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5,6-Dioxo-1,4,5,6-tetrahydropyrazine-2-carboxylic acid

  • CAS No. 77168-80-0

  • Cat. No. CS-0109434
  • Purity≥97%
  • MDL No.MFCD20654178

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

5,6-Dioxo-1,4,5,6-tetrahydropyrazine-2-carboxylic acid|CS-0109434

Structure of 77168-80-0

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General Information

  • CAS No. 77168-80-0
  • Cat. No. CS-0109434
  • Purity ≥97%
  • MDL No. MFCD20654178
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₄N₂O₄
  • Molecular Weight 156.10
  • Synonym(s) 5,6-Dihydroxypyrazine-2-carboxylic acid
  • SMILES O=C(C(NC1=O)=CNC1=O)O

Description

5,6-Dioxo-1,4,5,6-tetrahydropyrazine-2-carboxylic acid features a rigid, electron-deficient heterocyclic core that facilitates efficient conjugation in synthetic transformations. This scaffold integrates readily into complex molecular architectures, offering enhanced reactivity in cycloaddition and functionalization processes under standard conditions.

Application

5,6-Dioxo-1,4,5,6-tetrahydropyrazine-2-carboxylic acid serves as a versatile building block for heterocyclic synthesis, enabling access to pyrazine-based scaffolds through standard condensation and cyclization protocols. Its dual carbonyl and carboxylic acid functionalities provide orthogonal reactivity for peptide coupling, amide formation, and metal-catalyzed transformations. Bench-stable and readily purified by recrystallization, it functions effectively in multi-step syntheses requiring functional group tolerance and predictable reactivity.

Synthesis

  • Route1
    • null|null
      77168-78-6
    • ~9%
    • In-stock
      5,6-Dioxo-1,4,5,6-tetrahydropyrazine-2-carboxylic acid|CS-0109434
      77168-80-0

    References

    • Mano; Seo; Iami Chemical and Pharmaceutical Bulletin, 1980 , vol. 28, # 10 p. 3057 - 3063
  • Route2

    References

    • Mano; Seo; Iami Chemical and Pharmaceutical Bulletin, 1980 , vol. 28, # 10 p. 3057 - 3063
  • Route3

    References

    • Mano; Seo; Iami Chemical and Pharmaceutical Bulletin, 1980 , vol. 28, # 10 p. 3057 - 3063

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

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Computational Chemistry Data

  • TPSA   103.02
  • LogP   -1.2386
  • H_Acceptors   3
  • H_Donors   3
  • Rotatable_Bonds   1

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