Sulfone, sulfoxide compound

Sulfone is the general name for compounds formed by the combination of sulfonyl and hydrocarbyl, of which the general formula is R-SO2-R. The hydrocarbyl groups (R) can be identical or different, such as dimethyl sulfone (CH3 • SO2 • CH3), ethyl phenyl sulphone (C6H5 • SO2 • C2H5), diethyl sulfone, diphenyl sulfone, sulfolane, bisphenol S, etc. The sulfur in sulfones is of high valence; and sulfone is a stable crystalline organic compound which can’t be reduced into R2S. Sulfolane, dimethyl sulfone and bisphenol S are the most important sulfones in the industry. Sulfone is generally colorless and odorless stable solid. Lower carbon sulfone is soluble in water and most organic solvents. Sulfone can be prepared generally by the oxidation of thioether, the alkylation of sulfonate, the Diels-Alder reaction of sulfur dioxide or the reaction of aromatic hydrocarbons with sulfoxide chloride, etc.

Sulfone is widely used in pharmaceutical, plastics and basic organic synthesis industry. For example, solasulfone and dapsone are drugs for leprosy; bisphenol A polysulfone is a kind of plastic with excellent properties and sulfolane is an excellent solvent which can be used to clean industrial gases such as the removal of carbon dioxide and hydrogen sulfide; it’s also used as a solvent in the polymerization of acrylonitrile as well as in the extraction of aromatics from petroleum. Some sulfones have sedative and hypnotic effects, but with side effects. In addition to a heat resistance, oxidation resistance and light stability of bisphenol S, the hydroxyl in it has strong acidity because of the strong electron-withdrawing of the sulfonyl. Bisphenol S is mainly used as a fixative as well as the material of leather tanning agents, dyes, heat-resistant engineering plastics and crosslinking agents. It also can be used as a substitute for bisphenol A as the raw material of polycarbonate, epoxy resin, polyester resin and phenol resin.

Sulfoxide is the general name for compounds formed by the combination of sulfinyl and hydrocarbyl (R), such as dimethyl sulfoxide, diethyl sulfoxide, benzyl phenyl sulfoxide. The oxygen atom in sulfoxide is in an anion state with a strong polarity and a strong oxidizability. Sulfoxides may be optically active. They are solid at low temperatures and generally soluble in water, alcohol and ether. Sulfoxide can be reduced into sulfide, oxidized into the sulfone and salified with nitrate. It can be prepared generally by the oxidation of sulfide or the Friedel-Crafts reaction of an aromatic hydrocarbon with thionyl chloride.

Sulfoxide can take part in many important reactions.
