7545-50-8

Basic information

• Product Name: 3,3'-Diamino-4,4'-dihydroxydiphenyl sulfone
• Synonyms: BIS(3-AMINO-4-HYDROXYPHENYL) SULFONE;BIO-FARMA BF003087;3,3'-DIAMINO-4,4'-DIHYDROXYDIPHENYL SULFONE;4,4'-sulphonylbis[2-aminophenol];2-Amino-4-[(3-amino-4-hydroxybenzene)sulfonyl]phenol;3-Amino-4-hydroxyphenyl sulfone;4,4'-Sulfonylbis(2-aminophenol);2,2'-Diamino-4,4'-sulfonyldiphenol
• CAS NO: 7545-50-8
• Molecular Formula: C₁₂H₁₂N₂O₄S
• Molecular Weight: 280.3
• EINECS: 231-428-8
• Product Categories: Diphenyl Sulfones (for High-Performance Polymer Research);Functional Materials;Reagent for High-Performance Polymer Research
• Mol File: 7545-50-8.mol

Chemical Properties

• Melting Point: 231 °C
• Boiling Point: 596.9 °C at 760 mmHg
• Flash Point: 314.8 °C
• Appearance: Baby pink powder
• Density: 1.564 g/cm³
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: slightly sol. in Methanol
• PKA: 6.62±0.20(Predicted)
• CAS DataBase Reference: 3,3'-Diamino-4,4'-dihydroxydiphenyl sulfone(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3'-Diamino-4,4'-dihydroxydiphenyl sulfone(7545-50-8)
• EPA Substance Registry System: 3,3'-Diamino-4,4'-dihydroxydiphenyl sulfone(7545-50-8)

Safety Data

• Safety Statements: 22-24/25
• HazardClass: IRRITANT
• Hazardous Substances Data: 7545-50-8(Hazardous Substances Data)

Usage

General Description

3,3'-Diamino-4,4'-dihydroxydiphenyl sulfone is a chemical compound characterized by aromatic rings with amino and hydroxy substituents. Its structural formula gives it unique properties and distinct applications. Mostly, it is used in the preparation of other complex compounds due to its ability to participate in various chemical reactions. Importantly, this compound falls under the category of organosulfur compounds and can also be referred to as aromatic amines, aromatic alcohols or simply diphenyl sulfones. While it is highly useful in many industrial processes, caution should be taken when handling this compound due to potential health risks.

Synthetic route

3,3'-dibromo-4,4'-dihydroxydiphenyl sulfone (56486-79-4) → 3,3'-diamino-4,4'-dihydroxydiphenyl sulfone (7545-50-8)

Conditions	Yield
With ammonium hydroxide In 1-methyl-pyrrolidin-2-one at 150℃; Solvent; Temperature;	98%

3,3'-dinitro-4,4'-dihydroxydiphenylsulfone (7149-20-4) → 3,3'-diamino-4,4'-dihydroxydiphenyl sulfone (7545-50-8)

Conditions	Yield
With palladium 10% on activated carbon; hydrazine hydrate In 1,4-dioxane; ethanol at 95℃; for 24h; Inert atmosphere;	94%
With iron; ammonium chloride In water at 50℃; Concentration; Temperature; Large scale;	93%
With palladium on activated charcoal; ethanol Hydrogenation;

4,4'-sulfonediphenol (80-09-1) → 3,3'-diamino-4,4'-dihydroxydiphenyl sulfone (7545-50-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous H2SO4; HNO3 2: Na2S2O4; aqueous NH3 View Scheme

bis[3-methyl-4-hydroxyphenyl]sulfone (16346-97-7) → 3,3'-diamino-4,4'-dihydroxydiphenyl sulfone (7545-50-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: KMnO4; aqueous NaOH 2: aqueous H2SO4; HNO3 3: Na2S2O4; aqueous NH3 View Scheme

ortho-cresol (95-48-7) → 3,3'-diamino-4,4'-dihydroxydiphenyl sulfone (7545-50-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: H2SO4 / 180 °C / unter vermindertem Druck 2: KMnO4; aqueous NaOH 3: aqueous H2SO4; HNO3 4: Na2S2O4; aqueous NH3 View Scheme
Multi-step reaction with 4 steps 1: H2SO4 / 180 °C / unter vermindertem Druck 2: KMnO4; aqueous NaOH 3: aqueous H2SO4; HNO3 4: Na2S2O4; aqueous NH3 View Scheme

salicylic acid (69-72-7) → 3,3'-diamino-4,4'-dihydroxydiphenyl sulfone (7545-50-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: H2SO4 / 200 °C / unter vermindertem Druck 2: aqueous H2SO4; HNO3 3: Na2S2O4; aqueous NH3 View Scheme

