2-Acetylbutyrolactone
ABL · 3-acetyldihydrofuran-2(3H)-one · α-Acetyl-γ-butyrolactone · ACETYLBUTYROLACTONE · α-Acetylbutyrolactone · a-Acetyl-y-Butyrolactone · alpha-Acetylbutyrolactone · 2-ACETYL-GAMMA-BUTYROLACTONE
Identifiers & Physical Properties
| CAS No. | 517-23-7 |
|---|---|
| Molecular formula | C6H8O3 |
| Average molar mass | 128.13 g/mol |
| Monoisotopic mass | 128.04734412 g/mol |
| SMILES | CC(=O)C1CCOC1=O |
| InChIKey | OMQHDIHZSDEIFH-UHFFFAOYSA-N |
| PubChem CID | 10601 |
| ChEMBL | CHEMBL3187921 |
| ChEBI | CHEBI:179633 |
| EC No. | 208-235-2 |
| DTXSID | DTXSID6044436 |
Chemical & Physical Properties
| XLogP | 0.1 |
|---|---|
| Topological polar surface area | 43.4 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 3 |
| Rotatable bonds | 1 |
| Heavy atoms | 9 |
| Formal charge | 0 |
| Complexity | 150 |
| Chemical classes | Other Classes -> Lactones |
| Lipids | Fatty Acyls [FA] -> Fatty esters [FA07] -> Lactones [FA0704] |
| Physical Description | LiquidLiquid with an ester-like odor[Merck Index] Clear colorless to pale yellow liquid[Acros Organics MSDS] |
| 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 conditions | Keep in dark place,Sealed in dry,Room Temperature |
| Solubility | 200g/l310 g/L (20 ºC) |
| pKa (acidity coefficient) | 12.00±0.20(Predicted) |
| Physical state | Liquid |
| Color | Clear |
| Biological source | human |
| Merck | 14,83 |
| Specific Activity | 717-971nmol/min·mg |
| BRN | 112676 |
| Stability | Stable. Incompatible with strong oxidizing agents, strong bases. |
| InChI | 1S/C6H8O3/c1-4(7)5-2-3-9-6(5)8/h5H,2-3H2,1H3 |
| InChIKey | OMQHDIHZSDEIFH-UHFFFAOYSA-N |
| SMILES | CC(=O)C1CCOC1=O |
| LogP (partition coefficient) | -0.43 at 22℃ |
| CAS DataBase Reference | 517-23-7(CAS DataBase Reference) |
| EWG's Food Scores | 1 |
| FDA UNII | I3D73T5K0Q |
| NIST Chemistry Reference | 2(3H)-Furanone, 3-acetyldihydro-(517-23-7) |
| EPA Substance Registry System | 2(3H)-Furanone, 3-acetyldihydro- (517-23-7) |
| UNSPSC Code | 12352202 |
| NACRES | NA.32 |
| GHS pictogram | GHS07,GHS08 |
| Signal word | Danger |
| GHS hazard statements | H315-H319-H360D |
| GHS precautionary statements | P202-P264-P280-P302+P352-P305+P351+P338-P308+P313 |
| Target organs | Respiratory system |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type ABEK (EN14387) respirator filter |
| Hazard symbols | Xi,T |
| Risk statements (R) | 36/37/38-61 |
| Safety statements (S) | 26-36-37/39-45-53 |
| Water hazard class (WGK) | 1 |
| RTECS number | LU3456000 |
| TSCA inventory status | TSCA listed |
| Customs code | 29322980 |
| Storage class | 10 - Combustible liquids |
| Hazard class | Eye Irrit. 2Skin Irrit. 2STOT SE 3 |
| REACH registrations | Active |
Safety & Regulations
| GHS classification | This chemical does not meet GHS hazard criteria for 0.5% (1 of 202) of reports.WarningH315 (97.5%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 202 reports by companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatory information | Chemical: 2(3H)-Furanone, 3-acetyldihydro-2(3H)-Furanone, 3-acetyldihydro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2(3H)-Furanone, 3-acetyldihydro- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 26-11-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/257152-Acetyl-gamma-butyrolactone: Does not have an individual approval but may be used under an appropriate group standard |
| Hazards summary | A skin and mucous membrane irritant[Merck Index] A skin and strong eye irritant[ECHA REACH Registrations] An irritant[Acros Organics MSDS] See beta-Butyrolactone and Butyrolactone. |
| Hazard Classes and Categories | Skin Irrit. 2 (97.5%) |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type ABEK (EN14387) respirator filter |
| Water hazard class (WGK) | 1 |
| TSCA inventory status | TSCA listed |
| RTECS number | LU3456000 |
| Customs code | 29322980 |
| Risk statements (R) | 36/37/38-61 |
| Signal word | Danger |
| GHS pictogram | GHS07,GHS08 |
| Hazard symbols | Xi,T |
| Safety statements (S) | 26-36-37/39-45-53 |
| Storage class | 10 - Combustible liquids |
| Target organs | Respiratory system |
| GHS hazard statements | H315-H319-H360D |
| REACH registrations | Active |
| Hazard class | Eye Irrit. 2Skin Irrit. 2STOT SE 3 |
| GHS precautionary statements | P202-P264-P280-P302+P352-P305+P351+P338-P308+P313 |
Applications & Uses
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.
Uses
In synthesis of 3,4-disubstituted pyridines; of 5-(b-hydroxethyl)-4-methylthiazole.