127-63-9

Usage

Uses

Used in Pesticide Industry:
Diphenyl sulfone is used as an oviduct and acaricide, providing effective pest control in various agricultural applications.
Used in Chemical Industry:
Diphenyl sulfone is identified as a preferred solvent due to its chemical and thermal stability compared to dimethyl sulfoxide. This makes it suitable for various chemical processes and reactions.
Used in Organic Chemistry:
Diphenyl sulfone undergoes deoxygenation with Mg-MeOH at room temperature, which is a useful reaction in organic chemistry for the synthesis of various compounds.
Used in Polymer Processing:
Diphenyl sulfone is used as a high-temperature solvent, which is useful for processing highly rigid polymers such as PEEK (Polyether ether ketone) that only dissolve in very hot solvents. This allows for the manufacturing and shaping of these high-performance polymers in various industries.

Synthesis Reference(s)

The Journal of Organic Chemistry, 50, p. 1784, 1985 DOI: 10.1021/jo00210a053Synthesis, p. 342, 1974Tetrahedron Letters, 21, p. 689, 1980 DOI: 10.1016/S0040-4039(00)71446-8

Flammability and Explosibility

Notclassified

Purification Methods

Crystallise the sulfone from diethyl ether. It has been purified by zone melting. [Beilstein 6 H 300, 6 IV 1490.]

InChI:InChI=1/C12H10O2S/c13-15(14,11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H

Synthetic route

diphenyl sulfide (139-66-2) → diphenyl sulphone (127-63-9)

Conditions	Yield
With ruthenium trichloride; sodium periodate In tetrachloromethane; water; acetonitrile for 1h; Ambient temperature;	100%
With dihydrogen peroxide; methyltrioxorhenium(VII) In ethanol for 2h; Ambient temperature;	100%
With dihydrogen peroxide; [(η5-C5Me5)Mo(CO)3Cl] In acetonitrile at 35℃; for 5h;	100%

diphenyliodonium tetrafluoroborate + sodium benzenesulfonate (873-55-2) → iodobenzene (591-50-4) + diphenyl sulphone (127-63-9)

Conditions	Yield
In chloroform; water at 20℃; for 64h;	A n/a B 99%
In chloroform; water at 56℃; for 2.5h; Product distribution; other temperatures, other reaction time;	A 99 % Chromat. B 97%

1,1'-sulfinylbisbenzene (945-51-7) → diphenyl sulphone (127-63-9)

Conditions	Yield
With sodium hypochlorite; tetrabutyl-ammonium chloride In water; ethyl acetate Ambient temperature;	98%
With sodium hypochlorite In acetonitrile for 0.0833333h; Ambient temperature;	97%
With 2,2,4,4,6,6-hexachloro-1,3,5-triaza-2,4,6-triphosphorine; dihydrogen peroxide at 25℃; for 0.266667h; Neat (no solvent); chemoselective reaction;	97%

iodobenzene (591-50-4) + sodium benzenesulfonate (873-55-2) → diphenyl sulphone (127-63-9)

Conditions	Yield
With caesium carbonate In dimethyl sulfoxide at 110℃; for 24h; Ullmann Condensation; Green chemistry;	98%
With copper(l) iodide; potassium acetate; D-glucosamine hydrochloride In water; dimethyl sulfoxide at 100℃; Sealed tube; Green chemistry;	96%
With copper diacetate; potassium carbonate; N,N`-dimethylethylenediamine In dimethyl sulfoxide at 110℃; for 2h; Reagent/catalyst; Ullmann Condensation;	95%

C25H22NO2S2(1+)*ClO4(1-) → diphenyl sulphone (127-63-9) + S,S,S-triphenyloxosulfonium perchlorate + toluene-4-sulfonamide (70-55-3)

Conditions	Yield
With potassium hydroxide In methanol; water for 1h; Ambient temperature;	A 20% B 77% C 98%

pentaphenylbismuth (3049-07-8) → diphenyl sulphone (127-63-9) + benzene (71-43-2)

Conditions	Yield
With sulfur dioxide	A 95% B 97%

pentaphenylbismuth (3049-07-8) → C6H4(SOO)(Bi(C6H5)O2S) + diphenyl sulphone (127-63-9) + benzene (71-43-2)

