Cas no 155906-13-1 (2,5-Difluoro-4-iodoaniline)

2,5-Difluoro-4-iodoaniline is a halogenated aniline derivative featuring both fluorine and iodine substituents on the aromatic ring. This compound is valued in synthetic organic chemistry for its versatility as a building block in pharmaceutical and agrochemical applications. The presence of fluorine enhances electron-withdrawing properties, while the iodine atom offers reactivity for cross-coupling reactions, such as Suzuki or Sonogashira couplings. Its well-defined structure and high purity make it suitable for precise functionalization in complex molecule synthesis. The compound’s stability under standard conditions ensures reliable handling and storage, facilitating its use in research and industrial processes requiring regioselective aromatic substitutions.
2,5-Difluoro-4-iodoaniline structure
2,5-Difluoro-4-iodoaniline structure
Product Name:2,5-Difluoro-4-iodoaniline
CAS No:155906-13-1
MF:C6H4F2IN
MW:255.003940582275
MDL:MFCD07774188
CID:2093116
Update Time:2025-06-07

2,5-Difluoro-4-iodoaniline Chemical and Physical Properties

Names and Identifiers

    • 2,5-Difluoro-4-iodoaniline
    • 2,5-Difluoro-4-iodo-phenylamine
    • AK158273
    • 4-iodo-2,5-difluoroaniline
    • DQTJNHXTFILGGG-UHFFFAOYSA-N
    • 1397AJ
    • Benzenamine, 2,5-difluoro-4-iodo-
    • FCH1385286
    • AX8292135
    • MDL: MFCD07774188
    • Inchi: 1S/C6H4F2IN/c7-3-2-6(10)4(8)1-5(3)9/h1-2H,10H2
    • InChI Key: DQTJNHXTFILGGG-UHFFFAOYSA-N
    • SMILES: IC1=CC(=C(C=C1F)N)F

Computed Properties

  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 0
  • Complexity: 122
  • Topological Polar Surface Area: 26

2,5-Difluoro-4-iodoaniline Security Information

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Additional information on 2,5-Difluoro-4-iodoaniline

Professional Introduction to 2,5-Difluoro-4-iodoaniline (CAS No. 155906-13-1)

2,5-Difluoro-4-iodoaniline is a fluorinated aromatic amine derivative with the molecular formula C?H?F?IN?. This compound has garnered significant attention in the field of pharmaceutical chemistry and materials science due to its versatile structural properties and potential applications. As a key intermediate in organic synthesis, it plays a crucial role in the development of various chemical entities, including agrochemicals, pharmaceuticals, and advanced materials.

The chemical structure of 2,5-Difluoro-4-iodoaniline features a benzene ring substituted with two fluorine atoms at the 2- and 5-positions and an iodine atom at the 4-position, along with an amino group. This unique arrangement imparts distinct electronic and steric properties, making it a valuable building block for further functionalization. The presence of both fluorine and iodine atoms enhances its reactivity, enabling diverse synthetic pathways that are not achievable with simpler aromatic amines.

In recent years, 2,5-Difluoro-4-iodoaniline has been extensively studied for its role in medicinal chemistry. Its structural motifs have been incorporated into various drug candidates targeting different therapeutic areas. For instance, fluorinated aromatic compounds are known to exhibit improved metabolic stability and bioavailability, which are critical factors in drug design. The iodine atom serves as a handle for further transformations, such as cross-coupling reactions, which are widely used in the synthesis of complex molecular architectures.

One of the most notable applications of 2,5-Difluoro-4-iodoaniline is in the development of anticancer agents. Researchers have leveraged its reactivity to synthesize novel kinase inhibitors and other small-molecule drugs that disrupt cancer cell proliferation. The fluorine atoms contribute to the binding affinity of these compounds by modulating hydrophobic interactions and electronic effects. Additionally, the iodine moiety allows for post-synthetic modifications, enabling the creation of libraries of derivatives with tailored pharmacological properties.

The compound has also found utility in materials science, particularly in the fabrication of organic electronic devices. Fluorinated aromatic amines are employed as dopants and precursors for semiconducting materials due to their ability to enhance charge transport properties. The halogenated substituents in 2,5-Difluoro-4-iodoaniline facilitate π-conjugation and electron delocalization, making it an excellent candidate for applications in organic light-emitting diodes (OLEDs), field-effect transistors (OFETs), and other optoelectronic devices.

The synthesis of 2,5-Difluoro-4-iodoaniline typically involves multi-step organic transformations starting from commercially available precursors. Common methods include halogenation reactions followed by selective functional group interconversion. Advances in synthetic methodologies have enabled more efficient and scalable production processes, reducing costs and improving yields. These developments have made CAS No. 155906-13-1 more accessible to researchers worldwide.

In conclusion, 2,5-Difluoro-4-iodoaniline represents a fascinating compound with broad applications across multiple scientific disciplines. Its unique structural features make it an indispensable tool for chemists working on drug discovery, material science, and advanced chemical synthesis. As research continues to uncover new possibilities for this versatile intermediate, its importance is expected to grow even further.

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