Conditions | Yield |
---|---|
Stage #1: phenol With sulfuric acid; benzene-1,3-disulfonic acid In 1,3,5-trimethyl-benzene at 145 - 165℃; for 5h; Heating / reflux; Stage #2: at 170 - 185℃; under 525.053 Torr; for 2h; Product distribution / selectivity; | A 94% B n/a |
With sulfuric acid In 1,3,5-trimethyl-benzene at 145 - 165℃; for 5h; Product distribution / selectivity; Heating / reflux; | A 89% B n/a |
Stage #1: phenol With sulfuric acid In 1,3,5-trimethyl-benzene at 145 - 165℃; for 5h; Heating / reflux; Stage #2: at 170 - 185℃; under 525.053 Torr; for 2h; Product distribution / selectivity; | A 83% B n/a |
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; | 83% |
Conditions | Yield |
---|---|
With dihydrogen peroxide In water at 20℃; for 0.833333h; chemoselective reaction; | 94% |
With dihydrogen peroxide In methanol at 40℃; for 0.666667h; chemoselective reaction; | 90% |
With palladium; dihydrogen peroxide In methanol at 100℃; for 12h; Green chemistry; chemoselective reaction; | 87% |
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; | 74% |
Conditions | Yield |
---|---|
With sulfuric acid In ISOPER G at 50 - 165℃; for 7h; Product distribution / selectivity; water separating duct; | 80% |
With sulfuric acid at 100 - 110℃; Eintragen von Phenol in das Reaktionsgemisch bei 120-130grad/15-18 Torr; | |
With sulfuric acid |
Conditions | Yield |
---|---|
With sulfuric acid In chlorobenzene | 90% |
89.5% |
4,4'-Thiodiphenol
A
4,4'-sulfonediphenol
B
bis(4-hydroxyphenyl) sulfoxide
Conditions | Yield |
---|---|
With dihydrogen peroxide In water; acetonitrile at 30℃; for 5h; | A 10% B 60% |
With dihydrogen peroxide In ethanol at 25℃; for 9.3h; Green chemistry; | |
With dihydrogen peroxide In methanol at 30℃; for 2h; | A 6 %Chromat. B 91 %Chromat. |
Conditions | Yield |
---|---|
With sodium hydroxide; sulfuric acid In water | 92.6% |
4,5-dichloro-1-phenylpyridazin-6-one
A
4,4'-sulfonediphenol
B
chloridazon
Conditions | Yield |
---|---|
In water | A n/a B 91.3% |
Conditions | Yield |
---|---|
Stage #1: chlorobenzene With sulfur trioxide; dimethyl sulfate at 30℃; for 2h; Stage #2: With sodium hydroxide In water at 220℃; for 4h; |
4,4'-dichlorodiphenyl sulphone
A
4-(4-chloro-benzenesulfonyl)-phenol
B
4,4'-sulfonediphenol
Conditions | Yield |
---|---|
With sodium hydroxide In dimethyl sulfoxide at 100℃; for 1440h; | A 50% B 2% |
Conditions | Yield |
---|---|
With formaldehyd; thiourea In water |
Conditions | Yield |
---|---|
With sulfuric acid In chlorobenzene |
4,4'-dichlorodiphenyl sulphone
1-chloro-2-(4-chlorophenylsulfonyl)benzene
A
4,4'-sulfonediphenol
B
2,4'-dihydroxydiphenyl sulfone
Conditions | Yield |
---|---|
With water; sodium hydroxide at 220℃; for 4h; |
Conditions | Yield |
---|---|
With phenol; sulfuric acid at 195 - 210℃; for 2 - 20h; Product distribution / selectivity; | |
With phenol; benzene-1,2-disulfonic acid at 180℃; for 2 - 6h; Product distribution / selectivity; | |
With phenol; o-toluenesulfonic acid at 180 - 210℃; for 2 - 20h; Product distribution / selectivity; |
Conditions | Yield |
---|---|
With phenol; sulfuric acid at 195℃; for 2 - 6h; Product distribution / selectivity; | |
With phenol; o-toluenesulfonic acid at 195℃; for 2 - 6h; Product distribution / selectivity; |
Conditions | Yield |
---|---|
