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CS-W001157 4
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N3-C5-NHS ester

  • CAS No. 866363-70-4

  • Cat. No. CS-0105081
  • Purity≥96%
  • MDL No.MFCD25968077

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

N3-C5-NHS ester|CS-0105081

Structure of 866363-70-4

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General Information

  • CAS No. 866363-70-4
  • Cat. No. CS-0105081
  • Purity ≥96%
  • MDL No. MFCD25968077
  • Storage -20°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₄N₄O₄
  • Molecular Weight 254.24
  • Synonym(s) None
  • SMILES O=C(ON1C(CCC1=O)=O)CCCCCN=[N+]=[N-]

Description

N3-C5-NHS ester is a bifunctional crosslinker featuring a reactive NHS ester and an azide group separated by a five-atom aliphatic spacer. This design enables site-specific conjugation via copper-free click chemistry, facilitating efficient bioconjugation under physiological conditions. The spacer enhances solubility and reduces steric interference during labeling.

Application

N3-C5-NHS ester serves as a versatile, bench-stable linker for site-specific conjugation in synthetic chemistry. Its NHS ester moiety enables efficient coupling to primary amines under physiological conditions, while the azide group facilitates orthogonal click reactions with triarylphosphine or strained alkyne partners. This bifunctional reagent simplifies the construction of bioconjugates and functionalized scaffolds in medicinal chemistry and materials science workflows.

Synthesis

  • Route1

    References

    • Vasilyeva, Svetlana V.; Silnikov, Vladimir N.; Shatskaya, Natalia V.; Levina, Asya S.; Repkova, Marina N.; Zarytova, Valentina F. Bioorganic and Medicinal Chemistry, 2013 , vol. 21, # 3 p. 703 - 711
  • Route2

    References

    • Grandjean, Cyrille; Boutonnier, Alain; Guerreiro, Catherine; Fournier, Jean-Michel; Mulard, Laurence A. Journal of Organic Chemistry, 2005 , vol. 70, # 18 p. 7123 - 7132

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-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   112.44
  • LogP   1.4643
  • H_Acceptors   5
  • H_Donors   0
  • Rotatable_Bonds   7

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