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96-48-0

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Basic Information
CAS No.: 96-48-0
Name: 2(3H)-Furanone,dihydro-
Molecular Structure:
Molecular Structure of 96-48-0 (2(3H)-Furanone,dihydro-)
Formula: C4H6O2
Molecular Weight: 86.09
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;
EINECS: 202-509-5
Density: 1.128 g/cm3
Melting Point: -45 °C(lit.)
Boiling Point: 204 °C at 760 mmHg
Flash Point: 80.9 °C
Solubility: MISCIBLE
Appearance: colourless oily liquid
Hazard Symbols: HarmfulXn
Risk Codes: 22-36
Safety: 26-36-39
Transport Information:
PSA: 26.30000
LogP: 0.32340
Synthetic route
6117-80-2

1,4-butenediol

96-48-0

4-butanolide

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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%
1191-95-3

cyclobutanone

96-48-0

4-butanolide

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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%
110-63-4

Butane-1,4-diol

A

96-48-0

4-butanolide

B

71-36-3

butan-1-ol

Conditions
ConditionsYield
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
ConditionsYield
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%
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
ConditionsYield
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%
109-99-9

tetrahydrofuran

96-48-0

4-butanolide

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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%
36603-83-5

5-Chloro-dihydro-2(3H)-furanone

96-48-0

4-butanolide

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With manganese(IV) oxide In dichloromethane at 20℃; for 48h; Wittig olefination;A 5%
B n/a
C n/a
D 91%
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
ConditionsYield
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%
108-30-5

succinic acid anhydride

96-48-0

4-butanolide

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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%
96-48-0

4-butanolide

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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%

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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With sodium hydride100%
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
ConditionsYield
With sodium hydride100%
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
ConditionsYield
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
ConditionsYield
With trimethylsilyl iodide; iodine In chloroform-d1 for 1h; Ambient temperature;100%
96-48-0

4-butanolide

502-85-2

sodium 4-hydroxybutanoate

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With hydrogenchloride; ammonium chloride In tetrahydrofuran100%
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
99.5%
96-48-0

4-butanolide

109-73-9

N-butylamine

42042-67-1

N-butyl-4-hydroxybutyramide

Conditions
ConditionsYield
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
ConditionsYield
With sodium ethanolate In ethanol at 0 - 20℃; for 6.25h;99%
With sodium ethanolate In ethanol at 0 - 20℃;96%
With sodium methylate72%
96-48-0

4-butanolide

100-46-9

benzylamine

5291-77-0

1-benzyl-2-pyrrolidone

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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;
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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.