Product Name

  • Name

    Diphenyl sulfone

  • EINECS 204-853-1
  • CAS No. 127-63-9
  • Article Data501
  • CAS DataBase
  • Density 1.227 g/cm3
  • Solubility insoluble in hot water
  • Melting Point 123-129 °C(lit.)
  • Formula C12H10O2S
  • Boiling Point 378.5 °C at 760 mmHg
  • Molecular Weight 218.276
  • Flash Point 226.8 °C
  • Transport Information
  • Appearance white crystalline powder
  • Safety 26-36-37/39
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 127-63-9 (Diphenyl sulfone)
  • Hazard Symbols IrritantXi
  • Synonyms 1,1'-Sulfonylbis[benzene];DPS;Diphenyl sulphone;NSC627706;NSC 6780;Phenyl sulphone;Sulfobenzide;Diphenyl sulfone 98%;Phenyl sulfone(8CI);
  • PSA 42.52000
  • LogP 3.60020

Synthetic route

diphenyl sulfide
139-66-2

diphenyl sulfide

diphenyl sulphone
127-63-9

diphenyl sulphone

Conditions
ConditionsYield
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

diphenyliodonium tetrafluoroborate

sodium benzenesulfonate
873-55-2

sodium benzenesulfonate

A

iodobenzene
591-50-4

iodobenzene

B

diphenyl sulphone
127-63-9

diphenyl sulphone

Conditions
ConditionsYield
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%
...Expand
1,1'-sulfinylbisbenzene
945-51-7

1,1'-sulfinylbisbenzene

diphenyl sulphone
127-63-9

diphenyl sulphone

Conditions
ConditionsYield
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

iodobenzene

sodium benzenesulfonate
873-55-2

sodium benzenesulfonate

diphenyl sulphone
127-63-9

diphenyl sulphone

Conditions
ConditionsYield
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-)

C25H22NO2S2(1+)*ClO4(1-)

A

diphenyl sulphone
127-63-9

diphenyl sulphone

B

S,S,S-triphenyloxosulfonium perchlorate

S,S,S-triphenyloxosulfonium perchlorate

C

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

Conditions
ConditionsYield
With potassium hydroxide In methanol; water for 1h; Ambient temperature;A 20%
B 77%
C 98%
...Expand
pentaphenylbismuth
3049-07-8

pentaphenylbismuth

A

diphenyl sulphone
127-63-9

diphenyl sulphone

B

benzene
71-43-2

benzene

Conditions
ConditionsYield
With sulfur dioxideA 95%
B 97%
pentaphenylbismuth
3049-07-8

pentaphenylbismuth

A

C6H4(SOO)(Bi(C6H5)O2S)

C6H4(SOO)(Bi(C6H5)O2S)

B

diphenyl sulphone
127-63-9

diphenyl sulphone

C

benzene
71-43-2

benzene

Conditions
ConditionsYield
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%
...Expand
pentaphenylbismuth
3049-07-8

pentaphenylbismuth

sulfur dioxide
7446-09-5

sulfur dioxide

A

C12H9BiO4S2

C12H9BiO4S2

B

diphenyl sulphone
127-63-9

diphenyl sulphone

C

benzene
71-43-2

benzene

Conditions
ConditionsYield
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%
...Expand
diphenyliodonium tetrafluoroborate

diphenyliodonium tetrafluoroborate

sodium benzenesulfonate
873-55-2

sodium benzenesulfonate

diphenyl sulphone
127-63-9

diphenyl sulphone

Conditions
ConditionsYield
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

Diphenyliodonium triflate

sodium benzenesulfonate
873-55-2

sodium benzenesulfonate

diphenyl sulphone
127-63-9

diphenyl sulphone

Conditions
ConditionsYield
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

sodium benzenesulfonate

diphenyliodonium hexafluorophosphate
58109-40-3

diphenyliodonium hexafluorophosphate

diphenyl sulphone
127-63-9

diphenyl sulphone

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 90℃; for 24h; Schlenk technique; Inert atmosphere;96%
sodium benzenesulfonate
873-55-2

sodium benzenesulfonate

diphenyliodonium p-toluenesulfonate
6293-66-9

diphenyliodonium p-toluenesulfonate

diphenyl sulphone
127-63-9

diphenyl sulphone

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 90℃; for 24h; Schlenk technique; Inert atmosphere;96%
phenylsulfonyl fluoride
368-43-4

phenylsulfonyl fluoride

phenylmagnesium bromide

phenylmagnesium bromide

diphenyl sulphone
127-63-9

diphenyl sulphone

Conditions
ConditionsYield
In tetrahydrofuran for 4h; Ambient temperature;95%
diphenyl sulfide
139-66-2

