Conditions | Yield |
---|---|
With sulfuric acid; trifluoroacetic acid; trifluoroacetic anhydride; Η-β Zeochem at 10 - 53℃; for 4h; Product distribution / selectivity; | 100% |
With sulfuric acid at 20℃; for 4h; | 95.02% |
Stage #1: chlorobenzene With aluminum (III) chloride; thionyl chloride In water at 50 - 90℃; for 3h; Stage #2: With sulfuric acid; dihydrogen peroxide; acetic acid In water at 80℃; for 3h; | 93.8% |
Conditions | Yield |
---|---|
With dihydrogen peroxide; acetic acid at 80℃; for 2h; | 99.3% |
With tetrabutyl-ammonium chloride; dihydrogen peroxide In water at 95℃; for 5h; Temperature; Reagent/catalyst; | 97.8% |
With N-(n-butyl)tridemorph phosphotungstate; dihydrogen peroxide In benzene at 90℃; for 2h; Catalytic behavior; Temperature; | 96.2% |
4-chlorobenzenesulfonyl chloride
chlorobenzene
4,4'-dichlorodiphenyl sulphone
Conditions | Yield |
---|---|
iron(III) chloride at 144℃; for 0.333333h; microwave irradiation; | 95% |
With iron(III) chloride at 100 - 120℃; | |
With aluminium trichloride | |
With iron(III) chloride at 100 - 120℃; |
sodium p-chlorobenzenesulphinate
4,4'-dichlorodiphenyl sulphone
Conditions | Yield |
---|---|
With copper diacetate In acetonitrile at 60℃; for 3h; | 94% |
Conditions | Yield |
---|---|
With aluminum (III) chloride; thionyl chloride at 20℃; for 3h; Temperature; | 94% |
Conditions | Yield |
---|---|
With sodium bromate In water at 80℃; for 0.5h; Ionic liquid; | 92% |
With palladium; dihydrogen peroxide In methanol at 100℃; for 6h; Green chemistry; chemoselective reaction; | 90% |
With dihydrogen peroxide In methanol at 40℃; for 1.58333h; chemoselective reaction; | 89% |
p-chlorobenzenesulfonyl azide
chlorobenzene
4,4'-dichlorodiphenyl sulphone
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid In dichloromethane at 25℃; for 3h; regiospecific reaction; | 81% |
bis(4-chlorophenyl)sulfoxide
A
bis(4-chlorophenyl)sulfide
B
4,4'-dichlorodiphenyl sulphone
Conditions | Yield |
---|---|
With [ReOCl3(PPh3)2] In ethanol for 18h; Reflux; | A 33% B 65% |
With phenyltrifluorodiazoethane; oxygen; 5,15,10,20-tetraphenylporphyrin In dichloromethane; acetonitrile at 20℃; for 0.5h; Irradiation; |
sodium p-chlorobenzenesulphinate
bis(4-chlorophenyl)iodonium bromide
4,4'-dichlorodiphenyl sulphone
Conditions | Yield |
---|---|
With 1-butyl-3-methylimidazolium Tetrafluoroborate at 40℃; | 62% |
sodium p-chlorobenzenesulphinate
4,4'-dichlorodiphenyl sulphone
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 50℃; for 4h; | 55% |
chlorobenzene
A
4,4'-dichlorodiphenyl sulphone
B
1-chloro-2-(4-chlorophenylsulfonyl)benzene
Conditions | Yield |
---|---|
With cadmium(II) sulfate crystallohydrate; phosphorus pentoxide at 20℃; for 5h; Milling; Sealed tube; Green chemistry; | A 53% B 14% |
With sulfur trioxide; dimethyl sulfate at 50℃; for 1.33333h; exclusion of air humidity; |
Conditions | Yield |
---|---|
With potassium pyrosulfite; palladium diacetate; N-ethyl-N,N-diisopropylamine; tri tert-butylphosphoniumtetrafluoroborate In N,N-dimethyl-formamide at 100℃; for 20h; Inert atmosphere; | 19% |
