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Barbituric acid information


Barbituric acid
Names
Preferred IUPAC name
1,3-Diazinane-2,4,6-trione
Other names
  • 2,4,6(1H,3H,5H)-Pyrimidinetrione
  • Pyrimidine-2,4,6(1H,3H,5H)-trione
  • 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 checkY
3D model (JSmol)
  • Interactive image
3DMet
  • B01336
Beilstein Reference
120502
ChEBI
  • CHEBI:16294 checkY
ChEMBL
  • ChEMBL574699 checkY
ChemSpider
  • 5976 checkY
ECHA InfoCard 100.000.598 Edit this at Wikidata
EC Number
  • 200-658-0
Gmelin Reference
101571
KEGG
  • C00813 checkY
PubChem CID
  • 6211
UNII
  • WQ92Y2793G checkY
CompTox Dashboard (EPA)
  • DTXSID8020129 Edit this at Wikidata
InChI
  • InChI=1S/C4H4N2O3/c7-2-1-3(8)6-4(9)5-2/h1H2,(H2,5,6,7,8,9) checkY
    Key: HNYOPLTXPVRDBG-UHFFFAOYSA-N checkY
  • InChI=1/C4H4N2O3/c7-2-1-3(8)6-4(9)5-2/h1H2,(H2,5,6,7,8,9)
    Key: HNYOPLTXPVRDBG-UHFFFAOYAE
SMILES
  • O=C1NC(=O)NC(=O)C1
Properties
Chemical formula
C4H4N2O3
Molar mass 128.087 g·mol−1
Appearance White crystals
Melting point 245 °C (473 °F; 518 K)
Boiling point 260 °C (500 °F; 533 K)
Solubility in water
142 g/L (20 °C)
Acidity (pKa) 4.01 (H2O)[1]
Magnetic susceptibility (χ)
  • -78.6·10−6 cm3/mol crystal+2H20
  • -53.8·10−6 cm3/mol Anhy.
Hazards
GHS labelling:
Pictograms
GHS07: Exclamation mark
Signal word
Warning
Hazard statements
H315, H319, H335
Precautionary statements
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
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. The compound was first synthesised by Adolf von Baeyer.

  1. ^ Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. pp. 5–89. ISBN 978-1498754286.

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Barbituric acid

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Barbital

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ethyl iodide to the silver salt of malonylurea (barbituric acid) or possibly to a basic solution of the acid. The result was an odorless, slightly bitter...

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Balaban IE, "Improvements in the manufacture of substituted barbituric and thiobarbituric acids", issued 21 February 1951, assigned to Geigy  "Pentobarbital...

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Controlled Drugs and Substances Act

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(5-methyl-5-phenylbarbituric acid) Secobarbital (5-allyl-5-(1-methylbutyl)barbituric acid) Sigmodal (5-(2-bromoallyl)-5-(1-methylbutyl) barbituric acid) Talbutal...

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GABAA receptor positive allosteric modulator

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compounds, such as bromide. In 1903, the first psychoactive derivative of barbituric acid was synthesized and marketed for headaches. Within 30 years, many other...

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Pyrimidine

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until 1879, when Grimaux reported the preparation of barbituric acid from urea and malonic acid in the presence of phosphorus oxychloride. The systematic...

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Malonic acid

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reaction, malonic acid condenses with urea to form barbituric acid. Malonic acid may also be condensed with acetone to form Meldrum's acid, a versatile intermediate...

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Dimethyl malonate

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derivative of malonic acid. It is a common reagent for organic synthesis used, for example, as a precursor for barbituric acid. It is also used in the...

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Agarose gel electrophoresis

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buffering system may be used in specific applications, for example, barbituric acid-sodium barbiturate or Tris-barbiturate buffers may be used for in agarose...

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Buffer solution

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pH 3 to 8. A mixture containing citric acid, monopotassium phosphate, boric acid, and diethyl barbituric acid can be made to cover the pH range 2.6 to...

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Purpuric acid

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Purpuric acid is a nitrogenous acid related to barbituric acid that yields alloxan and uramil upon hydrolysis. It is noteworthy for its purple-red salts...

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Pigment yellow 139

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phthalonitrile to give diiminoisoindole, which in turn condenses with barbituric acid. K. Hunger. W. Herbst "Pigments, Organic" in Ullmann's Encyclopedia...

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Hexobarbital

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pharmacology of 5-ethyl-5(3-hydroxyisoamyl)-barbituric acid--a breakdown product of 5-ethyl-5-isoamyl-barbituric acid]". Arzneimittel-Forschung. 15 (6): 688–91...

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Pigment yellow 185

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in turn condenses first with N-methylcyanoacetamide and then with barbituric acid. Radtke, Volker; Erk, Peter; Sens, Benno (2009). "Isoindoline pigments"...

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Benzylbutylbarbiturate

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jurisdictions (including Japan) prohibit "any 5,5-disubstituted derivative of barbituric acid", this compound was deemed to be already illegal, despite being a novel...

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Ethchlorvynol

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methylparafynol and tert-amyl alcohol. It is not a benzodiazepine, carbamate, or barbituric acid derivative, and its molecular structure is considerably simpler. The...

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Violuric acid

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deeply colored. It was prepared by Adolf Baeyer by reaction of barbituric acid with nitrous acid. It can also be produced by condensation of alloxan with hydroxylamine...

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Adolf von Baeyer

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nitroso compounds (1869) and uric acid derivatives (1860 and onwards) (including the discovery of barbituric acid (1864), the parent compound of the...

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Secobarbital

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2007-12-02. US patent 1954429, Shonle HA, "Propyl-Methyl Carbinyl Allyl Barbituric Acid and its Salts", issued 1934-04-10, assigned to Eli Lilly  Dembosky...

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CHEB

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3-diazinane-2,4,6-trione Other names CHEB 5-(2-cyclohexylidene-ethyl)-5-ethyl barbituric acid 5-(2-cyclohexylidene-ethyl)-5-ethyl barbiturate BRN 0250312 Identifiers...

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Hydroxymethylfurfural

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Minoxidil

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2-dihydro-1-hydroxy-2-imino-4-piperidinopyrimidine, is synthesized from barbituric acid, the reaction of which with phosphorus oxychloride gives 2,4,6-trichloropyrimidine...

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ISBN 978-0-85404-182-4. Pentobarbital at CHEBI, described as "Barbituric acid substituted at C-5 by ethyl and sec-pentyl groups". Accessed on 2013-02-21...

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