gamma-Butyrolactone supplier

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Name
gamma-Butyrolactone
EINECS 202-509-5
CAS No. 96-48-0
Article Data494
CAS DataBase
Density 1.128 g/cm³
Solubility MISCIBLE
Melting Point -45 °C(lit.)
Formula C₄H₆O₂
Boiling Point 204 °C at 760 mmHg
Molecular Weight 86.0904
Flash Point 80.9 °C
Transport Information
Appearance colourless oily liquid
Safety 26-36-39
Risk Codes 22-36
Molecular Structure
Hazard Symbols Xn
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;
PSA 26.30000
LogP 0.32340

Synthetic route

: 6117-80-2
1,4-butenediol

: 96-48-0
4-butanolide

Conditions

Conditions	Yield
With 5 wt% Pd nanoparticles loaded on phosphate anion exchanged [Mg6Al2(OH)16]CO3*xH2O; air at 50℃; under 760.051 Torr; for 6h; Reagent/catalyst; Irradiation;	100%
With acetone; dihydridotetrakis(triphenylphosphine)ruthenium In toluene at 180℃; for 3h;	88 % Chromat.

: 3128-06-1
5-ketohexanoic acid

: 96-48-0
4-butanolide

Conditions

Conditions	Yield
With 5% active carbon-supported ruthenium; isopropyl alcohol at 160℃; for 0.416667h; Reagent/catalyst; Temperature; Microwave irradiation;	100%
With hydrogen In 1,4-dioxane at 180℃; under 37503.8 Torr; for 3h; Reagent/catalyst; Solvent; Autoclave;

: 98-01-1
furfural

: 110-63-4
Butane-1,4-diol

A: 534-22-5
2-methylfuran

B: 96-48-0
4-butanolide

Conditions

Conditions	Yield
With hydrogen; Cu-based catalyst at 210℃; Product distribution; Further Variations:; Temperatures; reaction in vapour phase, fixed bed reactor, coupled dehydrogenation reactions of title comp. and INO 160;	A 96.5% B 99.4%

...Expand

: 1191-95-3
cyclobutanone

: 96-48-0
4-butanolide

Conditions

Conditions	Yield
With oxone; silica gel In dichloromethane at 20℃; for 1h; Baeyer-Villiger oxidation;	99%
With acyltransferase from Mycobacterium smegmatis; dihydrogen peroxide; ethyl acetate In water at 35℃; for 2h; Baeyer-Villiger Ketone Oxidation; Enzymatic reaction;	99%
With 2,2,2-trifluoroethanol; dihydrogen peroxide for 24h; Ambient temperature;	98%

: 925-57-5
methyl 4-hydroxybutanoate

: 96-48-0
4-butanolide

Conditions

Conditions	Yield
With C16H25N3O2S In n-heptane for 3h; Reflux; Molecular sieve; Inert atmosphere;	99%
With C16H25N3O2S In n-heptane for 48h; Reflux; Molecular sieve;	99%
In hexane at 26℃; porcine pancreatic lipase (PPL);
With porcine pancreatic lipase (E.(1)C313) In diethyl ether at 26℃; Yield given;

: 497-23-4
2-buten-4-olide

: 96-48-0
4-butanolide

Conditions

Conditions	Yield
With hydrogen In methanol under 26252.6 Torr; for 2h; Reagent/catalyst; Autoclave;	99%
With 0.5% palladium on silica gel; hydrogen In methanol at 80℃; under 26252.6 Torr; Catalytic behavior; Kinetics; Reagent/catalyst; Autoclave;	92.6%
With Ni#NiO; hydrogen In ethanol at 80℃; under 22502.3 Torr; for 1h; Reagent/catalyst; Autoclave;	86.6%

: 110-16-7
maleic acid

A: 109-99-9
tetrahydrofuran

B: 96-48-0
4-butanolide

C: 110-63-4
Butane-1,4-diol

D: 110-15-6
succinic acid

E: 64-19-7
acetic acid

Conditions

Conditions	Yield
With hydrogen; 0.5 percent Pd on Rutile TiO2 at 110℃; Product distribution / selectivity;	A 0.37% B 0.28% C 0.37% D 98.89% E 0.08%

