Barbituric acid
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| style="background: #F8EABA; text-align: center;" colspan="2" | Barbituric acid |
|---|---|
| 160px | |
| Pyrimidine-2,4,6(1H,3H,5H)-trione | |
| Identifiers | |
| CAS number | 67-52-7 |
| PubChem | 6211 |
| SMILES | C1C(=O)NC(=O)NC1=O |
| Properties | |
| Molecular formula | C4H4N2O3 |
| Molar mass | 128.09 g/mol |
| Melting point |
245 °C |
| Hazards | |
| NFPA 704 |
|
| style="background: #F8EABA; text-align: center;" colspan="2" | 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-hydroxyuracyl 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 Malonic acid has since been replaced by diethyl malonate.
The synthesis of barbituric acid from urea and malonic acid
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
Edit
External linksEdit
- MSDS http://www.jtbaker.com [1]
- Barbituric acid J. B. Dickey and A. R. Gray Organic Syntheses, Coll. Vol. 2, p.60; Vol. 18, p.8 Online Article
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