1, The α-carbanion in sulfinyl can easily react with haloalkane, carbonyl compounds and olefins due to its high reactivity;
2, Sulfoxide along with acid anhydride can induce the Pummerer rearrangement;
3, Olefins and sulfinic acid can be generated after the thermal decomposition of sulfoxide with a β site containing hydrogen.

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Structure Chemical Name CAS MF
2,4'-DIHYDROXYDIPHENYL SULFONE 2,4'-DIHYDROXYDIPHENYL SULFONE 5397-34-2 C12H10O4S
4-Hydroxy-4'-isopropoxydiphenylsulfone 4-Hydroxy-4'-isopropoxydiphenylsulfone 95235-30-6 C15H16O4S
3-Nitrophenyl sulphone 3-Nitrophenyl sulphone 1228-53-1 C12H8N2O6S
Trimethylsulfoxonium iodide Trimethylsulfoxonium iodide 1774-47-6 C3H9IOS
Bis[4-(4-aminophenoxy)phenyl]sulfone Bis[4-(4-aminophenoxy)phenyl]sulfone 13080-89-2 C24H20N2O4S
Fluoromethyl phenyl sulfone Fluoromethyl phenyl sulfone 20808-12-2 C7H7FO2S
DIBENZOTHIOPHENE SULFONE DIBENZOTHIOPHENE SULFONE 1016-05-3 C12H8O2S
4-FLUOROPHENYL METHYL SULFONE 4-FLUOROPHENYL METHYL SULFONE 455-15-2 C7H7FO2S
METHYLTHIOMETHYL P-TOLYL SULFONE METHYLTHIOMETHYL P-TOLYL SULFONE 59662-65-6 C9H12O2S2
3,3'-Diamino-4,4'-dihydroxydiphenyl sulfone 3,3'-Diamino-4,4'-dihydroxydiphenyl sulfone 7545-50-8 C12H12N2O4S
1-(BROMOMETHYL)-4-(METHYLSULFONYL)BENZENE 1-(BROMOMETHYL)-4-(METHYLSULFONYL)BENZENE 53606-06-7 C8H9BrO2S
PHENYL VINYL SULFOXIDE PHENYL VINYL SULFOXIDE 20451-53-0 C8H8OS
BIS(4-NITROPHENYL) SULFONE BIS(4-NITROPHENYL) SULFONE 1156-50-9 C12H8N2O6S
3-METHOXYCARBONYL-3-SULFOLENE 3-METHOXYCARBONYL-3-SULFOLENE 67488-50-0 C6H8O4S
BENZYL METHYL SULFONE BENZYL METHYL SULFONE 3112-90-1 C8H10O2S
BIS[4-(2-HYDROXYETHOXY)PHENYL] SULFONE BIS[4-(2-HYDROXYETHOXY)PHENYL] SULFONE 27205-03-4 C16H18O6S
3-(TRIFLUOROMETHYLSULFONYL)ANILINE 3-(TRIFLUOROMETHYLSULFONYL)ANILINE 426-59-5 C7H6F3NO2S
4-Methylsulfuryl chlorobenzene 4-Methylsulfuryl chlorobenzene 98-57-7 C7H7ClO2S
Ethyl vinyl sulfone Ethyl vinyl sulfone 1889-59-4 C4H8O2S
2-(Ethylsulfonyl)-5-(1-pyrrolidinyl)aniline 2-(Ethylsulfonyl)-5-(1-pyrrolidinyl)aniline 1219972-54-9 C12H18N2O2S
Choline tosylate Choline tosylate 55357-38-5 C12H21NO4S
2,4-DIMETHYLSULFOLANE 2,4-DIMETHYLSULFOLANE 1003-78-7 C6H12O2S
METHYLSULFONYLACETONE METHYLSULFONYLACETONE 5000-46-4 C4H8O3S
3,4-DIBROMOSULFOLANE 3,4-DIBROMOSULFOLANE 15091-30-2 C4H6Br2O2S
3-METHYLSULFOLANE 3-METHYLSULFOLANE 872-93-5 C5H10O2S
4,4'-Bis(4-chlorophenyl)sulfonyl-1,1'-biphenyl 4,4'-Bis(4-chlorophenyl)sulfonyl-1,1'-biphenyl 22287-56-5 C24H16Cl2O4S2
Bis(4-hydroxyphenyl) Sulfone Bis(4-hydroxyphenyl) Sulfone 80-09-1 C12H10O4S
4-[(4-Benzyloxyphenyl)sulfonyl]phenol 4-[(4-Benzyloxyphenyl)sulfonyl]phenol 63134-33-8 C19H16O4S
4-FLUORONAPHTHALENE-1-SULFONYL CHLORIDE 4-FLUORONAPHTHALENE-1-SULFONYL CHLORIDE 316-69-8 C10H6ClFO2S
