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Barbituric acid

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style="background: #F8EABA; text-align: center;" colspan="2" Barbituric acid
160px
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

NFPA 704

1
2
0
 
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 Malonic acid has since been replaced by diethyl malonate.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.

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