Conditions | Yield |
---|---|
With sulfur trioxide; trifluoroacetic acid at 40 - 100℃; for 8.5h; Product distribution / selectivity; Inert atmosphere; | 11% |
With acetic anhydride at 100 - 120℃; for 3h; Product distribution / selectivity; | 2% |
unter kontinuierlicher Entfernung des gebildeten Wassers; |
methyl p-chlorobenzenesulphonate
4,4'-dichlorodiphenyl sulphone
Conditions | Yield |
---|---|
With sulfur trioxide anschliessendes Erwaermen mit Chlorbenzol; |
chlorobenzene
A
4,4'-dichlorodiphenyl sulphone
B
4-chlorobenzenesulfonyl chloride
Conditions | Yield |
---|---|
With chlorosulfonic acid | |
With chlorosulfonic acid at 25℃; | |
With chlorosulfonic acid; sulfuric acid Edukt 4:SO3; |
bis(4-chlorophenyl)sulfide
A
bis(4-chlorophenyl)sulfoxide
B
4,4'-dichlorodiphenyl sulphone
Conditions | Yield |
---|---|
With 1-oxo-10-tert-butyl-3,3,7,7-tetrakis(trifluoromethyl)-4,6-benzo-1-ioda-2,8-dioxabicyclo<3.3.0>octane at 130℃; for 24h; other substrates; |
chlorobenzene
A
4,4'-dichlorodiphenyl sulphone
B
bis(2-chlorophenyl) sulfone
C
1-chloro-2-(4-chlorophenylsulfonyl)benzene
Conditions | Yield |
---|---|
With antimony pentafluoride; fluorosulphonic acid at 50℃; for 1h; Yield given. Yields of byproduct given; |
chlorobenzene
A
4,4'-dichlorodiphenyl sulphone
B
p-chlorobenzenesulfonic anhydride
Conditions | Yield |
---|---|
With sulfur trioxide | A 6 % Chromat. B n/a |
aluminium trichloride
4-chlorobenzenesulfonyl chloride
chlorobenzene
4,4'-dichlorodiphenyl sulphone
chlorosulfonic acid
chlorobenzene
A
4,4'-dichlorodiphenyl sulphone
B
4-chloro-benzenesulfonic acid
C
4-chlorobenzenesulfonyl chloride
Conditions | Yield |
---|---|
at -5℃; auch bei Zusatz von wasserfreier Schwefelsaeure; |
4,4'-dichlorodiphenyl sulphone
Conditions | Yield |
---|---|
With sulfuric acid; acetic acid; sodium nitrite Behandeln der erhaltenen Diazoniumsalz-Loesung mit einer Loesung von CuCl in konz. wss. HCl; |
Conditions | Yield |
---|---|
With aluminium trichloride |
disulfuric acid
chlorobenzene
A
4,4'-dichlorodiphenyl sulphone
B
4-chloro-benzenesulfonic acid
Conditions | Yield |
---|---|
With sulfuric acid |
4-chlorobenzenesulfonyl chloride
chlorobenzene
A
4,4'-dichlorodiphenyl sulphone
B
1-chloro-2-(4-chlorophenylsulfonyl)benzene
Conditions | Yield |
---|---|
iron(III) chloride at 144℃; for 0.333333h; Product distribution / selectivity; Irradiation; |
5-p-(p-chlorophenylsulphonyl)phenyl-3-mercapto-1,2,4-triazole
A
4-Chlorophenyl phenyl sulfone
B
phenyl p-chlorophenyl sulfide
C
4,4'-dichlorodiphenyl sulphone
D
1-(4-chlorophenylsulfonyl)-4-cyanobenzene
Conditions | Yield |
---|---|
at 475℃; under 2 Torr; Pyrolysis; Inert atmosphere; | A 12.1 %Chromat. B 6 %Chromat. C 3.9 %Chromat. D 60.6 %Chromat. |
5-p-(p-chlorophenylsulphonyl)phenyl-3-mercapto-1,2,4-triazole
A
4-Chlorophenyl phenyl sulfone
B
4,4'-dichlorodiphenyl sulphone
C
4-((4- chlorophenyl) thio) benzo nitrile
D
1-(4-chlorophenylsulfonyl)-4-cyanobenzene
