80-09-1

Basic information

• Product Name: 4,4'-Sulfonyldiphenol
• Synonyms: BIS(4-HYDROXYPHENYL) SULPHONE;BIS(4-HYDROXYPHENYL) SULFONE;4,4-DIHYDROXYDIPHENYL SULPHONE;4,4'-DIHYDROXYDIPHENYLSULPHONE;4,4'-DIHYDROXYDIPHENYL SULFONE;4,4-DIHYDROXYDIPHENYL SULFONE;4,4'-SULFONYLDIPHENOL;4,4-SULFONYLDIPHENOL
• CAS NO: 80-09-1
• Molecular Formula: C₁₂H₁₀O₄S
• Molecular Weight: 250.27
• EINECS: 201-250-5
• Product Categories: 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
• Mol File: 80-09-1.mol
• Article Data: 50

Chemical Properties

• Melting Point: 245-250 °C(lit.)
• Boiling Point: 363.4°C (rough estimate)
• Flash Point: 259.4 °C
• Appearance: White to grayish-green/Crystalline Powder
• Density: 1.366
• Vapor Pressure: <0.0001 Pa (20 °C)
• Refractive Index: 1.5220 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: 1.1g/l
• PKA: 7?+-.0.15(Predicted)
• Water Solubility: 1.1 g/L (20 ºC)
• Stability: Stable. Incompatible with strong bases, acid chloride, acid anhydrides, strong oxidizing agents.
• BRN: 2052954
• CAS DataBase Reference: 4,4'-Sulfonyldiphenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-Sulfonyldiphenol(80-09-1)
• EPA Substance Registry System: 4,4'-Sulfonyldiphenol(80-09-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36-36/37/38
• Safety Statements: 26-39-36-37
• WGK Germany: 2
• RTECS: SM8925000
• TSCA: Yes
• Hazardous Substances Data: 80-09-1(Hazardous Substances Data)

Usage

Chemical Properties

White needle-like crystals. Freely soluble in aliphatic hydrocarbons, soluble in alcohols and ethers, slightly soluble in aromatics, insoluble in water. Bisphenol S molecule contains two hydroxyl groups and a strong electron-absorbing sulfone group, so the acidity is stronger than other phenols.

Uses

Different sources of media describe the Uses of 80-09-1 differently. You can refer to the following data:
1. 4,4'-Sulfonyldiphenol is commonly used as a reactant in epoxy reactions and is also used as a latent thermal catalyst for epoxy resin.
2. Bis(4-hydroxyphenyl) Sulfone is commonly used as a reactant in epoxy reactions and is also used as a latent thermal catalyst for epoxy resin.

Definition

4,4'-Sulfonyldiphenol is a sulfone that is diphenyl sulfone in which both of the para hydrogens have been replaced by hydroxy groups.

General Description

Bisphenol S (BPS), belonging to the class of bisphenols, is a structural analog of bisphenol A (BPA), used in a variety of industrial applications and products marketed as BPA-free. It is commonly identified in food and beverages, environmental samples, biological matrices, etc. It is also reported to be used in the production of epoxy resins. BPS is also found to be stable compared to BPA at elevated temperature and sunlight conditions.

Flammability and Explosibility

Nonflammable

Synthetic route

phenol (108-95-2) → 4,4'-sulfonediphenol (80-09-1) + 2,4'-dihydroxydiphenyl sulfone (5397-34-2)

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

4-bromo-phenol (106-41-2) → 4,4'-sulfonediphenol (80-09-1)

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%

4,4'-Thiodiphenol (2664-63-3) → 4,4'-sulfonediphenol (80-09-1)

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%

4-Iodophenol (540-38-5) → 4,4'-sulfonediphenol (80-09-1)

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%

phenol (108-95-2) → 4,4'-sulfonediphenol (80-09-1)

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

1,2-dichloro-benzene (95-50-1) + phenol (108-95-2) → 4,4'-sulfonediphenol (80-09-1)

Conditions	Yield
With sulfuric acid In chlorobenzene	90%
	89.5%

4,4'-Thiodiphenol (2664-63-3) → 4,4'-sulfonediphenol (80-09-1) + bis(4-hydroxyphenyl) sulfoxide (1774-34-1)

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.

pyrographite (7440-44-0) + 1,2-dichloro-benzene (95-50-1) + phenol (108-95-2) → 4,4'-sulfonediphenol (80-09-1)