With sulfuric acid In ISOPER H; 1,3,5-trimethyl-benzene at 50 - 170℃; for 4h; Product distribution / selectivity; water separating duct; | |
With sulfuric acid In ISOPER G at 50 - 167℃; for 7h; Product distribution / selectivity; water separating duct; |
Conditions | Yield |
---|---|
With hydrogen fluoride |
Conditions | Yield |
---|---|
With potassium hydroxide at 210 - 220℃; | |
With potassium hydroxide at 210 - 220℃; |
Conditions | Yield |
---|---|
With aluminium trichloride; xylene | |
With aluminum tri-bromide at 120 - 130℃; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: nickel(II) chloride hexahydrate; [2,2]bipyridinyl / N,N-dimethyl-formamide; acetonitrile / 0.08 h / 20 °C 1.2: air / 12 h / 20 °C 2.1: zinc(II) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; dihydrogen peroxide / methanol / 16 h / 80 °C View Scheme |
bis-(4-ethoxy-phenyl)-sulfone
4,4'-sulfonediphenol
Conditions | Yield |
---|---|
With aluminum tri-bromide at 120 - 130℃; |
Conditions | Yield |
---|---|
With sulfuric acid at 200℃; unter vermindertem Druck; |
Conditions | Yield |
---|---|
With sulfuric acid at 200℃; |
Conditions | Yield |
---|---|
With potassium permanganate | |
Multi-step reaction with 3 steps 1: Erwaermen auf dem Dampfbad 2: CrO3; water; acetic acid 3: aqueous HCl View Scheme | |
Multi-step reaction with 3 steps 1: Erwaermen auf dem Dampfbad 2: CrO3; water; acetic acid 3: aqueous HCl View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: AlCl3; carbon disulfide / anfangs bei 0grad 2: AlBr3 / 120 - 130 °C View Scheme | |
Multi-step reaction with 3 steps 1: AlCl3; carbon disulfide; SOCl2 2: CrO3; glacial acetic acid / 50 °C 3: AlBr3 / 120 - 130 °C View Scheme | |
Multi-step reaction with 5 steps 1: AlCl3; carbon disulfide; SOCl2 2: AlCl3 / 125 - 130 °C 3: Erwaermen auf dem Dampfbad 4: CrO3; water; acetic acid 5: aqueous HCl View Scheme | |
Multi-step reaction with 5 steps 1: AlCl3; carbon disulfide; SOCl2 2: AlCl3 / 125 - 130 °C 3: Erwaermen auf dem Dampfbad 4: CrO3; water; acetic acid 5: aqueous HCl View Scheme |
Conditions | Yield |
---|---|
With hydrogenchloride | |
With potassium hydroxide |
4,4'-sulfonediphenol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: CrO3; glacial acetic acid / 50 °C 2: AlBr3 / 120 - 130 °C View Scheme | |
Multi-step reaction with 4 steps 1: AlCl3 / 125 - 130 °C 2: Erwaermen auf dem Dampfbad 3: CrO3; water; acetic acid 4: aqueous HCl View Scheme | |
Multi-step reaction with 4 steps 1: AlCl3 / 125 - 130 °C 2: Erwaermen auf dem Dampfbad 3: CrO3; water; acetic acid 4: aqueous HCl View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: AlCl3; carbon disulfide; SOCl2 / 0 °C 2: AlCl3 / 125 - 130 °C 3: Erwaermen auf dem Dampfbad 4: CrO3; water; acetic acid 5: aqueous HCl View Scheme | |
Multi-step reaction with 5 steps 1: AlCl3; carbon disulfide; SOCl2 / 0 °C 2: AlCl3 / 125 - 130 °C 3: Erwaermen auf dem Dampfbad 4: CrO3; water; acetic acid 5: aqueous HCl View Scheme | |
Multi-step reaction with 2 steps 1: AlCl3; carbon disulfide / 0 °C 2: AlBr3 / 120 - 130 °C View Scheme |
4,4'-sulfonediphenol
2,2-bis(3,5-dibromo-4-hydroxyphenyl)sulfone
Conditions | Yield |
---|---|
With dihydrogen peroxide; bromine In dichloromethane; 2-methyl-propan-1-ol; water at 25 - 37℃; for 7.58333h; Temperature; | 99.5% |
With bromine; acetic acid at 85℃; for 2h; | 72% |
With bromine; iron Bromination; | 45.7% |
