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CS-W001157 4
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5-Oxotetrahydrofuran-2-carboxylic acid

  • CAS No. 4344-84-7

  • Cat. No. CS-0129013
  • Purity≥97%
  • MDL No.MFCD00066678

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

5-Oxotetrahydrofuran-2-carboxylic acid|CS-0129013

Structure of 4344-84-7

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General Information

  • CAS No. 4344-84-7
  • Cat. No. CS-0129013
  • Purity ≥97%
  • MDL No. MFCD00066678
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₆O₄
  • Molecular Weight 130.10
  • Synonym(s) Tetrahydro-5-oxo-2- furancarboxyli
  • SMILES O=C(C(CC1)OC1=O)O

Description

5-Oxotetrahydrofuran-2-carboxylic acid features a cyclic β-keto acid scaffold with enhanced stability and reactivity. This structure integrates a carbonyl group at the 5-position and a carboxylic acid at C2, enabling efficient functionalization in synthetic sequences. The molecule serves as a valuable intermediate for heterocyclic and peptidomimetic syntheses, particularly under mild conditions.

Application

5-Oxotetrahydrofuran-2-carboxylic acid serves as a versatile building block in synthetic organic chemistry, enabling efficient access to γ-lactone and tetrahydrofuran scaffolds. Its dual functionality—carboxylic acid and ketone—facilitates selective transformations, including nucleophilic additions and condensations, under mild conditions. The compound exhibits good bench stability and compatibility with common protecting group strategies, making it suitable for iterative synthesis of complex heterocycles and natural product analogs.

Synthesis

  • Route1

    References

    • Battersby, Alan R.; Cardwell, Kevin S.; Leeper, Finian J. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1986 , p. 1565 - 1580
  • Route2

    References

    • Lorenz, Peter; Conrad, Juergen; Bertrams, Julia; Berger, Melanie; Duckstein, Sarina; Meyer, Ulrich; Stintzing, Florian C. Phytochemical Analysis, 2012 , vol. 23, # 1 p. 60 - 71
  • Route3
    • L-Glutamine Amino acid impurity|CS-1738303
      56-85-9
    • ~97%
    • In-stock
      5-Oxotetrahydrofuran-2-carboxylic acid|CS-0129013
      4344-84-7

    References

    • Gouesnard, Jean-Paul Bulletin de la Societe Chimique de France, 1989 , # 1 p. 88 - 94

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   63.6
  • LogP   -0.2234
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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