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CS-W001157 4
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Methyl 1-methyl-1H-pyrazole-4-carboxylate

  • CAS No. 5952-93-2

  • Cat. No. CS-0061744
  • Purity≥98%
  • MDL No.None

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

Methyl 1-methyl-1H-pyrazole-4-carboxylate|CS-0061744

Structure of 5952-93-2

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General Information

  • CAS No. 5952-93-2
  • Cat. No. CS-0061744
  • Purity ≥98%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₈N₂O₂
  • Molecular Weight 140.14
  • Synonym(s) methyl 1-methylpyrazole-4-carboxylate
  • SMILES CN1C=C(C=N1)C(=O)OC

Description

Methyl 1-methyl-1H-pyrazole-4-carboxylate features a pyrazole core with complementary electron-rich and electrophilic sites, enabling direct functionalization in cross-coupling and cycloaddition reactions. The ester group enhances solubility in polar solvents, while the methyl substitution improves stability under standard handling conditions. This scaffold integrates readily into bioactive molecule synthesis.

Application

Methyl 1-methyl-1H-pyrazole-4-carboxylate serves as a versatile building block in medicinal chemistry, enabling efficient access to pyrazole-based scaffolds. Its methyl ester functionality facilitates direct coupling reactions and subsequent hydrolysis or reduction, while the electron-deficient pyrazole ring supports electrophilic substitution and transition-metal-catalyzed cross-couplings. The compound exhibits good bench stability and is amenable to purification via standard chromatographic methods, making it well-suited for iterative synthesis campaigns.

Synthesis

  • Route1
    • In-stock
      1-Methyl-1H-pyrazole-4-carboxylic acid|CS-W019444
      5952-92-1
    • null|null
      18107-18-1
    • ~77%
    • In-stock
      Methyl 1-methyl-1H-pyrazole-4-carboxylate|CS-0061744
      5952-93-2

    References

    • ARRAY BIOPHARMA INC.; GENENTECH, INC.; GRADL, Stefan; RUDOLPH, Joachim; REN, Li Patent: WO2011/25951 A1, 2011 ; Location in patent: Page/Page column 54 ; WO 2011/025951 A1
  • Route2
    • In-stock
      4-Iodo-1-methyl-1H-pyrazole|CS-W004080
      39806-90-1
    • null|null
      67-56-1
    • null|null
      201230-82-2
    • ~63%
    • In-stock
      Methyl 1-methyl-1H-pyrazole-4-carboxylate|CS-0061744
      5952-93-2

    References

    • Koos, Peter; Gross, Ulrike; Polyzos, Anastasios; O'Brien, Matthew; Baxendale, Ian; Ley, Steven V. Organic and Biomolecular Chemistry, 2011 , vol. 9, # 20 p. 6903 - 6908
  • Route3
    • In-stock
      Methyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate|CS-W022858
      110860-60-1
    • ~%
    • Methyl 5-chloro-1-methyl-1h-pyrazole-4-carboxylate|CS-0676697
      88398-85-0
    • In-stock
      Methyl 1-methyl-1H-pyrazole-4-carboxylate|CS-0061744
      5952-93-2

    References

    • Yamamoto, Susumu; Morimoto, Katsushi; Sato, Toshiaki Journal of Heterocyclic Chemistry, 1991 , vol. 28, # 6 p. 1545 - 1547

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   44.12
  • LogP   0.2067
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   1

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