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2,5-Dihydrothiophene Dioxide
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Name

2,5-Dihydrothiophene Dioxide

 EINECS 201-059-7
CAS No. 77-79-2 Density 1.3
PSA 42.52000 LogP 1.05180
Solubility Soluble Melting Point 65 - 66 C
Formula C4H6 O2 S Boiling Point Decomposes
Molecular Weight 118.156 Flash Point 112 C
Transport Information 25kgs Appearance white crystals
Safety 107004 Risk Codes R36/37/38;
Molecular Structure Molecular Structure of 77-79-2 (3-SULFOLENE) Hazard Symbols UN NO.
Synonyms

2,5-Dihydrothiophen-1,1-dioxide;2,5-Dihydrothiophene 1,1-dioxide; 2,5-Dihydrothiophene S,S-dioxide;2,5-Dihydrothiophene dioxide; 2,5-Dihydrothiophene sulfone; 3-Sulfolene;Butadiene sulfone; NSC 48532; NSC 56373; Sulfolene; Sulpholene; b-Sulfolene

Article Data 25

2,5-Dihydrothiophene Dioxide Synthetic route

16841-48-8

diallyl sulfone

77-79-2

3-Sulfolene

Conditions
ConditionsYield
With C34H43Cl2N3O2Ru In dichloromethane at 35℃; for 0.5h; Inert atmosphere;98%
Grubbs catalyst first generation In dichloromethane for 4h; Heating;97%
With C46H54Cl2FeN2O3Ru(1+)*I(1-) In dichloromethane at 35℃; for 0.5h;97%
106-99-0

buta-1,3-diene

77-79-2

3-Sulfolene

Conditions
ConditionsYield
With ferrocene; sulfur dioxide at 100℃; under 5250.53 - 20252 Torr; for 1h; Product distribution / selectivity;88%
With palladium(II) acetylacetonate; sulfur dioxide; triethylaluminum; triphenylphosphine In toluene at 100℃; for 10h;80%
With sulfur dioxide in Gegenwart von Polymerisationsinhibitoren;
53336-42-8

3-bromo-2,3-dihydro-thiophene-1,1-dioxide

(CH2=CH)2CuMgBr

(CH2=CH)2CuMgBr

A

77-79-2

3-Sulfolene

B

108919-88-6

4-vinyl-2-sulfolene

Conditions
ConditionsYield
In tetrahydrofuran at -78℃; for 2h;A 26%
B 41%
53336-42-8

3-bromo-2,3-dihydro-thiophene-1,1-dioxide

t-Bu2CuLi

t-Bu2CuLi

A

77-79-2

3-Sulfolene

B

1192-16-1

2,3-dihydrothiophene-1,1-dioxide

C

108919-90-0

4-tert-butyl-2-sulfolene

D

57278-92-9

(+/-)-2-(tert-butyl)-2,5-dihydrothiophene 1,1-dioxide

Conditions
ConditionsYield
In tetrahydrofuran at -78℃; for 2h;A 26%
B 13%
C 4%
D 4%
In tetrahydrofuran at -78℃; for 2h;A 26%
B 13%
C 18%
D 4%
...Expand
1708-32-3

2,5-dihydro-thiophene

77-79-2

3-Sulfolene

Conditions
ConditionsYield
With dihydrogen peroxide; acetic acid
53336-42-8

3-bromo-2,3-dihydro-thiophene-1,1-dioxide

67-64-1

acetone

A

77-79-2

3-Sulfolene

B

4055-13-4

2-(1-hydroxy-1-methylethyl)-3-sulfolene

Conditions
ConditionsYield
With magnesium; mercury dichloride In tetrahydrofuran Ambient temperature; Irradiation;
53336-42-8

3-bromo-2,3-dihydro-thiophene-1,1-dioxide

A

27092-46-2

thiophene-1,1-dioxide

B

77-79-2

3-Sulfolene

C

1192-16-1

2,3-dihydrothiophene-1,1-dioxide

Conditions
ConditionsYield
With potassium In toluene Ambient temperature;
53336-42-8

3-bromo-2,3-dihydro-thiophene-1,1-dioxide

77-79-2

3-Sulfolene

Conditions
ConditionsYield
With zinc In tetrahydrofuran Heating; Yield given;
77-79-2

3-Sulfolene

126-33-0

sulfolane

Conditions
ConditionsYield
With triethylsilane; 1% Pd on activated carbon In water at 45℃; for 20h; Green chemistry; chemoselective reaction;100%
With ethanol; platinum Hydrogenation;
With water; palladium Hydrogenation;
77-79-2

