Cas no 1003711-76-9 (4-nitropyridine-3-carbonitrile)

4-Nitropyridine-3-carbonitrile is a nitropyridine derivative featuring both a nitro group and a cyano functional group on its aromatic ring. This compound serves as a versatile intermediate in organic synthesis, particularly in the preparation of pharmaceuticals, agrochemicals, and heterocyclic compounds. The electron-withdrawing nitro and cyano groups enhance its reactivity, making it valuable for nucleophilic substitution and cyclization reactions. Its well-defined structure and high purity ensure consistent performance in research and industrial applications. The compound is typically handled under controlled conditions due to its potential sensitivity. Its utility in constructing complex molecular frameworks underscores its importance in synthetic chemistry.
4-nitropyridine-3-carbonitrile structure
1003711-76-9 structure
Product Name:4-nitropyridine-3-carbonitrile
CAS No:1003711-76-9
MF:C6H3N3O2
MW:149.106920480728
CID:1127869
PubChem ID:19707201
Update Time:2025-10-30

4-nitropyridine-3-carbonitrile Chemical and Physical Properties

Names and Identifiers

    • 4-nitropyridine-3-carbonitrile
    • 3-cyano-4-nitropyridine
    • 1003711-76-9
    • SCHEMBL8564318
    • DTXSID70599370
    • DB-058410
    • AKOS006328755
    • Inchi: 1S/C6H3N3O2/c7-3-5-4-8-2-1-6(5)9(10)11/h1-2,4H
    • InChI Key: RSWUDFDGDSLOGK-UHFFFAOYSA-N
    • SMILES: [O-][N+](C1C=CN=CC=1C#N)=O

Computed Properties

  • Exact Mass: 149.022526g/mol
  • Monoisotopic Mass: 149.022526g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 0
  • Complexity: 202
  • 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
  • Molecular Weight: 149.11g/mol
  • XLogP3: 0.4
  • Topological Polar Surface Area: 82.5?2

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Additional information on 4-nitropyridine-3-carbonitrile

Recent Advances in the Study of 4-Nitropyridine-3-Carbonitrile (CAS: 1003711-76-9) in Chemical Biology and Pharmaceutical Research

4-Nitropyridine-3-carbonitrile (CAS: 1003711-76-9) is a heterocyclic compound that has garnered significant attention in recent years due to its versatile applications in chemical biology and pharmaceutical research. This compound, characterized by its nitropyridine core and carbonitrile functional group, serves as a key intermediate in the synthesis of various bioactive molecules. Recent studies have explored its potential as a building block for drug discovery, particularly in the development of kinase inhibitors and antimicrobial agents. This research brief aims to summarize the latest findings related to 4-nitropyridine-3-carbonitrile, highlighting its synthetic utility, biological activities, and potential therapeutic applications.

One of the most notable advancements in the study of 4-nitropyridine-3-carbonitrile is its role in the synthesis of kinase inhibitors. Kinases are critical targets in cancer therapy, and the nitropyridine scaffold has been leveraged to design potent and selective inhibitors. Recent publications have demonstrated that derivatives of 4-nitropyridine-3-carbonitrile exhibit promising inhibitory activity against specific kinases, such as EGFR and VEGFR, which are implicated in tumor growth and angiogenesis. These findings underscore the compound's potential as a starting point for the development of novel anticancer agents.

In addition to its applications in oncology, 4-nitropyridine-3-carbonitrile has also been investigated for its antimicrobial properties. A 2023 study published in the Journal of Medicinal Chemistry reported that nitropyridine-based compounds, including 4-nitropyridine-3-carbonitrile derivatives, displayed broad-spectrum activity against resistant bacterial strains. The study highlighted the compound's ability to disrupt bacterial cell wall synthesis, making it a promising candidate for addressing the global challenge of antibiotic resistance. Further optimization of these derivatives could lead to the discovery of new classes of antibiotics.

The synthetic versatility of 4-nitropyridine-3-carbonitrile has also been a focal point of recent research. Advances in catalytic methods, such as transition-metal-catalyzed cross-coupling reactions, have enabled the efficient functionalization of the nitropyridine core. For instance, a 2022 study in Organic Letters detailed a palladium-catalyzed cyanation reaction that utilized 4-nitropyridine-3-carbonitrile as a precursor to generate highly functionalized pyridine derivatives. These synthetic methodologies not only expand the chemical space accessible to researchers but also facilitate the rapid exploration of structure-activity relationships in drug discovery.

Despite these promising developments, challenges remain in the practical application of 4-nitropyridine-3-carbonitrile. Issues such as solubility, stability, and bioavailability must be addressed to translate laboratory findings into clinically viable therapeutics. Recent efforts have focused on prodrug strategies and formulation technologies to overcome these limitations. For example, a 2023 patent application described a nanoparticle-based delivery system designed to enhance the bioavailability of nitropyridine derivatives, including 4-nitropyridine-3-carbonitrile, in preclinical models.

In conclusion, 4-nitropyridine-3-carbonitrile (CAS: 1003711-76-9) represents a valuable scaffold in chemical biology and pharmaceutical research. Its diverse applications in kinase inhibition, antimicrobial therapy, and synthetic chemistry highlight its potential to address unmet medical needs. Ongoing research efforts are expected to further elucidate its mechanisms of action and optimize its pharmacological properties, paving the way for its integration into next-generation therapeutics. This brief underscores the importance of continued investment in the study of this compound and its derivatives to unlock their full potential in medicine.

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