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CS-W001157 4
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Benzyl 3-oxoazetidine-1-carboxylate

  • CAS No. 105258-93-3

  • Cat. No. CS-M1635
  • Purity≥97%
  • MDL No.MFCD09954923

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

Benzyl 3-oxoazetidine-1-carboxylate|CS-M1635

Structure of 105258-93-3

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General Information

  • CAS No. 105258-93-3
  • Cat. No. CS-M1635
  • Purity ≥97%
  • MDL No. MFCD09954923
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₁NO₃
  • Molecular Weight 205.21
  • Synonym(s) N-CBZ-3-OXOAZETIDINE
  • SMILES O=C(N1CC(C1)=O)OCC2=CC=CC=C2

Description

Benzyl 3-oxoazetidine-1-carboxylate features a strained azetidine ring bearing a carbonyl group at the 3-position, enabling direct functionalization in synthetic sequences. The benzyl ester facilitates convenient deprotection under standard conditions. This scaffold integrates readily into complex molecular architectures requiring controlled reactivity and spatial constraints.

Application

Benzyl 3-oxoazetidine-1-carboxylate serves as a versatile building block in synthetic organic chemistry, enabling efficient access to strained azetidine scaffolds. Its ketone functionality facilitates nucleophilic addition and reductive amination, while the benzyl ester offers convenient protection and orthogonal deprotection. The compound exhibits good bench stability and compatibility with diverse reaction conditions, making it well-suited for iterative synthesis of bioactive heterocycles and medicinal chemistry libraries.

Synthesis

  • Route1

    References

    • EXELIXIS, INC. Patent: WO2008/124085 A2, 2008 ; Location in patent: Page/Page column 179 ; WO 2008/124085 A2
  • Route2
    • In-stock
      1-Benzhydrylazetidin-3-one|CS-W002715
      40320-60-3
    • null|null
      501-53-1
    • ~82%
    • In-stock
      Benzyl 3-oxoazetidine-1-carboxylate|CS-M1635
      105258-93-3

    References

    • Nitta, Yoshihiro; Yamaguchi, Tamie; Tanaka, Toshiko Heterocycles, 1986 , vol. 24, # 1 p. 25 - 28
  • Route3
    • null|null
      67865-70-7
    • ~31%
    • In-stock
      Benzyl 3-oxoazetidine-1-carboxylate|CS-M1635
      105258-93-3

    References

    • Wang, Jianbo; Hou, Yihua; Wu, Peng Journal of the Chemical Society - Perkin Transactions 1, 1999 , # 16 p. 2277 - 2280

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   46.61
  • LogP   1.2079
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   2

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