2-CHLOROETHYL P-TOLYL SULFONE 2-CHLOROETHYL P-TOLYL SULFONE 22381-53-9 C9H11ClO2S
Thionyl bromide Thionyl bromide 507-16-4 Br2OS
Allyl phenyl sulfone Allyl phenyl sulfone 16212-05-8 C9H10O2S
3,3'-Sulfonyldianiline 3,3'-Sulfonyldianiline 599-61-1 C12H12N2O2S
BIS(2-ETHYLHEXYL) SULFOXIDE BIS(2-ETHYLHEXYL) SULFOXIDE 82374-34-3 C16H34OS
ALDICARB-SULFOXIDE ALDICARB-SULFOXIDE 1646-87-3 C7H14N2O3S
DISULFOTON-SULFONE DISULFOTON-SULFONE 2497-06-5 C8H19O4PS3
Divinyl sulphone Divinyl sulphone 77-77-0 C4H6O2S
ISOTHIOCYANATOPHENYL SULFONE ISOTHIOCYANATOPHENYL SULFONE 4430-49-3 C14H8N2O2S3
2-CHLORO-4-(METHYLSULFONYL)ANILINE 2-CHLORO-4-(METHYLSULFONYL)ANILINE 13244-35-4 C7H8ClNO2S
2,2'-SULFONYLDIETHANOL 2,2'-SULFONYLDIETHANOL 2580-77-0 C4H10O4S
4-NITRODIPHENYL SULFONE 4-NITRODIPHENYL SULFONE 1146-39-0 C12H9NO4S
Phenyl chlorothionocarbonate Phenyl chlorothionocarbonate 1005-56-7 C7H5ClOS
4,4'-BIS(3-AMINOPHENOXY)DIPHENYL SULFONE 4,4'-BIS(3-AMINOPHENOXY)DIPHENYL SULFONE 30203-11-3 C24H20N2O4S
1-(BENZENESULFONYLMETHYL)-2-BROMOBENZENE 1-(BENZENESULFONYLMETHYL)-2-BROMOBENZENE 92022-50-9 C13H11BrO2S
TRIMETHYLSULFOXONIUM CHLORIDE TRIMETHYLSULFOXONIUM CHLORIDE 5034-06-0 C3H9ClOS
SULFOXIDE SULFOXIDE 120-62-7 C18H28O3S
DI-N-BUTYL SULFOXIDE DI-N-BUTYL SULFOXIDE 2168-93-6 C8H18OS
BENZYL PHENYL SULFONE BENZYL PHENYL SULFONE 3112-88-7 C13H12O2S
DI-N-OCTYL SULFONE DI-N-OCTYL SULFONE 7726-20-7 C16H34O2S
Tetramethylene sulfoxide Tetramethylene sulfoxide 1600-44-8 C4H8OS
1,1-dimethylethyl [[(2,4,6-trimethylphenyl)sulphonyl]oxy]carbamate 1,1-dimethylethyl [[(2,4,6-trimethylphenyl)sulphonyl]oxy]carbamate 36016-39-4 C14H21NO5S
3,3,4,4-Tetrachlorotetrahydrothiophene 1,1-dioxide 3,3,4,4-Tetrachlorotetrahydrothiophene 1,1-dioxide 3737-41-5 C4H4Cl4O2S
FENAMIPHOS SULFONE FENAMIPHOS SULFONE 31972-44-8 C13H22NO5PS
Tolyl diiodomethyl sulfone Tolyl diiodomethyl sulfone 20018-09-1 C8H8I2O2S
Ponazuril Ponazuril 69004-04-2 C18H14F3N3O6S
(-)-ANABASINE (-)-ANABASINE 494-52-0 C10H14N2
BENZENETHIOSULFONIC ACID S-PHENYL ESTER BENZENETHIOSULFONIC ACID S-PHENYL ESTER 1212-08-4 C12H10O2S2
BIS(4-FLUORO-3-NITROPHENYL) SULFONE BIS(4-FLUORO-3-NITROPHENYL) SULFONE 312-30-1 C12H6F2N2O6S
ISOPROPYL METHYL SULFONE ISOPROPYL METHYL SULFONE 4853-74-1 C4H10O2S
TERBUFOS-SULFONE TERBUFOS-SULFONE 56070-16-7 C9H21O4PS3
MMTS MMTS 33577-16-1 C3H8OS2
TRIMETHYLSULFOXONIUM BROMIDE TRIMETHYLSULFOXONIUM BROMIDE 25596-24-1 C3H9BrOS
DI-N-DODECYL SULFOXIDE DI-N-DODECYL SULFOXIDE 2168-96-9 C24H50OS
2-CHLOROETHYL 4-CHLOROPHENYL SULFONE 2-CHLOROETHYL 4-CHLOROPHENYL SULFONE 16191-84-7 C8H8Cl2O2S
3-N-HEPTYLTHIOPHENE 3-N-HEPTYLTHIOPHENE 65016-61-7 C11H18S
BUTOCARBOXIM SULFOXIDE BUTOCARBOXIM SULFOXIDE 34681-24-8 C7H14N2O3S
