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77-79-2 Usage

Chemical Properties

3-SULFOLENE is white crystalline solid

Uses

Different sources of media describe the Uses of 77-79-2 differently. You can refer to the following data:
1. 3-SULFOLENE was used in the isomerization of isoprene rubber. Sulfolene is also an analytical reagent used in the investigation of role of adducts in protein supercharging with sulfolane.
2. It is a source of cisoid butadiene for Diels-Alder reactions. This chemical is also a convenient source of sulfur dioxide. It is a solvent used in the petrochemical industry for the extraction of aromatics from hydrocarbon streams.

Check Digit Verification of cas no

The CAS Registry Mumber 77-79-2 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 7 respectively; the second part has 2 digits, 7 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 77-79:
(4*7)+(3*7)+(2*7)+(1*9)=72
72 % 10 = 2
So 77-79-2 is a valid CAS Registry Number.
InChI:InChI=1/C4H6O2S/c5-7(6)3-1-2-4-7/h1-2H,3-4H2

77-79-2 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (D0557)  3-Sulfolene  >98.0%(GC)

  • 77-79-2

  • 25g

  • 120.00CNY

  • Detail
  • TCI America

  • (D0557)  3-Sulfolene  >98.0%(GC)

  • 77-79-2

  • 500g

  • 525.00CNY

  • Detail
  • Alfa Aesar

  • (A13887)  3-Sulfolene, 98%   

  • 77-79-2

  • 100g

  • 179.0CNY

  • Detail
  • Alfa Aesar

  • (A13887)  3-Sulfolene, 98%   

  • 77-79-2

  • 500g

  • 564.0CNY

  • Detail
  • Alfa Aesar

  • (A13887)  3-Sulfolene, 98%   

  • 77-79-2

  • 1000g

  • 981.0CNY

  • Detail
  • Alfa Aesar

  • (A13887)  3-Sulfolene, 98%   

  • 77-79-2

  • 5000g

  • 3907.0CNY

  • Detail
  • Aldrich

  • (B84505)  Butadienesulfone  98%

  • 77-79-2

  • B84505-100G

  • 283.14CNY

  • Detail
  • Aldrich

  • (B84505)  Butadienesulfone  98%

  • 77-79-2

  • B84505-500G

  • 665.73CNY

  • Detail

77-79-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Butadiene sulfone

1.2 Other means of identification

Product number -
Other names 2,5-Dihydrothiophene 1,1-Dioxide

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Lubricants and lubricant additives
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:77-79-2 SDS

77-79-2Synthetic route

diallyl sulfone
16841-48-8

diallyl sulfone

3-Sulfolene
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%
buta-1,3-diene
106-99-0

buta-1,3-diene

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

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

(CH2=CH)2CuMgBr

(CH2=CH)2CuMgBr

A

3-Sulfolene
77-79-2

3-Sulfolene

B

4-vinyl-2-sulfolene
108919-88-6

4-vinyl-2-sulfolene

Conditions
ConditionsYield
In tetrahydrofuran at -78℃; for 2h;A 26%
B 41%
3-bromo-2,3-dihydro-thiophene-1,1-dioxide
53336-42-8

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

t-Bu2CuLi

t-Bu2CuLi

A

3-Sulfolene
77-79-2

3-Sulfolene

B

2,3-dihydrothiophene-1,1-dioxide
1192-16-1

2,3-dihydrothiophene-1,1-dioxide

C

4-tert-butyl-2-sulfolene
108919-90-0

4-tert-butyl-2-sulfolene

D

(+/-)-2-(tert-butyl)-2,5-dihydrothiophene 1,1-dioxide
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%
2,5-dihydro-thiophene
1708-32-3

2,5-dihydro-thiophene

3-Sulfolene
77-79-2

3-Sulfolene

Conditions
ConditionsYield
With dihydrogen peroxide; acetic acid
3-bromo-2,3-dihydro-thiophene-1,1-dioxide
53336-42-8

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

acetone
67-64-1

acetone

A

3-Sulfolene
77-79-2

3-Sulfolene

B

2-(1-hydroxy-1-methylethyl)-3-sulfolene
4055-13-4

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

Conditions
ConditionsYield
With magnesium; mercury dichloride In tetrahydrofuran Ambient temperature; Irradiation;
3-bromo-2,3-dihydro-thiophene-1,1-dioxide
53336-42-8

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

A

thiophene-1,1-dioxide
27092-46-2

thiophene-1,1-dioxide

B

3-Sulfolene
77-79-2

3-Sulfolene

C

2,3-dihydrothiophene-1,1-dioxide
1192-16-1

2,3-dihydrothiophene-1,1-dioxide

Conditions
ConditionsYield
With potassium In toluene Ambient temperature;
3-bromo-2,3-dihydro-thiophene-1,1-dioxide
53336-42-8