Conditions | Yield |
---|---|
at 750℃; under 2 Torr; Pyrolysis; Inert atmosphere; | A 16 %Chromat. B 4 %Chromat. C 5 %Chromat. D 40.2 %Chromat. |
5-p-(p-chlorophenylsulphonyl)phenyl-3-mercapto-1,2,4-triazole
A
4-Chlorophenyl phenyl sulfone
B
4,4'-dichlorodiphenyl sulphone
C
1-(4-chlorophenylsulfonyl)-4-cyanobenzene
Conditions | Yield |
---|---|
at 550℃; under 2 Torr; Pyrolysis; Inert atmosphere; | A 10.4 %Chromat. B 3.8 %Chromat. C 56 %Chromat. |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: sodium hydroxide / water / 2 h / Reflux 1.2: 50 °C / pH 10.85 2.1: sulfuric acid / water / pH 5 View Scheme |
4,4'-dichlorodiphenyl sulphone
Conditions | Yield |
---|---|
With sulfuric acid In water pH=5; |
4,4'-Dihydroxybiphenyl
4,4'-dichlorodiphenyl sulphone
polysulfone-block-poly(ethylene oxide), Mn = 56000 (GPC), Mw = 67000 (GPC), polydispersity = 1.9 (GPC); monomer(s): chlorine-terminated poly(ethylene oxide); 4,4'-dichlorodiphenyl sulfone; 4,4'-dihydroxybiphenyl
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl acetamide; toluene at 160℃; for 20h; | 100% |
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid In 1,2-dichloro-ethane | 99% |
With sodium nitrate; sulfuric acid at 80℃; | 95% |
With sulfuric acid; nitric acid In water at 20℃; for 6h; | 92% |
4,4'-dichlorodiphenyl sulphone
2-hydroxyethanethiol
2,2’-((sulfonylbis(4,1-phenylene))bis(sulfanediyl))bis(ethan-1-ol)
Conditions | Yield |
---|---|
With potassium carbonate In ISOPROPYLAMIDE at 150℃; for 5h; | 98% |
With sodium hydride In 1-methyl-pyrrolidin-2-one at 10 - 50℃; for 2h; | 90% |
Conditions | Yield |
---|---|
Stage #1: 4,4'-dichlorodiphenyl sulphone With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Stage #2: trimethyltin(IV)chloride In tetrahydrofuran at -78 - 20℃; | 97% |
4,4'-dichlorodiphenyl sulphone
phenylboronic acid
4,4''-sulfonyldi-1,1'-biphenyl
Conditions | Yield |
---|---|
With palladium diacetate; 1,3-bis-(diphenylphosphino)propane; cesium fluoride In various solvent(s) at 100℃; for 10h; | 95% |
4,4'-dichlorodiphenyl sulphone
(p-hydroxyphenyl)boronic acid
4,4'-bis(4-hydroxyphenyl)diphenyl sulfone
Conditions | Yield |
---|---|
With sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 90℃; for 20h; | 95% |
2,6-di-tert-butylphenol
4,4'-dichlorodiphenyl sulphone
4'-<(4-Chlorophenyl)sulfonyl>-3,5-di-tert-butyl-<1,1'-biphenyl>-4-ol
Conditions | Yield |
---|---|
With 2,3-diethynylquinoxaline; potassium tert-butylate; ammonia at -40℃; electrolysis, current density 1.5 A*dm-2; | 90% |
With 2,3-diethynylquinoxaline; potassium tert-butylate In ammonia at -38℃; electrosynthesis: cathode - platinum grid, 10 cm2, 1024 mesh/cm2; anode - magnesium rod, h = 8 cm, Φ = 1 cm; constant current density 0,5 A dm2, KBr as supporting electrolyte; | 90% |
Conditions | Yield |
---|---|
1-(2'-ethylhexyl)-4-dimethylaminopyridinium chloride In 1,2-dichloro-benzene at 150℃; for 2h; | 90% |
4,4'-dichlorodiphenyl sulphone
4,4'-dihydrazinodiphenyl sulfone
Conditions | Yield |
---|---|
