2-Acetylbutyrolactone Property

Melting point:

<25 °C

Boiling point:

107-108 °C5 mm Hg(lit.)

Density 

1.19 g/mL at 25 °C(lit.)

vapor pressure 

0.131Pa at 20℃

refractive index 

n20/D 1.459(lit.)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

200g/l

pka

12.00±0.20(Predicted)

form 

Liquid

color 

Clear

Water Solubility 

310 g/L (20 ºC)

Merck 

14,83

BRN 

112676

Stability:

Stable. Incompatible with strong oxidizing agents, strong bases.

LogP

-0.43 at 22℃

CAS DataBase Reference

517-23-7(CAS DataBase Reference)

NIST Chemistry Reference

2(3H)-Furanone, 3-acetyldihydro-(517-23-7)

EPA Substance Registry System

2(3H)-Furanone, 3-acetyldihydro- (517-23-7)

Safety

Hazard Codes 

Xi,T

Risk Statements 

36/37/38-61

Safety Statements 

26-36-37/39-45-53

WGK Germany 

1

RTECS 

LU3456000

TSCA 

Yes

HS Code 

29322980

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P202Do not handle until all safety precautions have been read and understood.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P308+P313IF exposed or concerned: Get medical advice/attention.

2-Acetylbutyrolactone Chemical Properties,Usage,Production

Description

It is an important intermediate involved in the synthesis of chemical and pharmaceutical products such as vitamin B, 3,4-substituted pyridine, 5-(2-Hydroxyethyl)-4-methylthiazole. In presence of 2-acetylbutyrolactone, reaction of tert-butyl isocyanide with dialkyl acetylenedicarboxylates leads to the formation of dialkyl (E)-2-{(tert-butylamino)[2-oxo-4,5-dihydro-3(2H)-furanylidene]methyl}-2-butenedioates.¹ Moreover, reaction of 2-acetylbutyrolactone with thiosemicarbazide and 3-(2-bromo-acetyl)-chromen-2-one in anhydrous ethanol produced 3-{2-[5-hydroxyl-4-(2-hydroxyl-ethyl)-3-methyl-pyrazol-1-yl]-thiazol-4-yl}-chromen-2-one in good yields.² In addition, 2-acetylbutyrolactone can also function as the raw material for synthesizing pilocarpine that is a leading therapeutic agent for the treatment of narrow and wide angle glaucoma.³ Besides, this chemical can also act as a fluorogenic reagent in the quantitative spectrofluorometric determination of primary amines, which has been demonstrated to be equally accurate and precise as the officially or other reported methods.⁴

Reference

1. Asghari, S.; Mohammadi, L., Reaction of tert-butyl isocyanide and dialkyl acetylenedicarboxylates in the presence of 2-acetylbutyrolactone. Synthesis of functionalized alpha-methylene-gamma-butyrolactones. Tetrahedron Lett. 2006, 47, 4297-4299.
2. Rao, V. R.; Kumar, P. V., Facile one-pot synthesis of 3-{25-hydroxy-4-(2-hydroxy-ethyl)-3-methyl-pyrazol-1-yl -thiazol-4-yl} -chromen-2-ones via a three-component reaction. Synth. Commun. 2006, 36, 2157-2161.
3. Horne, D. A.; Fugmann, B.; Yakushijin, K.; Buchi, G., A SYNTHESIS OF PILOCARPINE. J. Org. Chem. 1993, 58, 62-64.
4. Sabry, S. M., Application of 2-acetylbutyrolactone to spectrofluorinietry: Fluorescence properties of Schiff bases derived from 2-acetylbutyrolactone and spectrofluorimetric determination of primary amine-containing compounds. J. Pharm. Biomed. Anal. 2006, 40, 1057-1067.

Chemical Properties

Colorless to light yellow liqui

Uses

An intermediate in the synthesis of 2,4-disubstituted pyridines. A fluorogenic reagent for the spectrofluorimetric determination of primary amines.

Uses

In synthesis of 3,4-disubstituted pyridines; of 5-(b-hydroxethyl)-4-methylthiazole.

Definition

ChEBI: 3-Acetyldihydro-2(3H)-furanone is a gamma-lactone.

Flammability and Explosibility

Not classified