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Barbituric acid



Barbituric acid
IUPAC name Pyrimidine-2,4,6(1H,3H,5H)-trione
Other names 2,4,6(1H,3H,5H)-Pyrimidinetrione, 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
CAS number 67-52-7
PubChem 6211
EINECS number 200-658-0
SMILES C1C(=O)NC(=O)NC1=O
InChI InChI=1/C4H4N2O3/c7-2-1-3(8)6- 4(9)5-2/h1H2,(H2,5,6,7,8,9)
Properties
Molecular formula C4H4N2O3
Molar mass 128.09 g/mol
Appearance White crystals
Melting point

245 °C

Boiling point

260 °C

Solubility in water 142 g/l (20 °C)
Hazards
NFPA 704
1
2
0
 
R-phrases R36/38, R43
S-phrases S22, S26, S28
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

Barbituric acid or malonylurea or 4-hydroxyuracil is an organic compound based on a pyrimidine heterocyclic skeleton. It is an odorless powder soluble in hot water. Barbituric acid is the parent compound of a large class of barbiturates that have central nervous system depressant properties although barbituric acid itself is not pharmacologically active. The compound was discovered by the German chemist Adolf von Baeyer in 1864 by combining urea and malonic acid in a condensation reaction. Malonic acid has since been replaced by diethyl malonate.


On the carbon alpha it has reactive hydrogen atom. Using Knoevenagel condensation reaction, barbituric acid can form a large variety of barbiturate drugs that behave also as central nervous system depressants.

Barbituric acid is used in synthesis of riboflavin.

See also
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Barbituric_acid". A list of authors is available in Wikipedia.
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