Barbituric acid

Barbituric acid
Names
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
67-52-7 YesY
ChEBI CHEBI:16294 YesY
ChEMBL ChEMBL574699 YesY
ChemSpider 5976 YesY
EC Number 200-658-0
Jmol interactive 3D Image
KEGG C00813 YesY
PubChem 6211
UNII WQ92Y2793G YesY
Properties
C4H4N2O3
Molar mass 128.09 g·mol−1
Appearance White crystals
Melting point 245 °C (473 °F; 518 K)
Boiling point 260 °C (500 °F; 533 K)
142 g/l (20 °C)
Hazards
Safety data sheet External MSDS
R-phrases R36/38, R43
S-phrases S22, S26, S28
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
1
2
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Barbituric acid or malonylurea or 6-hydroxyuracil is an organic compound based on a pyrimidine heterocyclic skeleton. It is an odorless powder soluble in water. Barbituric acid is the parent compound of barbiturate drugs, although barbituric acid itself is not pharmacologically active.

Synthesis

The compound was discovered by the German chemist Adolf von Baeyer on December 4, 1864, the feast of Saint Barbara (who gave the compound its namesake), by combining urea and malonic acid in a condensation reaction.[1] Malonic acid has since been replaced by diethyl malonate,[2] as using the ester avoids the problem of having to deal with the acidity of the carboxylic acid and its unreactive carboxylate.

The synthesis of barbituric acid from malonic acid and urea

Properties

The α-carbon has a reactive hydrogen atom and is quite acidic (pKa = 4.01) even for a diketone species (cf. dimedone with pKa 5.23 and acetylacetone with pKa 8.95) because of the additional aromatic stabilization of the carbanion.

Uses

Using the Knoevenagel condensation reaction, barbituric acid can form a large variety of barbiturate drugs that behave as central nervous system depressants. 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, phenobarbital was first marketed in 1912.

Barbituric acid is one of four ingredients used to make riboflavin (vitamin B2).

Health and safety

Overdose of barbituric acid can cause respiratory problems and death.

See also

References

  1. ↑ Baeyer, Adolf (1864). "Untersuchungen über die Harnsäuregruppe". Annalen der Chemie und Pharmacie 131 (3): 291. doi:10.1002/jlac.18641310306.
  2. ↑ J. B. Dickey & A. R. Gray (1943). "Barbituric acid". Org. Synth.; Coll. Vol. 2, p. 60

Mahmudov K.T., Kopylovich M.N., Maharramov A.M., Kurbanova M.M., Gurbanov A.V., Pombeiro A.J.L. Barbituric acids as a useful tool for the construction of coordination and supramolecular compounds, Coordination Chemistry Reviews, 2014, 265, 1-37. DOI: 10.1016/j.ccr.2014.01.002 http://www.sciencedirect.com/science/article/pii/S0010854514000046

Mahmudov K.T., Kopylovich M.N., Maharramov A.M., Kurbanova M.M., Gurbanov A.V., Pombeiro A.J.L. Barbituric acids as a useful tool for the construction of coordination and supramolecular compounds, Coordination Chemistry Reviews, 2014, 265, 1-37. DOI: 10.1016/j.ccr.2014.01.002 http://www.sciencedirect.com/science/article/pii/S0010854514000046

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