| Identification | Back Directory | [Name]
Dihydrofuran-3(2H)-one | [CAS]
22929-52-8 | [Synonyms]
Oxolan-3-one
DIHYDRO-FURAN-3-ONE
3-OXOTETRAHYDROFURAN
Dihyro-3(2H)-Furanone
tetrahydrofuran-3-one
Dihydrofuran-3(2H)-one
DIHYDRO-3(2H)-FURANONE
3(2H)-FURANONE, DIHYDRO-
Triton X-100 / Octoxinol
Tetrahydrofuran-3-one,95%
3-Oxotetrahydrofuran, >95%
3-Oxo-1,4-epoxybutane, Oxolan-3-one | [EINECS(EC#)]
805-925-0 | [Molecular Formula]
C4H6O2 | [MDL Number]
MFCD07778393 | [MOL File]
22929-52-8.mol | [Molecular Weight]
86.09 |
| Chemical Properties | Back Directory | [Boiling point ]
68°C/60mmHg(lit.) | [density ]
1.1124 g/cm3(Temp: 420 °C) | [refractive index ]
1.4360-1.4400 | [Fp ]
56°C | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
Chloroform (Sparingly), Methanol (Slightly) | [form ]
Liquid | [color ]
Colorless to Yellow | [Stability:]
Volatile | [InChI]
InChI=1S/C4H6O2/c5-4-1-2-6-3-4/h1-3H2 | [InChIKey]
JLPJFSCQKHRSQR-UHFFFAOYSA-N | [SMILES]
O1CCC(=O)C1 |
| Hazard Information | Back Directory | [Chemical Properties]
Colorless transparent liquid | [Uses]
3-Oxotetrahydrofuran is a reagent in the preperation of dihydropteridinone which are orally active Polo-like kinase-2 (Plk-2) inhibitors. | [Definition]
ChEBI: Oxolan-3-one is an oxalane substituted by an oxo group at position 3. It is functionally related to an oxolane. | [Synthesis]
The general procedure for the synthesis of dihydro-3(2H)-furanone from 3-hydroxytetrahydrofuran was as follows: 3-hydroxytetrahydrofuran (3-OH-THF, 60.6 g, 0.68 mol, 1.0 eq.) was added to a 1 L three-necked flask, followed by the addition of dichloromethane (DCM, 620 mL) and 2,2,6,6-tetramethylpiperidin-1-oxyl radical (TEMPO 1.08 g, 0.0069 mol, 0.01 equiv). The reaction system was cooled to -5°C. Trichloroisocyanuric acid (TCCA, 159.6 g, 0.68 mol, 1.0 eq.) was added in batches while maintaining the temperature at -5°C to 0°C. The reaction mixture was gradually warmed up to room temperature and the reaction progress was monitored by gas chromatography-mass spectrometry (GC-MS). The reaction was completed after about 1 h. The product yield was 95% by GC area percentage analysis. | [References]
[1] Patent: WO2014/139080, 2014, A1. Location in patent: Page/Page column 8; 9
[2] Patent: WO2014/140017, 2014, A1. Location in patent: Page/Page column 7
[3] Patent: US2014/275579, 2014, A1. Location in patent: Paragraph 0033
[4] Patent: WO2006/67430, 2006, A1. Location in patent: Page/Page column 50
[5] Patent: WO2018/132905, 2018, A1. Location in patent: Paragraph 00420-00422 |
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