With hydrazine hydrate; triethylamine for 20h; Heating; | 90% |
With hydrazine hydrate; triethylamine for 24h; Reflux; | 90% |
4,4'-dichlorodiphenyl sulphone
2-Mercaptobenzothiazole
4,4'-di(2-benzothiazolylthio)diphenyl sulfone
Conditions | Yield |
---|---|
With sodium hydride In 1-methyl-pyrrolidin-2-one at 10 - 150℃; for 13h; | 90% |
Conditions | Yield |
---|---|
Stage #1: 3,5-dimethoxyphenol; 4,4'-dichlorodiphenyl sulphone With potassium carbonate In N,N-dimethyl acetamide; toluene at 140℃; for 4h; Dean-Stark; Inert atmosphere; Stage #2: In N,N-dimethyl-formamide at 150℃; for 1h; Dean-Stark; Inert atmosphere; | 90% |
With N,N-dimethyl acetamide; potassium carbonate In toluene at 150℃; for 15h; Temperature; Inert atmosphere; Reflux; |
4,4'-dichlorodiphenyl sulphone
ortho-cresol
4,4'-bis(2-methylphenyloxy)diphenylsulfone
Conditions | Yield |
---|---|
92% |
Conditions | Yield |
---|---|
With ammonium chloride In ethanol for 5h; Reflux; | 91.9% |
With ammonia; water; copper; copper(I) bromide at 200℃; | |
With ammonia; copper(II) sulfate; ethylene glycol at 245℃; |
4,4'-dichlorodiphenyl sulphone
4-tert-butylphenylboronic acid
Conditions | Yield |
---|---|
With sodium phosphate In water; isopropyl alcohol at 85℃; for 2h; Suzuki-Miyaura Coupling; | 90% |
4,4'-dichlorodiphenyl sulphone
sodium phenoxide
4,4'-sulfonylbis(phenoxybenzene)
Conditions | Yield |
---|---|
N-2-ethylhexyl chloride of 4(4-methylpiperidinyl)pyridine In 1,2-dichloro-benzene at 180℃; for 2h; | 87% |
(9,9’-(5-(4,4,5,5-tetramethyl-1,2,3-dioxaborolan-2-yl)-1,3-phenylene)bis(9H-carbazole))
4,4'-dichlorodiphenyl sulphone
Conditions | Yield |
---|---|
Stage #1: (9,9’-(5-(4,4,5,5-tetramethyl-1,2,3-dioxaborolan-2-yl)-1,3-phenylene)bis(9H-carbazole)); 4,4'-dichlorodiphenyl sulphone With Aliquat 336; potassium carbonate In water; toluene for 0.25h; Inert atmosphere; Stage #2: With tetrakis(triphenylphosphine) palladium(0) In water; toluene at 130℃; for 12h; Inert atmosphere; | 86% |
Conditions | Yield |
---|---|
With potassium carbonate at 180℃; for 18h; Temperature; Reagent/catalyst; Inert atmosphere; | 85.1% |
4,4'-dichlorodiphenyl sulphone
Conditions | Yield |
---|---|
Stage #1: 4,4'-dichlorodiphenyl sulphone; N1,N1,N3,N3-tetraphenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1,3-diamine With Aliquat 336; potassium carbonate In water; toluene for 0.25h; Inert atmosphere; Stage #2: With tetrakis(triphenylphosphine) palladium(0) In water; toluene at 130℃; for 12h; Inert atmosphere; | 85% |
Stage #1: 4,4'-dichlorodiphenyl sulphone; N1,N1,N3,N3-tetraphenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1,3-diamine With Aliquat 336; potassium carbonate In water; toluene for 0.25h; Inert atmosphere; Stage #2: With tetrakis(triphenylphosphine) palladium(0) In water; toluene at 130℃; for 12h; Inert atmosphere; | 85% |
4,4'-dichlorodiphenyl sulphone
Conditions | Yield |
---|---|
With sulfuric acid; sulfur trioxide at 75 - 160℃; for 4.5h; Large scale; | 83% |
