gamma-Butyrolactone

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
CAS Number	96-48-0 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:42639 ;
ChEMBL	ChEMBL95681 ;
ChemSpider	7029 ;
DrugBank	DB04699 ;
ECHA InfoCard	100.002.282
IUPHAR/BPS	5462;
KEGG	C01770 ;
PubChem CID	7302;
RTECS number	LU3500000;
UNII	OL659KIY4X ;
CompTox Dashboard (EPA)	DTXSID6020224 ;
	InChI InChI=1S/C4H6O2/c5-4-2-1-3-6-4/h1-3H2 Key: YEJRWHAVMIAJKC-UHFFFAOYSA-N ; InChI=1/C4H6O2/c5-4-2-1-3-6-4/h1-3H2 Key: YEJRWHAVMIAJKC-UHFFFAOYAC;
	SMILES O=C1OCCC1;
Properties
Chemical formula	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)
Solubility in water	Miscible
Solubility	Soluble in CCl4, methanol, ethanol, acetone, benzene, ethyl ether
log P	−0.76
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:
Hazard statements	H302, H318, H336
Precautionary statements	P264, P270, P280, P301+P312, P305+P351+P338, P403+P233, P501
Flash point	98 °C (208 °F; 371 K) (closed cup)
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	17.2 mL/kg (orally, rat)
Legal status	BR: Class B1 (Psychoactive drugs);
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Gamma-butyrolactone (GBL) or γ-butyrolactone 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.

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