2,5-Dihydrothiophene Dioxide supplier

Name
3-SULFOLENE
EINECS 201-059-7
CAS No. 77-79-2
Article Data25
CAS DataBase
Density 1.3
Solubility Soluble
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
PSA 42.52000
LogP 1.05180

Synthetic route

: 16841-48-8
diallyl sulfone

: 77-79-2
3-Sulfolene

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
In tetrahydrofuran at -78℃; for 2h;	A 26% B 41%

...Expand

: 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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With magnesium; mercury dichloride In tetrahydrofuran Ambient temperature; Irradiation;

...Expand

: 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

Conditions	Yield
With potassium In toluene Ambient temperature;

...Expand

: 53336-42-8
3-bromo-2,3-dihydro-thiophene-1,1-dioxide

: 77-79-2
3-Sulfolene

Conditions

Conditions	Yield
With zinc In tetrahydrofuran Heating; Yield given;

: 77-79-2
3-Sulfolene

: 126-33-0
sulfolane

Conditions

Conditions	Yield
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

Conditions	Yield
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

: 77-79-2
3-Sulfolene

: potassium (Z)-1,3-butadiene-1-sulfinate

Conditions

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 20℃; for 1h;	99.1%
With potassium methanolate In tetrahydrofuran at 110℃; for 0.166667h;

: 77-79-2
3-Sulfolene

: C4H5(2)HO2S

Conditions

Conditions	Yield
With n-butyllithium; water-d2; zinc(II) chloride 1.) THF, -105 deg C; 2.) THF, -78 deg C;	99%

: 77-79-2
3-Sulfolene

: 1532-97-4
4-bromoisoquinoline

: (E)-4-(buta-1,3-dien-1-yl)isoquinoline

Conditions

Conditions	Yield
Stage #1: 3-Sulfolene With o-phenylenebis(diphenylphosphine); potassium methanolate; palladium diacetate; potassium carbonate In tetrahydrofuran at 20℃; for 0.0833333h; Sealed tube; Inert atmosphere; Stage #2: 4-bromoisoquinoline In tetrahydrofuran at 20 - 110℃; for 17.3333h; Sealed tube; stereoselective reaction;	99%

: 77-79-2
3-Sulfolene

: 34784-04-8
5-bromoisoquinoline

: (E)-5-(buta-1,3-dien-1-yl)isoquinoline

Conditions

Conditions	Yield
Stage #1: 3-Sulfolene With o-phenylenebis(diphenylphosphine); potassium methanolate; palladium diacetate; potassium carbonate In tetrahydrofuran at 20℃; for 0.0833333h; Sealed tube; Inert atmosphere; Stage #2: 5-bromoisoquinoline In tetrahydrofuran at 20 - 110℃; for 17.3333h; Sealed tube; stereoselective reaction;	99%

: 77-79-2
3-Sulfolene

: 623-00-7
4-bromobenzenecarbonitrile

: (E)-1-(buta-1,3-dien-1-yl)-4-cyanobenzene

Conditions

Conditions	Yield
Stage #1: 3-Sulfolene With o-phenylenebis(diphenylphosphine); potassium methanolate; palladium diacetate; potassium carbonate In tetrahydrofuran at 20℃; for 0.0833333h; Sealed tube; Inert atmosphere; Stage #2: 4-bromobenzenecarbonitrile In tetrahydrofuran at 20 - 110℃; for 13.3333h; Catalytic behavior; Reagent/catalyst; Solvent; Sealed tube; diastereoselective reaction;	99%

: 77-79-2
3-Sulfolene

: 626201-15-8
4-cyanophenyl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate

: C11H11N

Conditions

Conditions	Yield
With dichloro bis(acetonitrile) palladium(II); potassium tert-butylate; potassium hydrogencarbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In tetrahydrofuran at 100℃; diastereoselective reaction;	99%

