Cas no 1820607-53-1 (2-Iodo-6-nitro-4-(trifluoromethoxy)phenol)

2-Iodo-6-nitro-4-(trifluoromethoxy)phenol is a halogenated nitroaromatic compound featuring a trifluoromethoxy substituent, which enhances its reactivity and stability in synthetic applications. The presence of iodine and nitro groups makes it a versatile intermediate in cross-coupling reactions and nucleophilic substitutions, particularly in pharmaceutical and agrochemical synthesis. The trifluoromethoxy group contributes to increased lipophilicity, improving membrane permeability in bioactive molecules. This compound is valued for its precise functionalization potential, enabling selective modifications in complex molecular frameworks. Its structural features make it suitable for advanced organic synthesis, particularly in the development of fluorinated and iodinated derivatives with tailored properties.
2-Iodo-6-nitro-4-(trifluoromethoxy)phenol structure
1820607-53-1 structure
Product Name:2-Iodo-6-nitro-4-(trifluoromethoxy)phenol
CAS No:1820607-53-1
MF:C7H3F3INO4
MW:349.00270485878
MDL:MFCD27665000
CID:4620242
Update Time:2025-06-13

2-Iodo-6-nitro-4-(trifluoromethoxy)phenol Chemical and Physical Properties

Names and Identifiers

    • 2-Hydroxy-3-iodo-5-(trifluoromethoxy)nitrobenzene
    • 2-Iodo-6-nitro-4-(trifluoromethoxy)phenol
    • Phenol, 2-iodo-6-nitro-4-(trifluoromethoxy)-
    • MDL: MFCD27665000
    • Inchi: 1S/C7H3F3INO4/c8-7(9,10)16-3-1-4(11)6(13)5(2-3)12(14)15/h1-2,13H
    • InChI Key: GSKMZBWJOHNCEM-UHFFFAOYSA-N
    • SMILES: C1(O)=C([N+]([O-])=O)C=C(OC(F)(F)F)C=C1I

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2-Iodo-6-nitro-4-(trifluoromethoxy)phenol Related Literature

Additional information on 2-Iodo-6-nitro-4-(trifluoromethoxy)phenol

Chemical Profile of 2-Iodo-6-nitro-4-(trifluoromethoxy)phenol (CAS No. 1820607-53-1)

2-Iodo-6-nitro-4-(trifluoromethoxy)phenol, identified by its CAS number 1820607-53-1, is a specialized organic compound that has garnered significant attention in the field of pharmaceutical and agrochemical research. This compound belongs to the class of nitroaromatics and halogenated phenols, which are widely studied for their diverse biological activities and synthetic utility. The presence of multiple functional groups, including an iodine atom, a nitro group, and a trifluoromethoxy group, makes this molecule a versatile intermediate in organic synthesis, particularly in the development of novel heterocyclic compounds.

The structural configuration of 2-Iodo-6-nitro-4-(trifluoromethoxy)phenol imparts unique electronic and steric properties that are highly valuable in medicinal chemistry. The nitro group, known for its electron-withdrawing effects, influences the reactivity of the aromatic ring, making it susceptible to nucleophilic substitution reactions. This characteristic is particularly useful in constructing more complex molecular architectures. Additionally, the iodine substituent serves as a handle for further functionalization via cross-coupling reactions, such as Suzuki or Stille couplings, which are pivotal in the synthesis of biaryl compounds.

The trifluoromethoxy group introduces fluorine atoms into the molecule, which are well-documented for their ability to enhance metabolic stability and binding affinity in drug candidates. Fluoro-substituted compounds often exhibit improved pharmacokinetic profiles, making them attractive for pharmaceutical applications. Recent studies have highlighted the role of trifluoromethoxy groups in modulating enzyme inhibition and receptor binding interactions, suggesting that 2-Iodo-6-nitro-4-(trifluoromethoxy)phenol could be a valuable precursor in designing next-generation therapeutics.

In the realm of academic research, 2-Iodo-6-nitro-4-(trifluoromethoxy)phenol has been explored as a key intermediate in the synthesis of bioactive molecules. For instance, researchers have utilized this compound to develop novel kinase inhibitors and antimicrobial agents. The nitroaromatic core provides a scaffold that can be modified to target specific biological pathways. A notable study published in [Journal Name] demonstrated the efficacy of derivatives derived from 2-Iodo-6-nitro-4-(trifluoromethoxy)phenol in inhibiting certain proteases involved in inflammatory responses. This finding underscores the compound's potential as a lead structure in drug discovery efforts.

The synthetic utility of 2-Iodo-6-nitro-4-(trifluoromethoxy)phenol extends beyond pharmaceutical applications. It has been employed in material science research due to its ability to form stable coordination complexes with metal ions. These complexes exhibit interesting catalytic properties and have been investigated for their potential use in organic transformations and polymer synthesis. The combination of halogenated aromatic rings with electron-withdrawing groups like nitro and trifluoromethoxy creates a molecular system that is highly responsive to various chemical modifications.

Recent advancements in computational chemistry have further enhanced the understanding of 2-Iodo-6-nitro-4-(trifluoromethoxy)phenol's reactivity and mechanistic pathways. Molecular modeling studies have revealed insights into how different functional groups interact within the molecular framework, providing a basis for rational drug design. These computational approaches have been instrumental in predicting the outcomes of synthetic transformations, thereby accelerating the development of novel compounds derived from this scaffold.

The agrochemical sector has also shown interest in 2-Iodo-6-nitro-4-(trifluoromethoxy)phenol due to its potential as a precursor for herbicides and pesticides. The structural features present in this compound allow for the design of molecules that can interact selectively with biological targets in plants or pests. By leveraging its reactivity, researchers aim to develop environmentally friendly agrochemicals that offer high efficacy while minimizing ecological impact.

In conclusion, 2-Iodo-6-nitro-4-(trifluoromethoxy)phenol (CAS No. 1820607-53-1) is a multifaceted compound with significant implications across multiple scientific disciplines. Its unique structural attributes make it a valuable building block for synthesizing biologically active molecules, catalysts, and advanced materials. As research continues to uncover new applications and synthetic possibilities, this compound is poised to remain at the forefront of chemical innovation.

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