13224-79-8

Basic information

• Product Name: 4-(3,4-diaminophenyl)sulfonylbenzene-1,2-diamine
• Synonyms: 4-(3,4-diaminophenyl)sulfonylbenzene-1,2-diamine;2-amino-4-[(3,4-diaminophenyl)sulfonyl]phenylamine;4,4'-Sulfonylbis(benzene-1,2-diaMine);1,2-diaMino-4-(3,4-diaMinophenyl)sulfonylbenzene
• CAS NO: 13224-79-8
• Molecular Formula: C12H14N4O2S
• Molecular Weight: 278.33
• Mol File: 13224-79-8.mol
• Article Data: 6

Chemical Properties

• Melting Point: 174 °C
• Boiling Point: 631.1°Cat760mmHg
• Flash Point: 335.5°C
• Appearance: /
• Density: 1.489g/cm³
• Vapor Pressure: 7.75E-16mmHg at 25°C
• Refractive Index: 1.731
• PKA: 2.36±0.10(Predicted)
• CAS DataBase Reference: 4-(3,4-diaminophenyl)sulfonylbenzene-1,2-diamine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(3,4-diaminophenyl)sulfonylbenzene-1,2-diamine(13224-79-8)
• EPA Substance Registry System: 4-(3,4-diaminophenyl)sulfonylbenzene-1,2-diamine(13224-79-8)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 13224-79-8(Hazardous Substances Data)

Usage

General Description

4-(3,4-diaminophenyl)sulfonylbenzene-1,2-diamine is a chemical compound that consists of a benzene ring with a sulfonamide group attached to one side and two amino groups attached to the other. 4-(3,4-diaminophenyl)sulfonylbenzene-1,2-diamine is commonly used in the production of dyes, particularly azo dyes, as well as in the synthesis of pharmaceutical compounds. It is also known for its potential use as a corrosion inhibitor in oil and gas production. Additionally, this compound has been studied for its potential antitumor and antimicrobial properties. Its unique structure and diverse range of applications make 4-(3,4-diaminophenyl)sulfonylbenzene-1,2-diamine an important compound in various fields of chemistry and industry.

InChI:InChI=1/C12H14N4O2S/c13-9-3-1-7(5-11(9)15)19(17,18)8-2-4-10(14)12(16)6-8/h1-6H,13-16H2

Synthetic route

N,N'-[4,4'-sulfinylbis(2-nitrobenzenamine)] (18491-91-3) → 3,3',4,4'-Tetraaminodiphenylsulfon (13224-79-8)

Conditions	Yield
With palladium 10% on activated carbon; hydrazine hydrate In ethanol at 60℃; for 24h; Inert atmosphere;	96%
With hydrazine hydrate; nickel In tetrahydrofuran; ethanol for 3h; Heating;	72%
With hydrazine hydrate; palladium on activated charcoal In isopropyl alcohol at 100℃; for 12h;	62%

acedapsone (77-46-3) → 3,3',4,4'-Tetraaminodiphenylsulfon (13224-79-8)

Conditions	Yield
With water; nitric acid und anschliessend mit SnCl2 und wss. HCl;

N,N'-[4,4'-sulfinylbis(2-nitrobenzenamine)] (18491-91-3) + tin dichloride → 3,3',4,4'-Tetraaminodiphenylsulfon (13224-79-8)

4,4'-dichlorodiphenyl sulphone (80-07-9) → 3,3',4,4'-Tetraaminodiphenylsulfon (13224-79-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: H2SO4; HNO3 2: alcohol; ammonia / 150 °C 3: tin dichloride View Scheme
Multi-step reaction with 3 steps 1: sulfuric acid; nitric acid / water / 6 h / 20 °C 2: ammonium hydroxide / water; dimethyl sulfoxide / 16 h / 140 °C / 3102.97 Torr / Inert atmosphere 3: palladium on activated charcoal; hydrazine hydrate / isopropyl alcohol / 12 h / 100 °C View Scheme
Multi-step reaction with 3 steps 1: sulfuric acid; nitric acid / 6 h / 20 °C 2: ammonium hydroxide / dimethyl sulfoxide / 16 h / 140 °C / 3102.97 Torr / Inert atmosphere 3: palladium on activated charcoal; hydrazine hydrate / isopropyl alcohol / 12 h / 100 °C View Scheme

bis(4-chloro-3-nitrophenyl)sulfone (1759-05-3) → 3,3',4,4'-Tetraaminodiphenylsulfon (13224-79-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: alcohol; ammonia / 150 °C 2: tin dichloride View Scheme
Multi-step reaction with 2 steps 1: ammonium hydroxide / dimethyl sulfoxide / 16 h / 140 °C / 3102.97 Torr / Inert atmosphere 2: palladium on activated charcoal; hydrazine hydrate / isopropyl alcohol / 12 h / 100 °C View Scheme

