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

Uses

Used in Chemical Synthesis:
3,3'-Diamino-4,4'-dihydroxydiphenyl sulfone is used as a building block for the preparation of other complex compounds due to its ability to engage in a wide range of chemical reactions.
Used in Pharmaceutical Industry:
3,3'-Diamino-4,4'-dihydroxydiphenyl sulfone is used as an intermediate in the synthesis of pharmaceuticals for its potential therapeutic applications.
Used in Dye Industry:
3,3'-Diamino-4,4'-dihydroxydiphenyl sulfone is used as a precursor in the production of dyes, taking advantage of its chemical reactivity and the color properties of its derivatives.
Used in Polymer Industry:
3,3'-Diamino-4,4'-dihydroxydiphenyl sulfone is used as a monomer in the polymerization process to create polymers with specific properties, such as enhanced thermal stability or improved mechanical strength.
It is important to handle 3,3'-Diamino-4,4'-dihydroxydiphenyl sulfone with care due to its potential health risks, and safety measures should be implemented during its use in various industrial processes.

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;

Upstream product

• 7149-20-4 3,3'-dinitro-4,4'-dihydroxydiphenylsulfone 
• 80-09-1 4,4'-sulfonediphenol 
• 16346-97-7 bis[3-methyl-4-hydroxyphenyl]sulfone 
• 69-72-7 salicylic acid 
• 2050-48-8 4,4'-dibromodiphenyl sulfone 
• 75853-45-1 4,4'-sulfonylbis(1-bromo-2-nitrobenzene) 
• 108-86-1 bromobenzene 
• 56486-79-4 3,3'-dibromo-4,4'-dihydroxydiphenyl sulfone 
• 95-48-7 ortho-cresol 

Relevant articles and documents

Preparation method for 3,3'-diamino-4,4'-dihydroxy diphenyl sulfone

The invention relates to a preparation method for 3,3'-diamino-4,4'-dihydroxy diphenyl sulfone. The preparation method comprises the following steps: dissolving 3,3'-dinitro-4,4'-dichloro diphenyl sulfone in a polar solvent, dimethyl sulfoxide, adding a sodium hydroxide solution and reacting completely, then regulating pH to 1-2 and precipitating a solid to obtain 3,3'-dinitro-4,4'-dihydroxy diphenyl sulfone; and dissolving the 3,3'-dinitro-4,4'-dihydroxy diphenyl sulfone in a polar solvent, dimethyl sulfoxide, adding an ammonium chloride aqueous solution and reduced iron powders, carrying out thermal filtering after raw materials are reacted completely, washing filter cakes with hot dimethyl sulfoxide, combining filtrate, distilling under reduced pressure to obtain a mixed solution of the dimethyl sulfoxide and water, and drying to obtain the 3,3'-diamino-4,4'-dihydroxy diphenyl sulfone. The method has the advantages of high yield, easiness in operation, good repeatability and the like. Meanwhile, raw materials are easy to purchase, requirements on production equipment are low, and solvents can be reused.

Preparation method of 3,3'-diamino-4,4'dyhydroxy diphenyl sulfone

The invention relates to a preparation method of 3,3'-diamino-4,4'-dyhydroxy diphenyl sulfone. 2-bromophenol and potassium hydrogen persulfate are heated to 50 DEG C to have a reaction in a mixed solution of trifluoromethanesulfonic acid, trifluoromethanesulfonic anhydride and chloroform, a solvent is evaporated under reduced pressure after the reaction of the raw materials is completely finished, the temperature is reduced, solids are precipitated, filtering is performed, a filter cake is washed with a sodium acetate aqueous solution, and 3,3'-dibromo-4,4'-dyhydroxy diphenyl sulfone is obtained after washing and drying; 3,3'-dibromo-4,4'-dyhydroxy diphenyl sulfone is dissolved in N-methyl pyrrolidone and has a reaction with ammonium hydroxide at the temperature of 150 DEG C, a solvent is evaporated after the reaction of the raw material is completely finished, a remaining reaction solution is poured into water, and 3,3'-diamino-4,4'-dyhydroxy diphenyl sulfone is prepared after filtering, washing and drying. The method has the advantages that a few reaction steps are required, raw materials are easy to purchase, requirements for production equipment are low, the yield is high, the operation is simple, the repeatability is good, the solvents can be recycled and the like.

The synthesis of diarylsulfones with simple arenes and K2S2O8 through double C-S bond formation

An unprecedented double C-S bond formation method has been developed to prepare both symmetric and unsymmetric diarylsulfones with simple arenes in a single step. This represents the first example that K2S2O8 can be employed as a highly effective sulfonating agent to synthesize diarylsulfones. The reaction demonstrates excellent reactivity, good functional group tolerance and high yields.

Bisfluoran chromogenic compounds, preparation thereof, and pressure-sensitive copy systems employing same

A substantially colorless bisfluoran chromogenic material having the structural formula STR1 wherein R1 and R2 each represent an alkyl group; X and Y each represent a hydrogen atom, a halogen atom, an hydroxyl group, an alkyl group, a nitro group, an amino group, an acyl group, or a carboalkoxy group; Z represents an oxy radical, a carbonyl group, an alkylene group, an alkylidene group, a sulfonyl group, or a thio radical; and n represents an integer from 0 to 1. The bisfluoran compounds are produced by reacting a 4-dialkylamino-2-hydroxy-2'-carboxybenzophenone with a diphenol wherein the diphenol is unsubstituted in at least one of the positions ortho to an hydroxyl group in each of the phenyl rings. The bisfluorans are used in pressure-sensitive copy systems comprising a support bearing microcapsules containing the bisfluorans, alone, or in combination with other color-forming materials.