diphenyl sulfide

A

1,1'-sulfinylbisbenzene
945-51-7

1,1'-sulfinylbisbenzene

B

diphenyl sulphone
127-63-9

diphenyl sulphone

Conditions
ConditionsYield
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

bromobenzene

sodium benzenesulfonate
873-55-2

sodium benzenesulfonate

diphenyl sulphone
127-63-9

diphenyl sulphone

Conditions
ConditionsYield
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

diphenyliodonium chloride

sodium benzenesulfonate
873-55-2

sodium benzenesulfonate

diphenyl sulphone
127-63-9

diphenyl sulphone

Conditions
ConditionsYield
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

2-(phenylsulfonyl)benzaldehyde

diphenyl sulphone
127-63-9

diphenyl sulphone

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran at -70 - 20℃; Inert atmosphere;95%
sodium phenylsulfonate
515-42-4

sodium phenylsulfonate

2-(trimethylsilyl)phenyl trifluoromethanesulfonate
88284-48-4

2-(trimethylsilyl)phenyl trifluoromethanesulfonate

diphenyl sulphone
127-63-9

diphenyl sulphone

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In acetonitrile at 20℃; for 3h; Reagent/catalyst; Inert atmosphere;95%
sodium benzenesulfonate
873-55-2

sodium benzenesulfonate

2-(trimethylsilyl)phenyl trifluoromethanesulfonate
88284-48-4

2-(trimethylsilyl)phenyl trifluoromethanesulfonate

diphenyl sulphone
127-63-9

diphenyl sulphone

Conditions
ConditionsYield
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

toluene-4-sulfonic acid phenyl ester

sodium benzenesulfonate
873-55-2

sodium benzenesulfonate

diphenyl sulphone
127-63-9

diphenyl sulphone

Conditions
ConditionsYield
With tetrakis(actonitrile)copper(I) hexafluorophosphate In dimethyl sulfoxide at 120℃; for 3h; Catalytic behavior; Reagent/catalyst; Solvent;95%
tert.-butylhydroperoxide
75-91-2

tert.-butylhydroperoxide

Martins sulfurane
32133-82-7

Martins sulfurane

A

di-tert-butyl peroxide
110-05-4

di-tert-butyl peroxide

B

diphenyl sulfide
139-66-2

diphenyl sulfide

C

1,1'-sulfinylbisbenzene
945-51-7

1,1'-sulfinylbisbenzene

D

diphenyl sulphone
127-63-9

diphenyl sulphone

E

1,1,1,3,3,3-hexafluoro-2-phenylisopropyl alcohol
718-64-9

1,1,1,3,3,3-hexafluoro-2-phenylisopropyl alcohol

F

isobutene
115-11-7

isobutene

Conditions
ConditionsYield
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
...Expand
benzene
71-43-2

benzene

A

diphenyl sulphone
127-63-9

diphenyl sulphone

B

phenylsulfonyl fluoride
368-43-4

phenylsulfonyl fluoride

Conditions
ConditionsYield
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

benzenesulfonyl chloride

phenylboronic acid
98-80-6

phenylboronic acid

diphenyl sulphone
127-63-9

diphenyl sulphone

Conditions
ConditionsYield
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

benzenesulfonyl chloride

benzene
71-43-2

benzene

diphenyl sulphone
127-63-9

diphenyl sulphone

Conditions
ConditionsYield
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

sodium benzenesulfonate

diphenyl sulphone
127-63-9

diphenyl sulphone

Conditions
ConditionsYield
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

benzene

diphenyl sulphone
127-63-9

diphenyl sulphone

Conditions
ConditionsYield
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 anhydride61%
S,S,S-triphenyloxosulfonium perchlorate

S,S,S-triphenyloxosulfonium perchlorate

A

biphenyl
92-52-4

biphenyl

B

diphenyl sulphone
127-63-9

diphenyl sulphone

Conditions
ConditionsYield
With potassium hydroxide In methanol; water for 24h; Ambient temperature;A 5%
B 92%
sodium benzenesulfonate
873-55-2

sodium benzenesulfonate

benzenediazonium tetrafluoroborate
369-57-3

benzenediazonium tetrafluoroborate

diphenyl sulphone
127-63-9

diphenyl sulphone

Conditions
ConditionsYield
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

benzenesufonyl hydrazide

diphenyl sulphone
127-63-9

diphenyl sulphone

Conditions
ConditionsYield
With 2C2H3O2(1-)*C26H30B10P2*Cu(2+) In toluene at 20℃; for 3h; Catalytic behavior; Solvent; Reagent/catalyst;92%
diphenyl sulphone
127-63-9