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

3-Sulfolene
77-79-2

3-Sulfolene

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

3-Sulfolene

sulfolane
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;
3-Sulfolene
77-79-2

3-Sulfolene

3-hydroxytetrahydrothiophene 1,1-dioxide
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
3-Sulfolene
77-79-2

3-Sulfolene

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

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

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran at 20℃; for 1h;99.1%
With potassium methanolate In tetrahydrofuran at 110℃; for 0.166667h;
3-Sulfolene
77-79-2

3-Sulfolene

C4H5(2)HO2S

C4H5(2)HO2S

Conditions
ConditionsYield
With n-butyllithium; water-d2; zinc(II) chloride 1.) THF, -105 deg C; 2.) THF, -78 deg C;99%
3-Sulfolene
77-79-2

3-Sulfolene

4-bromoisoquinoline
1532-97-4

4-bromoisoquinoline

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

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

Conditions
ConditionsYield
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%
3-Sulfolene
77-79-2

3-Sulfolene

5-bromoisoquinoline
34784-04-8

5-bromoisoquinoline

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

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

Conditions
ConditionsYield
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%
3-Sulfolene
77-79-2

3-Sulfolene

4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

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

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

Conditions
ConditionsYield
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%
3-Sulfolene
77-79-2

3-Sulfolene

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

4-cyanophenyl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate

C11H11N

C11H11N

Conditions
ConditionsYield
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%
3-Sulfolene
77-79-2

3-Sulfolene

diethyl Fumarate
623-91-6

diethyl Fumarate

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

trans-1,2-bis(ethoxycarbonyl)-4-cyclohexene

Conditions
ConditionsYield
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;
3-Sulfolene
77-79-2

3-Sulfolene

acrolein
107-02-8

acrolein

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

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

Conditions
ConditionsYield
With n-butyllithium; zinc dibromide 1.) THF, -105 deg C; 2.) THF, -78 deg C;97%
3-Sulfolene
77-79-2

3-Sulfolene

naphthalene-2-boronic acid
32316-92-0

naphthalene-2-boronic acid

C14H14O2S

C14H14O2S

Conditions
ConditionsYield
With C64H44Cl2F8Fe4Rh2; potassium hydroxide In 1,4-dioxane; water at 60℃; for 16h; Inert atmosphere; Schlenk technique; Sealed tube; enantioselective reaction;97%
3-Sulfolene
77-79-2

3-Sulfolene

2-Methylphenylboronic acid
16419-60-6

2-Methylphenylboronic acid

C11H14O2S

C11H14O2S

Conditions
ConditionsYield
With C64H44Cl2F8Fe4Rh2; potassium hydroxide In 1,4-dioxane; water at 60℃; for 16h; Inert atmosphere; Schlenk technique; Sealed tube; enantioselective reaction;97%
3-Sulfolene
77-79-2

3-Sulfolene

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

3-<(trifluoromethanesulfonyl)oxy>benzonitrile

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

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

Conditions
ConditionsYield
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%
3-Sulfolene
77-79-2

3-Sulfolene

acetonitrile
75-05-8

acetonitrile

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

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

Conditions
ConditionsYield
With sulfuryl dichloride for 4h; Ambient temperature;96%
3-Sulfolene
77-79-2

3-Sulfolene

p-chlorobenzenediazonium tetrafluoroborate
673-41-6

p-chlorobenzenediazonium tetrafluoroborate

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

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

Conditions
ConditionsYield
With palladium diacetate In methanol at 50℃; for 0.5h;96%
3-Sulfolene
77-79-2

3-Sulfolene

C15H12O4S2
143726-55-0

C15H12O4S2

C19H18O4S2

C19H18O4S2

Conditions
ConditionsYield
at 60℃; for 24h;96%
3-Sulfolene
77-79-2

3-Sulfolene

4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

C11H11N

C11H11N

Conditions
ConditionsYield
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%
3-Sulfolene
77-79-2

3-Sulfolene

p-aminomethylbenzoic acid
56-91-7

p-aminomethylbenzoic acid

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

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

Conditions
ConditionsYield
With potassium hydroxide In water at 55℃; for 23h;95%
3-Sulfolene
77-79-2

3-Sulfolene

benzaldehyde
100-52-7

benzaldehyde

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

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

Conditions
ConditionsYield
With n-butyllithium; zinc(II) chloride 1.) THF, -105 deg C; 2.) THF, -78 deg C;95%
3-Sulfolene
77-79-2