4,4'-dibromodiphenyl sulfone (2050-48-8) → 3,3'-diamino-4,4'-dihydroxydiphenyl sulfone (7545-50-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: sulfuric acid; potassium nitrate / 3 h / 80 °C 2: sodium hydroxide / dimethyl sulfoxide; water / 2 h / 50 °C 3: palladium 10% on activated carbon; hydrazine hydrate / ethanol; 1,4-dioxane / 24 h / 95 °C / Inert atmosphere View Scheme

4,4'-sulfonylbis(1-bromo-2-nitrobenzene) (75853-45-1) → 3,3'-diamino-4,4'-dihydroxydiphenyl sulfone (7545-50-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide / dimethyl sulfoxide; water / 2 h / 50 °C 2: palladium 10% on activated carbon; hydrazine hydrate / ethanol; 1,4-dioxane / 24 h / 95 °C / Inert atmosphere View Scheme

bromobenzene (108-86-1) → 3,3'-diamino-4,4'-dihydroxydiphenyl sulfone (7545-50-8)

Conditions

Yield

Multi-step reaction with 4 steps 1: trifluorormethanesulfonic acid; dipotassium peroxodisulfate; tetra(n-butyl)ammonium hydrogensulfate; trifluoroacetic anhydride / 1,2-dichloro-ethane / 8 h / 85 °C / Sealed tube 2: sulfuric acid; potassium nitrate / 3 h / 80 °C 3: sodium hydroxide / dimethyl sulfoxide; water / 2 h / 50 °C 4: palladium 10% on activated carbon; hydrazine hydrate / ethanol; 1,4-dioxane / 24 h / 95 °C / Inert atmosphere View Scheme

3,3'-diamino-4,4'-dihydroxydiphenyl sulfone (7545-50-8) + salicylaldehyde (90-02-8) → 4,4'-sulfonylbis(2-(-2-hydroxybenzylideneamino)phenol)

Conditions	Yield
Stage #1: 3,3'-diamino-4,4'-dihydroxydiphenyl sulfone; salicylaldehyde In methanol for 0.5h; Stage #2: In methanol for 6h; Reflux;	83%

4-Nitrophthalonitrile (31643-49-9) + 3,3'-diamino-4,4'-dihydroxydiphenyl sulfone (7545-50-8) → C28H16N6O4S

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 85℃; for 5h;	82%

3,3'-diamino-4,4'-dihydroxydiphenyl sulfone (7545-50-8) + ethyl cyanoacetimidate hydrochloride (55244-11-6) → C18H10N4O4S

Conditions	Yield
In methanol at 5℃; for 9h;	77%

8-formyl-7-hydroxycoumarin (2067-86-9) + 3,3'-diamino-4,4'-dihydroxydiphenyl sulfone (7545-50-8) → 8,8'-((1E,1'E)-((sulfonylbis(6-hydroxy-3,1-phenylene))bis(azanylylidene))bis(methanylylidene))bis(7-hydroxy-2H-chromen-2-one)

Conditions	Yield
In ethanol for 6h; Reflux;	76%

8-formyl-7-hydroxycoumarin (2067-86-9) + 3,3'-diamino-4,4'-dihydroxydiphenyl sulfone (7545-50-8) → C32H22N2O10S

Conditions	Yield
In ethanol for 8h; Reflux;	70%

3,3'-diamino-4,4'-dihydroxydiphenyl sulfone (7545-50-8) + 2-(4-(dibutylamino)phenyl)-6-hydroxybenzofuran-5-carbaldehyde → C58H58N4O8S

Conditions	Yield
With potassium cyanide; phenylboronic acid In methanol at 20℃; Inert atmosphere;	25%

3,3'-diamino-4,4'-dihydroxydiphenyl sulfone (7545-50-8) → Os(3,3'-diamino-4,4'-dihydroxydiphenylsulphone)(OH)2

Conditions	Yield
With osmium compound

3,3'-diamino-4,4'-dihydroxydiphenyl sulfone (7545-50-8) → {OsO2(3,3'-diamino-4,4'-dihydroxydiphenylsulphone)}Cl2

