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2-Acetylbutyrolactone

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2-Acetylbutyrolactone Basic information

Product Name:
2-Acetylbutyrolactone
Synonyms:
  • -(-2-Hydroxyethyl)acetoaceticacid-lactone
  • 2-Acetyl-4-hydroxybutyric acid gamma-lactone
  • 2-Acetylbutyrolacton
  • 2-Oxo-3-acetyltetrahydrofuran
  • -Acetyl-hydroxybutyricacid
  • alpha-(2-Hydroxyethyl)acetoacetic acid gamma-lactone
  • alpha-Acetobutyrolactone
  • alpha-Acetylbutyrolactone
CAS:
517-23-7
MF:
C6H8O3
MW:
128.13
EINECS:
208-235-2
Product Categories:
  • Organic solvents
  • Heterocycles
  • Carbonyl Compounds
  • Lactones
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • ketone
  • Furan&Benzofuran
  • Organic Building Blocks
Mol File:
517-23-7.mol
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2-Acetylbutyrolactone Chemical Properties

Melting point:
<25 °C
Boiling point:
107-108 °C5 mm Hg(lit.)
Density 
1.19 g/mL at 25 °C(lit.)
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.
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)
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Safety Information

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

MSDS

  • Language:English Provider:ABL
  • Language:English Provider:ACROS
  • Language:English Provider:SigmaAldrich
  • Language:English Provider:ALFA
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2-Acetylbutyrolactone Usage And Synthesis

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.

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