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CS-W001157 4
Total: USD 88.00

3,6-Dichloro-1,2,4,5-tetrazine

  • CAS No. 106131-61-7

  • Cat. No. CS-0049617
  • Purity≥95%
  • MDL No.None

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

3,6-Dichloro-1,2,4,5-tetrazine|CS-0049617

Structure of 106131-61-7

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General Information

  • CAS No. 106131-61-7
  • Cat. No. CS-0049617
  • Purity ≥95%
  • MDL No. None
  • Storage -20°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₂Cl₂N₄
  • Molecular Weight 150.95
  • Synonym(s) Dichloro-s-tetrazine
  • SMILES ClC1=NN=C(Cl)N=N1

Description

3,6-Dichloro-1,2,4,5-tetrazine features a highly reactive tetrazine core with two chlorine substituents at the 3 and 6 positions, enabling efficient inverse electron-demand Diels-Alder reactions. This bench-stable compound integrates readily into bioorthogonal labeling workflows, offering rapid conjugation kinetics with strained dienophiles. The electron-deficient framework enhances selectivity in complex biological environments.

Application

3,6-Dichloro-1,2,4,5-tetrazine serves as a versatile building block in synthetic organic chemistry, enabling efficient construction of nitrogen-rich heterocycles and functionalized scaffolds. Its reactive dichloro substituents facilitate selective nucleophilic substitution under mild conditions, offering high functional group tolerance and compatibility with common coupling protocols. The compound exhibits excellent bench stability and simplifies purification in multi-step syntheses, making it well-suited for the development of advanced intermediates in medicinal chemistry and materials science applications.

Synthesis

  • Route1
    • 3,6-Dihydrazino-1,2,4,5-tetrazine|CS-0253598
      5940-53-4
    • ~82%
    • In-stock
      3,6-Dichloro-1,2,4,5-tetrazine|CS-0049617
      106131-61-7

    References

    • Gong, Yong-Hua; Miomandre, Fabien; Meallet-Renault, Rachel; Badre, Sophie; Galmiche, Laurent; Tang, Jie; Audebert, Pierre; Clavier, Gilles European Journal of Organic Chemistry, 2009 , # 35 p. 6121 - 6128
  • Route2

    References

    • Dalla Via, Lisa; Gonzalez-Gomez, Jose Carlos; Perez-Montoto, Lazaro Guillermo; Santana, Lourdes; Uriarte, Eugenio; Marciani Magno, Sebastiano; Gia, Ornella Bioorganic and Medicinal Chemistry Letters, 2009 , vol. 19, # 10 p. 2874 - 2876

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   51.56
  • LogP   0.5734
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   0

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