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Ethyl 2-(oxetan-3-ylidene)acetate

  • CAS No. 922500-91-2

  • Cat. No. CS-0006466
  • Purity≥97%
  • MDL No.MFCD12755197

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

Ethyl 2-(oxetan-3-ylidene)acetate|CS-0006466

Structure of 922500-91-2

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General Information

  • CAS No. 922500-91-2
  • Cat. No. CS-0006466
  • Purity ≥97%
  • MDL No. MFCD12755197
  • Storage -20°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₁₀O₃
  • Molecular Weight 142.15
  • Synonym(s) Ethyl oxetan-3-ylideneacetate
  • SMILES CCOC(/C=C1COC\1)=O

Description

Ethyl 2-(oxetan-3-ylidene)acetate features a strained oxetane ring fused to an α,β-unsaturated ester system, enabling efficient cycloaddition reactions. This reactive scaffold integrates readily into complex molecular architectures via inverse electron-demand Diels–Alder processes, offering high chemoselectivity and mild reaction conditions. The molecule exhibits bench-stable handling with tolerance to moisture and air, simplifying use in synthetic workflows.

Application

Ethyl 2-(oxetan-3-ylidene)acetate serves as a versatile Michael acceptor and heterocyclic building block in synthetic organic chemistry. Its strained oxetane ring imparts enhanced reactivity, enabling efficient conjugate additions with nucleophiles under mild conditions. The molecule functions as a key intermediate in the construction of complex oxygen-containing heterocycles and bioactive scaffolds, offering excellent bench stability and compatibility with diverse functional groups.

Synthesis

  • Route1

    References

    • PFIZER LIMITED; BAGAL, Sharanjeet Kaur; KEMP, Mark Ian; MILLER, Duncan Charles; MURATA, Yoshihisa Patent: WO2013/61205 A2, 2013 ; Location in patent: Page/Page column 67 ;
  • Route2

    References

    • US2008/207573 A1, ; Page/Page column 87-88 ;

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

Quality Control

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Computational Chemistry Data

  • TPSA   35.53
  • LogP   0.5061
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   2

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