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Methyl 4-bromo-1H-pyrazole-3-carboxylate

  • CAS No. 81190-89-8

  • Cat. No. CS-W019707
  • Purity≥96%
  • MDL No.MFCD00466326

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

Methyl 4-bromo-1H-pyrazole-3-carboxylate|CS-W019707

Structure of 81190-89-8

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General Information

  • CAS No. 81190-89-8
  • Cat. No. CS-W019707
  • Purity ≥96%
  • MDL No. MFCD00466326
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₅BrN₂O₂
  • Molecular Weight 205.01
  • Synonym(s) 1H-Pyrazole-3-carboxylicacid, 4-bromo-, methyl ester
  • SMILES O=C(C1=NNC=C1Br)OC

Description

Methyl 4-bromo-1H-pyrazole-3-carboxylate features a brominated pyrazole core with a methyl ester group, enabling direct incorporation into Suzuki-Miyaura and other cross-coupling reactions. The electron-deficient pyrazole ring enhances reactivity, while the bench-stable ester facilitates handling and purification under standard conditions.

Application

Methyl 4-bromo-1H-pyrazole-3-carboxylate serves as a versatile building block in heterocyclic synthesis, enabling efficient access to substituted pyrazole scaffolds via palladium-catalyzed cross-coupling reactions. The bromo group facilitates reliable functionalization under standard Suzuki, Stille, or Negishi conditions, while the ester moiety offers compatibility with reduction, hydrolysis, and further derivatization. Its bench-stable nature and straightforward purification make it well-suited for iterative medicinal chemistry campaigns and process-scale applications.

Synthesis

  • Route1
    • null|null
      190263-45-7
    • ~72%
    • In-stock
      Methyl 4-bromo-1H-pyrazole-3-carboxylate|CS-W019707
      81190-89-8

    References

    • Erion, Mark D.; Rydzewski, Robert M. Nucleosides and Nucleotides, 1997 , vol. 16, # 3 p. 315 - 337

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   54.98
  • LogP   0.9588
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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