Barbituric acid

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)
3DMet
120502
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.598 Edit this at Wikidata
EC 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) checkY
    Key: HNYOPLTXPVRDBG-UHFFFAOYSA-N checkY
  • 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
C4H4N2O3
Molar mass 128.087 g·mol−1
Appearance White crystals
Melting point 245 °C (473 °F; 518 K)
Boiling point 260 °C (500 °F; 533 K)
142 g/L (20 °C)
Acidity (pKa) 4.01 (H2O)[1]
  • -78.6·10−6 cm3/mol crystal+2H20
  • -53.8·10−6 cm3/mol Anhy.
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
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).
checkY verify (what is checkY☒N ?)

Barbituric acid or malonylurea or 6-hydroxyuracil is an organic compound based on a pyrimidine heterocyclic 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.

  1. ^ Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. pp. 5–89. ISBN 978-1498754286.