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CS-W001157 4
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Isoxazole-5-carboxylic acid

  • CAS No. 21169-71-1

  • Cat. No. CS-W000637
  • Purity≥97%
  • MDL No.MFCD00156151

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

Isoxazole-5-carboxylic acid|CS-W000637

Structure of 21169-71-1

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General Information

  • CAS No. 21169-71-1
  • Cat. No. CS-W000637
  • Purity ≥97%
  • MDL No. MFCD00156151
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₄H₃NO₃
  • Molecular Weight 113.07
  • Synonym(s) 1,2-oxazole-5-carboxylic acid; Isoxazole-5-carboxylic acid
  • SMILES OC(C1=CC=NO1)=O

Description

Isoxazole-5-carboxylic acid features a rigid, electron-deficient isoxazole ring fused to a carboxylic acid group, enabling direct incorporation into heterocyclic scaffolds. This bench-stable motif serves as a key building block in medicinal chemistry, particularly for bioactive compounds requiring metabolic stability and hydrogen-bonding capacity.

Application

Isoxazole-5-carboxylic acid serves as a versatile heterocyclic building block in medicinal chemistry, enabling the synthesis of bioactive scaffolds through established coupling and functionalization reactions. Its carboxylic acid group facilitates direct amidation, esterification, and metal-catalyzed transformations, while the isoxazole ring provides structural rigidity and metabolic stability. The compound exhibits good bench stability and compatibility with standard purification methods, making it well-suited for use in iterative synthesis campaigns and API intermediate development.

Synthesis

  • Route1
    • In-stock
      Isoxazole|CS-W011365
      288-14-2
    • null|null
      124-38-9
    • ~92%
    • In-stock
      Isoxazole-5-carboxylic acid|CS-W000637
      21169-71-1

    References

    • Boogaerts, Ine I. F.; Nolan, Steven P. Journal of the American Chemical Society, 2010 , vol. 132, # 26 p. 8858 - 8859
  • Route2

    References

    • Martins, Marcos A. P.; Flores, Alex F. C.; Bastos, Giovani P.; Sinhorin, Adilson; Bonacorso, Helio G.; Zanatta, Nilo Tetrahedron Letters, 2000 , vol. 41, # 3 p. 293 - 297
  • Route3

    References

    • Adolphe-Pierre; Menager; Tombret; Verite; Lepage; Lafont Farmaco, 1998 , vol. 53, # 7 p. 513 - 518

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   63.33
  • LogP   0.3728
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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