Conditions	Yield
With osmium compound

3,3'-diamino-4,4'-dihydroxydiphenyl sulfone (7545-50-8) + neodymium(III) acetate (6192-13-8) → 2Nd(3+)*3SO2(C6H3(NH2)O)2(2-)*4H2O=Nd2(C12H10N2O4S)3*4H2O

Conditions	Yield
With sodium hydroxide In ethanol; water ethanolic soln. of the ligand, aqueous soln. of rare earth(III) acetate; mixing; adjusting pH to 7.0-8.5 (NaOH); crystn.;

3,3'-diamino-4,4'-dihydroxydiphenyl sulfone (7545-50-8) + samarium(III) acetate (10465-27-7) → 2Sm(3+)*3SO2(C6H3(NH2)O)2(2-)*4H2O=Sm2(C12H10N2O4S)3*4H2O

Conditions	Yield
With sodium hydroxide In ethanol; water ethanolic soln. of the ligand, aqueous soln. of rare earth(III) acetate; mixing; adjusting pH to 7.0-8.5 (NaOH); crystn.;

3,3'-diamino-4,4'-dihydroxydiphenyl sulfone (7545-50-8) + praseodymium(3+) acetate (6192-12-7) → 2Pr(3+)*3SO2(C6H3(NH2)O)2(2-)*4H2O=Pr2(C12H10N2O4S)3*4H2O

Conditions	Yield
With sodium hydroxide In ethanol; water ethanolic soln. of the ligand, aqueous soln. of rare earth(III) acetate; mixing; adjusting pH to 7.0-8.5 (NaOH); crystn.;

3,3'-diamino-4,4'-dihydroxydiphenyl sulfone (7545-50-8) + cerium(III) acetate (537-00-8, 19475-87-7, 57023-24-2) → 2Ce(3+)*3SO2(C6H3(NH2)O)2(2-)*4H2O=Ce2(C12H10N2O4S)3*4H2O

Conditions	Yield
With sodium hydroxide In ethanol; water ethanolic soln. of the ligand, aqueous soln. of rare earth(III) acetate; mixing; adjusting pH to 7.0-8.5 (NaOH); crystn.;

5-norbornene-2,3-dicarboxylic anhydride (826-62-0, 85081-15-8, 85081-16-9) + oxybis(benzoic acid) (2215-89-6) + 3,3'-diamino-4,4'-dihydroxydiphenyl sulfone (7545-50-8) → PA-3

Conditions	Yield
Stage #1: oxybis(benzoic acid); 3,3'-diamino-4,4'-dihydroxydiphenyl sulfone With benzotriazol-1-ol In 1-methyl-pyrrolidin-2-one Stage #2: 5-norbornene-2,3-dicarboxylic anhydride In 1-methyl-pyrrolidin-2-one Product distribution / selectivity;

3,3'-diamino-4,4'-dihydroxydiphenyl sulfone (7545-50-8) + ethyl 3-ethoxy-3-iminopropanoate hydrochloride (2318-25-4) → C22H20N2O8S

Conditions	Yield
In methanol at 10 - 60℃; for 55h;
In methanol at 60℃; for 55h;
In methanol at 10 - 60℃; for 55h;

3,3'-diamino-4,4'-dihydroxydiphenyl sulfone (7545-50-8) → C64H66N4O8S

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol / 55 h / 10 - 60 °C 2: piperidine / toluene / 19 h / 100 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: methanol / 55 h / 60 °C 2: piperidine / toluene / 19 h / 100 °C View Scheme
Multi-step reaction with 2 steps 1: methanol / 55 h / 10 - 60 °C 2: piperidine / toluene / 19 h / 100 °C / Inert atmosphere View Scheme

3,3'-diamino-4,4'-dihydroxydiphenyl sulfone (7545-50-8) → C64H50N4O8S

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol / 55 h / 10 - 60 °C 2: piperidine / toluene / 6 h / 105 °C View Scheme
Multi-step reaction with 2 steps 1: methanol / 55 h / 60 °C 2: piperidine / toluene / 6 h / 105 °C View Scheme

4-(Diethylamino)salicylaldehyde (17754-90-4) + 3,3'-diamino-4,4'-dihydroxydiphenyl sulfone (7545-50-8) + ethyl 2-cyanoacetate (105-56-6) → C40H34N4O8S

Conditions	Yield
With benzoic acid In pentan-1-ol at 120℃; for 15h;
With benzoic acid In pentan-1-ol at 120℃; for 15h;