Cas no 1228093-54-6 (1,2-Difluoro-4-iodo-5-methoxybenzene)

1,2-Difluoro-4-iodo-5-methoxybenzene is a fluorinated and iodinated aromatic compound with a methoxy substituent, offering unique reactivity for synthetic applications. Its structure combines electron-withdrawing fluorine and iodine groups with an electron-donating methoxy group, making it a versatile intermediate in cross-coupling reactions, such as Suzuki or Sonogashira couplings. The fluorine atoms enhance stability and influence regioselectivity in further functionalization, while the iodine serves as a reactive handle for metal-catalyzed transformations. This compound is particularly valuable in pharmaceutical and agrochemical research, where selective aromatic substitution is critical. Its well-defined reactivity profile ensures predictable outcomes in complex synthetic pathways.
1,2-Difluoro-4-iodo-5-methoxybenzene structure
1228093-54-6 structure
Product Name:1,2-Difluoro-4-iodo-5-methoxybenzene
CAS No:1228093-54-6
MF:C7H5F2IO
MW:270.015281438828
MDL:MFCD23135546
CID:1040740
PubChem ID:46220900
Update Time:2025-05-26

1,2-Difluoro-4-iodo-5-methoxybenzene Chemical and Physical Properties

Names and Identifiers

    • 1,2-Difluoro-4-iodo-5-methoxybenzene
    • 1,2-Difluoro-4-iodo-5-methoxy-benzene
    • AKOS016007183
    • MFCD23135546
    • CS-0194129
    • Benzene, 1,2-difluoro-4-iodo-5-methoxy-
    • E92597
    • DB-345491
    • AB93368
    • DTXSID10673123
    • 1228093-54-6
    • MDL: MFCD23135546
    • Inchi: 1S/C7H5F2IO/c1-11-7-3-5(9)4(8)2-6(7)10/h2-3H,1H3
    • InChI Key: ZPQSYQHIOJOCIT-UHFFFAOYSA-N
    • SMILES: IC1C=C(C(=CC=1OC)F)F

Computed Properties

  • Exact Mass: 269.93532g/mol
  • Monoisotopic Mass: 269.93532g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 1
  • Complexity: 134
  • 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: 2.7
  • Topological Polar Surface Area: 9.2?2

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Additional information on 1,2-Difluoro-4-iodo-5-methoxybenzene

Introduction to 1,2-Difluoro-4-iodo-5-methoxybenzene (CAS No: 1228093-54-6)

1,2-Difluoro-4-iodo-5-methoxybenzene, identified by its Chemical Abstracts Service (CAS) number 1228093-54-6, is a fluorinated aromatic compound that has garnered significant attention in the field of pharmaceutical and materials chemistry. This molecule, featuring both fluoro and iodo substituents on a benzene ring with a methoxy group at the fifth position, exhibits unique electronic and steric properties that make it a valuable intermediate in synthetic chemistry. The presence of fluorine atoms enhances the lipophilicity and metabolic stability of the compound, while the iodine atom serves as a versatile handle for further functionalization via cross-coupling reactions.

The structural motif of 1,2-Difluoro-4-iodo-5-methoxybenzene positions it as a key building block in the synthesis of more complex organic molecules. Its dual halogenation pattern allows for selective modifications at different positions, enabling chemists to tailor the compound for specific applications. In recent years, this compound has been explored in the development of novel agrochemicals, pharmaceuticals, and advanced materials due to its reactivity and structural versatility.

One of the most compelling aspects of 1,2-Difluoro-4-iodo-5-methoxybenzene is its utility in transition-metal-catalyzed cross-coupling reactions. The iodine atom can be readily displaced by other nucleophiles under mild conditions, facilitating the construction of biaryl systems and other complex scaffolds. These reactions are particularly valuable in medicinal chemistry, where biaryl structures are prevalent in bioactive molecules. For instance, recent studies have demonstrated the use of this compound in synthesizing kinase inhibitors, which are critical in targeted cancer therapies.

Moreover, the fluoro substituents in 1,2-Difluoro-4-iodo-5-methoxybenzene contribute to its pharmacokinetic properties. Fluorine atoms are known to influence metabolic pathways and binding affinities, making them indispensable in drug design. The methoxy group further enhances solubility and bioavailability, which are crucial factors in pharmaceutical development. Researchers have leveraged these properties to create derivatives with improved pharmacological profiles.

In the realm of materials science, 1,2-Difluoro-4-iodo-5-methoxybenzene has been investigated for its potential applications in organic electronics. The electron-withdrawing nature of fluorine and iodine can modulate the electronic properties of conjugated polymers and small molecules used in optoelectronic devices. Recent advances in this area have shown that incorporating this compound into polymer backbones can lead to enhanced charge transport properties, making it promising for use in organic light-emitting diodes (OLEDs) and photovoltaic cells.

The synthesis of 1,2-Difluoro-4-iodo-5-methoxybenzene typically involves multi-step processes that require careful optimization to achieve high yields and purity. Common synthetic routes include halogenation of pre-functionalized benzenes followed by methylation and fluorination steps. Advances in catalytic methods have enabled more efficient synthetic pathways, reducing waste and improving scalability. These improvements align with the growing emphasis on green chemistry principles in industrial applications.

Recent research has also highlighted the role of 1,2-Difluoro-4-iodo-5-methoxybenzene in medicinal chemistry beyond kinase inhibitors. Studies have shown its utility in developing antiviral agents and antimicrobial compounds. The ability to introduce diverse functional groups via cross-coupling reactions allows for rapid screening of novel drug candidates. For example, derivatives of this compound have been tested for their efficacy against resistant bacterial strains, showcasing its potential as a scaffold for antibiotic development.

The impact of 1,2-Difluoro-4-iodo-5-methoxybenzene extends to agrochemical research as well. Its structural features make it suitable for synthesizing herbicides and fungicides with improved selectivity and environmental compatibility. By modifying its halogenation pattern and substituent placement, researchers can develop compounds that target specific pests while minimizing ecological impact.

In conclusion,1,2-Difluoro-4-iodo-5-methoxybenzene (CAS No: 1228093-54-6) is a versatile intermediate with broad applications across pharmaceuticals、materials science,and agrochemicals。Its unique structural features,including fluoro、iodo,and methoxy substituents,make it a valuable tool for synthetic chemists。The growing body of research on this compound underscores its importance in modern chemical innovation,and future studies are likely to uncover even more exciting possibilities for its use.

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