Dihydrofuran-3(2H)-one Chemical Properties

Boiling point:

68°C/60mmHg(lit.)

Density 

1.1124 g/cm3(Temp: 420 °C)

refractive index 

1.4360-1.4400

Flash point:

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

Safety Information

Hazard Codes 

Xn

Risk Statements 

11-19-36/37/38-22

Safety Statements 

16-26-36/37/39-23

RIDADR 

1993

HazardClass 

3

PackingGroup 

III

HS Code 

2932190090

Dihydrofuran-3(2H)-one Usage And Synthesis

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

Dihydrofuran-3(2H)-one(22929-52-8)Related Product Information

• 2-Methyltetrahydrofuran
• TETRAHYDRO-3-FURANMETHANOL
• Tetrahydrofurfuryl bromide
• Tetrahydrofuran
• Poly(tetrahydrofuran)
• 3-METHYLTETRAHYDROFURAN
• Furan
• Furazolidone
• 4-Methoxy-2,5-dimethyl-3(2H)-furanone
• Furaneol acetate
• 2-Methyltetrahydrofuran-3-one
• TETRONIC ACID
• DEHYDROASCORBIC ACID
• DIHYDRO-4,4-DIMETHYL-2,3-FURANDIONE
• D-(-)-PANTOLACTONE
• gamma-Octanoic lactone
• 3-CHLORO-2,4(3H,5H)-FURANDIONE
• 1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-RIBO-3-HEXULOFURANOSE