Name: 2-Acetylbutyrolactone
SKU: 517-23-7

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Basic Information

Molecular Structure:
CAS No.:	517-23-7
Name:	2-Acetylbutyrolactone

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

Synthetic route

: α-acetyl-γ-butyrolactone sodium

A: 60-35-5
acetamide

B: 517-23-7
3-acetyl-2-oxo-4,5-dihydrofuran

Conditions

Conditions	Yield
With ethyl hydrazine hydrochloride In methanol at 10 - 20℃; for 2h; Temperature;	A 98.9% B 98.29%

: 96-48-0
4-butanolide

: 79-20-9
acetic acid methyl ester

: 517-23-7
3-acetyl-2-oxo-4,5-dihydrofuran

Conditions

Conditions	Yield
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%

: 96-48-0
4-butanolide

: 141-78-6
ethyl acetate

: 517-23-7
3-acetyl-2-oxo-4,5-dihydrofuran

Conditions

Conditions	Yield
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;

: 96-48-0
4-butanolide

: 75-07-0
acetaldehyde

: 517-23-7
3-acetyl-2-oxo-4,5-dihydrofuran

Conditions

Conditions	Yield
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%

: 75-21-8
oxirane

: 105-45-3
acetoacetic acid methyl ester

: 517-23-7
3-acetyl-2-oxo-4,5-dihydrofuran

Conditions

Conditions	Yield
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%

: 96-48-0
4-butanolide

: 108-24-7
acetic anhydride

: 517-23-7
3-acetyl-2-oxo-4,5-dihydrofuran

Conditions

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%

: 75-21-8
oxirane

: 64-17-5
ethanol

: 1007476-32-5
sodium ethyl acetylacetate enolate

: 517-23-7
3-acetyl-2-oxo-4,5-dihydrofuran

...Expand

: 75-21-8
oxirane

: 1007476-32-5
sodium ethyl acetylacetate enolate

: 517-23-7
3-acetyl-2-oxo-4,5-dihydrofuran

Conditions

Conditions	Yield
With ethanol

: 64-17-5
ethanol

: 1007476-32-5
sodium ethyl acetylacetate enolate

: 107-07-3
2-chloro-ethanol

: 517-23-7
3-acetyl-2-oxo-4,5-dihydrofuran

...Expand

: 75-21-8
oxirane

: 141-97-9
ethyl acetoacetate

: 517-23-7
3-acetyl-2-oxo-4,5-dihydrofuran

Conditions

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

Raw Materials

2280-44-6

75-21-8

107-07-3

141-52-6

75-36-5

7647-01-0

64-17-5

105-45-3

Downstream Products

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Specification

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 %.

2-Acetylbutyrolactone can be prepared by oxirane with acetoacetic acid methyl ester.

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 %.

2-Acetylbutyrolactone can react with methanol to get 2-methyl-4,5-dihydro-furan-3-carboxylic acid methyl ester.

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

517-23-7

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Specification