: 77-79-2
3-Sulfolene

: 623-91-6
diethyl Fumarate

: 4841-85-4, 5048-50-0, 13043-60-2, 56000-17-0
trans-1,2-bis(ethoxycarbonyl)-4-cyclohexene

Conditions

Conditions	Yield
In ethanol at 120℃; for 16h; Diels-Alder reaction;	97%
	90%
With hydroquinone In ethanol at 130℃; in sealed bomb reactor;
In ethanol at 125℃; for 24h; Diels-Alder Cycloaddition;
at 90℃; for 120h;

: 77-79-2
3-Sulfolene

: 107-02-8
acrolein

: (R)-1-((R)-1,1-Dioxo-2,3-dihydro-1H-1λ6-thiophen-3-yl)-prop-2-en-1-ol

Conditions

Conditions	Yield
With n-butyllithium; zinc dibromide 1.) THF, -105 deg C; 2.) THF, -78 deg C;	97%

: 77-79-2
3-Sulfolene

: 32316-92-0
naphthalene-2-boronic acid

: C14H14O2S

Conditions

Conditions	Yield
With C64H44Cl2F8Fe4Rh2; potassium hydroxide In 1,4-dioxane; water at 60℃; for 16h; Inert atmosphere; Schlenk technique; Sealed tube; enantioselective reaction;	97%

: 77-79-2
3-Sulfolene

: 16419-60-6
2-Methylphenylboronic acid

: C11H14O2S

Conditions

Conditions	Yield
With C64H44Cl2F8Fe4Rh2; potassium hydroxide In 1,4-dioxane; water at 60℃; for 16h; Inert atmosphere; Schlenk technique; Sealed tube; enantioselective reaction;	97%

: 77-79-2
3-Sulfolene

: 66152-74-7
3-<(trifluoromethanesulfonyl)oxy>benzonitrile

: (E)-3-(buta-1,3-dien-1-yl)benzonitrile

Conditions

Conditions	Yield
Stage #1: 3-Sulfolene With potassium tert-butylate In tetrahydrofuran at 20℃; for 1h; Stage #2: With o-phenylenebis(diphenylphosphine); palladium diacetate In tetrahydrofuran at 20℃; for 0.25h; Inert atmosphere; Stage #3: 3-<(trifluoromethanesulfonyl)oxy>benzonitrile With potassium hydrogencarbonate In tetrahydrofuran at 20 - 100℃; Sealed tube; Inert atmosphere; stereoselective reaction;	97%

: 77-79-2
3-Sulfolene

: 75-05-8
acetonitrile

: 87605-39-8
2,2,2-Trichloro-N-((3R,4S)-4-chloro-1,1-dioxo-tetrahydro-1λ6-thiophen-3-yl)-acetimidoyl chloride

Conditions

Conditions	Yield
With sulfuryl dichloride for 4h; Ambient temperature;	96%

: 77-79-2
3-Sulfolene

: 673-41-6
p-chlorobenzenediazonium tetrafluoroborate

: 3-(4-Chloro-phenyl)-2,3-dihydro-thiophene 1,1-dioxide

Conditions

Conditions	Yield
With palladium diacetate In methanol at 50℃; for 0.5h;	96%

: 77-79-2
3-Sulfolene

: 143726-55-0
C15H12O4S2

: C19H18O4S2

Conditions

Conditions	Yield
at 60℃; for 24h;	96%

: 77-79-2
3-Sulfolene

: 623-00-7
4-bromobenzenecarbonitrile

: C11H11N

Conditions

Conditions	Yield
With dichloro bis(acetonitrile) palladium(II); potassium tert-butylate; potassium hydrogencarbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In tetrahydrofuran at 110℃; Reagent/catalyst; diastereoselective reaction;	96%

