Cas no 125163-12-4 (4-Fluoro-5-methoxy-2-nitroaniline)

4-Fluoro-5-methoxy-2-nitroaniline is a fluorinated nitroaniline derivative with a methoxy substituent, offering unique reactivity and selectivity in synthetic applications. Its molecular structure, featuring both electron-withdrawing (nitro, fluoro) and electron-donating (methoxy) groups, makes it a versatile intermediate in the synthesis of pharmaceuticals, agrochemicals, and specialty dyes. The fluorine atom enhances metabolic stability and binding affinity in bioactive compounds, while the nitro group facilitates further functionalization via reduction or substitution. The methoxy group contributes to solubility and steric modulation. This compound is particularly valuable in heterocyclic chemistry and as a precursor for complex aromatic systems, ensuring high purity and consistent performance in research and industrial processes.
4-Fluoro-5-methoxy-2-nitroaniline structure
125163-12-4 structure
Product Name:4-Fluoro-5-methoxy-2-nitroaniline
CAS No:125163-12-4
MF:C7H7FN2O3
MW:186.140485048294
MDL:MFCD00247494
CID:856236
PubChem ID:53216869
Update Time:2025-05-20

4-Fluoro-5-methoxy-2-nitroaniline Chemical and Physical Properties

Names and Identifiers

    • 4-Fluoro-5-methoxy-2-nitroaniline
    • 4-Fluoro-5-methoxy-2-nitro-phenylamine
    • BenzenaMine, 4-fluoro-5-Methoxy-2-nitro-
    • DTXSID80682000
    • CS-0207816
    • SCHEMBL2313882
    • BCP33209
    • DB-349238
    • E87511
    • AKOS006346289
    • BS-19661
    • 4-Fluoro-5-methoxy-2-nitro-aniline
    • 125163-12-4
    • FRMLKSWJWIKLPO-UHFFFAOYSA-N
    • MFCD00247494
    • MDL: MFCD00247494
    • Inchi: 1S/C7H7FN2O3/c1-13-7-3-5(9)6(10(11)12)2-4(7)8/h2-3H,9H2,1H3
    • InChI Key: FRMLKSWJWIKLPO-UHFFFAOYSA-N
    • SMILES: FC1=CC(=C(C=C1OC)N)[N+](=O)[O-]

Computed Properties

  • Exact Mass: 186.04411
  • Monoisotopic Mass: 186.04407025g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 2
  • Complexity: 197
  • 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: 1.7
  • Topological Polar Surface Area: 81.1?2

Experimental Properties

  • PSA: 78.39

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Additional information on 4-Fluoro-5-methoxy-2-nitroaniline

Professional Introduction to 4-Fluoro-5-methoxy-2-nitroaniline (CAS No. 125163-12-4)

4-Fluoro-5-methoxy-2-nitroaniline is a specialized organic compound that has garnered significant attention in the field of pharmaceutical and chemical research due to its unique structural and functional properties. This compound, identified by its Chemical Abstracts Service (CAS) number CAS No. 125163-12-4, is a derivative of aniline and features a nitro group, a fluoro substituent, and a methoxy group, which collectively contribute to its reactivity and potential applications.

The structural configuration of 4-fluoro-5-methoxy-2-nitroaniline makes it a valuable intermediate in the synthesis of various pharmacologically active molecules. The presence of the nitro group at the 2-position enhances its electrophilicity, making it susceptible to reduction or transformation into other functional groups such as amines or amides. Additionally, the fluoro substituent at the 4-position can influence the metabolic stability and binding affinity of the compound when incorporated into larger molecular frameworks.

In recent years, there has been growing interest in exploring the therapeutic potential of fluorinated aromatic compounds. The fluorine atom's ability to modulate lipophilicity and metabolic pathways has made such compounds attractive candidates for drug development. For instance, studies have demonstrated that fluorine substitution can improve the bioavailability and binding affinity of drug molecules, leading to more effective therapeutic outcomes.

4-Fluoro-5-methoxy-2-nitroaniline has been investigated in several research contexts, particularly in the synthesis of kinase inhibitors and other small-molecule drugs targeting specific biological pathways. The nitro group's reactivity allows for further functionalization, enabling chemists to design complex molecules with tailored properties. Moreover, the methoxy group at the 5-position can serve as a handle for further derivatization, such as etherification or sulfation, expanding the compound's utility in medicinal chemistry.

One notable application of 4-fluoro-5-methoxy-2-nitroaniline is in the development of anticancer agents. Researchers have leveraged its structural features to create novel inhibitors that target enzymes involved in tumor growth and progression. The combination of fluorine and nitro groups provides a balance between reactivity and stability, allowing for efficient synthesis and optimization of lead compounds.

The synthesis of 4-fluoro-5-methoxy-2-nitroaniline typically involves multi-step organic reactions starting from readily available precursors. Common synthetic routes include nitration followed by selective fluorination and methylation. Advanced techniques such as palladium-catalyzed cross-coupling reactions have also been employed to introduce additional functional groups with high precision.

In terms of industrial applications, 4-fluoro-5-methoxy-2-nitroaniline serves as a key intermediate in the production of specialty chemicals used in agrochemicals and materials science. Its unique electronic properties make it suitable for applications in organic electronics, where it can be used to develop novel conductive polymers or liquid crystal materials.

The safety profile of 4-fluoro-5-methoxy-2-nitroaniline is another critical aspect that has been thoroughly evaluated in research settings. While handling this compound requires standard laboratory precautions due to its reactivity, it does not pose significant health risks under controlled conditions. Proper storage and handling protocols ensure that researchers can work with it safely while minimizing environmental impact.

The future prospects for 4-fluoro-5-methoxy-2-nitroaniline are promising, with ongoing research focusing on expanding its applications in drug discovery and material science. Innovations in synthetic methodologies are expected to further enhance its accessibility and utility, paving the way for new breakthroughs in pharmaceutical development.

In conclusion, 4-fluoro-5-methoxy-2-nitroaniline (CAS No. 125163-12-4) is a versatile compound with significant potential across multiple scientific disciplines. Its unique structural features make it an invaluable tool for researchers seeking to develop novel therapeutics and advanced materials. As our understanding of its properties continues to grow, so too will its role in shaping the future of chemical research.

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