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
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)
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.
N-Bromosuccinimide Price
- Product number
- A13409
- Product name
- α-Acetylbutyrolactone
- Purity
- ≥99%
- Packaging
- 100g
- Price
- $42.4
- Updated
- 2025/07/31
- Product number
- A13409
- Product name
- α-Acetylbutyrolactone
- Purity
- ≥99%
- Packaging
- 500g
- Price
- $46.8
- Updated
- 2025/07/31
- 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
- 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
- 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
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
- 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
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View Lastest Price from 2-Acetylbutyrolactone manufacturers
- 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
- Product
- 2-Acetylbutyrolactone 517-23-7
- Price
- US $0.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 5000mt
- Release date
- 2022-02-17
- 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