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CS-W001157 4
Total: USD 88.00

3-Oxo-3,4-dihydropyrazine-2-carboxylic acid

  • CAS No. 20737-42-2

  • Cat. No. CS-W019268
  • Purity≥97%
  • MDL No.None

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

3-Oxo-3,4-dihydropyrazine-2-carboxylic acid|CS-W019268

Structure of 20737-42-2

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General Information

  • CAS No. 20737-42-2
  • Cat. No. CS-W019268
  • Purity ≥97%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₄N₂O₃
  • Molecular Weight 140.10
  • Synonym(s) 3-Hydroxypyrazine-2-carboxylic acid
  • SMILES O=C(C1=NC=CNC1=O)O

Description

3-Oxo-3,4-dihydropyrazine-2-carboxylic acid features a fused heterocyclic core with a ketone at the 3-position and a carboxylic acid at the 2-position, enabling versatile conjugation in synthetic routes. The electron-deficient pyrazine ring supports efficient coupling reactions, while the adjacent carbonyl group enhances reactivity in nucleophilic additions. This scaffold serves as a key intermediate in medicinal chemistry for constructing bioactive molecules.

Application

3-Oxo-3,4-dihydropyrazine-2-carboxylic acid serves as a versatile building block in medicinal chemistry, enabling the construction of pyrazine-containing scaffolds via standard condensation and cyclization protocols. Its carboxylic acid and enone functionalities offer orthogonal reactivity for peptide coupling, derivatization, and transition-metal-catalyzed transformations. Bench-stable and readily purified by recrystallization, it functions reliably in multi-step syntheses of heterocyclic drug candidates.

Synthesis

  • Route1

    References

    • BOEHRINGER INGELHEIM INTERNATIONAL GMBH Patent: US2012/94976 A1, 2012 ; Location in patent: Page/Page column 35-36 ;
  • Route2

    References

    • Journal of the American Chemical Society, , vol. 67, p. 802,804
  • Route3

    References

    • Journal of the Chemical Society, , p. 1379,1380 Journal of the American Chemical Society, , vol. 71, p. 78,79, 80

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H319
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   83.05
  • LogP   -0.5319
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   1

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