactivity has been the subject of several mechanistic investigations. A 2024 publication in Organic Letters detailed a palladium-catalyzed cross-coupling reaction involving 2-Bromo-1-(difluoromethoxy)-4-fluorobenzene, which enabled the efficient construction of complex biaryl structures. The study provided insights into the influence of the difluoromethoxy group on the reaction kinetics and selectivity, offering valuable guidelines for the design of similar transformations.

Looking ahead, the versatility of 2-Bromo-1-(difluoromethoxy)-4-fluorobenzene is expected to drive further innovation in drug discovery and chemical biology. Ongoing research is exploring its potential in the development of covalent inhibitors, proteolysis-targeting chimeras (PROTACs), and other emerging therapeutic modalities. As the field continues to evolve, this compound is likely to remain a focal point of interdisciplinary research efforts aimed at addressing unmet medical needs.

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