3-Sulfolene

C15H12O4S2

C15H12O4S2

C19H18O4S2

C19H18O4S2

Conditions
ConditionsYield
at 60℃; for 24h;95%
3-Sulfolene
77-79-2

3-Sulfolene

C26H18O4S2

C26H18O4S2

C30H24O4S2

C30H24O4S2

Conditions
ConditionsYield
at 60℃; for 24h;95%
3-Sulfolene
77-79-2

3-Sulfolene

3-methoxyphenylboronic acid
10365-98-7

3-methoxyphenylboronic acid

C11H14O3S

C11H14O3S

Conditions
ConditionsYield
With C64H44Cl2F8Fe4Rh2; potassium hydroxide In 1,4-dioxane; water at 60℃; for 16h; Inert atmosphere; Schlenk technique; Sealed tube; enantioselective reaction;95%
3-Sulfolene
77-79-2

3-Sulfolene

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

1-bromo-3,5-dichlorobenzene

C10H8Cl2

C10H8Cl2

Conditions
ConditionsYield
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%
3-Sulfolene
77-79-2

3-Sulfolene

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

ethyl 5-bromo-3-pyridinecarboxylate

C12H13NO2

C12H13NO2

Conditions
ConditionsYield
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%
3-Sulfolene
77-79-2

3-Sulfolene

C13H10O4S2
143726-50-5

C13H10O4S2

C17H16O4S2
143726-57-2

C17H16O4S2

Conditions
ConditionsYield
at 60℃; for 24h;94%
at 70℃;
3-Sulfolene
77-79-2

3-Sulfolene

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

2-methyl-1,4-benzodithiin tetroxide

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

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

Conditions
ConditionsYield
at 60℃;94%
3-Sulfolene
77-79-2

3-Sulfolene

4-bromobenzenediazonium tetrafluoroborate
673-40-5

4-bromobenzenediazonium tetrafluoroborate

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

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

Conditions
ConditionsYield
With palladium diacetate In methanol at 50℃; for 0.5h;94%
3-Sulfolene
77-79-2

3-Sulfolene

C22H14O4S2
143726-54-9

C22H14O4S2

C26H20O4S2

C26H20O4S2

Conditions
ConditionsYield
at 60℃; for 24h;94%
3-Sulfolene
77-79-2

3-Sulfolene

4-Bromophenylboronic acid
5467-74-3

4-Bromophenylboronic acid

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

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

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

77-79-2Relevant articles and documents

Synthesis of symmetrical sulfones from rongalite: Expansion to cyclic sulfones by ring-closing metathesis

Kotha, Sambasivarao,Khedkar, Priti,Ghosh, Arun Kumar

, p. 3581 - 3585 (2005)

A simple method for the synthesis of symmetrical sulfones using rongalite has been developed. Terminally olefinic sulfone derivatives were subjected to ring-closing metathesis (RCM) reactions to generate cyclic sulfones. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.

A six-coordinated cationic ruthenium carbyne complex with liable pyridine ligands: Synthesis, structure, catalytic investigation, and DFT study on initiation mechanism

Liu, Guiyan,Zheng, Lu,Shao, Mingbo,Zhang, Huizhu,Qiao, Weixia,Wang, Xiaojia,Liu, Bowen,Zhao, Haitao,Wang, Jianhui

supporting information, p. 4718 - 4725 (2014/06/24)

A novel six-coordinated high-valence cationic ruthenium carbyne complex bearing two liable pyridine ligands was prepared in high yield by the reaction of the ruthenium-based complex (IMesH2)(Cl)2(C 5H5N)2RuCHPh [IMesH2=1,3-dimesityl- 4,5-dihydroimida-zol-2-ylidene] with excess iodine as an oxidant in CH 2Cl2 at 25 °C under N2. The new ruthenium carbyne-based complex shows moderate to good catalytic activity for ring-closing metathesis reactions. Importantly, no double bond isomerization by-product was produced at elevated reaction temperatures (100 °C-137 °C) in the reaction catalyzed by the synthesized ruthenium carbyne complex. A mechanism involving the in situ conversion of the ruthenium carbyne through the addition of an iodide to the carbyne carbon was also proposed, and DFT calculations were performed to explain the initiating mechanism.

A unique ruthenium carbyne complex: A highly thermo-endurable catalyst for olefin metathesis

Wang, Jianhui,Shao, Mingbo,Zheng, Lu,Qiao, Weixia,Wang, Jingjing

supporting information, p. 2743 - 2750,8 (2012/12/12)

A cationic ruthenium carbyne complex was prepared and was found to initiate olefin metathesis reactions with good activities, which throws a new light on the design of a new type of ruthenium catalyst for RCM reactions. More importantly, no double bond isomerized by-product was observed even at elevated temperatures in reactions catalyzed by the new carbyne complex. A mechanism involving the in situ conversion of the ruthenium carbyne to a ruthenium carbene complex via addition of an iodide to the carbyne carbon was also proposed.

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