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CS-W001157 4
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3-Pyrazolylacetic acid

  • CAS No. 102732-63-8

  • Cat. No. CS-D0159
  • Purity≥96%
  • MDL No.MFCD03161180

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

3-Pyrazolylacetic acid|CS-D0159

Structure of 102732-63-8

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General Information

  • CAS No. 102732-63-8
  • Cat. No. CS-D0159
  • Purity ≥96%
  • MDL No. MFCD03161180
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₆N₂O₂
  • Molecular Weight 126.11
  • Synonym(s) 2-(1H-Pyrazol-3-yl)acetic acid
  • SMILES O=C(O)CC1=NNC=C1

Description

3-Pyrazolylacetic acid integrates a pyrazole heterocycle with a carboxylic acid side chain, enabling direct functionalization at the 3-position. This scaffold delivers enhanced solubility and stability in aqueous systems while supporting efficient coupling reactions under mild conditions. The molecule features a rigid, planar pyrazole ring that facilitates π-stacking interactions in supramolecular assemblies.

Application

3-Pyrazolylacetic acid serves as a versatile building block in medicinal chemistry, enabling the construction of pyrazole-containing heterocycles via standard coupling and functionalization reactions. Its carboxylic acid functionality facilitates direct amidation, esterification, and derivatization under mild conditions, while the pyrazole ring offers robust metabolic stability and hydrogen-bonding capacity. The compound exhibits excellent bench stability and is readily purified by recrystallization or chromatography, making it ideal for scalable synthesis workflows.

Synthesis

  • Route1
    • 2-(1h-Pyrazol-3-yl)acetohydrazide|CS-0217211
      144677-14-5
    • ~89%
    • In-stock
      3-Pyrazolylacetic acid|CS-D0159
      102732-63-8

    References

    • F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BAKER-GLENN, Charles; BURDICK, Daniel Jon; CHAMBERS, Mark; CHAN, Bryan K.; CHEN, Huifen; ESTRADA, Anthony; SWEENEY, Zachary Kevin Patent: WO2013/164321 A1, 2013 ; Location in patent: Page/Page column 39 ;
  • Route2
    • 2-(1H-Pyrazol-3-yl)acetonitrile|CS-0055272
      135237-01-3
    • ~%
    • In-stock
      3-Pyrazolylacetic acid|CS-D0159
      102732-63-8

    References

    • Jones; Mann Journal of the American Chemical Society, 1953 , vol. 75, p. 4048,4050
  • Route3

    References

    • Barker, John M; Huddleston, Patrick R; Wood, Michael L Journal of Chemical Research, Miniprint, 1992 , # 9 p. 2383 - 2396

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   65.98
  • LogP   0.0368
  • H_Acceptors   2
  • H_Donors   2
  • Rotatable_Bonds   2

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