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CS-W001157 4
Total: USD 88.00

3-Methylisoxazole-5-carboxylic acid

  • CAS No. 4857-42-5

  • Cat. No. CS-W005033
  • Purity≥98%
  • MDL No.MFCD00464222

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

3-Methylisoxazole-5-carboxylic acid|CS-W005033

Structure of 4857-42-5

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General Information

  • CAS No. 4857-42-5
  • Cat. No. CS-W005033
  • Purity ≥98%
  • MDL No. MFCD00464222
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₅NO₃
  • Molecular Weight 127.10
  • Synonym(s) None
  • SMILES O=C(O)C=1ON=C(C1)C

Description

3-Methylisoxazole-5-carboxylic acid features a fused heterocyclic core with complementary electron-rich and electron-deficient regions, enabling versatile coupling reactions. The carboxylic acid group provides a robust handle for amide formation, while the methyl substituent enhances solubility and metabolic stability. This scaffold integrates readily into bioactive molecules, offering favorable pharmacokinetic profiles in medicinal chemistry applications.

Application

3-Methylisoxazole-5-carboxylic acid serves as a versatile heterocyclic building block for medicinal chemistry and materials science. Its orthogonal reactivity enables direct functionalization at the carboxylic acid group, facilitating amide coupling, esterification, or activation for nucleophilic substitution. The methyl and isoxazole functionalities provide structural rigidity and favorable pharmacophore properties, enhancing metabolic stability in bioactive molecule design. Bench-stable and readily purified by recrystallization, it integrates seamlessly into standard synthetic workflows for API intermediates and advanced catalysts.

Synthesis

  • Route1
    • Ethyl 3-methylisoxazole-5-carboxylate|CS-0085260
      63366-79-0
    • ~89%
    • In-stock
      3-Methylisoxazole-5-carboxylic acid|CS-W005033
      4857-42-5

    References

    • MILLENNIUM PHARMACEUTICALS, INC. Patent: WO2006/91674 A1, 2006 ; Location in patent: Page/Page column 79 ; WO 2006/091674 A1
  • Route2

    References

    • Choi, Min Jeong; No, Eun Sun; Thorat, Dhanaji Achyutrao; Jang, Jae Wan; Yang, Hakkyun; Lee, Jaeick; Choo, Hyunah; Kim, Soo Jin; Lee, Chang Sik; Ko, Soo Young; Lee, Jiyoun; Nam, Ghilsoo; Pae, Ae Nim Journal of Medicinal Chemistry, 2013 , vol. 56, # 22 p. 9008 - 9018
  • Route3
    • null|null
      135351-18-7
    • ~95%
    • In-stock
      3-Methylisoxazole-5-carboxylic acid|CS-W005033
      4857-42-5

    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

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   63.33
  • LogP   0.68122
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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