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Gamma-Butyrolactone

γ-Butyrolactone (GBL) 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, e.g. methyl-2-pyrrolidone. GBL In humans it acts as a prodrug for γ-hydroxybutyric acid (GHB), and it is used as a recreational intoxicant with effects similar to barbiturates.

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Further Information

Names

Preferred IUPAC name: Oxolan-2-one

Other names

Dihydrofuran-2(3)-one
GBL
Butyrolactone
1,4-Lactone
4-Butyrolactone
4-Hydroxybutyric acid lactone
gamma-Hydroxybutyric acid lactone

Identifiers

CAS Number: 96-48-0

JSmol: Interactive image

ChEBI: CHEBI:42639

ChEMBL: ChEMBL95681

ChemSpider: 7029

DrugBank: DB04699

ECHA InfoCard: 100.002.282

IUPHAR/BPS: 5462

KEGG: C01770

PubChem: 7302

RTECS number: LU3500000

UNII: OL659KIY4X

Properties

Chemical formula: C4H6O2

Molar mass: 86.09 g·mol

Appearance: Colorless liquid

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)

Solubility in water: Miscible

Solubility: CCl

log : -0.76

K: 4.5

Refractive index: 1.435, 1.4341 (20 °C)

Viscosity: 1.7 cp (25 °C)

Hazards

hazards: Harmful

GHS hazard statements: H318 H302 H336

GHS precautionary statements: P264 P270 P280 P301+312 P305+351+338 P403+233 P501

Flash point: 98 °C (208 °F; 371 K) (closed cup)

median dose: 17.2 mL/kg (orally, rat)

Except where otherwise noted, data are given for materials in their(at 25 °C [77 °F], 100 kPa).Except where otherwise noted, data are given for materials in their(at 25 °C [77 °F], 100 kPa).