2-Acetylbutyrolactone

Base Information

• Chemical Name: 2-Acetylbutyrolactone
• CAS No.: 517-23-7
• Deprecated CAS: 98634-97-0
• Molecular Formula: C6H8O3
• Molecular Weight: 128.128
• Hs Code.: 29322980
• European Community (EC) Number: 208-235-2
• NSC Number: 2019
• UNII: I3D73T5K0Q
• DSSTox Substance ID: DTXSID6044436
• Nikkaji Number: J6.575G
• Wikipedia: 2-Acetylbutyrolactone
• Wikidata: Q10863668
• Metabolomics Workbench ID: 4339
• ChEMBL ID: CHEMBL3187921
• Mol file: 517-23-7.mol

Synonyms:2-acetylbutyrolactone;4,5-dihydro-3-acetylfuran-2(3H)-one;alpha-acetyl-gamma-butyrolactone

Chemical Property of 2-Acetylbutyrolactone

Chemical Property:

• Appearance/Colour: Colorless to light yellow liquid
• Vapor Pressure: 0.0186mmHg at 25°C
• Melting Point: <25 °C
• Refractive Index: 1.4580 - 1.4620
• Boiling Point: 253.078 °C at 760 mmHg
• PKA: 12.00±0.20(Predicted)
• Flash Point: 128.244 °C
• PSA: 43.37000
• Density: 1.191 g/cm³
• LogP: 0.13850
• Storage Temp.: -20?C Freezer, Under Inert Atmosphere
• Solubility.: 200g/l
• Water Solubility.: 310 g/L (20 ºC)
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 128.047344113
• Heavy Atom Count: 9
• Complexity: 150

Purity/Quality:

99.00% ^*data from raw suppliers

BCR/ABL ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,T
• Statements: 36/37/38-61
• Safety Statements: 26-36-37/39-45-53

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Lactones
• Canonical SMILES: CC(=O)C1CCOC1=O
• 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
• Uses: An intermediate in the synthesis of 2,4-disubstituted pyridines. A fluorogenic reagent for the spectrofluorimetric determination of primary amines. In synthesis of 3,4-disubstituted pyridines; of 5-(b-hydroxethyl)-4-methylthiazole.

Technology Process of 2-Acetylbutyrolactone

There total 19 articles about 2-Acetylbutyrolactone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.9%

α-acetyl-γ-butyrolactone sodium → acetamide (60-35-5) + 3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7,594837-91-9,98634-97-0,313643-49-1)

Guidance literature:

With ethyl hydrazine hydrochloride; In methanol; at 10 - 20 ℃; for 2h; Temperature;

Reference yield: 96.0%

4-butanolide (96-48-0) + acetic acid methyl ester (79-20-9) → 3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7,594837-91-9,98634-97-0,313643-49-1)

Guidance literature:

4-butanolide; acetic acid methyl ester; With sodium methylate; In methanol; at 45 - 90 ℃; for 10h; under 750.075 Torr; Inert atmosphere; Large scale;

With carbon dioxide; In methanol; water; at 0 - 35 ℃; for 0.5h; under 6000.6 Torr; Temperature; Pressure; Reagent/catalyst; Large scale;

Reference yield: 93.0%

4-butanolide (96-48-0) + ethyl acetate (141-78-6) → 3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7,594837-91-9,98634-97-0,313643-49-1)

Guidance literature:

With sodium ethanolate; at 75 ℃; for 10h; Reflux;

upstream raw materials:

oxirane

ethanol

sodium ethyl acetylacetate enolate

2-chloro-ethanol

Downstream raw materials:

3-acetyl-3-methyl-dihydro-furan-2-one

2-acetyl-2-allyl-γ-butyrolactone

α-methylene-γ-butyrolactone

6-β-hydroxyethyl-2,5-dimethyl-7-oxo-pyrazolo[1,5-a]pyrimidine

Refernces

• 1、 -. "Preparation method of alpha-acetyl-gamma-butyrolactone". Paragraph 0053-0123. . Retrieved 2020/09/16.
• 2、 -. "Synthesis method for alpha-acetyl gamma-butyrolactone". Paragraph 0022-0047. . Retrieved 2018/04/21.