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CS-W001157 4
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4-Oxo-4H-pyran-2-carboxylic acid

  • CAS No. 499-05-8

  • Cat. No. CS-0100194
  • Purity≥96%
  • MDL No.MFCD00059958

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

4-Oxo-4H-pyran-2-carboxylic acid|CS-0100194

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General Information

  • CAS No. 499-05-8
  • Cat. No. CS-0100194
  • Purity ≥96%
  • MDL No. MFCD00059958
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₄O₄
  • Molecular Weight 140.09
  • Synonym(s) γ-Pyrone-2-carboxylic Acid
  • SMILES O=C(O)C1=CC(C=CO1)=O

Description

4-Oxo-4H-pyran-2-carboxylic acid features a conjugated β-keto acid moiety integrated within a pyran ring, enabling participation in Michael additions and condensation reactions. This electron-deficient heterocycle serves as a key scaffold for synthesizing bioactive molecules, particularly in medicinal chemistry and natural product analogs.

Application

4-Oxo-4H-pyran-2-carboxylic acid serves as a versatile building block in heterocyclic synthesis, enabling efficient access to bioactive pyranoid frameworks. Its enolizable carbonyl and carboxylic acid functionalities support diverse transformations, including Michael additions, esterifications, and cyclizations. The compound exhibits good bench stability and facilitates straightforward purification, making it well-suited for medicinal chemistry campaigns and API intermediate development.

Synthesis

  • Route1

    References

    • Tajima, Kiyohiko Tetrahedron Letters, 1986 , vol. 27, # 50 p. 6095 - 6098
  • Route2
    • null|null
      95722-14-8
    • ~65%
    • In-stock
      4-Oxo-4H-pyran-2-carboxylic acid|CS-0100194
      499-05-8
    • null|null
      76539-65-6

    References

    • Tajima, Kiyohiko Chemistry Letters, 1985 , p. 49 - 52
  • Route3
    • null|null
      1246616-74-9
    • ~47%
    • In-stock
      4-Oxo-4H-pyran-2-carboxylic acid|CS-0100194
      499-05-8

    References

    • Obydennov, Dmitrii L.; Roeschenthaler, Gerd-Volker; Sosnovskikh, Vyacheslav Ya. Tetrahedron Letters, 2013 , vol. 54, # 48 p. 6545 - 6548

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   67.51
  • LogP   0.338
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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