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3-Nitro-1H-pyrazole-4-carbonitrile

  • CAS No. 39205-87-3

  • Cat. No. CS-0044034
  • Purity≥97%
  • MDL No.MFCD00195039

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

3-Nitro-1H-pyrazole-4-carbonitrile|CS-0044034

Structure of 39205-87-3

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General Information

  • CAS No. 39205-87-3
  • Cat. No. CS-0044034
  • Purity ≥97%
  • MDL No. MFCD00195039
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₄H₂N₄O₂
  • Molecular Weight 138.08
  • Synonym(s) 1H-Pyrazole-4-carbonitrile,3-nitro-(9CI)
  • SMILES [N+](=O)([O-])C1=N[NH]C=C1C#N

Description

3-Nitro-1H-pyrazole-4-carbonitrile features a dual functional group motif—electron-deficient nitro and nitrile moieties—positioned ortho to each other on the pyrazole ring. This arrangement enhances reactivity in transition-metal-catalyzed couplings and facilitates incorporation into bioactive heterocycles. The compound exhibits bench-stable handling characteristics and high solubility in polar organic solvents, streamlining use in synthetic workflows.

Application

3-Nitro-1H-pyrazole-4-carbonitrile serves as a versatile heterocyclic building block for medicinal chemistry and materials science. Its dual electron-withdrawing nitro and nitrile groups enable selective functionalization at C3 and C4 positions, facilitating nucleophilic substitution, metal-catalyzed coupling, and cyclization reactions. The compound exhibits good bench stability and is compatible with standard purification protocols, making it well-suited for iterative synthesis of pyrazole-based scaffolds in API development.

Synthesis

  • Route1
    • 3-Amino-4-pyrazolecarbonitrile Allopurinol Impurity|CS-0229543
      16617-46-2
    • ~89%
    • In-stock
      3-Nitro-1H-pyrazole-4-carbonitrile|CS-0044034
      39205-87-3

    References

    • Vinogradov, V. M.; Cherkasova, T. I.; Dalinger, I. L.; Shevelev, S. A. Russian Chemical Bulletin, 1993 , vol. 42, # 9 p. 1552 - 1554 Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1993 , # 9 p. 1616 - 1618

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   95.61
  • LogP   0.18958
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   1

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