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Ethyl 1H,4H,5H,6H-cyclopenta[c]pyrazole-3-carboxylate

  • CAS No. 5932-31-0

  • Cat. No. CS-0049555
  • Purity≥97%
  • MDL No.None

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

Ethyl 1H,4H,5H,6H-cyclopenta[c]pyrazole-3-carboxylate|CS-0049555

Structure of 5932-31-0

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General Information

  • CAS No. 5932-31-0
  • Cat. No. CS-0049555
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₂N₂O₂
  • Molecular Weight 180.20
  • Synonym(s) Ethyl 1,4,5,6-tetrahydrocyclopenta[c]pyrazole-3-carboxylate
  • SMILES CCOC(=O)C1=NNC2=C1CCC2

Description

Ethyl 1H,4H,5H,6H-cyclopenta[c]pyrazole-3-carboxylate features a rigid fused bicyclic core with a pyrazole ring flanked by cyclopentane, delivering structural integrity for synthetic applications. The ester group enables facile derivatization, while the scaffold exhibits enhanced metabolic stability and favorable solubility in organic solvents. This compound serves as a key intermediate in heterocyclic synthesis, particularly for bioactive molecule development.

Application

Ethyl 1H,4H,5H,6H-cyclopenta[c]pyrazole-3-carboxylate serves as a versatile heterocyclic building block for medicinal chemistry and synthetic organic research. The cyclopenta[c]pyrazole core provides a rigid, planar scaffold with defined regiochemistry, enabling efficient functionalization at the C3 position. The ester group facilitates subsequent transformations including hydrolysis, reduction, or coupling reactions. Its stability under standard reaction conditions and compatibility with diverse coupling protocols make it a practical reagent for constructing complex polycyclic systems and targeted API precursors.

Synthesis

  • Route1
    • null|null
      120-92-3
    • null|null
      95-92-1
    • ~90%
    • In-stock
      Ethyl 1H,4H,5H,6H-cyclopenta[c]pyrazole-3-carboxylate|CS-0049555
      5932-31-0

    References

    • Wilson, Robert D.; Cleator, Ed; Ashwood, Michael S.; Bio, Matthew M.; Brands, Karel M.J.; Davies, Antony J.; Dolling, Ulf-H; Emerson, Khateeta M.; Gibb, Andrew D.; Hands, David; McKeown, Arlene E.; Oliver, Steven F.; Reamer, Robert A.; Sheen, Faye J.; Stewart, Gavin W.; Zhou, George X. Organic Process Research and Development, 2009 , vol. 13, # 3 p. 543 - 547
  • Route2

    References

    • Wu, Deyan; Jin, Fangfang; Lu, Weiqiang; Zhu, Jin; Li, Cui; Wang, Wei; Tang, Yun; Jiang, Hualiang; Huang, Jin; Liu, Guixia; Li, Jian Chemical Biology and Drug Design, 2012 , vol. 79, # 6 p. 897 - 906
  • Route3
    • Ethyl cyclopentyl(oxo)acetate|CS-0061535
      33537-18-7
    • ~%
    • In-stock
      Ethyl 1H,4H,5H,6H-cyclopenta[c]pyrazole-3-carboxylate|CS-0049555
      5932-31-0

    References

    • WO2006/52569 A1, ; Page/Page column 74 ;

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-H320-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   54.98
  • LogP   1.0751
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   2

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