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CS-W001157 4
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2,4-Dioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile

  • CAS No. 4425-56-3

  • Cat. No. CS-W002248
  • Purity≥98%
  • MDL No.MFCD00128255

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

2,4-Dioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile|CS-W002248

Structure of 4425-56-3

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General Information

  • CAS No. 4425-56-3
  • Cat. No. CS-W002248
  • Purity ≥98%
  • MDL No. MFCD00128255
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₃N₃O₂
  • Molecular Weight 137.10
  • Synonym(s) 5-Cyanouracil
  • SMILES N#Cc1c[nH]c(=O)[nH]c1=O

Description

This tetrahydropyrimidine derivative features a conjugated dioxo-carbonitrile system, enabling direct integration into heterocyclic scaffolds. The electron-deficient pyrimidine core facilitates nucleophilic addition and cycloaddition reactions under mild conditions. Bench-stable and moisture-tolerant, it serves as a key intermediate in the synthesis of bioactive nitrogen-containing compounds.

Application

2,4-Dioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile serves as a versatile building block in heterocyclic synthesis, enabling efficient access to pyrimidine-based scaffolds through nucleophilic addition and cyclization reactions. Its dual carbonyl and nitrile functionalities offer high reactivity in multicomponent condensations and support functional group tolerance under standard synthetic conditions. Bench-stable and readily purified by recrystallization, it functions as a key intermediate in the construction of biologically relevant heterocycles and is compatible with scalable reaction protocols.

Synthesis

  • Route1
    • Ethyl (2-cyano-3-ethoxyacryloyl)carbamate|CS-0456903
      1187-34-4
    • ~%
    • In-stock
      2,4-Dioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile|CS-W002248
      4425-56-3

    References

    • Shaw Journal of the Chemical Society, 1955 , p. 1834,1838

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   89.51
  • LogP   -1.06512
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   0

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