2-Acetylbutyrolactone

Description Reference

Product Name: 2-Acetylbutyrolactone
CAS No.: 517-23-7
Chemical Name: 2-Acetylbutyrolactone
Synonyms: ABL;3-acetyldihydrofuran-2(3H)-one;ABL1;ACETYLBUTYROLACTONE;2-Acetylbutyrolacton;-Acetyl-hydroxybutyricacid;2-Oxo-3-acetyltetrahydrofuran;JTK7;p190;CHDSKM
CBNumber: CB8101532
Molecular Formula: C6H8O3
Formula Weight: 128.13
MOL File: 517-23-7.mol

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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
biological source: human
Water Solubility: 310 g/L (20 ºC)
Merck: 14,83
Specific Activity: 717-971nmol/min·mg
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)

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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

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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.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: A13409
Product name: α-Acetylbutyrolactone
Purity: ≥99%
Packaging: 100g
Price: $42.4
Updated: 2025/07/31

Sigma-Aldrich

Product number: A13409
Product name: α-Acetylbutyrolactone
Purity: ≥99%
Packaging: 500g
Price: $46.8
Updated: 2025/07/31

Sigma-Aldrich

Product number: SRP5279
Product name: ABL1, active, His tagged human
Purity: PRECISIO<SUP>®</SUP>, recombinant, expressed in baculovirus infected <I>Sf</I>9 cells, ≥7
Packaging: 10 μg
Price: $456
Updated: 2025/07/31

Sigma-Aldrich

Product number: A0608
Product name: ABL1 (27-end), active, His-tagged from mouse
Purity: PRECISIO? Kinase, recombinant, expressed in baculovirus infected Sf9 cells, ≥70% (SDS-PAGE), buffered aqueous glycerol solution
Packaging: 10μG
Price: $457
Updated: 2025/07/31

Sigma-Aldrich

Product number: SRP5279
Product name: ABL1, active, His tagged human
Purity: PRECISIO?, recombinant, expressed in baculovirus infected Sf9 cells, ≥70% (SDS-PAGE), buffered aqueous glycerol solution
Packaging: 10μG
Price: $498
Updated: 2023/06/20

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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.¹Moreover, 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

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.
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.
Horne, D. A.; Fugmann, B.; Yakushijin, K.; Buchi, G., A SYNTHESIS OF PILOCARPINE. J. Org. Chem. 1993, 58, 62-64.
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

Biological Activity

ABL1 protooncogene encodes a cytoplasmic and nuclear protein tyrosine kinase th at has been implicated in processes of cell differentiation, cell division, cell adhesion, and stress response. Activity of ABL protein is negatively regulated by its SH3 domain and deletion of the SH3 domain turns ABL1 into an oncogene. Translocation and head-to-tail fusion of the BCR and ABL1 genes is present in many cases of chronic myelogeneous leukemia. The DNA-binding activity of the ubiquitously expressed ABL1 tyrosine kinase is regulated by CDK1-mediated phosphorylation, suggesting a cell cycle function for ABL1.

Synthesis

75-21-8

105-45-3

517-23-7

Example 2: Ethylene oxide (EO, 25.0 g, 1.4 eq.) was slowly added to a methanol (MeOH, 144.0 g) solution of methyl acetoacetate (MAA, 46.9 g, 0.40 mol) followed by triethylamine (TEA, 40.7 g, 1.0 eq.) at 5°C. The reaction mixture was warmed up to 60 °C within 0.5 h and maintained at this temperature for 2.5 h. The reaction mixture was then heated up to 60 °C within 0.5 h and maintained at this temperature for 2.5 h. Quantitative GC analysis showed 50.8% conversion of MAA and 72.9% selectivity of α-acetyl-γ-butyrolactone (ABL). Example 4: Ethylene oxide (EO, 35.3 g, 2.0 eq.) was slowly added to a methanol (MeOH, 144 g) solution of methyl acetoacetate (MAA, 47.0 g, 0.40 mol) at 5 °C, followed by triethylamine (TEA, 42.4 g, 1.0 eq.). The reaction mixture was warmed up to 60 °C within 0.5 h and maintained at this temperature for 4.5 h. The reaction mixture was then heated up to 60 °C within 0.5 h and maintained at this temperature for 4.5 h. Quantitative GC analysis showed 67.7% conversion of MAA and 75.0% selectivity of α-acetyl-γ-butyrolactone (ABL). Examples 7-27: The reaction was carried out according to the method of Example 1 by adjusting the amount of ethylene oxide (EO), the optional addition of the catalysts and additives specified in Table 1, and the reaction times specified in Table 1. Table 1 details the reaction conditions, conversion and selectivity data for Examples 7-27. All reactions of Examples 7-26 were carried out at 60°C using 11 equivalents of methanol as solvent and 0.40 equivalents of MAA. Examples 27 and 28, on the other hand, used 0.10 eq. of MAA and 1 eq. of EO at 60 °C, using 11 eq. of methanol as solvent. Example of Example 28: Example of optimal reaction conditions using triethylamine (TEA) as a catalyst: 37 g of methanol was added to a 250 mL autoclave, pressurized with 2-3 bar nitrogen and heated to 65 °C. Subsequently, a solution of MAA (39.9 g, 0.34 mol, 1 eq.) and triethylamine (TEA, 34.4 g, 0.34 mol, 1 eq.) in methanol (27 g) with ethylene oxide (EO, 30.1 g, 0.68 mol, 2 eq.) was added simultaneously via two pumps over 11 min. After 2 h of reaction, analysis by GC showed a selectivity of 77% for ABL and a yield of 52.3% based on the added MAA. The conditions for this series of reactions ranged from 65 to 95 °C, addition times from 9 to 13 min, concentrations of MAA in the solvent from 1.3 to 2.1 mol/L, TEA/MAA molar ratios from 0.7 to 1.3, and EO/MAA molar ratios from 1.7 to 2.2.The results of this series of reactions showed MAA conversions ranging from 65.6 to 85.0%, ABL selectivities of 47.5-77.4% and the yield of ABL based on MAA was 40.4-52.3%.

