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Barbiturate
Violuric acid
Другие языки:

    Violuric acid

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    Violuric acid
    Violursäure.svg
    Violuric acid monohydrate.jpg
    Names
    IUPAC name
    6-Hydroxy-5-nitroso-1H-pyrimidine-2,4-dione
    Other names
    2,4,5,6(1H,3H)-Pyrimidinetetrone 5-oxime
    5-Hydroxyiminobarbituric acid
    5-Isonitrosobarbituric acid
    Alloxan 5-oxime
    Identifiers
    3D model (JSmol)
    ChemSpider
    ECHA InfoCard 100.001.584
    EC Number
    • 201-741-4
    PubChem CID
    UNII
    • InChI=1S/C4H3N3O4/c8-2-1(7-11)3(9)6-4(10)5-2/h(H3,5,6,8,9,10)
      Key: HRRVLSKRYVIEPR-UHFFFAOYSA-N
    • C1(=C(NC(=O)NC1=O)O)N=O
    Properties
    C4H3N3O4 (anhydrous)
    C4H3N3O4·H2O (monohydrate)
    Molar mass 157.08 g/mol (anhydrous)
    175.10 g/mol (monohydrate)
    Appearance Off-white yellow or yellow cream solid
    Odor Odorless
    Melting point 247 °C (477 °F; 520 K) (decomposes)
    Boiling point Decomposes
    0.704 g/100 mL (20 °C)
    Solubility Soluble in alcohols
    Vapor pressure ~0 mmHg
    Acidity (pKa) 4.7
    Hazards
    Occupational safety and health (OHS/OSH):
    Main hazards
    		 Irritant
    GHS labelling:
    GHS07: Exclamation mark
    Warning
    H315, H319, H335
    P261, P305+P351+P338
    Related compounds
    Related compounds
    		 Barbituric acid
    Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

    Violuric acid is an organic compound with the formula HON=C(CONH)2CO. It crystallizes as white or off-white monohydrate. The compound has attracted attention because its salts are deeply colored.

    Reactions

    It readily deprotonated to give salts of the anion [ON=C(CONH)2CO]−, which are often deeply colored.

    Preparation

    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. as typical for forming the oxime of other carbonyl compounds.

    Analytical reagents

    Structure of the ferrous complex with three violurate ligands.

    Violuric acid and many of its derivatives, such as thiovioluric acid, 1,3-dimethylvioluric acid, and diphenylthiovioluric acid, have historically been used as analytical reagents for specrophotometric determination and titration of various metals and metal-ions. It was also used as a novel staining/spraying agent for inorganic paper chromatography to identify and separate metals based on color. Most derivitaves of violuric acid will also typically form brightly colored salts with most metals and nitrogen bases.

    Because of the characteristic and diverse colors that violuric acid forms with alkali metals, it has been used photometrically to determine the amount of sodium in blood serum.


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