: 77-79-2
3-Sulfolene

: 56-91-7
p-aminomethylbenzoic acid

: 4-(N-(3-tetrahydrothiophenyl-1,1-dioxide)aminomethyl)benzoic acid

Conditions

Conditions	Yield
With potassium hydroxide In water at 55℃; for 23h;	95%

: 77-79-2
3-Sulfolene

: 100-52-7
benzaldehyde

: (R)-((S)-1,1-Dioxo-2,3-dihydro-1H-1λ6-thiophen-3-yl)-phenyl-methanol

Conditions

Conditions	Yield
With n-butyllithium; zinc(II) chloride 1.) THF, -105 deg C; 2.) THF, -78 deg C;	95%

: 77-79-2
3-Sulfolene

: C15H12O4S2

: C19H18O4S2

Conditions

Conditions	Yield
at 60℃; for 24h;	95%

: 77-79-2
3-Sulfolene

: C26H18O4S2

: C30H24O4S2

Conditions

Conditions	Yield
at 60℃; for 24h;	95%

: 77-79-2
3-Sulfolene

: 10365-98-7
3-methoxyphenylboronic acid

: C11H14O3S

Conditions

Conditions	Yield
With C64H44Cl2F8Fe4Rh2; potassium hydroxide In 1,4-dioxane; water at 60℃; for 16h; Inert atmosphere; Schlenk technique; Sealed tube; enantioselective reaction;	95%

: 77-79-2
3-Sulfolene

: 19752-55-7
1-bromo-3,5-dichlorobenzene

: C10H8Cl2

Conditions

Conditions	Yield
With dichloro bis(acetonitrile) palladium(II); potassium tert-butylate; potassium hydrogencarbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In tetrahydrofuran at 110℃; diastereoselective reaction;	95%

: 77-79-2
3-Sulfolene

: 20986-40-7
ethyl 5-bromo-3-pyridinecarboxylate

: C12H13NO2

Conditions

Conditions	Yield
With dichloro bis(acetonitrile) palladium(II); potassium tert-butylate; potassium hydrogencarbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In tetrahydrofuran at 110℃; diastereoselective reaction;	95%

: 77-79-2
3-Sulfolene

: 143726-50-5
C13H10O4S2

: 143726-57-2
C17H16O4S2

Conditions

Conditions	Yield
at 60℃; for 24h;	94%
at 70℃;

: 77-79-2
3-Sulfolene

: 158225-49-1
2-methyl-1,4-benzodithiin tetroxide

: (4aR,10aS)-4a-Methyl-1,4,4a,10a-tetrahydro-thianthrene 5,5,10,10-tetraoxide

Conditions

Conditions	Yield
at 60℃;	94%

: 77-79-2
3-Sulfolene

: 673-40-5
4-bromobenzenediazonium tetrafluoroborate

: 3-(4-Bromo-phenyl)-2,3-dihydro-thiophene 1,1-dioxide

Conditions

Conditions	Yield
With palladium diacetate In methanol at 50℃; for 0.5h;	94%

: 77-79-2
3-Sulfolene

: 143726-54-9
C22H14O4S2

: C26H20O4S2

Conditions

Conditions	Yield
at 60℃; for 24h;	94%

: 77-79-2
3-Sulfolene

: 5467-74-3
4-Bromophenylboronic acid

: 3-(4-bromophenyl)tetrahydrothiophene 1,1-dioxide

Conditions

Conditions	Yield
With C64H44Cl2F8Fe4Rh2; potassium hydroxide In 1,4-dioxane; water at 60℃; for 16h; Inert atmosphere; Schlenk technique; Sealed tube; enantioselective reaction;	94%

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 SO_x.
Hazard Codes:
Irritant Xi
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.

Product Name

3-SULFOLENE

Synthetic route

2,5-Dihydrothiophene Dioxide Chemical Properties

2,5-Dihydrothiophene Dioxide Uses

2,5-Dihydrothiophene Dioxide Production

2,5-Dihydrothiophene Dioxide Toxicity Data With Reference

2,5-Dihydrothiophene Dioxide Consensus Reports

2,5-Dihydrothiophene Dioxide Safety Profile

2,5-Dihydrothiophene Dioxide Specification

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