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tert-Butyl(2-cyanoethyl)carbamate

  • CAS No. 53588-95-7

  • Cat. No. CS-0171919
  • Purity≥97%
  • MDL No.None

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

tert-Butyl(2-cyanoethyl)carbamate|CS-0171919

Structure of 53588-95-7

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General Information

  • CAS No. 53588-95-7
  • Cat. No. CS-0171919
  • Purity ≥97%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₁₄N₂O₂
  • Molecular Weight 170.21
  • Synonym(s) tert-butyl N-(2-cyanoethyl)carbamate
  • SMILES CC(C)(OC(NCCC#N)=O)C

Description

tert-Butyl(2-cyanoethyl)carbamate serves as a robust, bench-stable protecting group for primary amines in synthetic workflows. The carbamate moiety enables selective N-alkylation and subsequent cleavage under mild acidic conditions. Its electron-deficient cyano group enhances reactivity in nucleophilic transformations, while the tert-butyl group provides steric shielding and ease of removal. This combination delivers precise control in peptide synthesis and complex molecule assembly.

Application

tert-Butyl(2-cyanoethyl)carbamate serves as a robust, bench-stable protecting group for primary amines, enabling efficient incorporation of cyano functionality in peptide and small-molecule synthesis. It facilitates selective N-alkylation, undergoes mild acidolysis to release the free amine, and exhibits excellent compatibility with diverse reaction conditions. Its orthogonal cleavage profile supports sequential functionalization strategies in complex molecule assembly.

Synthesis

  • Route1

    References

    • ALMIRALL, S.A.; GRIMA POVEDA, Pedro Manuel; AGUILAR IZQUIERDO, Nuria; MIR CEPEDA, Marta; CARRASCAL RIERA, Marta; TERRICABRAS BELART, Emma; GRACIA FERRER, Jordi; CASALS COLL, Gaspar Patent: WO2011/35900 A1, 2011 ; Location in patent: Page/Page column 71 ; WO 2011/035900 A1
  • Route2
    • In-stock
      Di-tert-butyl dicarbonate|CS-0017817
      24424-99-5
    • null|null
      352-96-5
    • ~73%
    • In-stock
      tert-Butyl(2-cyanoethyl)carbamate|CS-0171919
      53588-95-7

    References

    • Brutsche; Hartke Archiv der Pharmazie, 1993 , vol. 326, # 5 p. 271 - 276
  • Route3

    References

    • Houssin; Bernier; Henichart Journal of Heterocyclic Chemistry, 1984 , vol. 21, # 3 p. 681 - 683

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   62.12
  • LogP   1.42478
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   2

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