3-Sulfolene

13031-76-0

3-hydroxytetrahydrothiophene 1,1-dioxide

Conditions
ConditionsYield
With potassium hydroxide In water at 20℃; for 16h; Inert atmosphere;100%
With sodium hydroxide at 40℃; for 12h; Inert atmosphere;95.6%
With water; potassium hydroxide at 40℃; for 4h;88%
With sodium hydroxide In water at 20℃; for 24h;87%
With potassium hydroxide

2,5-Dihydrothiophene Dioxide Chemical Properties

Chemistry informtion about 2,5-Dihydrothiophene Dioxide (CAS NO.77-79-2) is:
IUPAC Name: 2,5-Dihydrothiophene 1,1-Dioxide
Synonyms: Sulfolene ; 1-Thia-3-Cyclopentene1,1-Dioxide ; 2,5-Dihydrothiophene Dioxide ; 2,5-Dihydrothiophenedioxide ; 2,5-Dihydrothiophenesulfone ; Beta-Sulfolene ; Nci-C04557 ; Sulfol-3-Ene
Product Categories: Sulfur Compounds (for Synthesis) ; Synthetic Organic Chemistry 
MF: C4H6O2S
MW: 118.15
EINECS: 201-059-7 
Density: 1.333 g/cm3 
Melting Point: 65-66 °C(lit.) 
Flash Point: 188.4 °C
Boiling Point: 299.2 °C at 760 mmHg
Vapour Pressure: 0.00215 mmHg at 25°C 
Enthalpy of Vaporization: 51.76 kJ/mol
Merck: 14,8956
BRN: 107004
Stability: Stable, but decomposes above the melting point. Combustible. Incompatible with strong oxidizing agents.
Following is the molecular structure of 2,5-Dihydrothiophene Dioxide (CAS NO.77-79-2) is:

2,5-Dihydrothiophene Dioxide Uses

 In electrochemical fluorination, 2,5-Dihydrothiophene Dioxide (CAS NO.77-79-2) can increase the yield of perfluorooctanesulfonyl fluoride by about 70%. It is "highly soluble in anhydrous HF and increases the conductivity of the electrolyte solution." In this application, it undergoes a ring opening and is fluorinated to form perfluorobutanesulfonyl fluoride.

2,5-Dihydrothiophene Dioxide Production

Raw materials are Sulfur dioxide --> Hydroquinone --> 1,3-Butadiene ,preparation products is Sulfolane .

2,5-Dihydrothiophene Dioxide Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 1700mg/kg (1700mg/kg)   Pharmaceutical Chemistry Journal Vol. 12, Pg. 1568, 1978.
mouse LD50 oral 1600mg/kg (1600mg/kg) behavioral: somnolence (general depressed activity) behavioral: convulsions or effect on seizure threshold gastrointestinal: change in structure or function of esophagus National Technical Information Service. Vol. OTS0534337,
rabbit LD50 skin > 5gm/kg (5000mg/kg)   Toxicology and Applied Pharmacology. Vol. 28, Pg. 313, 1974.
rat LD50 intraperitoneal 3200mg/kg (3200mg/kg) behavioral: somnolence (general depressed activity) behavioral: convulsions or effect on seizure threshold gastrointestinal: changes in structure or function of salivary glands National Technical Information Service. Vol. OTS0534337,
rat LD50 oral 2547mg/kg (2547mg/kg) behavioral: tremor behavioral: ataxia gastrointestinal: changes in structure or function of salivary glands National Technical Information Service. Vol. OTS0546574,

2,5-Dihydrothiophene Dioxide Consensus Reports

NCI Carcinogenesis Bioassay (gavage); No Evidence: mouse, rat NCITR*    National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCI-CG-TR-102 ,1978. . Reported in EPA TSCA Inventory.

2,5-Dihydrothiophene Dioxide Safety Profile

Moderately toxic by ingestion and intraperitoneal routes. When heated to decomposition it emits toxic fumes of SOx.
Hazard Codes:
IrritantXi
Risk Statements:
R41:Risk of serious damage to the eyes. 
Safety Statements:
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S37/39:Wear suitable gloves and eye/face protection.
WGK Germany: 1
RTECS: XM9100000

2,5-Dihydrothiophene Dioxide Specification

2,5-Dihydrothiophene Dioxide (CAS NO.77-79-2) is a white crystalline solid.
First Aid Measures:
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin: Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion: Get medical aid. Wash mouth out with water.
Inhalation: Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. 
Handling and Storage:
Handling: Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Avoid contact with eyes, skin, and clothing. Avoid ingestion and inhalation.
Storage: Store in a cool, dry place. Keep container closed when not in use.

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