Γ-Butyrolactone
| Names | |
|---|---|
| Preferred IUPAC name
Oxolan-2-one | |
| Other names
Dihydrofuran-2(3H)-one GBL Butyrolactone 1,4-Lactone 4-Butyrolactone 4-Hydroxybutyric acid lactone gamma-Hydroxybutyric acid lactone | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| DrugBank | |
| ECHA InfoCard | 100.002.282 |
| KEGG | |
PubChem CID |
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| RTECS number |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C4H6O2 | |
| Molar mass | 86.090 g·mol−1 |
| Appearance | Colorless liquid |
| Odor | Weak characteristic odor, comparable to stale water, synthetic melon aroma or burnt plastic |
| Density | 1.1286 g/mL (15 °C), 1.1296 g/mL (20 °C) |
| Melting point | −43.53 °C (−46.35 °F; 229.62 K) |
| Boiling point | 204 °C (399 °F; 477 K) |
| Miscible | |
| Solubility | Soluble in CCl4, methanol, ethanol, acetone, benzene, ethyl ether |
| log P | −0.76 |
| Vapor pressure | 1.5 kPa (20 °C) |
| Acidity (pKa) | 4.5 |
Refractive index (nD) |
1.435, 1.4341 (20 °C) |
| Viscosity | 1.7 cP (25 °C) |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards |
Toxic and flammable |
| GHS labelling: | |
| Danger | |
| H302, H318, H336 | |
| P264, P270, P280, P301+P312, P305+P351+P338, P403+P233, P501 | |
| NFPA 704 (fire diamond) | |
| Flash point | 98 °C (208 °F; 371 K) (closed cup) |
| 455 °C (851 °F; 728 K) | |
| Explosive limits | 3.6% v/v (lower) 16% v/v (upper) |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose) |
1540 mg/kg (oral, rat) >5640 mg/kg (dermal, rabbit) |
LC50 (median concentration) |
>2.68 mg/kg (rat, 4h) |
| Safety data sheet (SDS) | Fisher Scientific |
| Legal status |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references | |
γ-Butyrolactone (GBL) or gamma-butyrolactone is an organic compound with the formula O=CO(CH2)3. It is a hygroscopic, colorless, water-miscible liquid with a weak characteristic odor. It is the simplest 4-carbon lactone. It is mainly used as an intermediate in the production of other chemicals, such as N-methyl-2-pyrrolidone.
In humans, GBL acts as a prodrug for gamma-hydroxybutyric acid (GHB) and is often used as a recreational drug. GHB acts as a central nervous system (CNS) depressant with effects similar to those of barbiturates.