...Expand

: 110-63-4
Butane-1,4-diol

A: 96-48-0
4-butanolide

B: 71-36-3
butan-1-ol

Conditions

Conditions	Yield
With hydrogen; Cu-based catalyst at 190℃; Product distribution; Further Variations:; Temperatures; reaction in vapour phase, fixed bed reactor;	A 98.8% B 0.8%

: 110-16-7
maleic acid

A: 109-99-9
tetrahydrofuran

B: 96-48-0
4-butanolide

C: 67-56-1
methanol

D: 110-63-4
Butane-1,4-diol

E: 617-48-1
malic acid

F: 110-15-6
succinic acid

G: 64-19-7
acetic acid

H: 71-36-3
butan-1-ol

Conditions

Conditions	Yield
With hydrogen; 0.5percent Pd on Rutile TiO2 at 110℃; Product distribution / selectivity;	A 0.45% B 0.06% C 0% D 0.21% E 0.36% F 98.73% G 0.04% H 0.08%

...Expand

: 110-16-7
maleic acid

A: 109-99-9
tetrahydrofuran

B: 96-48-0
4-butanolide

C: 110-63-4
Butane-1,4-diol

D: 591-81-1
4-hydroxybutanoic acid

E: 110-15-6
succinic acid

F: 64-19-7
acetic acid

G: 71-36-3
butan-1-ol

Conditions

Conditions	Yield
With hydrogen; 0.5percent Pd on Rutile TiO2 at 110℃; Product distribution / selectivity;	A 0.77% B 0.38% C 0.24% D 0.05% E 98.28% F 0.02% G 0.26%

...Expand

: 109-99-9
tetrahydrofuran

: 96-48-0
4-butanolide

Conditions

Conditions	Yield
With trans-{dioxoruthenium(VI)(N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)propylenediamine)}(perchlorate)2 In acetonitrile at 25℃; for 1h;	98%
Stage #1: tetrahydrofuran With bromine In dichloromethane; water for 1h; Reflux; Stage #2: With dihydrogen peroxide In dichloromethane; water for 1h; Reflux;	98%
With manganese (VII)-oxide In tetrachloromethane; acetone at -45℃;	86%

: 110-63-4
Butane-1,4-diol

: 96-48-0
4-butanolide

Conditions

Conditions	Yield
With phosphoric acid tributyl ester at 119.84℃; under 9375.94 Torr; for 8h; Catalytic behavior; Reagent/catalyst; Autoclave;	98%
With Cu-Al hydrotalcite In 1,4-dioxane at 220℃; under 12001.2 Torr; for 0.045h;	98%
With Hoveyda-Grubbs catalyst second generation; potassium hydroxide; tricyclohexylphosphine In toluene at 110℃; for 24h; Reagent/catalyst; Schlenk technique; Inert atmosphere;	98%

: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

A: 109-99-9
tetrahydrofuran

B: 13436-45-8
2-methoxytetrahydrofuran

C: 96-48-0
4-butanolide

D: 71-23-8
propan-1-ol

E: 64001-06-5
2-(4'-hydroxybutoxy)-tetrahydrofuran

F: 110-63-4
Butane-1,4-diol

G: 71-36-3
butan-1-ol

Conditions

Conditions	Yield
With hydrogen; copper catalyst, T 4489, Sud-Chemie AG, Munich at 150 - 280℃; under 187519 Torr; Neat liquid(s) and gas(es)/vapour(s);	A 1% B n/a C 0.4% D n/a E n/a F 98% G 0.5%

...Expand

: 36603-83-5
5-Chloro-dihydro-2(3H)-furanone

: 96-48-0
4-butanolide

Conditions

Conditions	Yield
With palladium on activated carbon; hydrogen at 200℃; under 760.051 Torr; for 149h; Temperature; Reagent/catalyst;	97.98%

: 160194-31-0
4-(tert-butyldimethylsilyl)but-3-yn-1-ol

: 96-48-0
4-butanolide

Conditions

Conditions	Yield
With 8-isopropyl-quinoline-N-oxide; [Au(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)(NTf2)] In fluorobenzene; 1,2-dichloro-ethane at 60℃; for 5h;	96%

: 108-31-6
maleic anhydride

: 96-48-0
4-butanolide

Conditions

Conditions	Yield
With hydrogen In 1,4-dioxane at 159.84℃; under 37503.8 Torr; Reagent/catalyst; Autoclave;	95.94%
at 275℃; under 51485.6 Torr; Hydrogenation.an einen Nickel-Chrom-Molybdaen-Katalysator;
With cobalt at 200℃; under 102971 Torr; Hydrogenation;