References

[1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1985, p. 2585 - 2598
[2] Patent: EP1911752, 2008, A1. Location in patent: Page/Page column 6; 7; 7-8; 8
[3] Patent: EP1911752, 2008, A1. Location in patent: Page/Page column 6; 7; 8; 8-9
[4] Patent: EP1911752, 2008, A1. Location in patent: Page/Page column 7; 8; 9
[5] Patent: EP1911752, 2008, A1. Location in patent: Page/Page column 7; 8

2-Acetylbutyrolactone Preparation Products And Raw materials

Raw materials

Ethyl acetoacetate Acetyl ketene ETHYLENE OXIDE Methyl acetoacetate Vinyl acetate Sodium hydroxide METHANE Gamma Butyrolactone

Preparation Products

Thiamine chloride 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one Fursultiamine

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View Lastest Price from 2-Acetylbutyrolactone manufacturers

Shandong Vital Biotechnology Co., Ltd.

Product: 2-Acetylbutyrolactone 517-23-7
Price: US $0.00-0.00/kg
Min. Order: 1kg
Purity: 98%
Supply Ability: 100tons
Release date: 2025-11-20

Jinan Finer Chemical Co., Ltd

Product: 2-Acetylbutyrolactone 517-23-7
Price: US $0.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 5000mt
Release date: 2022-02-17

Qingdao RENAS Polymer Material Co., Ltd.

Product: 2-Acetylbutyrolactone 517-23-7
Price: US $0.00/kg
Min. Order: 20kg
Purity: 99%
Supply Ability: 20 tons
Release date: 2025-03-24

517-23-7, 2-AcetylbutyrolactoneRelated Search:

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 ABL PROTEIN TYROSINE KINASE,ABL PROTEIN TYROSINE KINASE, RECOMBINANT, E COLI ABL-21 Acid Blue 9 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

-(-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

alpha-Acetyl-gamma-hydroxybutyric acid gamma-lactone

2-ACETYL-GAMA-BUTYROLACTONE

2-ACETYL-GAMMA-BUTYROLACTONE

2-ACETYLBUTYROLACTONE

2-ACETYL-4-BUTANOLIDE

2-ACETOBUTANOATE-4-LACTONE

AKOS BBS-00004292

AKOS NCG-0049

ALPHA-ACETYL-GAMMA-BUTYROLACTONE

ALPHA-ACETYL-GAMMA-HYDROXYBUTYRIC ACID LACTONE

ABL

ACETYLBUTYROLACTONE

3-Acetyloxolane-2-one

3-acetyl-dihydro-2(3h)-furanone

3-ACETYL-DIHYDRO-FURAN-2-ONE

OMEGA-ACETYL-GAMMA-BUTYROLACTONE

2-acetyl-4-butyrolactone

2-Acetyl-gaMMa-butyrolactone for synthesis

3-Acetotetrahydrofuranone-2

NSC 2019

α-Acetyl-γ-hydroxybutyric Acid γ-Lactone

2-AcetylbutyrolaCLone

2-ACETYL-G-BUTYROLACTONE FOR SYNTHESIS

The2- acetyl-butyrolactone

α-Acetylbutyrolactone, 98%+

Anti-Abl-interactor protein 1

Anti-eps8 binding

Anti-interactor protein AblBP4

Anti-Nap1 binding protein NAP1BP

Anti-spectrin SH3 domain binding protein 1 SSH3BP1

ABL1, active, His tagged human

bcr/abl

ABL1 (27-end), active, His-tagged from mouse

ANTI-C ABL (ABL1)(C-TERMINAL) antibody produced in rabbit

Anti-eps8 binding protein

Abelson murine leukemia viral oncogene homolog 1

ABL1

ANTI-PHOSPHO-ABL(Y204) antibody produced in rabbit

JTK7

Monoclonal Anti-ABL1 antibody produced in mouse

ANTI-PHOSPHO-ABL(Y412) antibody produced in rabbit

Anti-Abelson interactor 1

3-acetyldihydrofuran-2(3H)-one

butyroL

Alpha - acetyl - -butyllactone

3-Acetyl-2-(3H)-4,-5-dihydrofuranone

3-Acetyl-2(3H)-4,5-dihydrofuranone

3-acetyldihydro-2(3h)-furanon

3-Acetyltetrahydro-2-furanone

-Acetobutyrolacton