Conditions	Yield
With sulfur dioxide In liquid sulphur dioxide 15 min; GLC, volatiles removal (vacuum), washing (benzene), drying; elem. anal.;	A n/a B 95% C 97%

pentaphenylbismuth (3049-07-8) + sulfur dioxide (7446-09-5) → C12H9BiO4S2 + diphenyl sulphone (127-63-9) + benzene (71-43-2)

Conditions	Yield
In neat (no solvent) soln. (liquid SO2) lost purple color within 15 min;; evapn. (SO2); identification of C6H6 and SO2(C6H5)2 by liquid chromy.; residue washed with benzene and dried; elem. anal. of unidentified Bi-compound;;	A n/a B 95% C 97%

diphenyliodonium tetrafluoroborate + sodium benzenesulfonate (873-55-2) → diphenyl sulphone (127-63-9)

Conditions	Yield
In N,N-dimethyl-formamide at 90℃; for 24h; Schlenk technique; Inert atmosphere;	96%
With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 50℃; for 4h;	71%

Diphenyliodonium triflate (66003-76-7) + sodium benzenesulfonate (873-55-2) → diphenyl sulphone (127-63-9)

Conditions	Yield
In N,N-dimethyl-formamide at 90℃; for 24h; Solvent; Temperature; Schlenk technique; Inert atmosphere;	96%
With PEG-400 at 50℃; for 0.166667h; Microwave irradiation; Sealed tube;	94%
In 1,4-dioxane at 80℃; for 24h;	79%

sodium benzenesulfonate (873-55-2) + diphenyliodonium hexafluorophosphate (58109-40-3) → diphenyl sulphone (127-63-9)

Conditions	Yield
In N,N-dimethyl-formamide at 90℃; for 24h; Schlenk technique; Inert atmosphere;	96%

sodium benzenesulfonate (873-55-2) + diphenyliodonium p-toluenesulfonate (6293-66-9) → diphenyl sulphone (127-63-9)

Conditions	Yield
In N,N-dimethyl-formamide at 90℃; for 24h; Schlenk technique; Inert atmosphere;	96%

phenylsulfonyl fluoride (368-43-4) + phenylmagnesium bromide → diphenyl sulphone (127-63-9)

Conditions	Yield
In tetrahydrofuran for 4h; Ambient temperature;	95%

diphenyl sulfide (139-66-2) → 1,1'-sulfinylbisbenzene (945-51-7) + diphenyl sulphone (127-63-9)

Conditions	Yield
With sodium hypochlorite pentahydrate In water; acetonitrile at 20℃; for 0.416667h; Green chemistry;	A 95% B 5%
With chloro-trimethyl-silane In acetonitrile at -15℃; for 18h; Oxidation;	A 94% B 1 % Spectr.
With phenylphosphonate; dihydrogen peroxide; methyl tri-n-octyl ammonium hydrogen sulfate; sodium tungstate at 0℃; for 9h;	A 94% B 6%

bromobenzene (108-86-1) + sodium benzenesulfonate (873-55-2) → diphenyl sulphone (127-63-9)

Conditions	Yield
With pyridine; copper(I) bromide at 80℃; for 12h; Reagent/catalyst; Solvent;	95%
With C93H189NO41; copper(I) bromide In water at 90℃; for 8h;	95%
With 1,10-Phenanthroline; copper ferrite In N,N-dimethyl-formamide at 110℃; for 12h; Green chemistry;	85%

diphenyliodonium chloride (1483-72-3) + sodium benzenesulfonate (873-55-2) → diphenyl sulphone (127-63-9)

Conditions	Yield
In N,N-dimethyl-formamide at 90℃; for 24h; Schlenk technique; Inert atmosphere;	95%
With 1-butyl-3-methylimidazolium Tetrafluoroborate at 40℃;	73%

2-(phenylsulfonyl)benzaldehyde (126076-76-4) → diphenyl sulphone (127-63-9)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at -70 - 20℃; Inert atmosphere;	95%

sodium phenylsulfonate (515-42-4) + 2-(trimethylsilyl)phenyl trifluoromethanesulfonate (88284-48-4) → diphenyl sulphone (127-63-9)