: 5061-21-2
α-bromo-γ-butyrolactone

: 96-48-0
4-butanolide

Conditions

Conditions	Yield
With DMBI In tetrahydrofuran for 4h; Heating;	95%
With nickel In tetrahydrofuran at 20℃; for 0.75h;	95%
With triethyl borane; tri-n-butyl-tin hydride In hexane; toluene at -78℃; for 0.5h;	90%

: 110-15-6
succinic acid

A: 96-48-0
4-butanolide

B: 110-63-4
Butane-1,4-diol

Conditions

Conditions	Yield
With C36H54IrN2P2(1+)*C24H20B(1-); hydrogen; sodium hydride In toluene at 180℃; under 7500.75 - 45004.5 Torr; for 18h; Reagent/catalyst; Temperature; Pressure; Autoclave; Sealed tube;	A 5% B 95%
Stage #1: succinic acid In 1,4-dioxane at 500℃; for 4h; Stage #2: With hydrogen In 1,4-dioxane at 200℃; under 60006 Torr; for 5h; Catalytic behavior; Reagent/catalyst;	A n/a B 64.7%
With hydrogen In water at 130℃; under 37503.8 Torr; for 12h; Pressure; Reagent/catalyst; Temperature; Autoclave;	A 34% B 23%

: 13325-10-5
4-Aminobutanol

: 96-48-0
4-butanolide

Conditions

Conditions	Yield
With hydrogenchloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; laccase from Trametes versicolor In water for 15h; pH=5.5; Enzymatic reaction; chemoselective reaction;	95%

: 3879-08-1
4-hydroxybutanoic acid hydrazide

: 96-48-0
4-butanolide

Conditions

Conditions	Yield
With benzeneseleninic acid In dichloromethane for 1.75h;	91%

: 110-63-4
Butane-1,4-diol

: 1099-45-2
ethyl (triphenylphosphoranylidene)acetate

A: 1092929-40-2
(Z)-6-hydroxy-hex-2-enoic acid ethyl ester

B: 96-48-0
4-butanolide

C: 15898-58-5
octa-2,6-dienedioic acid diethyl ester

D: 13038-15-8
(E)-6-hydroxy-hex-2-enoic acid ethyl ester

Conditions

Conditions	Yield
With manganese(IV) oxide In dichloromethane at 20℃; for 48h; Wittig olefination;	A 5% B n/a C n/a D 91%

...Expand

: 110-16-7
maleic acid

A: 109-99-9
tetrahydrofuran

B: 96-48-0
4-butanolide

C: 110-63-4
Butane-1,4-diol

D: 591-81-1
4-hydroxybutanoic acid

E: 617-48-1
malic acid

F: 110-15-6
succinic acid

G: 64-19-7
acetic acid

Conditions

Conditions	Yield
With hydrogen; 0.5percent Pd/2.0percent Re on Rutile TiO2 at 110℃; Product distribution / selectivity;	A 1.27% B 4.78% C 1.55% D 1.24% E 0.48% F 90.6% G 0.08%

...Expand

: 108-30-5
succinic acid anhydride

: 96-48-0
4-butanolide

Conditions

Conditions	Yield
With hydrogen In 1,4-dioxane at 199.84℃; under 37503.8 Torr; for 5h; Catalytic behavior; Activation energy; Temperature;	90.1%
With lithium borohydride In tetrahydrofuran for 0.25h;	68%
With lithium borohydride In tetrahydrofuran at 25℃; for 0.25h; Mechanism; other cyclic anhydrides;	68%

: 591-81-1
4-hydroxybutanoic acid

: 96-48-0
4-butanolide

Conditions

Conditions	Yield
With sulfuric acid In chloroform at 60℃; for 1h; pH=0.5; pH-value; Solvent; Temperature;	90%
bei der Destillation;
With hydrogenchloride In ethanol at 25℃; Rate constant;
With cis-nitrous acid at 25℃; Rate constant;
With hydrogenchloride at 35℃; Equilibrium constant; Further Variations:; Temperatures;

