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CS-W001157 4
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4-Oxo-2-azetidinecarboxylic acid

  • CAS No. 98019-65-9

  • Cat. No. CS-W019929
  • Purity≥97%
  • MDL No.MFCD00798160

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

4-Oxo-2-azetidinecarboxylic acid|CS-W019929

Structure of 98019-65-9

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General Information

  • CAS No. 98019-65-9
  • Cat. No. CS-W019929
  • Purity ≥97%
  • MDL No. MFCD00798160
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₄H₅NO₃
  • Molecular Weight 115.09
  • Synonym(s) 4-OXOAZETIDINE-2-CARBOXYLIC ACID
  • SMILES O=C(C(C1)NC1=O)O

Description

4-Oxo-2-azetidinecarboxylic acid is a strained, electron-deficient β-lactam derivative featuring a ketone at the C4 position and a carboxylic acid at C2. This unique combination enables direct incorporation into peptide macrocycles and bioconjugation workflows, offering enhanced reactivity in amide bond formation under mild conditions. The molecule exhibits bench-stable handling characteristics with high functional group tolerance.

Application

4-Oxo-2-azetidinecarboxylic acid serves as a valuable building block in medicinal chemistry, enabling the synthesis of bioactive β-lactam derivatives and constrained peptide mimetics. Its strained azetidine ring facilitates efficient cyclization reactions and exhibits favorable reactivity in amide bond formation. The ketone functionality provides a handle for selective transformations, while the carboxylic acid group supports direct derivatization or salt formation, enhancing solubility and purification. This compound offers robust bench stability and compatibility with standard synthetic protocols, making it well-suited for iterative library synthesis and process development.

Synthesis

  • Route1

    References

    • US4564609 A1, ;

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-H335
Precautionary Statements : P260-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   66.4
  • LogP   -1.0405
  • H_Acceptors   2
  • H_Donors   2
  • Rotatable_Bonds   1

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