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| 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 | |
| EINECS number | |
| SMILES | C1C(=O)NC(=O)NC1=O |
| 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 Malonic acid has since been replaced by diethyl malonate.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.
This article is licensed under the GNU Free Documentation License. It uses material from Wikipedia