Conditions	Yield
With sodium hydroxide; sulfuric acid In water	92.6%

4-amino-5-chloro-1-phenylpyridazin-6-one (chloridazon) + 4,5-dichloro-1-phenylpyridazin-6-one (1698-53-9) → 4,4'-sulfonediphenol (80-09-1) + chloridazon (1698-60-8)

Conditions	Yield
In water	A n/a B 91.3%

chlorobenzene (108-90-7) → 4,4'-sulfonediphenol (80-09-1) + 2,4'-dihydroxydiphenyl sulfone (5397-34-2)

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 (80-07-9) → 4-(4-chloro-benzenesulfonyl)-phenol (7402-67-7) + 4,4'-sulfonediphenol (80-09-1)

Conditions	Yield
With sodium hydroxide In dimethyl sulfoxide at 100℃; for 1440h;	A 50% B 2%

phenol-2-sulfonic acid (609-46-1) → 4,4'-sulfonediphenol (80-09-1)

Conditions	Yield
With formaldehyd; thiourea In water

benzene-1,3-disulfonic acid (98-48-6) + phenol (108-95-2) → 4,4'-sulfonediphenol (80-09-1)

Conditions	Yield
With sulfuric acid In chlorobenzene

4,4'-dichlorodiphenyl sulphone (80-07-9) + 1-chloro-2-(4-chlorophenylsulfonyl)benzene (38980-51-7) → 4,4'-sulfonediphenol (80-09-1) + 2,4'-dihydroxydiphenyl sulfone (5397-34-2)

Conditions	Yield
With water; sodium hydroxide at 220℃; for 4h;

bisphenol S → 4,4'-sulfonediphenol (80-09-1) + 2,4'-dihydroxydiphenyl sulfone (5397-34-2)

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;

bisphenol S → 4,4'-sulfonediphenol (80-09-1) + 2,4'-dihydroxydiphenyl sulfone (5397-34-2)

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;

phenol (108-95-2) → phenol sulfonic acid + 4,4'-sulfonediphenol (80-09-1) + 2,4'-dihydroxydiphenyl sulfone (5397-34-2)

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;

fluorosulphonic acid (HFSO3) + phenol (108-95-2) → 4,4'-sulfonediphenol (80-09-1) + 2,4'-dihydroxydiphenyl sulfone (5397-34-2)

Conditions	Yield
With hydrogen fluoride

benzene-1,3-disulfonic acid (98-48-6) → 4,4'-sulfonediphenol (80-09-1)

4,4'-dichlorodiphenyl sulphone (80-07-9) → 4,4'-sulfonediphenol (80-09-1)

Conditions	Yield
With potassium hydroxide at 210 - 220℃;
With potassium hydroxide at 210 - 220℃;

bis(p-anisyl)sulfone (3112-80-9) → 4,4'-sulfonediphenol (80-09-1)

Conditions	Yield
With aluminium trichloride; xylene
With aluminum tri-bromide at 120 - 130℃;

4-sulfanylphenol (637-89-8) + (p-hydroxyphenyl)boronic acid (71597-85-8) → 4,4'-sulfonediphenol (80-09-1)

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 (66294-58-4) → 4,4'-sulfonediphenol (80-09-1)

Conditions	Yield
With aluminum tri-bromide at 120 - 130℃;

salicylic acid (69-72-7) → 4,4'-sulfonediphenol (80-09-1)

Conditions	Yield
With sulfuric acid at 200℃; unter vermindertem Druck;

p-hydoroxybenzenesulfonic acid (98-67-9) + phenol (108-95-2) → 4,4'-sulfonediphenol (80-09-1)

Conditions	Yield
With sulfuric acid at 200℃;

bis(4-hydroxyphenyl) sulfoxide (1774-34-1) → 4,4'-sulfonediphenol (80-09-1)

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

Phenetole (103-73-1) → 4,4'-sulfonediphenol (80-09-1)

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

4,4'-diacetoxydiphenylsulfone (5456-51-9) → 4,4'-sulfonediphenol (80-09-1)

Conditions	Yield
With hydrogenchloride
With potassium hydroxide

bis-(4-ethoxy-phenyl)-sulfoxide → 4,4'-sulfonediphenol (80-09-1)

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

methoxybenzene (100-66-3) → 4,4'-sulfonediphenol (80-09-1)

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 (80-09-1) → 2,2-bis(3,5-dibromo-4-hydroxyphenyl)sulfone (39635-79-5)

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 (80-09-1) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → 4,4'-Di-(trimethylsilylhydroxy)-diphenylsulfon (71918-64-4)

