Cas no 875238-74-7 (2-Bromo-4-nitro-1-(trifluoromethyl)benzene)

2-Bromo-4-nitro-1-(trifluoromethyl)benzene is a halogenated aromatic compound featuring a bromo substituent, a nitro group, and a trifluoromethyl group on a benzene ring. This structure imparts unique reactivity, making it valuable as an intermediate in organic synthesis, particularly in pharmaceutical and agrochemical applications. The presence of electron-withdrawing groups (nitro and trifluoromethyl) enhances its utility in nucleophilic substitution reactions, while the bromo group allows for further functionalization via cross-coupling methodologies. Its stability under standard conditions and well-defined reactivity profile make it a reliable building block for constructing complex molecules. The compound is typically handled under controlled conditions due to its potential sensitivity.
2-Bromo-4-nitro-1-(trifluoromethyl)benzene structure
875238-74-7 structure
Product Name:2-Bromo-4-nitro-1-(trifluoromethyl)benzene
CAS No:875238-74-7
MF:C7H3BrF3NO2
MW:270.003431558609
MDL:MFCD16606317
CID:1026698
PubChem ID:66545383
Update Time:2025-06-13

2-Bromo-4-nitro-1-(trifluoromethyl)benzene Chemical and Physical Properties

Names and Identifiers

    • 2-Bromo-4-nitro-1-(trifluoromethyl)benzene
    • 3-BROMO-4-TRIFLUOROMETHYLNITROBENZENE
    • WPUMBZRKLJGMIJ-UHFFFAOYSA-N
    • CL8899
    • 3872AC
    • 2-Bromo-4-nitro-1-(trifluoromethyl)benzene (ACI)
    • Toluene, 2-bromo-α,α,α-trifluoro-4-nitro- (5CI)
    • DTXSID20735180
    • 3-bromo-4-(trifluoromethyl)nitrobenzene
    • AKOS015995520
    • DB-364803
    • 2-Bromo-4-nitrobenzotrifluoride
    • SCHEMBL15123102
    • CS-0041268
    • EN300-170119
    • SY119837
    • MFCD16606317
    • DS-14260
    • 875238-74-7
    • MDL: MFCD16606317
    • Inchi: 1S/C7H3BrF3NO2/c8-6-3-4(12(13)14)1-2-5(6)7(9,10)11/h1-3H
    • InChI Key: WPUMBZRKLJGMIJ-UHFFFAOYSA-N
    • SMILES: [O-][N+](C1C=C(Br)C(C(F)(F)F)=CC=1)=O

Computed Properties

  • Exact Mass: 268.92993g/mol
  • Monoisotopic Mass: 268.92993g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 0
  • Complexity: 228
  • 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
  • Topological Polar Surface Area: 45.8
  • XLogP3: 3.3

Experimental Properties

  • Density: 1.788
  • Boiling Point: 257.5±40.0°C at 760 mmHg
  • Flash Point: 110℃

2-Bromo-4-nitro-1-(trifluoromethyl)benzene Security Information

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2-Bromo-4-nitro-1-(trifluoromethyl)benzene Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Hydrofluoric acid ,  Sulfur tetrafluoride ;  -196 °C → rt; 24 h, 85 °C; 85 °C → rt
1.2 Reagents: Sodium bicarbonate Solvents: Water ;  0 °C
Reference
Deoxofluorination of (Hetero)aromatic Acids
Trofymchuk, Serhii; et al, Journal of Organic Chemistry, 2020, 85(5), 3110-3124

2-Bromo-4-nitro-1-(trifluoromethyl)benzene Raw materials

2-Bromo-4-nitro-1-(trifluoromethyl)benzene Preparation Products

Additional information on 2-Bromo-4-nitro-1-(trifluoromethyl)benzene

Research Brief on 2-Bromo-4-nitro-1-(trifluoromethyl)benzene (CAS: 875238-74-7) in Chemical and Biomedical Applications

2-Bromo-4-nitro-1-(trifluoromethyl)benzene (CAS: 875238-74-7) is a halogenated nitroaromatic compound that has garnered significant attention in recent chemical and biomedical research due to its versatile reactivity and potential applications in drug discovery and material science. This research brief synthesizes the latest findings on this compound, focusing on its synthesis, reactivity, and emerging applications in pharmaceutical and agrochemical development.

Recent studies have highlighted the role of 2-Bromo-4-nitro-1-(trifluoromethyl)benzene as a key intermediate in the synthesis of complex organic molecules. Its unique structure, featuring both bromo and nitro substituents on a trifluoromethylated benzene ring, enables diverse chemical transformations, including nucleophilic aromatic substitutions and cross-coupling reactions. A 2023 study published in the Journal of Medicinal Chemistry demonstrated its utility in constructing novel heterocyclic scaffolds with potential antimicrobial activity.

In pharmaceutical research, this compound has shown promise as a building block for developing kinase inhibitors. Computational docking studies suggest that derivatives of 2-Bromo-4-nitro-1-(trifluoromethyl)benzene can interact with the ATP-binding sites of various protein kinases, making it a valuable template for cancer drug development. Ongoing preclinical evaluations are investigating its derivatives for selective inhibition of tyrosine kinases associated with solid tumors.

The compound's stability under physiological conditions has also made it attractive for radiopharmaceutical applications. Recent work at several research institutions has explored its potential as a precursor for PET tracer development, particularly for imaging inflammation markers. The trifluoromethyl group enhances lipophilicity, potentially improving blood-brain barrier penetration for neurological applications.

From a safety perspective, new toxicological data (2024) indicates that proper handling protocols are essential when working with this compound. While it shows moderate acute toxicity in standard assays, its environmental persistence warrants careful consideration in industrial applications. Researchers are actively developing greener synthetic routes to minimize hazardous byproducts during its production.

Looking forward, the unique electronic properties imparted by the combination of electron-withdrawing groups (nitro and trifluoromethyl) and the bromine leaving group position this molecule as a strategic intermediate for next-generation materials. Several patents filed in 2024 describe its incorporation into organic semiconductors and liquid crystal displays, suggesting expanding applications beyond traditional chemical synthesis.

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