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CS-W001157 4
Total: USD 88.00

2-(2,4-Dioxothiazolidin-5-yl)acetic acid

  • CAS No. 875-97-8

  • Cat. No. CS-0376624
  • Molecule weight175.16
  • Purity≥98%
  • MDL No.MFCD01165868

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

2-(2,4-Dioxothiazolidin-5-yl)acetic acid|CS-0376624

Structure of 875-97-8

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General Information

  • CAS No. 875-97-8
  • Cat. No. CS-0376624
  • Purity ≥98%
  • MDL No. MFCD01165868
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₅NO₄S
  • Molecular Weight 175.16
  • Synonym(s) 2-[(5S)-2,4-dioxothiazolidin-5-yl]acetate
  • SMILES O=C(O)CC(SC(N1)=O)C1=O

Description

This thiazolidinedione derivative features a reactive acetic acid side chain, enabling direct conjugation in bioconjugation workflows. The 2,4-dioxothiazolidin-5-yl moiety imparts enhanced stability and electrophilic character, facilitating efficient coupling with nucleophiles under physiological conditions.

Application

2-(2,4-Dioxothiazolidin-5-yl)acetic acid serves as a versatile building block for thiazolidine-based heterocycles, enabling efficient access to medicinally relevant scaffolds. Its reactive β-ketoacid moiety facilitates cyclization and functional group interconversions under mild conditions, offering robust utility in synthetic routes targeting bioactive molecules. The compound exhibits good bench stability and compatibility with standard purification methods, supporting reliable use in iterative synthesis workflows.

Synthesis

  • Route1
    • null|null
      108-31-6
    • null|null
      17356-08-0
    • ~70%
    • In-stock
      2-(2,4-Dioxothiazolidin-5-yl)acetic acid|CS-0376624
      875-97-8

    References

    • Koppireddi, Satish; Komsani, Jayaram Reddy; Avula, Sreenivas; Pombala, Sujitha; Vasamsetti, Satishbabu; Kotamraju, Srigiridhar; Yadla, Rambabu European Journal of Medicinal Chemistry, 2013 , vol. 66, p. 305 - 313
  • Route2
    • 2-(2-amino-4-oxo-4,5-dihydrothiazol-5-yl)acetic acid|CS-0451171
      33176-41-9
    • ~82%
    • In-stock
      2-(2,4-Dioxothiazolidin-5-yl)acetic acid|CS-0376624
      875-97-8

    References

    • Jawale, Dhanaji V.; Pratap, Umesh R.; Rahuja, Neha; Srivastava, Arvind K.; Mane, Ramrao A. Bioorganic and Medicinal Chemistry Letters, 2012 , vol. 22, # 1 p. 436 - 439
  • Route3
    • 2-(2,4-Dioxo-5-thiazolidinylidene)acetic acid|CS-0067341
      5374-29-8
    • ~%
    • In-stock
      2-(2,4-Dioxothiazolidin-5-yl)acetic acid|CS-0376624
      875-97-8

    References

    • Deghenghi,R.; Daneault,G. Canadian Journal of Chemistry, 1960 , vol. 38, p. 1255 - 1260

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319
Precautionary Statements : P264-P280-P302+P352-P362+P364

Quality Control

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Computational Chemistry Data

  • TPSA   83.47
  • LogP   -0.1873
  • H_Acceptors   4
  • H_Donors   2
  • Rotatable_Bonds   2

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