1,3-diazinane-2,4,6-trione

• ChemBase ID: 126024
• Molecular Formular: C4H4N2O3
• Molecular Mass: 128.08616
• Monoisotopic Mass: 128.022192
• SMILES: O=C1NC(=O)NC(=O)C1
• Canonical SMILES: O=C1CC(=O)NC(=O)N1
• InChI: InChI=1S/C4H4N2O3/c7-2-1-3(8)6-4(9)5-2/h1H2,(H2,5,6,7,8,9)
• InChIKey: HNYOPLTXPVRDBG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3-diazinane-2,4,6-trione
• IUPAC Traditional name: barbituric acid
• Synonyms: Malonylurea; Barbituric acid; 2,4,6(1H,3H,5H)-Pyrimidinetrione; 1,2,3,4,5,6-Hexahydro-2,4,6-pyrimidinetrione; 2,4,6-Pyrimidinetriol; 6-Hydroxyuracil; Hexahydropyrimidine-2,4,6-trione; NSC 7889; 2,4,6(1H,3H,5H)-Pyrimidinetrione; 2,4,6-Trioxohexahydropyrimidine; 2,4,6-Trihydroxypyrimidine; 2,4,6-Trioxypyrimidine; 2,4,6-Pyrimidinetrioe; 2,4,6-Pyrimidinetrione; Pyrimidinetrioe; 2,4,6-Trihydroxy-1,3-diazine; N,N′-Malonyluree; Malonyluree; 6-Hydroxyuracie; 6-Hydroxy-Hydrouracie; N,N′-(1,3-dioxo-1,3-propanediyl)urea; Barbituric acid; 2,4,6-三羟基嘧啶; 丙二酰脲; 巴比妥酸

Database IDs

• CAS Number: 67-52-7
• EC Number: 200-658-0
• MDL Number: MFCD00006666
• Beilstein Number: 120502
• Merck Index: 14963
• PubChem SID: 162220367; 24847314; 24851157
• PubChem CID: 6211
• CHEBI ID: 16294
• CHEMBL: 574699
• Chemspider ID: 5976
• KEGG ID: C00813
• Unique Ingredient Identifier: WQ92Y2793G
• Wikipedia Title: Barbituric_acid

CALCULATED PROPERTIES

• Acid pKa: 3.9489894
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -2.8161807
• LogD (pH = 7.4): -4.1899095
• Log P: -1.2710431
• Molar Refractivity: 25.9748 cm^3
• Polarizability: 10.119884 Å^3
• Polar Surface Area: 75.27 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 142 g/l (20 °C) in water
• Apperance: White crystals
• Melting Point: 245 °C; 248-252 °C (dec.)(lit.); ca 250°C dec.
• Boiling Point: 260 °C
• Flash Point: 150 °C; 150°C(302°F); 302 °F

Safety Information

• RTECS: CP8000000
• German water hazard class: 1
• Risk Statements: R36/38, R43
• Safety Statements: S22, S26, S28
• TSCA Listed: 是
• NFPA704:
  

  1

  2

  0
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Drug Control: regulated under CDSA - not available from Sigma-Aldrich Canada

Product Information

• Purity: ≥99.0% (HPLC); ≥99.5%; ≥99.5% (HPLC); 98%; 99%
• Grade: purum; ReagentPlus®
• Ignition Residue: ≤0.05%
• Impurities: ≤2.0% water
• Cation Traces: Ca: ≤10 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤5 mg/kg; Fe: ≤5 mg/kg; Mg: ≤10 mg/kg; Mn: ≤5 mg/kg; Ni: ≤5 mg/kg; Pb: ≤5 mg/kg; Zn: ≤5 mg/kg
• Antion Traces: chloride (Cl-): ≤50 mg/kg; sulfate (SO42-): ≤500 mg/kg
• Quality: for spectrophotometric det. of cyanide
• Empirical Formula (Hill Notation): C4H4N2O3

DETAILS

Sigma Aldrich - B208

Packaging
Packaged in glass bottles

Sigma Aldrich - 11710

Other Notes
Sales restrictions may apply

Sigma Aldrich - 185698

Packaging
25, 100, 500 g in poly bottle
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - B118650

Barbituric acid is a parent compound of barbiturate drugs. Unsubstituted barbituric acid has no hypnotic properties.

REFERENCES

• Luo, Y., et al.: J. Med. Chem., 53, 3846 (2010)
• Tomasic, T., et al.: Eur. J. Med. Chem., 45, 1667 (2010)
• Gilbert, A., et al.: Bioorg. Med. Chem. Lett., 20, 636 (2010)