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1-[(Tert-butoxy)carbonyl]-3-cyanoazetidine-3-carboxylic acid

  • CAS No. 1158759-45-5

  • Cat. No. CS-0052696
  • Molecule weight226.23
  • Purity≥98%
  • MDL No.None

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

1-[(Tert-butoxy)carbonyl]-3-cyanoazetidine-3-carboxylic acid|CS-0052696

Structure of 1158759-45-5

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General Information

  • CAS No. 1158759-45-5
  • Cat. No. CS-0052696
  • Purity ≥98%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₄N₂O₄
  • Molecular Weight 226.23
  • Synonym(s) 1-Boc-3-cyanoazetidine-3-carboxylic acid
  • SMILES CC(C)(C)OC(=O)N1CC(C1)(C#N)C(O)=O

Description

This azetidine derivative features a tert-butoxycarbonyl-protected amine and a cyano group at the 3-position, enabling direct incorporation into peptide synthesis. The strained azetidine ring enhances reactivity in coupling reactions, while the carbamate moiety provides stability under standard conditions. Designed for efficient functionalization in medicinal chemistry applications.

Application

1-[(Tert-butoxy)carbonyl]-3-cyanoazetidine-3-carboxylic acid serves as a versatile building block for the synthesis of azetidinyl scaffolds in medicinal chemistry. The tert-butyl ester provides bench stability and facilitates orthogonal deprotection, while the cyano group enables downstream functionalization via nucleophilic addition or cyclization. Its compatibility with standard coupling reactions and ease of purification make it suitable for iterative synthesis of complex heterocycles and peptide-like architectures.

Safety Information

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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   90.63
  • LogP   0.83168
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   1

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