imidazolidine-2,4,5-trione

• ChemBase ID: 102679
• Molecular Formular: C3H2N2O3
• Molecular Mass: 114.05958
• Monoisotopic Mass: 114.00654193
• SMILES: O=C1NC(=O)C(=O)N1
• Canonical SMILES: O=C1NC(=O)C(=O)N1
• InChI: InChI=1S/C3H2N2O3/c6-1-2(7)5-3(8)4-1/h(H2,4,5,6,7,8)
• InChIKey: ZFLIKDUSUDBGCD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: imidazolidine-2,4,5-trione
• IUPAC Traditional name: imidazolidinetrione
• Synonyms: Imidazolidinetrione; PARABANIC ACID; Oxalylurea; Trioxoimidazolidine; Parabanic acid; OXALYLUREA; 2,4,5-Imidazolidinetrione; 乙二酰脲; 仲班酸

Database IDs

• CAS Number: 120-89-8
• EC Number: 204-434-3
• MDL Number: MFCD00014493
• PubChem SID: 162088719; 24278003
• PubChem CID: 67126

CALCULATED PROPERTIES

• Acid pKa: 7.0895514
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -1.2145833
• LogD (pH = 7.4): -1.6771277
• Log P: -1.2036774
• Molar Refractivity: 21.4256 cm^3
• Polarizability: 8.344828 Å^3
• Polar Surface Area: 75.27 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Ethanol; Hot Water; Methanol
• Apperance: White Crystalline Solid
• Melting Point: 241-243°C dec.; 249 °C (dec.)(lit.)

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 99%
• Empirical Formula (Hill Notation): C3H2N2O3

DETAILS

MP Biomedicals - 02102574

Crystalline

MP Biomedicals - 05217270

MP Biomedicals Rare Chemical collection

Sigma Aldrich - P209

Packaging
1, 5 g in glass bottle
Application
Reactant for:
• Enantiospecific assembly of homochiral, hexanuclear palladium complexes1
• Mitsunobu reactions2
• Quantitative cascade condensation reactions3Reactant for synthesis of:
• Pyridine derivatives4
• Nitroesters5
• Parabanic acid derivatives6

Toronto Research Chemicals - P191000

Parabanic acid appears to be an important marker of free radical reactions in vivo and may be used to monitor free radical activity and to evaluate pharmacological therapy with radical scavengers.

REFERENCES

• Koumoto, Y., et al.: J. Biol. Chem., 276, 29688 (2001)
• Gibon, Y., et al.: Plant Cell, 16, 3304 (2001)
• Kaplan, F., et al.: Plant J., 44, 730 (2001)
• Ishii, N., et al.: Science, 316, 593 (2001)