diphenyl sulphone

3,3'-dinitrodiphenyl sulfone
1228-53-1

3,3'-dinitrodiphenyl sulfone

Conditions
ConditionsYield
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 sulphone

diphenyl sulfide
139-66-2

diphenyl sulfide

Conditions
ConditionsYield
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

1-methyl-piperazine

diphenyl sulphone
127-63-9

diphenyl sulphone

1-methyl-4-phenylpiperazine
3074-43-9

1-methyl-4-phenylpiperazine

Conditions
ConditionsYield
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

diphenyl sulphone

sulfur trioxide
7446-11-9

sulfur trioxide

benzenesulfonic acid
98-11-3

benzenesulfonic acid

Conditions
ConditionsYield
With sulfuric acid In water; benzene93%
With phosphoric acid; sulfuric acid In water; benzene87%

Diphenyl sulfone Consensus Reports

Reported in EPA TSCA Inventory.

Diphenyl sulfone Specification

The Phenyl sulfone is an organic compound with the formula C12H10O2S. The IUPAC name of this chemical is benzenesulfonylbenzene. With the CAS registry number 127-63-9, it is also named as 1,1'-Sulfonyldibenzene. The product's categories are Biochemistry;Color Former & Related Compounds; Diphenyl Sulfones (for High-Performance Polymer Research); Functional Materials; Reagent for High-Performance Polymer Research; Reagents for Oligosaccharide Synthesis; Sensitizer. Besides, it is a white crystalline powder, which is mainly used as a medicine intermediate and pesticide intermediate.

Physical properties about Phenyl sulfone are: (1)ACD/LogP: 2.40; (2)ACD/LogD (pH 5.5): 2.4; (3)ACD/LogD (pH 7.4): 2.4; (4)ACD/BCF (pH 5.5): 39.26; (5)ACD/BCF (pH 7.4): 39.26; (6)ACD/KOC (pH 5.5): 481.5; (7)ACD/KOC (pH 7.4): 481.5; (8)#H bond acceptors: 2; (9)#Freely Rotating Bonds: 2; (10)Polar Surface Area: 42.52 Å2; (11)Index of Refraction: 1.593; (12)Molar Refractivity: 60.27 cm3; (13)Molar Volume: 177.7 cm3; (14)Polarizability: 23.89×10-24cm3; (15)Surface Tension: 43.6 dyne/cm; (16)Density: 1.227 g/cm3; (17)Flash Point: 226.8 °C; (18)Enthalpy of Vaporization: 60.18 kJ/mol; (19)Boiling Point: 378.5 °C at 760 mmHg; (20)Vapour Pressure: 1.36E-05 mmHg at 25°C.

Preparation: this chemical can be prepared by diphenylsulfane. This reaction will need reagent (t-BuO)3Al, t-BuOOH and solvent benzene. The reaction time is 30 min. The yield is about 88%.



Uses of Phenyl sulfone: it can be used to produce 1-methyl-4-phenyl-piperazine at room temperature. It will need reagent n-BuLi and solvent hexane, tetrahydrofuran with reaction time of 30 min. The yield is about 93%.

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O=S(=O)(c1ccccc1)c2ccccc2
(2)InChI: InChI=1/C12H10O2S/c13-15(14,11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H
(3)InChIKey: KZTYYGOKRVBIMI-UHFFFAOYAU
(4)Std. InChI: InChI=1S/C12H10O2S/c13-15(14,11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H
(5)Std. InChIKey: KZTYYGOKRVBIMI-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 313mg/kg (313mg/kg)   Drugs in Japan Vol. -, Pg. 503, 1995.
mouse LD50 intravenous 320mg/kg (320mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#01761,
mouse LD50 oral 375mg/kg (375mg/kg)   Drugs in Japan Vol. -, Pg. 503, 1995.
mouse LD50 subcutaneous 329mg/kg (329mg/kg)   Drugs in Japan Vol. -, Pg. 503, 1995.
rabbit LDLo oral 4700mg/kg (4700mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

KIDNEY, URETER, AND BLADDER: OTHER CHANGES IN URINE COMPOSITION		 National Technical Information Service. Vol. OTS0555048,
rat LC inhalation > 1700mg/m3/8H (1700mg/m3)   National Technical Information Service. Vol. OTS0533717,
rat LD50 unreported > 2gm/kg (2000mg/kg)   Residue Reviews. Vol. 36, Pg. 240, 1971.
rat LDLo oral 2250mg/kg (2250mg/kg) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA		 National Technical Information Service. Vol. OTS0533717,

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