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CS-W001157 4
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5-Phenylisoxazole-3-carboxylic acid

  • CAS No. 14441-90-8

  • Cat. No. CS-W022424
  • Purity≥97%
  • MDL No.MFCD00464221

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

5-Phenylisoxazole-3-carboxylic acid|CS-W022424

Structure of 14441-90-8

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General Information

  • CAS No. 14441-90-8
  • Cat. No. CS-W022424
  • Purity ≥97%
  • MDL No. MFCD00464221
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₇NO₃
  • Molecular Weight 189.17
  • Synonym(s) 5-phenyl-3-isoxazolecarboxylate
  • SMILES OC(=O)C1=NOC(=C1)C1=CC=CC=C1

Description

5-Phenylisoxazole-3-carboxylic acid features a rigid isoxazole core fused to a phenyl ring and a carboxylic acid group, enabling integration into bioactive scaffolds. This electron-deficient heterocycle supports diverse coupling reactions and serves as a key building block in medicinal chemistry and materials science applications.

Application

5-Phenylisoxazole-3-carboxylic acid serves as a versatile building block for heterocyclic synthesis, enabling efficient access to bioactive scaffolds through standard coupling and functionalization reactions. The molecule exhibits robust bench stability and facilitates straightforward purification, making it well-suited for medicinal chemistry applications. Its ortho-functionalized isoxazole core supports diverse transformations, including amide formation and metal-catalyzed cross-couplings, with predictable reactivity profiles in standard synthetic workflows.

Synthesis

  • Route1
    • Ethyl 5-phenylisoxazole-3-carboxylate|CS-0085317
      7063-99-2
    • ~95%
    • In-stock
      5-Phenylisoxazole-3-carboxylic acid|CS-W022424
      14441-90-8

    References

    • Chapal, Nicolas; McNicol, Patricia; Jette, Lucie Patent: US2006/223884 A1, 2006 ; Location in patent: Page/Page column 58 ;
  • Route2

    References

    • Veeraswamy; Kurumurthy; Santhosh Kumar; Sambasiva Rao; Thelakkat, Kavya; Kotamraju, Srigiridhar; Narsaiah Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2012 , vol. 51, # 9 p. 1369 - 1375
  • Route3
    • Ethyl-5-phenyl-isoxazole-4-carboxylate|CS-0757644
      50784-69-5
    • ~%
    • In-stock
      5-Phenylisoxazole-3-carboxylic acid|CS-W022424
      14441-90-8

    References

    • EP1216980 A1, ; EP 1216980 A1

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07,GHS08
Signal Word : Danger
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H317-H319-H334-H335
Precautionary Statements : P261-P264-P270-P271-P272-P280-P284-P302+P352-P304+P340-P330-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   63.33
  • LogP   2.0398
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   2

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