: 110-15-6
succinic acid

: 96-48-0
4-butanolide

Conditions

Conditions	Yield
With 5% active carbon-supported ruthenium; hydrogen at 150℃; under 26252.6 Torr;	90%
With butanediamide; hydrogen In Triethylene glycol dimethyl ether at 205℃; under 6750.68 Torr; for 2h; Reagent/catalyst; Autoclave;	30%
With D-glucose; hydrogen In Triethylene glycol dimethyl ether at 205℃; under 6750.68 Torr; for 2h; Autoclave;	27.5%

: 821-11-4, 6117-80-2, 110-64-5
1,4-butenediol

: 96-48-0
4-butanolide

Conditions

Conditions	Yield
With [RuCl2(PPh3)2(2-PyCH21,3,5-triaza-7-phosphadamantane)].Br; potassium hydroxide In water for 48h; Reagent/catalyst; Schlenk technique; Reflux; Inert atmosphere; Green chemistry;	90%
With potassium hydroxide; tricyclohexylphosphine In toluene at 110℃; for 24h; Schlenk technique;

: 108-31-6
maleic anhydride

A: 96-48-0
4-butanolide

B: 71-36-3
butan-1-ol

Conditions

Conditions	Yield
With hydrogen In 1,4-dioxane at 159.84℃; under 37503.8 Torr; Reagent/catalyst; Autoclave;	A 89.9% B 6.83%

: 628-22-8
4-hydroxy-1-butanitrile

: 96-48-0
4-butanolide

Conditions

Conditions	Yield
With ; water In 1,2-dimethoxyethane at 140℃; for 24h;	89%

: 110-15-6
succinic acid

A: 109-99-9
tetrahydrofuran

B: 96-48-0
4-butanolide

C: 110-63-4
Butane-1,4-diol

D: 71-36-3
butan-1-ol

Conditions

Conditions	Yield
With hydrogen In 1,4-dioxane at 139.84℃; under 60006 Torr; for 96h; Catalytic behavior; Reagent/catalyst; Time; Temperature; Autoclave; Overall yield = 100 %;	A 0.2% B 3.1% C 89% D 7.6%
With hydrogen; 1.0percent Pd/ 3.0percent Re on Rutile TiO2 at 164 - 185℃; for 21 - 237h; Product distribution / selectivity;	A 2.95% B 0% C 81.5% D 3.35%
With hydrogen; 0percent Pd/5.0percent Re on Rutile TiO2 at 170 - 185℃; for 90 - 825h; Product distribution / selectivity;	A 3.38% B 0% C 64.14% D 2.86%

...Expand

: 4-{[(1Z,3E)-2-(2-furylcarbonyl)-5-oxo-1,5-diphenylpenta-1,3-dienyl]amino}butanoic acid

A: 96-48-0
4-butanolide

B: 3-(2-furylcarbonyl)-2,6-diphenylpyridine

Conditions

Conditions	Yield
In ethanol at 78℃; for 4h;	A n/a B 89%

: 96-48-0
4-butanolide

: 100-46-9
benzylamine

: 19340-88-6
N-benzyl-4-hydroxybutanamide

Conditions

Conditions	Yield
With bis(trifluoromethane)sulfonimide lithium In chloroform at 85℃; for 40h;	100%
Stage #1: benzylamine With diisobutylaluminium hydride In tetrahydrofuran; toluene Stage #2: 4-butanolide In tetrahydrofuran at 20℃; for 0.5h;	98%
In benzene for 12h; Reflux;	98%

: 123-75-1
pyrrolidine

: 96-48-0
4-butanolide

: 73200-24-5
4-hydroxy-1-(pyrrolidin-1-yl)butan-1-one

Conditions

Conditions	Yield
With triethylamine Inert atmosphere; Reflux;	100%
With triethylamine for 16h; Reflux;	94%
In benzene for 3h; Heating;	90%

: 110-89-4
piperidine

: 96-48-0
4-butanolide

: 86452-60-0
4-hydroxy-1-(piperidin-1-yl)butan-1-one

Conditions

Conditions	Yield
With bis(trifluoromethane)sulfonimide lithium In chloroform at 85℃; for 40h;	100%
In acetonitrile at 30℃; under 6750540 Torr; for 96h;	99%
In acetonitrile at 30℃; under 6750540 Torr; for 168h;	99%

