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CAS No.: | 517-23-7 |
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Name: | 2-Acetylbutyrolactone |
Article Data: | 32 |
Molecular Structure: | |
Formula: | C6H8O3 |
Molecular Weight: | 128.128 |
Synonyms: | Acetoaceticacid, 2-(2-hydroxyethyl)-, g-lactone (6CI,7CI);2-Acetyl-g-butyrolactone;2-Acetylbutanolide;2-Oxo-3-acetyltetrahydrofuran;3-Acetyl-4,5-dihydro-2(3H)-furanone;3-Acetyl-4,5-dihydrofuran-2-one;3-Acetyldihydro-2(3H)-furanone;3-Acetyldihydrofuran-2-one;3-Acetyltetrahydro-2-furanone;Dihydro-3-acetyl-2(3H)-furanone;NSC 2019;a-(2-Hydroxyethyl)acetoacetic acidg-lactone;a-Acetobutyrolactone;a-Acetyl-g-butyrolactone;a-Acetyl-g-hydroxybutyric acid g-lactone;a-Acetylbutyrolactone; |
EINECS: | 208-235-2 |
Density: | 1.191 g/cm3 |
Melting Point: | <25 °C |
Boiling Point: | 253.078 °C at 760 mmHg |
Flash Point: | 128.244 °C |
Solubility: | 310 g/L (20 °C) in water |
Appearance: | Colorless to light yellow liquid |
Hazard Symbols: | Xi |
Risk Codes: | 36/37/38 |
Safety: | 26-36-37/39 |
PSA: | 43.37000 |
LogP: | 0.13850 |
Conditions | Yield |
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With ethyl hydrazine hydrochloride In methanol at 10 - 20℃; for 2h; Temperature; | A 98.9% B 98.29% |
Conditions | Yield |
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Stage #1: 4-butanolide; acetic acid methyl ester With sodium methylate In methanol at 45 - 90℃; under 750.075 Torr; for 10h; Inert atmosphere; Large scale; Stage #2: With carbon dioxide In methanol; water at 0 - 35℃; under 6000.6 Torr; for 0.5h; Temperature; Pressure; Reagent/catalyst; Large scale; | 96% |
Conditions | Yield |
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With sodium ethanolate at 75℃; for 10h; Reflux; | 93% |
Stage #1: 4-butanolide; ethyl acetate With sodium methylate at 50 - 100℃; for 5h; Autoclave; Stage #2: With sulfuric acid at -5 - 5℃; for 5h; pH=6 - 7; | 83% |
With sodium at 80℃; for 8h; Mechanism; |
Conditions | Yield |
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With sodium hydrogencarbonate In ethyl acetate at 60 - 95℃; under 750.075 - 7500.75 Torr; for 3.5h; Solvent; Temperature; Reagent/catalyst; Autoclave; | 79.31% |
Conditions | Yield |
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With sodium hydroxide In ethanol; water at -5 - 0℃; for 50h; | 78% |
With triethylamine In methanol at 5 - 95℃; under 1500.15 - 2250.23 Torr; for 2.15 - 5h; Product distribution / selectivity; | 40.4% |
With N,N,N',N'-tetramethylguanidine In methanol at 5 - 65℃; under 1500.15 - 2250.23 Torr; for 1.15 - 6.18333h; Product distribution / selectivity; | 30.8% |
Conditions | Yield |
---|---|
Stage #1: 4-butanolide With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.25h; Inert atmosphere; Stage #2: acetic anhydride In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; | 42% |
oxirane
ethanol
sodium ethyl acetylacetate enolate
3-acetyl-2-oxo-4,5-dihydrofuran
Conditions | Yield |
---|---|
With ethanol |
ethanol
sodium ethyl acetylacetate enolate
2-chloro-ethanol
3-acetyl-2-oxo-4,5-dihydrofuran
Conditions | Yield |
---|---|
With sodium hydroxide 1.) water, EtOH, 0 deg C, 30 min, 2.) 0 - 5 deg C, 72 h; Yield given. Multistep reaction; | |
With sodium hydroxide; sulfuric acid In water; ethylene glycol |
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The 2-Acetylbutyrolactone, with the CAS registry number 517-23-7, is also known as 3-Acetyldihydro-2(3H)-furanone. It belongs to the product categories of Ketone; Furan & Benzofuran; Carbonyl Compounds; Lactones; Organic Building Blocks; Heterocycles; Intermediates & Fine Chemicals; Pharmaceuticals. Its EINECS registry number is 208-235-2. This chemical's molecular formula is C6H8O3 and molecular weight is 128.13. What's more, its IUPAC name is called 3-Acetyloxolan-2-one. It should be stored in a cool, dry and sealed place.
Physical properties about 2-Acetylbutyrolactone are: (1)ACD/LogP: -1.217; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.22; (4)ACD/LogD (pH 7.4): -1.22; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 5.19; (8)ACD/KOC (pH 7.4): 5.19; (9)#H bond acceptors: 3; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 43.37 Å2; (13)Index of Refraction: 1.459; (14)Molar Refractivity: 29.388 cm3; (15)Molar Volume: 107.507 cm3; (16)Polarizability: 11.65×10-24cm3; (17)Surface Tension: 39.39 dyne/cm; (18)Density: 1.192 g/cm3; (19)Flash Point: 128.244 °C; (20)Enthalpy of Vaporization: 49.045 kJ/mol; (21)Boiling Point: 253.078 °C at 760 mmHg; (22)Vapour Pressure: 0.019 mmHg at 25 °C.
Preparation of 2-Acetylbutyrolactone: this chemical can be prepared by oxirane with acetoacetic acid methyl ester. This reaction needs reagent sodium hydroxide and solvents H2O, ethanol at temperature of -5 – 0 °C. The reaction time is 50 hours. The yield is 78 %.
Uses of 2-Acetylbutyrolactone: (1) it is an important intermediate to synthesize vitamin B,3,4 - disubstituted pyridine and 5-(β-hydroxyethyl) -4- methyl-thiazole. (2) it is used to produce other chemicals. For example, it can react with methanol to get 2-methyl-4,5-dihydro-furan-3-carboxylic acid methyl ester. The reaction occurs with reagent hydrogen chloride and other condition of heating for 4 days. The yield is 19 %.
When you are dealing with this chemical, you should be very careful. This chemical is inflammation to the skin, eyes and respiratory system or other mucous membranes. Therefore, you should wear suitable protective clothing, gloves and eye/face protection. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1) SMILES: O=C1OCCC1C(=O)C
(2) InChI: InChI=1S/C6H8O3/c1-4(7)5-2-3-9-6(5)8/h5H,2-3H2,1H3
(3) InChIKey: OMQHDIHZSDEIFH-UHFFFAOYSA-N