oxolane-2,4-dione

• ChemBase ID: 77773
• Molecular Formular: C4H4O3
• Molecular Mass: 100.07276
• Monoisotopic Mass: 100.01604399
• SMILES: O=C1CC(=O)CO1
• Canonical SMILES: O=C1OCC(=O)C1
• InChI: InChI=1S/C4H4O3/c5-3-1-4(6)7-2-3/h1-2H2
• InChIKey: JCGNDDUYTRNOFT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: oxolane-2,4-dione
• IUPAC Traditional name: oxolane-2,4-dione
• Synonyms: beta-Tetronic acid; Furan-2,4-dione; β-Tetronic acid; 4-Hydroxy-2(5H)-furanone; Tetrahydrofuran-2,4-dione; Tetronic acid; 2,4(3H,5H)-Furandione; 2,4(3H,5H)-Furandione; Tetronic acid; β-特窗酸; 2,4-二氧四氢呋喃; 4-羟基-2(5H)-呋喃酮; 特窗酸; 4-羟乙酰乙酸内酯; 季酮酸

Database IDs

• CAS Number: 4971-56-6; 541-57-1
• EC Number: 225-617-4; 208-785-3
• MDL Number: MFCD00010086
• Beilstein Number: 108442
• PubChem SID: 162042642
• PubChem CID: 521261

CALCULATED PROPERTIES

• Acid pKa: 6.9981575
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.06549617
• LogD (pH = 7.4): -0.46707818
• Log P: -0.15426867
• Molar Refractivity: 20.7489 cm^3
• Polarizability: 8.355237 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 141-143 °C (dec.)(lit.); ca 140°C dec.

Safety Information

• Storage Warning: Irritant
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A

Product Information

• Purity: 96%; 98%
• Empirical Formula (Hill Notation): C4H4O3

DETAILS

Sigma Aldrich - 254592

Application
Strongly acidic building block for heterocyclic systems1 including medicinal intermediates.2

REFERENCES

• Equivalent to the -lactone of 4-hydroxyacetoacetic acid.
• Selective O-alkylation is promoted by CsF under mild conditions: Synlett, 843 (1995).
• Versatile precursor of a variety of substituted and ring-fused furans and butenolides; see, e.g.: J. Org. Chem., 48, 1914 (1983); Synthesis, 155 (1996).