Barbituric acid
From Wikipedia, the free encyclopedia
| 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 on 4. December 1864 -- the feast of St Barbara and therefore the name given to the compound -- 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 Malonic acid has since been replaced by diethyl malonate.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.
As of 2007, more than 2550 barbiturates and related compounds have been synthesised, with 50 to 55 in clinical use around the world at present. The first to be used in medicine was barbital (Veronal®) starting in 1903, and the second, phenobarbitone a.k.a. phenobarbital was first marketed in 1912.
[edit] See also
[edit] External links
- 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