Conditions	Yield
With tetrabutyl ammonium fluoride In acetonitrile at 20℃; for 3h; Reagent/catalyst; Inert atmosphere;	95%

sodium benzenesulfonate (873-55-2) + 2-(trimethylsilyl)phenyl trifluoromethanesulfonate (88284-48-4) → diphenyl sulphone (127-63-9)

Conditions	Yield
With tetrabutyl ammonium fluoride In acetonitrile at 30℃; for 3h; Reagent/catalyst; Time; Inert atmosphere;	95%
With cesium fluoride In acetonitrile at 80℃; for 2h; Solvent; Reagent/catalyst; Temperature; Inert atmosphere;	85%

toluene-4-sulfonic acid phenyl ester (640-60-8) + sodium benzenesulfonate (873-55-2) → diphenyl sulphone (127-63-9)

Conditions	Yield
With tetrakis(actonitrile)copper(I) hexafluorophosphate In dimethyl sulfoxide at 120℃; for 3h; Catalytic behavior; Reagent/catalyst; Solvent;	95%

tert.-butylhydroperoxide (75-91-2) + Martins sulfurane (32133-82-7) → di-tert-butyl peroxide (110-05-4) + diphenyl sulfide (139-66-2) + 1,1'-sulfinylbisbenzene (945-51-7) + diphenyl sulphone (127-63-9) + 1,1,1,3,3,3-hexafluoro-2-phenylisopropyl alcohol (718-64-9) + isobutene (115-11-7)

Conditions	Yield
With 2,2-diphenyl-1-picrylhydrazine In chloroform-d1 at -78℃; Product distribution; chemiluminescence, other peroxides;	A n/a B 2% C 94% D 2% E n/a F n/a

benzene (71-43-2) → diphenyl sulphone (127-63-9) + phenylsulfonyl fluoride (368-43-4)

Conditions	Yield
With antimony pentafluoride; fluorosulphonic acid at 50℃; for 1h;	A 94% B 4%
With antimony pentafluoride; fluorosulphonic acid at 50℃; for 1h; Product distribution; influence of HSO3F-SbF5 composition;

benzenesulfonyl chloride (98-09-9) + phenylboronic acid (98-80-6) → diphenyl sulphone (127-63-9)

Conditions	Yield
With potassium carbonate; palladium dichloride In acetone at 25℃; for 0.583333h; Suzuki-Miyaura reaction;	94%
With bromo(1,10-phenanthroline)copper(I); potassium carbonate In dichloromethane; water at 25℃; for 0.166667h;	72%

benzenesulfonyl chloride (98-09-9) + benzene (71-43-2) → diphenyl sulphone (127-63-9)

Conditions	Yield
With [BTBA]Cl-FeCl3 at 60℃; for 0.05h; Friedel-Crafts sulfonylation;	93%
With tin(II) trifluoromethanesulfonate at 120℃; for 8h; Friedel-Crafts sulfonylation;	89%
iron(III) chloride at 160℃; microwave irradiation;	88%

sodium benzenesulfonate (873-55-2) → diphenyl sulphone (127-63-9)

Conditions	Yield
With copper diacetate In acetonitrile at 60℃; for 3h;	93%
Multi-step reaction with 2 steps 1: hydrogenchloride / water / pH 2 - 3 / Inert atmosphere 2: copper; isopentyl nitrite / acetonitrile / 12 h / 0 - 25 °C / Schlenk technique; Inert atmosphere View Scheme

benzene (71-43-2) → diphenyl sulphone (127-63-9)

Conditions	Yield
With chlorosulfonic acid; 1-hexyl-3-methylimidazolium hexafluorophosphate at 30℃; for 2h; Temperature; Reagent/catalyst;	92%
With dipotassium peroxodisulfate; trifluorormethanesulfonic acid; tetra(n-butyl)ammonium hydrogensulfate; trifluoroacetic anhydride In 1,2-dichloro-ethane at 80℃; for 6h; Reagent/catalyst; Sealed tube;	81%
With sulfuric acid; trifluoroacetic anhydride	61%

