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CS-W001157 4
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3-Oxocyclobutane-1-carbonitrile

  • CAS No. 20249-16-5

  • Cat. No. CS-W004195
  • Purity≥98%
  • MDL No.MFCD01087798

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

3-Oxocyclobutane-1-carbonitrile|CS-W004195

Structure of 20249-16-5

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General Information

  • CAS No. 20249-16-5
  • Cat. No. CS-W004195
  • Purity ≥98%
  • MDL No. MFCD01087798
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₅NO
  • Molecular Weight 95.10
  • Synonym(s) None
  • SMILES N#CC1CC(=O)C1

Description

3-Oxocyclobutane-1-carbonitrile is a strained cyclic ketonitrile featuring a reactive carbonyl group and a nitrile functionality within a four-membered ring. This configuration enables participation in cycloadditions and nucleophilic additions, facilitating access to complex heterocyclic scaffolds. The molecule exhibits enhanced reactivity due to ring strain and electronic polarization between the carbonyl and nitrile moieties.

Application

3-Oxocyclobutane-1-carbonitrile serves as a versatile synthetic building block for strained ring systems and heterocyclic scaffolds. Its dual functionality—ketone and nitrile groups—enables selective transformations, including nucleophilic additions and cyclizations, under mild conditions. The molecule exhibits good bench stability and facilitates efficient purification, making it well-suited for iterative synthesis in medicinal chemistry and process development workflows.

Synthesis

  • Route1

    References

    • ASTRAZENECA AB Patent: US2012/122843 A1, 2012 ; Location in patent: Page/Page column 39 ;
  • Route2
    • null|null
      339529-30-5
    • ~79%
    • In-stock
      3-Oxocyclobutane-1-carbonitrile|CS-W004195
      20249-16-5

    References

    • Tishkov, Alexander A.; Lyapkalo, Il'ya M.; Ioffe, Sema L.; Strelenko, Yuri A.; Tartakovsky, Vladimir A. Tetrahedron, 2001 , vol. 57, # 11 p. 2221 - 2230
  • Route3
    • null|null
      22020-87-7
    • ~%
    • In-stock
      3-Oxocyclobutane-1-carbonitrile|CS-W004195
      20249-16-5

    References

    • Tetrahedron, , vol. 57, # 11 p. 2221 - 2230

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS06,GHS09
Signal Word : Danger
UN#: 3077
Class : 9
Packing Group : Ⅲ
Hazard Statements : H301+H331-H410
Precautionary Statements : P261-P264-P270-P271-P273-P304+P340-P330-P391-P405-P501

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Computational Chemistry Data

  • TPSA   40.86
  • LogP   0.48908
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   0

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