Cas no 159454-73-6 (6-Methoxy-3-nitroquinoline)

6-Methoxy-3-nitroquinoline is a heterocyclic organic compound featuring a quinoline core substituted with a methoxy group at the 6-position and a nitro group at the 3-position. This compound serves as a versatile intermediate in organic synthesis, particularly in the preparation of pharmaceuticals, agrochemicals, and specialty chemicals. Its electron-withdrawing nitro group and electron-donating methoxy group contribute to its reactivity in nucleophilic and electrophilic substitution reactions. The compound’s well-defined structure and stability make it suitable for use in cross-coupling reactions and as a building block for more complex quinoline derivatives. It is typically handled under standard laboratory conditions, with attention to appropriate safety measures due to its nitro functionality.
6-Methoxy-3-nitroquinoline structure
6-Methoxy-3-nitroquinoline structure
Product Name:6-Methoxy-3-nitroquinoline
CAS No:159454-73-6
MF:C10H8N2O3
MW:204.18212223053
MDL:MFCD06411221
CID:1031848
PubChem ID:1519394
Update Time:2025-10-28

6-Methoxy-3-nitroquinoline Chemical and Physical Properties

Names and Identifiers

    • 6-Methoxy-3-nitroquinoline
    • quinoline, 6-methoxy-3-nitro-
    • 3-nitro-6-methoxyquinoline
    • 6-Methoxy-3-nitro-quinoline
    • 159454-73-6
    • SCHEMBL2815910
    • STK664875
    • MFCD06411221
    • DTXSID70364020
    • AKOS003388212
    • DB-350571
    • LS-08482
    • SB69024
    • LMMZXVJDJDOXEA-UHFFFAOYSA-N
    • ALBB-025299
    • MDL: MFCD06411221
    • Inchi: 1S/C10H8N2O3/c1-15-9-2-3-10-7(5-9)4-8(6-11-10)12(13)14/h2-6H,1H3
    • InChI Key: LMMZXVJDJDOXEA-UHFFFAOYSA-N
    • SMILES: O(C)C1C=CC2C(=CC(=CN=2)[N+](=O)[O-])C=1

Computed Properties

  • Exact Mass: 204.05354
  • Monoisotopic Mass: 204.05349212g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 15
  • Rotatable Bond Count: 1
  • Complexity: 241
  • 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: 1.9
  • Topological Polar Surface Area: 67.9?2

Experimental Properties

  • PSA: 65.26

6-Methoxy-3-nitroquinoline Pricemore >>

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Additional information on 6-Methoxy-3-nitroquinoline

Comprehensive Analysis of 6-Methoxy-3-nitroquinoline (CAS No. 159454-73-6): Properties, Applications, and Research Insights

6-Methoxy-3-nitroquinoline (CAS No. 159454-73-6) is a specialized nitroquinoline derivative that has garnered significant attention in pharmaceutical and agrochemical research due to its unique structural features and reactivity. This compound belongs to the quinoline family, a class of heterocyclic aromatic compounds known for their broad biological activities. The presence of both methoxy and nitro functional groups at specific positions on the quinoline backbone enhances its potential as a versatile intermediate in synthetic chemistry.

In recent years, the demand for 6-Methoxy-3-nitroquinoline has surged, particularly in the development of antimicrobial agents and fluorescence probes. Researchers are actively exploring its role in designing novel small-molecule inhibitors targeting enzymes involved in metabolic pathways. A notable trend in scientific literature highlights its utility in cancer research, where its derivatives exhibit promising anti-proliferative effects. This aligns with the growing public interest in targeted therapies and precision medicine, topics frequently searched in academic and healthcare forums.

The synthesis of 6-Methoxy-3-nitroquinoline typically involves nitration reactions of pre-functionalized quinoline precursors under controlled conditions. Advanced techniques like HPLC purification and NMR characterization ensure high purity (>98%), a critical factor for its application in high-throughput screening assays. Its molecular weight of 204.18 g/mol and lipophilic nature (LogP ~2.1) make it suitable for crossing biological membranes, a property highly valued in drug discovery pipelines.

From an industrial perspective, 6-Methoxy-3-nitroquinoline serves as a key building block for crop protection chemicals, addressing the global need for sustainable pest management solutions. Its derivatives have shown efficacy against plant pathogens, resonating with the agricultural sector's focus on eco-friendly alternatives to traditional pesticides. This connection to green chemistry principles has further amplified its relevance in patent filings and R&D investments.

Environmental and safety studies indicate that 6-Methoxy-3-nitroquinoline exhibits moderate stability under ambient conditions, with recommended storage in amber glass containers to prevent photodegradation. While not classified as hazardous under standard protocols, proper laboratory handling practices (e.g., PPE usage) are advised during experimentation. These precautions align with the increasing public scrutiny of chemical safety and workplace regulations, frequently searched topics in occupational health databases.

Emerging applications include its use in material science, where its conjugated system contributes to the development of organic semiconductors for flexible electronics. This intersects with the booming interest in wearable technology and IoT devices, making it a compound of multidisciplinary importance. Analytical methods such as LC-MS and X-ray crystallography have been instrumental in elucidating its solid-state properties and interaction mechanisms.

In conclusion, 6-Methoxy-3-nitroquinoline (CAS No. 159454-73-6) represents a compelling case study in the convergence of medicinal chemistry, agricultural innovation, and advanced materials. Its adaptability to diverse research needs—from drug design to smart materials—positions it as a valuable asset in contemporary scientific endeavors. Future studies may explore its structure-activity relationships further, potentially unlocking new therapeutic or technological breakthroughs.

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