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gamma-Butyrolactone

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Name gamma-Butyrolactone EINECS 202-509-5
CAS No. 96-48-0 Density 1.128 g/cm3
Solubility Melting Point -45 °C(lit.)
Formula C4H6O2 Boiling Point 204 °C at 760 mmHg
Molecular Weight 86.09 Flash Point 80.9 °C
Transport Information Appearance colourless oily liquid
Safety 26-36-39 Risk Codes 22-36
Molecular Structure Molecular Structure of 96-48-0 (2(3H)-Furanone,dihydro-) Hazard Symbols HarmfulXn
Synonyms

1,4-Butanolide;1-Oxacyclopentan-2-one;2,3,4,5-Tetrahydro-2-furanone;2-Oxolanone;2-Oxotetrahydrofuran;4,5-Dihydro-2(3H)-furanone;4-Butanolide;4-Deoxytetronicacid;4-Hydroxybutanoic acid lactone;4-Hydroxybutyric acid lactone;Butanoicacid, 4-hydroxy-, g-lactone;Butyric acid lactone;Butyrolactone;Dihydro-2(3H)-furanone;NIH 10540;NSC 4592;Paint Clean G;Tetrahydro-2-furanone;g-BL;g-Butalactone;g-Butyrolactone;g-Butyryllactone;g-Hydroxybutyric acid lactone;1,4-Butyrolactone;gamma-Butyrolactone;

 

Consensus Reports

 IARC Cancer Review: Group 3 IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 (1987),p. 56.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal No Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 11 (1976),p. 231.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . EPA Genetic Toxicology Program. Reported in EPA TSCA Inventory.

Specification

The gamma-Butyrolactone is an organic compound with the formula C4H6O2. The IUPAC name of this chemical is oxolan-2-one. With the CAS registry number 96-48-0, it is also named as 1-Oxacyclopentan-2-one. The product's category is Pharmaceutical Intermediates. Besides, gamma-Butyrolactone (γ-butyrolactone or GBL) is a hygroscopic colorless oily liquid with a weak characteristic odor and is soluble in water, which should be stored in a cool and ventilated place.

Physical properties about gamma-Butyrolactone are: (1)ACD/LogP: -0.76; (2)ACD/LogD (pH 5.5): -0.76; (3)ACD/LogD (pH 7.4): -0.76; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 9.15; (7)ACD/KOC (pH 7.4): 9.15; (8)#H bond acceptors: 2; (9)Polar Surface Area: 26.3 Å2; (10)Index of Refraction: 1.442; (11)Molar Refractivity: 20.18 cm3; (12)Molar Volume: 76.2 cm3; (13)Polarizability: 8×10-24cm3; (14)Surface Tension: 35.4 dyne/cm; (15)Density: 1.128 g/cm3; (16)Flash Point: 80.9 °C; (17)Enthalpy of Vaporization: 44.02 kJ/mol; (18)Boiling Point: 204 °C at 760 mmHg; (19)Vapour Pressure: 0.27 mmHg at 25°C.

Preparation of gamma-Butyrolactone: gamma-Butyrolactone can be prepared by gamma-hydroxybutyric acid (GHB) by removal of water or by distillation from such a mixture. It may also be obtained via oxidation of tetrahydrofuran (THF). One such process, which affords GBL in yields of up to 80%, utilises bromine generated in situ from an aqueous solution of sodium bromate and potassium hydrogen sulfate. Another process can proceed by using commercially-available calcium hypochlorite in the presence of activating acetic acid and an appropriate solvent such as acetonitrile.

Uses of gamma-Butyrolactone: GHB (gamma hydroxybutyrate) and GBL (gamma butyrolactone) are substances which are often used as recreational drugs. GHB has two effects, at low doses it has a euphoric effect (which is why it is sometimes referred to as liquid ecstasy). At higher doses it acts like a sedative and can make the user unconscious very quickly.

When you are using this chemical, please be cautious about it as the following: It is harmful if swallowed. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Besides, this chemical is irritating to eyes. When you are using it, wear suitable protective clothing and eye/face protection.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C1OCCC1
(2)InChI: InChI=1/C4H6O2/c5-4-2-1-3-6-4/h1-3H2
(3)InChIKey: YEJRWHAVMIAJKC-UHFFFAOYAC
(4)Std. InChI: InChI=1S/C4H6O2/c5-4-2-1-3-6-4/h1-3H2
(5)Std. InChIKey: YEJRWHAVMIAJKC-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 skin > 5gm/kg (5000mg/kg)   GAF Material Safety Data Sheet.
mouse LD50 intraperitoneal 1100mg/kg (1100mg/kg) BEHAVIORAL: GENERAL ANESTHETIC

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Archivum Immunologiae et Therapiae Experimentalis. Vol. 13, Pg. 70, 1965.
mouse LD50 oral 1460mg/kg (1460mg/kg) BEHAVIORAL: GENERAL ANESTHETIC

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 64(2), Pg. 3, 1999.
mouse LDLo parenteral 1600mg/kg (1600mg/kg)   "Summary Tables of Biological Tests," National Research Council Chemical-Biological Coordination Center. Vol. 7, Pg. 687, 1955.
rabbit LDLo intravenous 500mg/kg (500mg/kg)   Archivum Immunologiae et Therapiae Experimentalis. Vol. 13, Pg. 70, 1965.
rat LC50 inhalation > 5100mg/m3/4H (5100mg/m3)   National Technical Information Service. Vol. OTS0534527,
rat LD50 intraperitoneal 1gm/kg (1000mg/kg) BEHAVIORAL: GENERAL ANESTHETIC

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Archivum Immunologiae et Therapiae Experimentalis. Vol. 13, Pg. 70, 1965.
rat LD50 oral 1540mg/kg (1540mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 31(1), Pg. 49, 1987.

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