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.)

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

form 

Liquid

pka

12.00±0.20(Predicted)

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 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:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

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.

Definition

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

Flammability and Explosibility

Not classified

2-Acetylbutyrolactone(517-23-7)Related Product Information

• N-ACETYL-L-TYROSINE ETHYL ESTER
• Acetyl coenzyme A sodium salt
• Dihydromyrcenol
• Acetylacetone
• Acetyl chloride
• tributyl acetocitrate
• Gamma Butyrolactone
• ALPHA-ACETYL-ALPHA-METHYL-GAMMA-BUTYROLACTONE
• Iragon Blue ABL9
• ABL PROTEIN TYROSINE KINASE,ABL PROTEIN TYROSINE KINASE, RECOMBINANT, E COLI
• ABL-21
• butalactin
• OXO-(2-OXO-TETRAHYDRO-FURAN-3-YL)-ACETIC ACID ETHYL ESTER
• Dihydro-3-(3-pyridoyl)-2-(3H)-furanone
• okilactomycin
• SETOSUSIN
• 2-CHLOROACETYL BUTYROLACTONE
• RK-682