S,S,S-triphenyloxosulfonium perchlorate → biphenyl (92-52-4) + diphenyl sulphone (127-63-9)

Conditions	Yield
With potassium hydroxide In methanol; water for 24h; Ambient temperature;	A 5% B 92%

sodium benzenesulfonate (873-55-2) + benzenediazonium tetrafluoroborate (369-57-3) → diphenyl sulphone (127-63-9)

Conditions	Yield
With tert.-butylnitrite; eosin; methanesulfonic acid In water; acetonitrile at 20℃; for 12h; Irradiation; Inert atmosphere;	92%
With copper exchanged fluorapatite In methanol at 20℃; for 12h; Green chemistry;	88%

benzenesufonyl hydrazide (80-17-1) → diphenyl sulphone (127-63-9)

Conditions	Yield
With 2C2H3O2(1-)*C26H30B10P2*Cu(2+) In toluene at 20℃; for 3h; Catalytic behavior; Solvent; Reagent/catalyst;	92%

diphenyl sulphone (127-63-9) → 3,3'-dinitrodiphenyl sulfone (1228-53-1)

Conditions	Yield
With sulfuric acid; nitric acid at 20℃; for 24h;	97%
bei der Nitrierung;
With sulfuric acid; nitric acid
durch Nitrieren;
With sulfuric acid; nitric acid

diphenyl sulphone (127-63-9) → diphenyl sulfide (139-66-2)

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; samarium diiodide In tetrahydrofuran at 20℃; for 0.0166667h;	93%
With iodine; magnesium In methanol at 20℃; for 1.5h;	82%
With lithium aluminium tetrahydride; titanium tetrachloride In tetrahydrofuran at -78 - 20℃; for 0.5h;	75%
With pyridine-4-carbonitrile; bis(pinacol)diborane In pentane at 80℃; for 36h; Inert atmosphere; Sealed tube;	67%
With sulfur

1-methyl-piperazine (109-01-3) + diphenyl sulphone (127-63-9) → 1-methyl-4-phenylpiperazine (3074-43-9)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane 1.) 0 deg C, 30 min; room temp., 1 h, 2.) reflux, overnight;	93%

diphenyl sulphone (127-63-9) + sulfur trioxide (7446-11-9) → benzenesulfonic acid (98-11-3)

Conditions	Yield
With sulfuric acid In water; benzene	93%
With phosphoric acid; sulfuric acid In water; benzene	87%

Upstream product

• 93-59-4 Perbenzoic acid 
• 67-66-3 chloroform 
• 139-66-2 diphenyl sulfide 
• 60-29-7 diethyl ether 
• 368-43-4 phenylsulfonyl fluoride 
• 945-51-7 1,1'-sulfinylbisbenzene 
• 515-42-4 sodium phenylsulfonate 
• 2674-04-6 diphenyl cadmium 
• 98-09-9 benzenesulfonyl chloride 
• 595-90-4 tetraphenyltin(IV) 
• 555-54-4 diphenylmagnesium 
• 587-85-9 diphenylmercury(II) 
• 71-43-2 benzene 
• 2845-62-7 benzenesulphonyl isocyanate 

Downstream Products

• 1829-40-9 hexaphenyldisiloxanne 
• 1048-08-4 tetraphenylsilane 
• 18920-16-6 hexa-Si-phenyl-Si,Si'-m-phenylene-bis-silane 
• 791-31-1 triphenylhydroxysilane 
• 4096-20-2 N-phenyl piperidine 
• 58844-73-8 2-(phenylsulfonyl)benzoic acid 
• 22219-00-7 2,2'-sulfinatodibenzoate 
• 634-90-2 1,2,3,5-tetrachlorobenzene 
• 92-52-4 biphenyl 
• 139-66-2 diphenyl sulfide 
• 608-93-5 pentachlorobenzene 
• 17051-72-8 (o-chlorophenyl)phenylsulfone 
• 1228-53-1 3,3'-dinitrodiphenyl sulfone 
• 1132-39-4 diphenylselenide 

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