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Topic summary

Barbituric acid

Barbituric acid
Sample of barbituric acid
Names Preferred IUPAC name
1,3-Diazinane-2,4,6-trione
Other names
  • 2,4,6(1H,3H,5H)-Pyrimidinetrione
  • Pyrimidine-2,4,6(1H,3H,5H)-trione
  • 2,4,6-Trioxohexahydropyrimidine
  • 2,4,6-Trihydroxypyrimidine
  • 2,4,6-Trioxypyrimidine
  • 2,4,6-Pyrimidinetriol
  • 2,4,6-Pyrimidinetrione
  • Pyrimidinetriol
  • 2,4,6-Trihydroxy-1,3-diazine
  • N,N-Malonylurea
  • Malonylurea
  • 6-Hydroxyuracil
  • 6-Hydroxy-hydrouracil
  • N,N-(1,3-Dioxo-1,3-propanediyl)urea
Identifiers
3D model (JSmol)
120502 ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.000.598EC Number
  • 200-658-0
101571 KEGG
UNII
  • InChI=1S/C4H4N2O3/c7-2-1-3(8)6-4(9)5-2/h1H2,(H2,5,6,7,8,9)
    Key: HNYOPLTXPVRDBG-UHFFFAOYSA-N
  • InChI=1/C4H4N2O3/c7-2-1-3(8)6-4(9)5-2/h1H2,(H2,5,6,7,8,9)
    Key: HNYOPLTXPVRDBG-UHFFFAOYAE
  • O=C1NC(=O)NC(=O)C1
Properties C4H4N2O3Molar mass128.087 g·mol Appearance White crystals Melting point245 °C (473 °F; 518 K) Boiling point260 °C (500 °F; 533 K) 142 g/L (20 °C) Acidity (pKa) 4.01 (H2O)
  • −78.6·10 cm/mol crystal+2H20
  • −53.8·10 cm/mol Anhy.
Hazards GHS labelling: WarningH315, H319, H335P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501NFPA 704 (fire diamond)
2
1
0
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Barbituric acid or malonylurea or 6-hydroxyuracil is an organic compound based on a pyrimidineheterocyclic skeleton. It is an odorless powder soluble in water. Barbituric acid is the parent compound of barbiturate drugs, although barbituric acid itself is not pharmacologically active. The compound was first synthesised by Adolf von Baeyer.

Wikipedia source