With bromine; acetic acid at 85℃; | |
With bromine |
4,4'-sulfonediphenol
1,1,1,3,3,3-hexamethyl-disilazane
4,4'-Di-(trimethylsilylhydroxy)-diphenylsulfon
Conditions | Yield |
---|---|
In toluene Reflux; | 99% |
trifluoromethylsulfonic anhydride
4,4'-sulfonediphenol
4,4'-sulfonylbis(phenyltrifluoromethanesulfonate)
Conditions | Yield |
---|---|
Stage #1: 4,4'-sulfonediphenol With pyridine In dichloromethane at 0℃; for 0.166667h; Inert atmosphere; Stage #2: trifluoromethylsulfonic anhydride In dichloromethane at 0℃; Inert atmosphere; | 98.6% |
With pyridine at 0 - 20℃; | 96% |
Inert atmosphere; |
4,4'-sulfonediphenol
allyl tosylate
3,3′-diallyl-4,4′-dihydroxydiphenylsulfone
Conditions | Yield |
---|---|
With tetrabutyl-ammonium chloride; potassium carbonate In N,N-dimethyl-formamide at 110 - 120℃; for 8h; Large scale; | 98.5% |
With potassium carbonate In N,N-dimethyl-formamide | 30.4 parts (92.1%) |
4,4'-sulfonediphenol
3-chloroprop-1-ene
4,4’-sulfonylbis((allyloxy)benzene)
Conditions | Yield |
---|---|
With potassium iodide; sodium hydroxide In methanol at 35 - 65℃; for 5h; Reagent/catalyst; Solvent; | 98% |
Stage #1: 4,4'-sulfonediphenol With sodium hydroxide for 0.166667h; Stage #2: 3-chloroprop-1-ene at 60 - 100℃; for 5h; Inert atmosphere; Sealed tube; | 93% |
With sodium hydroxide In methanol at 45℃; | |
With sodium hydroxide In water at 55 - 60℃; under 600.06 - 750.075 Torr; for 8h; Concentration; Temperature; Time; | 612 g |
Stage #1: 4,4'-sulfonediphenol With sodium hydroxide In water; toluene at 80℃; for 8h; Stage #2: 3-chloroprop-1-ene at 75℃; for 8h; |
Conditions | Yield |
---|---|
In 1,2-dichloro-benzene at 180.5℃; for 39h; Inert atmosphere; | 98% |
In 1,2-dichloro-benzene (Ar) chloro boron subphthalocyanine and bisphenol in 1,2-dichlorobenzenewere heated at reflux (180.5°C) for 39 h; react. mixt. was cooled, solvent was totary evapd., purification from hot toluene; | 98% |
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol at 70℃; for 24h; | 98% |
4,4'-sulfonediphenol
chloroacetic acid ethyl ester
diethyl 2,2'-(sulfonylbis(4,1-phenylene)bis(oxy))diacetate
Conditions | Yield |
---|---|
Stage #1: 4,4'-sulfonediphenol With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 0.5h; Stage #2: chloroacetic acid ethyl ester In N,N-dimethyl-formamide at 120℃; | 97% |
fluorosulfonyl fluoride
4,4'-sulfonediphenol
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; | 97% |
4,4'-sulfonediphenol
<2H9>trimethylsulphoxonium iodide
Conditions | Yield |
---|---|
With potassium carbonate at 65℃; for 18h; Sealed tube; | 96.9% |
Conditions | Yield |
---|---|
Stage #1: 4,4'-sulfonediphenol; epichlorohydrin With tetramethylammonium bromide at 100℃; for 3h; Inert atmosphere; Stage #2: With sodium hydroxide at 60℃; for 3h; Inert atmosphere; | 96% |
Conditions | Yield |
---|---|
Stage #1: 4,4'-sulfonediphenol With chlorine; sodium hydroxide for 0.166667h; Stage #2: propene at 60 - 100℃; for 5h; Inert atmosphere; Sealed tube; | 96% |
Conditions | Yield |
---|---|
Stage #1: 4,4'-sulfonediphenol With potassium hydroxide In toluene at 100℃; for 2h; Inert atmosphere; Reflux; Stage #2: 4-nitro-N-methyl-phthalimide With 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate In toluene at 110℃; for 6h; Inert atmosphere; | 94.2% |
With potassium carbonate In N,N-dimethyl acetamide; toluene for 6h; Reflux; |
