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tert-Butyl 3-methyleneazetidine-1-carboxylate

  • CAS No. 934664-41-2

  • Cat. No. CS-W022997
  • Purity≥97%
  • MDL No.MFCD12031229

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

tert-Butyl 3-methyleneazetidine-1-carboxylate|CS-W022997

Structure of 934664-41-2

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General Information

  • CAS No. 934664-41-2
  • Cat. No. CS-W022997
  • Purity ≥97%
  • MDL No. MFCD12031229
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₅NO₂
  • Molecular Weight 169.22
  • Synonym(s) 3-Methyleneazetidine-1-carboxylic Acid tert-Butyl Ester
  • SMILES O=C(N1CC(C1)=C)OC(C)(C)C

Description

tert-Butyl 3-methyleneazetidine-1-carboxylate features a strained azetidine ring with an exocyclic methylene group, enabling direct functionalization at the 3-position. This reactive scaffold integrates readily into diverse synthetic sequences, offering efficient access to nitrogen-containing heterocycles under mild conditions. The tert-butyl ester provides stability and ease of manipulation during multi-step transformations.

Application

tert-Butyl 3-methyleneazetidine-1-carboxylate serves as a versatile, bench-stable building block for the synthesis of strained azetidine scaffolds. Its exocyclic methylene group enables efficient [2+2] cycloadditions and Michael-type additions, facilitating access to functionalized nitrogen heterocycles. The tert-butyl ester provides excellent solubility and compatibility with standard purification methods, while the azetidine core offers high reactivity in late-stage functionalization workflows.

Synthesis

  • Route1
    • In-stock
      tert-Butyl 3-oxoazetidine-1-carboxylate|CS-D0675
      398489-26-4
    • null|null
      1779-49-3
    • ~97%
    • In-stock
      tert-Butyl 3-methyleneazetidine-1-carboxylate|CS-W022997
      934664-41-2

    References

    • EXELIXIS, INC. Patent: WO2008/124085 A2, 2008 ; Location in patent: Page/Page column 190 ; WO 2008/124085 A2

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   29.54
  • LogP   1.7933
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   0

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