Cas no 475272-62-9 (6-methoxy-5-nitro-pyridine-2-carboxylic acid)

6-Methoxy-5-nitro-pyridine-2-carboxylic acid is a nitro-substituted pyridine derivative with a methoxy group at the 6-position and a carboxylic acid functionality at the 2-position. This compound serves as a versatile intermediate in organic synthesis, particularly in the preparation of pharmaceuticals, agrochemicals, and specialty chemicals. Its nitro and carboxylic acid groups provide reactive sites for further functionalization, enabling the construction of complex heterocyclic frameworks. The methoxy substituent enhances solubility and influences electronic properties, making it useful in fine chemical applications. High purity grades are available to meet stringent research and industrial requirements. Proper handling and storage are recommended due to its reactivity.
6-methoxy-5-nitro-pyridine-2-carboxylic acid structure
475272-62-9 structure
Product Name:6-methoxy-5-nitro-pyridine-2-carboxylic acid
CAS No:475272-62-9
MF:C7H6N2O5
MW:198.13294172287
MDL:MFCD18261308
CID:931097
PubChem ID:22565233
Update Time:2025-08-04

6-methoxy-5-nitro-pyridine-2-carboxylic acid Chemical and Physical Properties

Names and Identifiers

    • 6-Methoxy-5-nitropicolinic acid
    • 2-Pyridinecarboxylicacid,6-methoxy-5-nitro-(9CI)
    • 6-methoxy-5-nitro-2-Pyridinecarboxylic acid
    • 6-methoxy-5-nitropyridine-2-carboxylic acid
    • USBYKQLQDLTNGK-UHFFFAOYSA-N
    • NE58231
    • AK127179
    • ST2418977
    • Z1741982330
    • 6-methoxy-5-nitro-pyridine-2-carboxylic acid
    • C75267
    • A872126
    • AKOS016012877
    • EN300-142134
    • CS-0040710
    • MFCD18261308
    • SCHEMBL4651273
    • SB53766
    • 475272-62-9
    • DTXSID90626511
    • DB-070824
    • DS-5475
    • 6-Methoxy-5-nitropicolinicacid
    • MDL: MFCD18261308
    • Inchi: 1S/C7H6N2O5/c1-14-6-5(9(12)13)3-2-4(8-6)7(10)11/h2-3H,1H3,(H,10,11)
    • InChI Key: USBYKQLQDLTNGK-UHFFFAOYSA-N
    • SMILES: O(C)C1C(=CC=C(C(=O)O)N=1)[N+](=O)[O-]

Computed Properties

  • Exact Mass: 198.02767130g/mol
  • Monoisotopic Mass: 198.02767130g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 6
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 2
  • Complexity: 239
  • 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
  • Topological Polar Surface Area: 105
  • XLogP3: 0.8

Experimental Properties

  • Density: 1.512±0.06 g/cm3 (20 oC 760 Torr),
  • Solubility: Slightly soluble (6.7 g/l) (25 o C),

6-methoxy-5-nitro-pyridine-2-carboxylic acid Security Information

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Additional information on 6-methoxy-5-nitro-pyridine-2-carboxylic acid

Recent Advances in the Application of 6-Methoxy-5-nitro-pyridine-2-carboxylic acid (CAS: 475272-62-9) in Chemical Biology and Pharmaceutical Research

6-Methoxy-5-nitro-pyridine-2-carboxylic acid (CAS: 475272-62-9) has recently emerged as a key intermediate in the synthesis of novel bioactive compounds, particularly in the development of kinase inhibitors and antimicrobial agents. This heterocyclic carboxylic acid derivative has garnered significant attention due to its unique structural features, which enable diverse chemical modifications and interactions with biological targets. Recent studies have highlighted its potential in addressing drug resistance challenges and enhancing therapeutic efficacy.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the utility of 6-methoxy-5-nitro-pyridine-2-carboxylic acid as a building block for the synthesis of potent EGFR inhibitors. The researchers utilized this compound to develop a series of pyridine-based derivatives showing nanomolar activity against resistant EGFR mutations. The nitro and methoxy functional groups were found to be critical for maintaining binding affinity while improving metabolic stability compared to earlier generation inhibitors.

In antimicrobial research, a team from the University of Cambridge reported in ACS Infectious Diseases (2024) that derivatives of 475272-62-9 exhibited promising activity against multidrug-resistant Gram-positive pathogens. The compound's ability to chelate metal ions essential for bacterial virulence factors was identified as a novel mechanism of action. This finding opens new avenues for developing antibiotics that can bypass conventional resistance mechanisms.

Recent synthetic methodology developments have significantly improved the accessibility of 6-methoxy-5-nitro-pyridine-2-carboxylic acid. A Nature Protocols paper (2023) described an optimized three-step synthesis from commercially available 2-chloro-6-methoxypyridine, achieving an overall yield of 68% with excellent purity. This advancement addresses previous challenges in large-scale production and has facilitated broader investigation of its pharmaceutical applications.

The compound's potential in targeted drug delivery systems was explored in a 2024 Advanced Materials publication. Researchers conjugated 475272-62-9 to polymeric nanoparticles, creating pH-responsive carriers that demonstrated enhanced tumor accumulation and controlled drug release. The nitro group's reduction potential in hypoxic environments was leveraged to trigger payload release specifically in tumor tissues.

Ongoing clinical trials (Phase I/II) are investigating a small molecule immunomodulator derived from 6-methoxy-5-nitro-pyridine-2-carboxylic acid for autoimmune diseases. Preliminary results presented at the 2024 American Chemical Society meeting showed favorable safety profiles and dose-dependent modulation of inflammatory cytokines. This application represents a significant expansion of the compound's therapeutic potential beyond its initial use as a synthetic intermediate.

Future research directions for 475272-62-9 include exploration of its photophysical properties for diagnostic applications and further optimization of its derivatives for CNS penetration. The compound's versatility continues to make it a valuable scaffold in medicinal chemistry, with several patent applications filed in 2024 covering novel derivatives and their therapeutic uses.

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