PHENYL TRANS-STYRYL SULFONE PHENYL TRANS-STYRYL SULFONE 16212-06-9 C14H12O2S
DIXYLYL SULFONE DIXYLYL SULFONE 27043-27-2 C16H18O2S
FENBENDAZOLE SULFONE FENBENDAZOLE SULFONE 54029-20-8 C15H13N3O4S
Triclabendazole sulfoxide Triclabendazole sulfoxide 100648-13-3 C14H9Cl3N2O2S
CHLOROMETHYL PHENYL SULFOXIDE CHLOROMETHYL PHENYL SULFOXIDE 7205-94-9 C7H7ClOS
CHLOROMETHYL PHENYL SULFONE CHLOROMETHYL PHENYL SULFONE 7205-98-3 C7H7ClO2S
2-CHLOROETHYL PHENYL SULFONE 2-CHLOROETHYL PHENYL SULFONE 938-09-0 C8H9ClO2S
2-FLUOROPHENYLMETHYLSULFONE 2-FLUOROPHENYLMETHYLSULFONE 654-47-7 C7H7FO2S
DAPSONE HYDROXYLAMINE DAPSONE HYDROXYLAMINE 32695-27-5 C12H12N2O3S
NITROMETHYL PHENYL SULFONE NITROMETHYL PHENYL SULFONE 21272-85-5 C7H7NO4S
2-CHLOROETHYL 4-FLUOROPHENYL SULFONE 2-CHLOROETHYL 4-FLUOROPHENYL SULFONE 33330-46-0 C8H8ClFO2S
(R)-(+)-Methyl p-tolyl sulfoxide (R)-(+)-Methyl p-tolyl sulfoxide 1519-39-7 C8H10OS
METHIOCARB SULFONE METHIOCARB SULFONE 2179-25-1 C11H15NO4S
ETHYNYL P-TOLYL SULFONE ETHYNYL P-TOLYL SULFONE 13894-21-8 C9H8O2S
Methyl vinyl sulfone Methyl vinyl sulfone 3680-02-2 C3H6O2S
4,4'-DIBROMO DIPHENYL SULFONE 4,4'-DIBROMO DIPHENYL SULFONE 2050-48-8 C12H8Br2O2S
PHENYL TRANS-STYRYL SULFONE  99 PHENYL TRANS-STYRYL SULFONE 99 5418-11-1 C14H12O2S
3-METHYL-2,5-DIHYDROTHIOPHENE-1,1-DIOXIDE 3-METHYL-2,5-DIHYDROTHIOPHENE-1,1-DIOXIDE 1193-10-8 C5H8O2S
BIS[4-(2-HYDROXYETHOXY)-3,5-DIBROMOPHENYL] SULFONE BIS[4-(2-HYDROXYETHOXY)-3,5-DIBROMOPHENYL] SULFONE 53714-39-9 C16H14Br4O6S
BROMOMETHYL PHENYL SULFONE BROMOMETHYL PHENYL SULFONE 19169-90-5 C7H7BrO2S
3-AMINOTETRAHYDRO-1H-1LAMBDA6-THIOPHENE-1,1-DIONE HYDROCHLORIDE 3-AMINOTETRAHYDRO-1H-1LAMBDA6-THIOPHENE-1,1-DIONE HYDROCHLORIDE 51642-03-6 C4H10ClNO2S
DI-P-TOLYL SULFONE DI-P-TOLYL SULFONE 599-66-6 C14H14O2S
3-SULFOLENE 3-SULFOLENE 77-79-2 C4H6O2S
FENTHION-OXON-SULFOXIDE FENTHION-OXON-SULFOXIDE 6552-13-2 C10H15O5PS
N-MONOACETYL-4,4'-DIAMINODIPHENYL SULFONE N-MONOACETYL-4,4'-DIAMINODIPHENYL SULFONE 565-20-8 C14H14N2O3S
TERBUFOS-SULFOXIDE TERBUFOS-SULFOXIDE 10548-10-4 C9H21O3PS3
(S)-(-)-METHYL P-TOLYL SULFOXIDE (S)-(-)-METHYL P-TOLYL SULFOXIDE 5056-07-5 C8H10OS
ETHYL ISOPROPYL SULFONE ETHYL ISOPROPYL SULFONE 4853-75-2 C5H12O2S
SULPROFOS-SULFOXIDE SULPROFOS-SULFOXIDE 34643-47-5 C12H19O3PS3
METHYL (PHENYLSULFINYL)ACETATE METHYL (PHENYLSULFINYL)ACETATE 14090-83-6 C9H10O3S
TRANS-1,2-BIS(PHENYLSULFONYL)ETHYLENE TRANS-1,2-BIS(PHENYLSULFONYL)ETHYLENE 963-16-6 C14H12O4S2
PHORATE SULFONE PHORATE SULFONE 2588-04-7 C7H17O4PS3
4-METHOXYPHENYLMETHYLSULFONE 4-METHOXYPHENYLMETHYLSULFONE 3517-90-6 C8H10O3S
TRIMETHYLSILYLBENZENESULFONATE TRIMETHYLSILYLBENZENESULFONATE 17872-92-3 C10H16O2SSi
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