Cas no 29682-14-2 (methyl 5-nitropyridine-2-carboxylate)

Methyl 5-nitropyridine-2-carboxylate is a nitropyridine derivative with significant utility as an intermediate in organic synthesis and pharmaceutical research. Its key structural features—a nitro group at the 5-position and a methyl ester at the 2-position—make it a versatile building block for constructing more complex heterocyclic compounds. The compound is particularly valuable in medicinal chemistry for the development of bioactive molecules, including potential antimicrobial and antitumor agents. Its high purity and stability under standard conditions ensure reliable performance in reactions such as nucleophilic substitutions and reductions. The product is commonly used in academic and industrial settings for targeted synthesis and structure-activity relationship studies.
methyl 5-nitropyridine-2-carboxylate structure
29682-14-2 structure
Product Name:methyl 5-nitropyridine-2-carboxylate
CAS No:29682-14-2
MF:C7H6N2O4
MW:182.133541584015
MDL:MFCD09062740
CID:852700
PubChem ID:12457882
Update Time:2025-06-14

methyl 5-nitropyridine-2-carboxylate Chemical and Physical Properties

Names and Identifiers

    • Methyl 5-nitropicolinate
    • 2-Pyridinecarboxylic acid, 5-nitro-, methyl ester
    • Methyl 5-nitro-2-pyridinecarboxylate
    • methyl 5-nitropyridine-2-carboxylate
    • 5-Nitro-2-methoxycarbonylpyridine
    • 5-Nitropyridine-2-carboxylic acid methyl ester
    • CHEMBL2022009
    • DTXSID60499057
    • SB10169
    • GS-5003
    • SCHEMBL1403615
    • WBJDJRHSHXTRAT-UHFFFAOYSA-N
    • W17169
    • AKOS006330598
    • DB-068148
    • Z1198184840
    • 5-nitro-pyridine-2-carboxylic acid methyl ester
    • SY150280
    • STK689715
    • EN300-129493
    • MFCD09062740
    • 29682-14-2
    • CS-0061867
    • MDL: MFCD09062740
    • Inchi: 1S/C7H6N2O4/c1-13-7(10)6-3-2-5(4-8-6)9(11)12/h2-4H,1H3
    • InChI Key: WBJDJRHSHXTRAT-UHFFFAOYSA-N
    • SMILES: O(C)C(C1C=CC(=CN=1)[N+](=O)[O-])=O

Computed Properties

  • Exact Mass: 182.03300
  • Monoisotopic Mass: 182.03275668g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 3
  • Complexity: 213
  • 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: 0.9
  • Topological Polar Surface Area: 85?2

Experimental Properties

  • Density: 1.375±0.06 g/cm3 (20 oC 760 Torr),
  • Melting Point: 150-153 oC
  • Solubility: Slightly soluble (13 g/l) (25 o C),
  • PSA: 85.01000
  • LogP: 1.29960

methyl 5-nitropyridine-2-carboxylate Customs Data

  • HS CODE:2933399090
  • Customs Data:

    China Customs Code:

    2933399090

    Overview:

    2933399090. Other compounds with non fused pyridine rings in structure. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to, Please indicate the appearance of Urotropine, 6- caprolactam please indicate the appearance, Signing date

    Summary:

    2933399090. other compounds containing an unfused pyridine ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

methyl 5-nitropyridine-2-carboxylate Pricemore >>

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Additional information on methyl 5-nitropyridine-2-carboxylate

Recent Advances in the Application of Methyl 5-Nitropyridine-2-Carboxylate (CAS 29682-14-2) in Chemical Biology and Pharmaceutical Research

Methyl 5-nitropyridine-2-carboxylate (CAS 29682-14-2) is a versatile chemical intermediate that has garnered significant attention in recent years due to its potential applications in chemical biology and pharmaceutical research. This compound, characterized by its nitro and ester functional groups, serves as a key building block in the synthesis of various heterocyclic compounds, which are often explored for their biological activities. Recent studies have highlighted its utility in the development of novel therapeutic agents, particularly in the fields of oncology, infectious diseases, and neurological disorders.

One of the most notable advancements involving methyl 5-nitropyridine-2-carboxylate is its role in the synthesis of kinase inhibitors. Kinases are critical targets in cancer therapy, and researchers have leveraged the reactivity of this compound to design potent and selective inhibitors. For instance, a 2023 study published in the Journal of Medicinal Chemistry demonstrated the use of methyl 5-nitropyridine-2-carboxylate as a precursor in the synthesis of pyridine-based inhibitors targeting the epidermal growth factor receptor (EGFR), a protein implicated in various cancers. The study reported improved inhibitory activity and reduced off-target effects compared to previous generations of inhibitors.

In addition to its applications in oncology, methyl 5-nitropyridine-2-carboxylate has been explored as a scaffold for antimicrobial agents. A recent publication in Bioorganic & Medicinal Chemistry Letters detailed the synthesis of a series of nitropyridine derivatives using this compound, which exhibited potent activity against drug-resistant bacterial strains. The researchers attributed the enhanced efficacy to the electron-withdrawing nitro group, which facilitates interactions with bacterial enzymes. These findings underscore the potential of methyl 5-nitropyridine-2-carboxylate in addressing the growing challenge of antibiotic resistance.

Beyond its therapeutic applications, methyl 5-nitropyridine-2-carboxylate has also been investigated for its utility in chemical biology. A 2022 study in ACS Chemical Biology described its use as a fluorescent probe for detecting reactive oxygen species (ROS) in cellular environments. The nitro group in the compound undergoes reduction in the presence of ROS, leading to a measurable change in fluorescence. This property makes it a valuable tool for studying oxidative stress, which is implicated in numerous diseases, including neurodegenerative disorders and cardiovascular conditions.

The synthetic versatility of methyl 5-nitropyridine-2-carboxylate has further been demonstrated in the development of prodrugs. Prodrugs are inactive compounds that are metabolized into active drugs within the body, often improving bioavailability or reducing side effects. A recent study in European Journal of Medicinal Chemistry highlighted the use of this compound in the design of prodrugs for central nervous system (CNS) agents. The researchers successfully synthesized a prodrug that exhibited enhanced blood-brain barrier penetration, paving the way for improved treatments for neurological disorders.

Despite its promising applications, challenges remain in the large-scale production and optimization of methyl 5-nitropyridine-2-carboxylate-based compounds. Issues such as yield, purity, and scalability need to be addressed to facilitate their transition from the laboratory to clinical use. However, ongoing research efforts, including the development of novel synthetic routes and catalytic methods, are expected to overcome these hurdles. For example, a 2023 study in Organic Process Research & Development reported a more efficient and environmentally friendly synthesis of methyl 5-nitropyridine-2-carboxylate using green chemistry principles, which could significantly enhance its industrial applicability.

In conclusion, methyl 5-nitropyridine-2-carboxylate (CAS 29682-14-2) continues to be a compound of great interest in chemical biology and pharmaceutical research. Its diverse applications, ranging from kinase inhibitors to antimicrobial agents and fluorescent probes, highlight its potential to contribute to the development of next-generation therapeutics. As research progresses, it is anticipated that this compound will play an increasingly important role in addressing unmet medical needs and advancing our understanding of biological systems.

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