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CS-W001157 4
Total: USD 88.00

4-Cyano-1-methylpyrazole

  • CAS No. 66121-71-9

  • Cat. No. CS-W019316
  • Purity≥98%
  • MDL No.MFCD04969704

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

4-Cyano-1-methylpyrazole|CS-W019316

Structure of 66121-71-9

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General Information

  • CAS No. 66121-71-9
  • Cat. No. CS-W019316
  • Purity ≥98%
  • MDL No. MFCD04969704
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₅N₃
  • Molecular Weight 107.11
  • Synonym(s) 1-methyl-1H-pyrazole-4-carbonitrile
  • SMILES CN1C=C(C=N1)C#N

Description

4-Cyano-1-methylpyrazole is a bench-stable heterocycle featuring a nitrile group at the 4-position and a methyl substituent at the 1-position. This combination imparts enhanced electron-withdrawing character and improved solubility in organic solvents, enabling efficient integration into medicinal chemistry campaigns. The molecule serves as a bioisostere for carboxylic acids and amides, facilitating targeted modulation of target affinity and metabolic stability.

Application

4-Cyano-1-methylpyrazole serves as a versatile heterocyclic building block in medicinal chemistry, enabling efficient access to pyrazole-based scaffolds through nucleophilic substitution and transition-metal-catalyzed coupling reactions. Its cyano group enhances electrophilicity for C–C bond formation, while the methylpyrazole core provides metabolic stability and favorable pharmacokinetic properties. The compound exhibits excellent bench stability and ease of purification, facilitating integration into multi-step synthetic sequences for API development.

Synthesis

  • Route1
    • Methyl 4-cyano-1-methyl-1H-pyrazole-5-carboxylate|CS-0094730
      70910-18-8
    • ~75%
    • In-stock
      4-Cyano-1-methylpyrazole|CS-W019316
      66121-71-9

    References

    • Huisgen, Rolf; Mitra, Abhijit; Moran, Joaquin Rodriguez Chemische Berichte, 1987 , vol. 120, p. 159 - 170
  • Route2
    • null|null
      149139-41-3
    • null|null
      60-34-4
    • ~61%
    • In-stock
      4-Cyano-1-methylpyrazole|CS-W019316
      66121-71-9

    References

    • Jachak, Madhukar; Kriessmann, Ulrike; Mittelbach, Martin; Junek, Hans Monatshefte fuer Chemie, 1993 , vol. 124, p. 199 - 208
  • Route3
    • null|null
      43193-15-3
    • ~86%
    • In-stock
      4-Cyano-1-methylpyrazole|CS-W019316
      66121-71-9

    References

    • Attaryan; Sahakyan; Tamazyan; Ayvazyan; Asratyan Russian Journal of General Chemistry, 2012 , vol. 82, # 10 p. 1720 - 1723 Zh. Obshch. Khim., 2012 , vol. 82, # 10 p. 1716 - 1719,4

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

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Computational Chemistry Data

  • TPSA   41.61
  • LogP   0.29178
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   0

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