: 96-48-0
4-butanolide

: 117968-50-0
(2S,5S)-2,5-dimethylpyrrolidine

: 139108-39-7
(2S,5S)-1-(4-hydroxybutanoyl)-2,5-dimethylpyrrolidine

Conditions

Conditions	Yield
With triethylamine for 12h; Heating;	100%
With triethylamine for 48h; Heating;	96%

: 96-48-0
4-butanolide

: 109-89-7
diethylamine

: 86452-59-7
N,N-Diethyl-4-hydroxy-butyramide

Conditions

Conditions	Yield
In acetonitrile at 30℃; under 6750540 Torr; for 96h;	100%
Stage #1: diethylamine With diisobutylaluminium hydride In tetrahydrofuran; toluene Stage #2: 4-butanolide In tetrahydrofuran at 45℃; for 2h;	72%

: 96-48-0
4-butanolide

: 109-94-4
formic acid ethyl ester

: 51270-64-5, 54211-97-1, 93698-26-1
sodium salt of (Z)-3-(hydroxymethylene)dihydro-2(3H)-furanone

Conditions

Conditions	Yield
With sodium hydride	100%
With sodium In diethyl ether at -20 - -15℃; for 5h;

: 96-48-0
4-butanolide

: 109-94-4
formic acid ethyl ester

: 54211-97-1
sodium salt of (E)-3-(hydroxymethylene)dihydro-2(3H)-furanone

Conditions

Conditions	Yield
With sodium hydride	100%
With ethanol; sodium hydride In 1,2-dimethoxyethane at 40℃; for 22h; cross-Claisen acylation;	97%
With sodium methylate In diethyl ether for 12h;	69%
With sodium hydroxide In 1,2-dimethoxyethane at 60℃; for 16h;	66%

: 96-48-0
4-butanolide

: 110-63-4
Butane-1,4-diol

Conditions

Conditions	Yield
With sodium aluminum tetrahydride In tetrahydrofuran at 0℃; for 0.0833333h;	100%
With C31H33ClN2O3RuS; potassium tert-butylate; hydrogen In isopropyl alcohol at 60℃; under 37503.8 Torr; for 48h; Inert atmosphere;	100%
With C39H39N6ORu(1+)*Br(1-); potassium methanolate; hydrogen In tetrahydrofuran at 100℃; under 37503.8 Torr; for 16h; Reagent/catalyst;	100%

: 96-48-0
4-butanolide

: 67764-03-8
4-iodobutanoate de trimethylsilyle

Conditions

Conditions	Yield
With trimethylsilyl iodide; iodine In chloroform-d1 for 1h; Ambient temperature;	100%

: 96-48-0
4-butanolide

: 502-85-2
sodium 4-hydroxybutanoate

Conditions

Conditions	Yield
With water; sodium hydroxide at 20℃; Inert atmosphere;	100%
With ethanol; sodium hydroxide at 20℃; for 2h;	95%
With sodium hydroxide at 45 - 60℃; for 12h;	95%

: 96-48-0
4-butanolide

: 127421-48-1
iodosilyl 4-iodobutyrate

Conditions

Conditions	Yield
With diiodosilane; iodine In chloroform-d1 at 50℃; for 0.166667h;	100%

: 96-48-0
4-butanolide

: 75-04-7
ethylamine

: 42042-64-8
N-ethyl-4-hydroxybutanamide

Conditions

Conditions	Yield
In tetrahydrofuran at 50℃; for 22h;	100%
In tetrahydrofuran at 20℃; Acylation;
With ammonia In methanol at 20℃;

: 96-48-0
4-butanolide

: 13325-10-5
4-Aminobutanol

: 4-hydroxy-N-(4-hydroxybutyl)butanamide

Conditions

Conditions	Yield
In 5,5-dimethyl-1,3-cyclohexadiene Reflux;	100%
In various solvent(s) for 18h; Heating;

: 96-48-0
4-butanolide

: 63255-29-8
Lithium γ-hydroxybutyrate

Conditions

Conditions	Yield
With lithium hydroxide monohydrate In methanol; water at 20℃; for 16h;	100%
With lithium hydroxide In methanol; water at 20℃; for 16h;	100%
With lithium hydroxide; water In methanol at 20℃;

