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5-Nitro-2-oxo-1,2-dihydropyridine-3-carboxylic acid

  • CAS No. 6854-07-5

  • Cat. No. CS-W017019
  • Purity≥96%
  • MDL No.MFCD05669267

*For research and further manufacturing use only, not for direct human use.

5-Nitro-2-oxo-1,2-dihydropyridine-3-carboxylic acid|CS-W017019

Structure of 6854-07-5

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General Information

  • CAS No. 6854-07-5
  • Cat. No. CS-W017019
  • Purity ≥96%
  • MDL No. MFCD05669267
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₄N₂O₅
  • Molecular Weight 184.11
  • Synonym(s) 5-nitro-2-oxo-1,2-dihydropyridine-3-carboxylate
  • SMILES O=C(C1=CC([N+]([O-])=O)=CNC1=O)O

Description

5-Nitro-2-oxo-1,2-dihydropyridine-3-carboxylic acid features a conjugated dihydropyridine core with orthogonal electron-withdrawing groups: a nitro substituent at C5 and a carboxylic acid at C3. This combination imparts enhanced electrophilicity and metabolic stability, enabling direct incorporation into heterocyclic scaffolds. The molecule exhibits favorable solubility in polar solvents and maintains bench-stability under standard conditions, facilitating use in synthetic medicinal chemistry workflows.

Application

5-Nitro-2-oxo-1,2-dihydropyridine-3-carboxylic acid serves as a versatile building block in heterocyclic synthesis, enabling efficient access to substituted pyridine derivatives. Its nitro and carboxylic acid functionalities provide orthogonal reactivity for downstream transformations, including reduction, coupling, and cyclization reactions. The molecule exhibits good bench stability and facilitates straightforward purification, making it well-suited for use in medicinal chemistry and process development workflows.

Synthesis

  • Route1

    References

    • CURIS, INC. Patent: WO2006/50506 A1, 2006 ; Location in patent: Page/Page column 124 ;
  • Route2
    • 1,2-Dihydro-5-nitro-2-oxo-3-pyridinecarbonitrile|CS-0213124
      31309-38-3
    • ~%
    • In-stock
      5-Nitro-2-oxo-1,2-dihydropyridine-3-carboxylic acid|CS-W017019
      6854-07-5

    References

    • Journal of the American Chemical Society, , vol. 77, p. 1045
  • Route3
    • 2-Ethoxy-5-nitronicotinonitrile|CS-1074944
      265664-09-3
    • ~%
    • In-stock
      5-Nitro-2-oxo-1,2-dihydropyridine-3-carboxylic acid|CS-W017019
      6854-07-5

    References

    • Journal of the American Chemical Society, , vol. 77, p. 1045

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   113.3
  • LogP   -0.0187
  • H_Acceptors   4
  • H_Donors   2
  • Rotatable_Bonds   2

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