Conditions | Yield |
---|---|
Stage #1: 4,4'-sulfonediphenol With potassium carbonate In acetone for 1h; Inert atmosphere; Reflux; Stage #2: allyl bromide In acetone Reflux; Inert atmosphere; | 94% |
With sodium hydroxide; tetramethylammonium bromide In water; toluene at 49.9 - 59.9℃; for 15h; | |
In methanol; water; toluene | 30.5 parts (91.2%) |
With potassium carbonate In acetone at 80℃; Inert atmosphere; |
trifluoromethane sulfonyl chloride
4,4'-sulfonediphenol
4,4'-sulfonylbis(phenyltrifluoromethanesulfonate)
Conditions | Yield |
---|---|
Stage #1: trifluoromethane sulfonyl chloride; 4,4'-sulfonediphenol With triethylamine In chloroform at 0 - 20℃; for 6h; Stage #2: With ammonium chloride In chloroform; water | 94% |
Conditions | Yield |
---|---|
With sodium hydroxide In water at 55 - 60℃; under 600.06 - 750.075 Torr; for 8h; Time; | 93.85% |
4,4'-sulfonediphenol
3-chloroprop-1-ene
A
4,4’-sulfonylbis((allyloxy)benzene)
Conditions | Yield |
---|---|
With sodium hydroxide In water at 55 - 60℃; under 600.06 - 750.075 Torr; for 8h; Concentration; Temperature; Time; | A n/a B 93.5% |
With sodium hydroxide In water at 55 - 60℃; under 600.06 - 750.075 Torr; for 4h; Concentration; Temperature; Time; | A 73.98% B 25.32% |
4,4'-sulfonediphenol
ethylene glycol
2,2’-((sulfonylbis(4,1-phenylene))bis(oxy))bis(ethan-1-ol)
Conditions | Yield |
---|---|
With tetrabutoxytitanium; aluminum (III) chloride; bismuth at 150℃; for 1h; Temperature; Reagent/catalyst; | 93.1% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 0.5h; Acetylation; | 93% |
at 130℃; im geschlossenen Rohr; | |
With acetic acid |
Conditions | Yield |
---|---|
With ammonia In water | A n/a B 92.3% |
With ammonia In water | A n/a B 90% |
4,4'-sulfonediphenol
tert-butyldimethylsilyl chloride
(4,4'-sulfonylbis(4,1-phenylene)bis(oxy))bis(tert-butyldimethylsilane)
Conditions | Yield |
---|---|
With 1H-imidazole; dmap In dichloromethane; N,N-dimethyl-formamide for 3h; | 92% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20 - 70℃; Inert atmosphere; | 92% |
5-bromo-2-methyl-2,3-dihydro-1H-isoindole-1,3-dione
4,4'-sulfonediphenol
Conditions | Yield |
---|---|
Stage #1: 4,4'-sulfonediphenol With sodium hydroxide In o-xylene at 90℃; for 2.5h; Inert atmosphere; Stage #2: 5-bromo-2-methyl-2,3-dihydro-1H-isoindole-1,3-dione In dimethyl sulfoxide at 150℃; for 6h; | 91.1% |
4,4'-sulfonediphenol
2-propynyl chloride
4,4′-sulfonylbis((prop-2-yn-1-yloxy)benzene)
Conditions | Yield |
---|---|
With sodium carbonate In N,N-dimethyl-formamide at 65℃; for 24h; | 91% |
4,4'-sulfonediphenol
Conditions | Yield |
---|---|
With fluorosulfonyl fluoride; triethylamine In dichloromethane at 20℃; for 12h; | 91% |
With 1-(fluorosulfuryl)-2,3-dimethyl-1H-imidazol-3-ium trifluoromethanesulfonate; triethylamine In acetonitrile at 80℃; for 8h; | 79.5% |
Stage #1: 4,4'-sulfonediphenol With triethylamine In acetonitrile at 20℃; for 0.166667h; Stage #2: With 1-(fluorosulfuryl)-2,3-dimethyl-1H-imidazol-3-ium trifluoromethanesulfonate In acetonitrile for 1h; | 77% |
Stage #1: 4,4'-sulfonediphenol With triethylamine In acetonitrile at 20℃; for 0.166667h; Stage #2: With 1-(fluorosulfuryl)-2,3-dimethyl-1H-imidazol-3-ium trifluoromethanesulfonate In acetonitrile for 1h; Inert atmosphere; | 77% |
Reported in EPA TSCA Inventory.