Conditions	Yield
In toluene Reflux;	99%

trifluoromethylsulfonic anhydride (358-23-6) + 4,4'-sulfonediphenol (80-09-1) → 4,4'-sulfonylbis(phenyltrifluoromethanesulfonate) (17763-90-5)

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 (80-09-1) + allyl tosylate (4873-09-0) → 3,3′-diallyl-4,4′-dihydroxydiphenylsulfone (41481-66-7)

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 (80-09-1) + 3-chloroprop-1-ene (107-05-1) → 4,4’-sulfonylbis((allyloxy)benzene) (41481-63-4)

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;

4,4'-sulfonediphenol (80-09-1) + subphthalocyanine (36530-06-0) → (B(N6C24H12))2O2C6H4SO2C6H4

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%

4,4'-sulfonediphenol (80-09-1) + 1-chloro-3-hydroxypropane (627-30-5) → C18H22O6S

Conditions	Yield
With potassium hydroxide In ethanol at 70℃; for 24h;	98%

4,4'-sulfonediphenol (80-09-1) + chloroacetic acid ethyl ester (105-39-5) → diethyl 2,2'-(sulfonylbis(4,1-phenylene)bis(oxy))diacetate (38775-52-9)

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 (640723-20-2, 2699-79-8, 12769-73-2) + 4,4'-sulfonediphenol (80-09-1) → 4,4'-sulfonylbis(4,1-phenylene) disulfofluoridate

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	97%

4,4'-sulfonediphenol (80-09-1) + <2H9>trimethylsulphoxonium iodide (23726-00-3) → 4,4'-sulfonylbis((methoxy-d3)benzene)

Conditions	Yield
With potassium carbonate at 65℃; for 18h; Sealed tube;	96.9%

4,4'-sulfonediphenol (80-09-1) + epichlorohydrin (106-89-8) → C20H22O4S

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%

propene (187737-37-7) + 4,4'-sulfonediphenol (80-09-1) → 4,4’-sulfonylbis((allyloxy)benzene) (41481-63-4)

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%

4-nitro-N-methyl-phthalimide (41663-84-7) + 4,4'-sulfonediphenol (80-09-1) → C30H20N2O8S

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;

4,4'-sulfonediphenol (80-09-1) + allyl bromide (106-95-6) → 4,4’-sulfonylbis((allyloxy)benzene) (41481-63-4)

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 (421-83-0) + 4,4'-sulfonediphenol (80-09-1) → 4,4'-sulfonylbis(phenyltrifluoromethanesulfonate) (17763-90-5)

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%

4,4'-sulfonediphenol (80-09-1) + 3-chloroprop-1-ene (107-05-1) → 4-allyloxy-4'-hydroxydiphenyl-sulfone

Conditions	Yield
With sodium hydroxide In water at 55 - 60℃; under 600.06 - 750.075 Torr; for 8h; Time;	93.85%

4,4'-sulfonediphenol (80-09-1) + 3-chloroprop-1-ene (107-05-1) → 4,4’-sulfonylbis((allyloxy)benzene) (41481-63-4) + 4-allyloxy-4'-hydroxydiphenyl-sulfone

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 (80-09-1) + ethylene glycol (107-21-1) → 2,2’-((sulfonylbis(4,1-phenylene))bis(oxy))bis(ethan-1-ol) (27205-03-4)

Conditions	Yield
With tetrabutoxytitanium; aluminum (III) chloride; bismuth at 150℃; for 1h; Temperature; Reagent/catalyst;	93.1%

4,4'-sulfonediphenol (80-09-1) + acetyl chloride (75-36-5) → 4,4'-diacetoxydiphenylsulfone (5456-51-9)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 0.5h; Acetylation;	93%
at 130℃; im geschlossenen Rohr;
With acetic acid

4,5-dichloro-1-phenylpyridazin-6-one (1698-53-9) + 4,4'-sulfonediphenol (80-09-1) → 4-amino-5-chloro-1-phenylpyridazin-6-one (chloridazon) + chloridazon (1698-60-8)

Conditions	Yield
With ammonia In water	A n/a B 92.3%
With ammonia In water	A n/a B 90%

4,4'-sulfonediphenol (80-09-1) + tert-butyldimethylsilyl chloride (18162-48-6) → (4,4'-sulfonylbis(4,1-phenylene)bis(oxy))bis(tert-butyldimethylsilane) (154116-76-4)

Conditions	Yield
With 1H-imidazole; dmap In dichloromethane; N,N-dimethyl-formamide for 3h;	92%

2-chloro-5-nitropyridine (4548-45-2) + 4,4'-sulfonediphenol (80-09-1) → 4,4'-bis(5-nitro-2-pyridinoxy)diphenyl sulfone

