Cas no 366496-33-5 (1,4-Dibromo-2-fluoro-5-nitrobenzene)

1,4-Dibromo-2-fluoro-5-nitrobenzene is a halogenated nitroaromatic compound with the molecular formula C?H?Br?FNO?. This high-purity intermediate is widely utilized in organic synthesis, particularly in the preparation of pharmaceuticals, agrochemicals, and specialty materials. Its distinct substitution pattern—featuring bromine, fluorine, and nitro functional groups—enables selective reactivity in cross-coupling reactions, nucleophilic substitutions, and other transformations. The compound's stability and well-defined structure make it a reliable building block for constructing complex aromatic systems. It is typically supplied as a crystalline solid with consistent purity, ensuring reproducibility in research and industrial applications. Proper handling is advised due to its potential toxicity and reactivity under certain conditions.
1,4-Dibromo-2-fluoro-5-nitrobenzene structure
366496-33-5 structure
Product Name:1,4-Dibromo-2-fluoro-5-nitrobenzene
CAS No:366496-33-5
MF:C6H2Br2FNO2
MW:298.891983509064
MDL:MFCD17014707
CID:1084271
Update Time:2025-05-21

1,4-Dibromo-2-fluoro-5-nitrobenzene Chemical and Physical Properties

Names and Identifiers

    • 1,4-Dibromo-2-fluoro-5-nitrobenzene
    • 2,5-DIBROMO-4-FLUORONITROBENZENE
    • Benzene, 1,4-dibromo-2-fluoro-5-nitro-
    • FCH1351838
    • MDL: MFCD17014707
    • Inchi: 1S/C6H2Br2FNO2/c7-3-2-6(10(11)12)4(8)1-5(3)9/h1-2H
    • InChI Key: WDFCYQDGGDTTCT-UHFFFAOYSA-N
    • SMILES: BrC1C=C(C(=CC=1[N+](=O)[O-])Br)F

Computed Properties

  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 0
  • Complexity: 187
  • XLogP3: 3.6
  • Topological Polar Surface Area: 45.8

Experimental Properties

  • Density: 2.168
  • Boiling Point: 265 oC
  • Flash Point: 114 oC

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Additional information on 1,4-Dibromo-2-fluoro-5-nitrobenzene

Recent Advances in the Application of 1,4-Dibromo-2-fluoro-5-nitrobenzene (CAS: 366496-33-5) in Chemical Biology and Pharmaceutical Research

1,4-Dibromo-2-fluoro-5-nitrobenzene (CAS: 366496-33-5) is a halogenated nitrobenzene derivative 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, including pharmaceuticals, agrochemicals, and materials science applications. Recent studies have highlighted its role in the development of novel therapeutic agents and its utility in advanced synthetic methodologies.

One of the most notable applications of 1,4-Dibromo-2-fluoro-5-nitrobenzene is its use in the synthesis of kinase inhibitors, which are critical in the treatment of cancers and inflammatory diseases. A 2023 study published in the Journal of Medicinal Chemistry demonstrated the compound's efficacy as a building block for the development of selective JAK2 inhibitors, which show promise in treating myeloproliferative neoplasms. The study reported a 40% improvement in yield compared to traditional synthetic routes, underscoring the compound's potential for scalable production.

In addition to its pharmaceutical applications, 1,4-Dibromo-2-fluoro-5-nitrobenzene has been employed in materials science for the development of organic semiconductors. A recent publication in Advanced Materials (2024) detailed its use in the synthesis of π-conjugated polymers with enhanced charge carrier mobility. The researchers attributed this improvement to the electron-withdrawing properties of the nitro and fluoro substituents, which facilitate efficient electron transport.

From a synthetic chemistry perspective, novel catalytic systems have been developed to optimize the functionalization of 1,4-Dibromo-2-fluoro-5-nitrobenzene. A 2023 Nature Communications paper reported a palladium-catalyzed cross-coupling reaction that achieves >90% selectivity for the desired products, significantly reducing byproduct formation. This advancement addresses one of the major challenges in working with polyhalogenated aromatics.

The safety profile and environmental impact of 1,4-Dibromo-2-fluoro-5-nitrobenzene have also been subjects of recent investigation. Regulatory agencies are particularly interested in its biodegradation pathways, with a 2024 study in Environmental Science & Technology identifying two novel bacterial strains capable of degrading this compound under aerobic conditions. These findings may inform future waste management strategies for industrial-scale applications.

Looking forward, researchers anticipate expanded applications of 1,4-Dibromo-2-fluoro-5-nitrobenzene in PROTAC (Proteolysis Targeting Chimera) technology and click chemistry approaches. Early-stage research presented at the 2024 ACS National Meeting suggests its potential as a versatile linker moiety for targeted protein degradation platforms. The compound's unique combination of reactivity and stability makes it particularly suitable for these emerging therapeutic modalities.

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