Stage #1: 4,4'-dichlorodiphenyl sulphone With fuming sulphuric acid at 110℃; for 6h; Stage #2: With sodium chloride In water | |
Stage #1: 4,4'-dichlorodiphenyl sulphone With sulfuric acid; sulfur trioxide Stage #2: With sodium chloride |
Conditions | Yield |
---|---|
With 2.9-dimethyl-1,10-phenanthroline; nickel(II) perchlorate hexahydrate; tetrabutylammomium bromide In N,N-dimethyl acetamide at 20℃; for 10h; Glovebox; Sealed tube; Electrochemical reaction; Inert atmosphere; regioselective reaction; | 83% |
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran for 72h; Reflux; Inert atmosphere; | 81.8% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 150℃; for 9h; | 80% |
Molecular Structure:
Molecular Formula: C12H8Cl2O2S
Molecular Weight: 287.1617
IUPAC Name: 1-Chloro-4-(4-chlorophenyl)sulfonylbenzene
Synonyms of Bis(p-chlorophenyl) sulfone (CAS NO.80-07-9): 1,1'-Sulfonylbis(4-chlorobenzene) ; 4,4'-Dichlorodiphenyl sulfone ; 4,4'-Dichlorodiphenyl sulphone ; 4-06-00-01587 (Beilstein Handbook Reference) ; 4-Chloro-1-(4-chlorophenylsulfonyl)benzene ; 4-Chlorophenyl sulfone ; AI3-01386 ; AI3-02901 ; BRN 2052955 ; Benzene, 1,1'-sulfonylbis(4-chloro- ; Bis(4-chlorophenyl) sulfone ; CCRIS 8813 ; Di-p-chlorophenyl sulfone ; EINECS 201-247-9 ; HSDB 5233 ; NSC 23899 ; Sulfone, bis(p-chlorophenyl) ; p,p'-Dichlorodiphenyl sulfone ; p-Chlorophenyl sulfone
CAS NO: 80-07-9
Classification Code: Tumor data
Melting point: 143-146 °C
Index of Refraction: 1.61
Molar Refractivity: 69.93 cm3
Molar Volume: 201.6 cm3
Surface Tension: 48.1 dyne/cm
Density: 1.423 g/cm3
Flash Point: 211.2 °C
Enthalpy of Vaporization: 64.75 kJ/mol
Boiling Point: 419.9 °C at 760 mmHg
Vapour Pressure: 7.18E-07 mmHg at 25°C
Bis(p-chlorophenyl) sulfone (CAS NO.80-07-9) is used to product 4,4'-diamino-diphenyl sulfone. It is also used as a raw material for engineering plastics polysulfone.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | oral | 24gm/kg (24000mg/kg) | BEHAVIORAL: TREMOR | Helvetica Chimica Acta. Vol. 29, Pg. 1317, 1946. |
rat | LDLo | oral | 7500mg/kg (7500mg/kg) | GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" | National Technical Information Service. Vol. OTS0533718, |
Reported in EPA TSCA Inventory.
The safety information of Bis(p-chlorophenyl) sulfone (CAS NO.80-07-9) is as follows:
Hazard Codes:Xi ,C
Hazard Note:Harmful/Corrosive/Moisture Sensitive
Risk Statements:36/37/38
36/37/38:Irritating to eyes, respiratory system and skin
Safety Statements:22-24/25-37/39-26
22:Do not breathe dust
24/25:Avoid contact with skin and eyes
37/39:Wear suitable gloves and eye/face protection
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
WGK Germany:2
RTECS:WR3450000
HS Code:29309070
Mildly toxic by ingestion. See also SULFONATES. When heated to decomposition it emits very toxic fumes of Cl− and SOx.
Storage information of Bis(p-chlorophenyl) sulfone (CAS NO.80-07-9):
Store in a cool, dry place. Store in a tightly closed container.
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