: 96-48-0
4-butanolide

: 100-58-3
phenylmagnesium bromide

: 1023-94-5
1,1-diphenylbutan-1,4-diol

Conditions

Conditions	Yield
With hydrogenchloride; ammonium chloride In tetrahydrofuran	100%
Stage #1: 4-butanolide; phenylmagnesium bromide In tetrahydrofuran; diethyl ether at -78 - 20℃; Inert atmosphere; Stage #2: With water; ammonium chloride In tetrahydrofuran; diethyl ether at 10℃; Cooling with ice;
In tetrahydrofuran Grignard reaction; Reflux;

: 96-48-0
4-butanolide

: 591-19-5
3-bromoaniline

: 38348-83-3
1-(3-bromophenyl)-2-pyrrolidinone

Conditions

Conditions	Yield
With hydrogenchloride In water at 160℃; for 36h;	100%

: 96-48-0
4-butanolide

: 15570-12-4
3-methoxybenzenethiol

: 4-((3-methoxyphenyl)thio)butanoic acid sodium salt

Conditions

Conditions	Yield
With ethanol; sodium for 24h; Inert atmosphere; Reflux;	100%
With sodium In ethanol for 24h; Inert atmosphere; Reflux;	100%

: 96-48-0
4-butanolide

: 74-89-5
methylamine

: 872-50-4
1-methyl-pyrrolidin-2-one

Conditions

Conditions	Yield
With water; ZSM-5 at 280℃;	99%
In water at 300℃; under 75007.5 Torr; Concentration;	99.9%
at 255℃; under 15001.5 Torr; for 3h;	98.2%

: 96-48-0
4-butanolide

: 74-89-5
methylamine

: 37941-69-8
γ-hydroxybutyric acid monomethylamide

Conditions

Conditions	Yield
at 20℃; for 1.5h;	99%
	99.5%
With water at 0 - 5℃; for 2h;	95.5%

: 96-48-0
4-butanolide

: 124-40-3
dimethyl amine

: 37941-69-8
γ-hydroxybutyric acid monomethylamide

Conditions

Conditions	Yield
	99.5%

: 96-48-0
4-butanolide

: 109-73-9
N-butylamine

: 42042-67-1
N-butyl-4-hydroxybutyramide

Conditions

Conditions	Yield
With bis(trifluoromethane)sulfonimide lithium In chloroform at 85℃; for 40h;	99%

: 96-48-0
4-butanolide

: 95-92-1
oxalic acid diethyl ester

: 42564-36-3
oxo-(2-oxotetrahydrofuran-3-yl)acetic acid ethyl ester

Conditions

Conditions	Yield
With sodium ethanolate In ethanol at 0 - 20℃; for 6.25h;	99%
With sodium ethanolate In ethanol at 0 - 20℃;	96%
With sodium methylate	72%

: 96-48-0
4-butanolide

: 100-46-9
benzylamine

: 5291-77-0
1-benzyl-2-pyrrolidone

Conditions

Conditions	Yield
With 1-butyl-3-methylimidazolium Tetrafluoroborate In 1,4-dioxane at 220℃; for 0.583333h; Microwave irradiation;	99%
for 24h; Heating;	79%
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; sodium acetate In toluene at 110℃; for 36h; Reagent/catalyst; Inert atmosphere; Glovebox; Molecular sieve; Schlenk technique;	65%

: 96-48-0
4-butanolide

: 507-63-1
1-iodoheptadecafluorooctane

: 112678-33-8
2-Heptadecafluorooctyl-tetrahydro-furan-2-ol

Conditions

Conditions	Yield
With methyllithium; lithium bromide In diethyl ether at -78℃; for 1h;	99%
With methyllithium In diethyl ether at -78℃; for 1h;	99%

: 96-48-0
4-butanolide

: 107-11-9
1-amino-2-propene

: 98435-58-6
N-allyl 4-hydroxybutyramide

Conditions

Conditions	Yield
at 120 - 130℃; for 3h;	99%
at 120 - 130℃; for 3h;	99%
With bis(trifluoromethane)sulfonimide lithium In chloroform at 85℃; for 40h;	99%
In benzene for 12h; Inert atmosphere; Reflux;

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.

gamma-Butyrolactone 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.

Product Name

gamma-Butyrolactone

Synthetic route

gamma-Butyrolactone Consensus Reports

gamma-Butyrolactone Specification

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