Cas no 194344-29-1 (2-Iodo-4-nitro-1-(trifluoromethoxy)benzene)

2-Iodo-4-nitro-1-(trifluoromethoxy)benzene structure
194344-29-1 structure
Product Name:2-Iodo-4-nitro-1-(trifluoromethoxy)benzene
CAS No:194344-29-1
MF:C7H3F3INO3
MW:333.003304719925
MDL:MFCD13194454
CID:2619875
PubChem ID:56604200
Update Time:2025-07-18

2-Iodo-4-nitro-1-(trifluoromethoxy)benzene Chemical and Physical Properties

Names and Identifiers

    • SY128821
    • 3-Iodo-4-(trifluoromethoxy)nitrobenzene
    • C7H3F3INO3
    • MFCD13194454
    • PS-10462
    • 194344-29-1
    • Benzene, 2-iodo-4-nitro-1-(trifluoromethoxy)-
    • AC5126
    • CS-0083333
    • AKOS027324464
    • 2-Iodo-4-nitro-1-(trifluoromethoxy)benzene
    • MDL: MFCD13194454
    • Inchi: 1S/C7H3F3INO3/c8-7(9,10)15-6-2-1-4(12(13)14)3-5(6)11/h1-3H
    • InChI Key: UCHXFOSROGVONK-UHFFFAOYSA-N
    • SMILES: IC1C=C(C=CC=1OC(F)(F)F)[N+](=O)[O-]

Computed Properties

  • Exact Mass: 332.91098g/mol
  • Monoisotopic Mass: 332.91098g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 15
  • Rotatable Bond Count: 3
  • Complexity: 243
  • 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: 55?2

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Additional information on 2-Iodo-4-nitro-1-(trifluoromethoxy)benzene

Professional Introduction to 2-Iodo-4-nitro-1-(trifluoromethoxy)benzene (CAS No. 194344-29-1)

2-Iodo-4-nitro-1-(trifluoromethoxy)benzene, with the chemical formula C?H?ClF?INO?, is a highly versatile aromatic compound that has garnered significant attention in the field of pharmaceutical and agrochemical research. Its unique structural features, comprising an iodo substituent, a nitro group, and a trifluoromethoxy moiety, make it a valuable intermediate in the synthesis of various biologically active molecules. This compound has found applications in medicinal chemistry, particularly in the development of novel therapeutic agents targeting diverse disease pathways.

The structure of 2-Iodo-4-nitro-1-(trifluoromethoxy)benzene exhibits a rich electronic distribution due to the presence of electron-withdrawing and electron-donating groups. The iodo atom at the 2-position enhances electrophilic aromatic substitution reactions, while the nitro group at the 4-position introduces strong electron-withdrawing effects. The trifluoromethoxy group at the 1-position contributes both electron-donating and electron-withdrawing influences, depending on its position relative to other substituents. This complex interplay of electronic effects makes the compound highly reactive and adaptable for further functionalization.

In recent years, 2-Iodo-4-nitro-1-(trifluoromethoxy)benzene has been extensively studied for its potential in drug discovery. Its derivatives have been explored as intermediates in the synthesis of kinase inhibitors, anticancer agents, and antimicrobial compounds. The trifluoromethoxy group, in particular, is known for its ability to enhance metabolic stability and binding affinity in drug candidates. For instance, studies have demonstrated its utility in generating novel small-molecule inhibitors targeting protein kinases involved in cancer progression.

One notable application of 2-Iodo-4-nitro-1-(trifluoromethoxy)benzene is in the development of tyrosine kinase inhibitors (TKIs), which play a crucial role in treating various types of cancer. Researchers have leveraged its reactive iodine atom to introduce further modifications through cross-coupling reactions such as Suzuki-Miyaura coupling, allowing for the construction of complex molecular architectures. These modifications have led to the discovery of several lead compounds with promising preclinical activity against tumor cell lines.

The synthesis of 2-Iodo-4-nitro-1-(trifluoromethoxy)benzene typically involves multi-step organic transformations starting from commercially available precursors. A common synthetic route includes nitration followed by halogenation and subsequent methoxylation. The precise control of reaction conditions is essential to achieve high yields and purity, as side reactions can lead to undesired byproducts. Advances in catalytic systems and green chemistry principles have improved the efficiency and sustainability of these synthetic processes.

Recent advancements in computational chemistry have also enhanced our understanding of 2-Iodo-4-nitro-1-(trifluoromethoxy)benzene's reactivity and mechanistic pathways. Molecular modeling studies have revealed insights into how different substituents influence its electronic properties and interactions with biological targets. These insights are invaluable for designing optimized synthetic strategies and predicting the biological activity of derived compounds.

The pharmaceutical industry has shown particular interest in 2-Iodo-4-nitro-1-(trifluoromethoxy)benzene due to its potential as a building block for next-generation therapeutics. Its structural features align well with current trends in drug design, where fluorinated aromatic compounds are favored for their improved pharmacokinetic properties. Several academic and industrial groups have reported novel derivatives with enhanced potency and selectivity against disease-causing targets.

In conclusion, 2-Iodo-4-nitro-1-(trifluoromethoxy)benzene (CAS No. 194344-29-1) represents a significant asset in synthetic chemistry and drug discovery. Its unique structural attributes enable diverse functionalization strategies, making it a cornerstone for developing innovative therapeutic agents. As research continues to uncover new applications and synthetic methodologies, this compound is poised to remain a key intermediate in pharmaceutical innovation.

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