1. Introduction of 4,4'-Sulfonyldiphenol
4,4'-Sulfonyldiphenol is commonly used as a reactant in epoxy reactions, and is used in curing fast-drying epoxy resin glues. The IUPAC Name of 4,4'-Sulfonyldiphenol is 4-(4-Hydroxyphenyl)sulfonylphenol.
2. Properties of 4,4'-Sulfonyldiphenol
H bond acceptors: 4
H bond donors: 2
Freely Rotating Bonds: 4
Polar Surface Area: 60.98 Å2
Index of Refraction: 1.645
Molar Refractivity: 63.33 cm3
Molar Volume: 174.6 cm3
Surface Tension: 60.7 dyne/cm
Density: 1.432 g/cm3
Flash Point: 259.4 °C
Enthalpy of Vaporization: 80.43 kJ/mol
Boiling Point: 505.3 °C at 760 mmHg
Vapour Pressure: 7.8E-11 mmHg at 25°C
Melting Point: 245-250 °C(lit.)
Water Solubility: 1.1 g/L (20°C)
Appearance: light yellow crystalline powder
Stability: Stable. Incompatible with strong bases, acid chloride, acid anhydrides, strong oxidizing agents.
Product Categories of 4,4'-Sulfonyldiphenol (CAS NO.80-09-1): Aromatics;Sulphur Derivatives;API intermediates;Color Former & Related Compounds;Developer;Diphenyl Sulfones (for High-Performance Polymer Research);Functional Materials;Reagent for High-Performance Polymer Research
3. Structure Descriptors of 4,4'-Sulfonyldiphenol
4. Toxicity of 4,4'-Sulfonyldiphenol
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
guinea pig | LD50 | skin | > 1mg/kg (1mg/kg) | National Technical Information Service. Vol. OTS0534330, | |
mouse | LD50 | intraperitoneal | 200mg/kg (200mg/kg) | National Technical Information Service. Vol. OTS0534330, | |
mouse | LD50 | oral | 1600mg/kg (1600mg/kg) | National Technical Information Service. Vol. OTS0534330, | |
rabbit | LD50 | skin | > 10250mg/kg (10250mg/kg) | BIOFAX Industrial Bio-Test Laboratories, Inc., Data Sheets. Vol. 601-05501, Pg. 1974, | |
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 | LD50 | intraperitoneal | 400mg/kg (400mg/kg) | National Technical Information Service. Vol. OTS0534330, | |
rat | LD50 | oral | 4556mg/kg (4556mg/kg) | BIOFAX Industrial Bio-Test Laboratories, Inc., Data Sheets. Vol. 601-05501, Pg. 1974, |
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-39-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36: Wear suitable protective clothing.
S39: Wear eye / face protection.
WGK Germany: 2
RTECS: SM8925000
HS Code: 29309070
Mildly toxic by ingestion. A skin and eye irritant. When heated to decomposition it emits toxic fumes of SOx.
6. Preparation of 4,4'-Sulfonyldiphenol
4,4'-Sulfonyldiphenol can produced by the reaction of two equivalents of phenol with one equivalent of sulfuric acid.
7. Use of 4,4'-Sulfonyldiphenol
4,4'-Sulfonyldiphenol is mainly used as monomer for synthesizing polysulfone resin. It can be also directly applied in coatings, leather modifier, dye intermediates, metal electroplating light agent, etc.
8. Other details of 4,4'-Sulfonyldiphenol
General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. Dangerous fire hazard in the form of dust when exposed to heat or flame.
Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or chemical foam.
Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage: Store in a cool, dry place. Store in a tightly closed container.
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