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 (90224-73-0) + 4,4'-sulfonediphenol (80-09-1) → C30H20N2O8S

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 (80-09-1) + 2-propynyl chloride (624-65-7) → 4,4′-sulfonylbis((prop-2-yn-1-yloxy)benzene) (73303-45-4)

Conditions	Yield
With sodium carbonate In N,N-dimethyl-formamide at 65℃; for 24h;	91%

4,4'-sulfonediphenol (80-09-1) → 4,4'-sulfonylbis(4,1-phenylene) disulfofluoridate

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%

Upstream product

• 66294-58-4 bis-(4-ethoxy-phenyl)-sulfone 
• 80-07-9 4,4'-dichlorodiphenyl sulphone 
• 3112-80-9 bis(p-anisyl)sulfone 
• 1774-34-1 bis(4-hydroxyphenyl) sulfoxide 
• 16346-97-7 bis[3-methyl-4-hydroxyphenyl]sulfone 
• 5456-51-9 4,4'-diacetoxydiphenylsulfone 
• 98-67-9 p-hydoroxybenzenesulfonic acid 
• 108-38-3 m-xylene 
• 609-46-1 phenol-2-sulfonic acid 
• 108-88-3 toluene 
• 69-72-7 salicylic acid 
• 80-08-0 dapsone 
• 71-43-2 benzene 
• 108-95-2 phenol 

Downstream Products

• 27205-03-4 2,2’-((sulfonylbis(4,1-phenylene))bis(oxy))bis(ethan-1-ol) 
• 121678-10-2 bis-(4-hippuroyloxy-phenyl)-sulfone 
• 114842-17-0 bis-(4-nicotinoyloxy-phenyl)-sulfone 
• 3112-80-9 bis(p-anisyl)sulfone 
• 2868-44-2 2-hydroxy-5-(4-hydroxy-benzenesulfonyl)-benzyl alcohol 
• 806659-83-6 4-[4-(5-bromo-pentyloxy)-benzenesulfonyl]-phenol 
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• 120548-46-1 bis-[4-(3-acetylamino-benzoyloxy)-phenyl]-sulfone 
• 119925-79-0 bis-[4-(3-nitro-trans-cinnamoyloxy)-phenyl]-sulfone 
• 122217-95-2 bis-[4-(2-acetoxy-4-acetylamino-benzoyloxy)-phenyl]-sulfone 
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Relevant articles and documents

One-step hydroxylation of aryl and heteroaryl fluorides using mechanochemistry

Simple use of KOH allows the direct F to OH exchange of aromatic and heteroaromatic substrates under mechanochemical conditions. The reaction is performed in the absence of solvent with potassium hydroxide as OH source. As a result, this approach is both more atom economical and environmentally friendly than previously described methods for this transformation.

Preparation process of low-cost and environment-friendly bisphenol S

The invention discloses a preparation process of bisphenol S with low cost and environmental protection. When the corrosion-resistant paint is sprayed into the interior of the reaction kettle, N atoms and O atoms of the reinforcing filler can interact with the metal ions to form a chelate. The acid resistance of the reaction kettle is higher, and the preparation cost is further reduced.

Macrocyclic sulfone derivatives: Synthesis, characterization, in vitro biological evaluation and molecular docking

An artificial series of macrocycles based on 4,4′-sulfonyldiphenol intermediate was synthesized using a multistep procedure involving oxidation of bisphenol sulfide, etherification of phenolic hydroxyl groups, and final ring closure with different diamines. Different chemical species having aromatic, heteroaromatic, and aliphatic characters were incorporated into macrocyclic frameworks in the final step of ring closure. This simple and easily executable synthetic strategy was applied to synthesize 15 macrocycles (5a-o) in excellent yields. Characterization of the synthesized products was achieved through well-known modern spectroscopic techniques such as IR, NMR, and Mass. Macrocycles 5m and 5n were found to show significant AChE inhibition with IC50 values of 76.9 ± 0.24 and 71.2 ± 0.77 μM, respectively. Macrocycle 5n was also found to be an active inhibitor of butyrylcholinesterase (BChE) with IC50 score of 55.3 ± 0.54 μM. Among others, macrocycle 5l cyclized with o-phenylenediamine demonstrated moderate inhibition with IC50 value of 81.1 ± 0.54 μM. Increasing interest in studying interactions of macrocycles with different enzymatic targets compelled us to design and synthesize sulfone-based macrocycles that might prove as highly potent class of biologically active compounds.