Violuric acid
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Names | |
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IUPAC name
6-Hydroxy-5-nitroso-1H-pyrimidine-2,4-dione
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Other names
2,4,5,6(1H,3H)-Pyrimidinetetrone 5-oxime
5-Hydroxyiminobarbituric acid 5-Isonitrosobarbituric acid Alloxan 5-oxime | |
Identifiers | |
3D model (JSmol)
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ChemSpider | |
ECHA InfoCard | 100.001.584 ![]() |
EC Number |
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PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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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)[1] | |
Solubility | Soluble in alcohols |
Vapor pressure | ~0 mmHg |
Acidity (pKa) | 4.7 |
Hazards | |
Main hazards | Irritant |
GHS labelling: | |
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Signal word
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Warning |
H315, H319, H335 | |
P261, P305+P351+P338 | |
Related compounds | |
Related compounds
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Barbituric acid |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Infobox references | |
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.[2]
Reactions[]
It readily deprotonated to give salts of the anion [ON=C(CONH)2CO]-, which are often deeply colored.[3][4]
Preparation[]
It was prepared by Adolf Baeyer by reaction of barbituric acid with nitrous acid.[5] It can also be produced by condensation of alloxan with hydroxylamine.[4][6] as typical for forming the oxime of other carbonyl compounds.
References[]
- ^ "Registration Dossier - ECHA".
- ^ Guille, Kathy; Harrington, Ross W.; Clegg, William (2007). "Violuric acid monohydrate: A second polymorph with more extensive hydrogen bonding". Acta Crystallographica Section C Crystal Structure Communications. 63 (6): o327–o329. doi:10.1107/S010827010701743X. PMID 17551193.
- ^ Nichol, Gary S.; Clegg, William (2007). "Ammonium Violurate: A Compact Structure with Extensive Hydrogen Bonding in Three Dimensions". Acta Crystallographica Section C Crystal Structure Communications. 63 (10): o609–o612. doi:10.1107/S0108270107044241. PMID 17917236.
- ^ a b Liebing, Phil; Stein, Franziska; Hilfert, Liane; Lorenz, Volker; Oliynyk, Karyna; Edelmann, Frank T. (2019). "Synthesis and Structural Investigation of Brightly Colored Organoammonium Violurates". Zeitschrift für Anorganische und Allgemeine Chemie. 645: 36–43. doi:10.1002/zaac.201800439. S2CID 104376844.
- ^ Baeyer, Adolf (1863). "Untersuchungen über die Harnsäuregruppe". Annalen der Chemie und Pharmacie. 127 (2): 199–236. doi:10.1002/jlac.18631270214.
- ^ Guinchard, J. (1899). "Ueber die farbigen Salze aus Violursäure und anderen ringförmigen Oximidoketonen". Berichte der Deutschen Chemischen Gesellschaft. 32 (2): 1723–1741. doi:10.1002/cber.18990320260.
Categories:
- Barbiturates
- Nitroso compounds
- Oximes