3,3',4,4'-Tetraaminodiphenylsulfon (13224-79-8) + 10-hydroxy-10-oxo-10H-10λ5-phenoxaphosphine-2,8-dicarboxylic acid (97193-04-9) → poly{2-[6-(1H-1,3-benzoimidazol-5-ylsulfonyl)-1H-1,3-benzoimidazol-2-yl]-10-hydroxy-10H-10λ5-phenoxaphosphine 10-oxide}, [η] = 0.85 dLg-1 in H2SO4 at 25 grad C, solution polycondensation

Conditions	Yield
With phosphorus pentoxide at 80 - 140℃; for 19h;	100%

3,3',4,4'-Tetraaminodiphenylsulfon (13224-79-8) + 10-hydroxy-10-oxo-10H-10λ5-phenoxaphosphine-2,8-dicarboxylic acid (97193-04-9) → poly{2-[6-(1H-1,3-benzoimidazol-5-ylsulfonyl)-1H-1,3-benzoimidazol-2-yl]-10-hydroxy-10H-10λ5-phenoxaphosphine 10-oxide}, [η] = 2.35 dLg-1 in H2SO4 at 25 grad C, solution polycondensation

Conditions	Yield
With PPA at 100 - 180℃; for 25h;	100%

benzoic acid (65-85-0) + 3,3',4,4'-Tetraaminodiphenylsulfon (13224-79-8) → 2,2'-diphenyl-5,5'-sulfonyldibenzimidazole (68575-20-2)

Conditions	Yield
With Eaton′s Reagent at 120℃; for 1h; Inert atmosphere;	93%

3,3',4,4'-Tetraaminodiphenylsulfon (13224-79-8) → C12H8N6O2S

Conditions	Yield
With acetic acid; sodium nitrite at 50℃; Inert atmosphere;	85%

formic acid (64-18-6) + 3,3',4,4'-Tetraaminodiphenylsulfon (13224-79-8) → C14H10N4O2S

Conditions	Yield
In acetic acid Heating;	71%

acetic acid (64-19-7) + 3,3',4,4'-Tetraaminodiphenylsulfon (13224-79-8) → C16H14N4O2S

Conditions	Yield
In acetic acid Heating;	64%

1,3-Dicarbomethoxy-S-methylisothiourea (34840-23-8) + 3,3',4,4'-Tetraaminodiphenylsulfon (13224-79-8) → C18H16N6O6S

Conditions	Yield
In ethanol Heating;	62%

1,3-dicarbethoxy-S-methylisothiourea (34840-26-1) + 3,3',4,4'-Tetraaminodiphenylsulfon (13224-79-8) → C20H20N6O6S

Conditions	Yield
In ethanol Heating;	58%

tetrakis(salicylaldehydato)zirconium(IV) (65531-97-7) + 3,3',4,4'-Tetraaminodiphenylsulfon (13224-79-8) → catena-poly[zirconium(IV)(μ-N,N',N''N'''-tetrasalicylidene-3,3',4,4'-tetraaminobiphenylsulfonato-O,N,N',O':O'',N;;,N''',O''')]

Conditions	Yield
In dimethyl sulfoxide Ar-atmosphere; equimolar amts., stirring at 60°C for 9 h; pptn. on MeOH addn., collection (filtration), washing (MeOH), drying (vac.), repptn. with MeOH, drying (vac., 100°C);	52%

1,3-Dicarbomethoxy-S-methylisothiourea (34840-23-8) + 3,3',4,4'-Tetraaminodiphenylsulfon (13224-79-8) → C18H16N6O6S (102790-42-1)

Conditions	Yield
With toluene-4-sulfonic acid In methanol for 3h; Heating; Yield given;

C8H5ClN2O2*ClH (1099749-34-4) + 3,3',4,4'-Tetraaminodiphenylsulfon (13224-79-8) → C28H18Cl2N6O6S (1099749-17-3)

Conditions	Yield
With acetic acid In water; isopropyl alcohol at 75 - 78℃;

C8H5N3O3*ClH + 3,3',4,4'-Tetraaminodiphenylsulfon (13224-79-8) → C28H18N8O8S (1099749-18-4)

Conditions	Yield
With acetic acid In water; isopropyl alcohol at 75 - 78℃;

Upstream product

• 77-46-3 acedapsone 
• 18491-91-3 N,N'-[4,4'-sulfinylbis(2-nitrobenzenamine)] 
• 80-07-9 4,4'-dichlorodiphenyl sulphone 
• 1759-05-3 bis(4-chloro-3-nitrophenyl)sulfone 
• 98-60-2 4-chlorobenzenesulfonyl chloride 
• 108-90-7 chlorobenzene 
• 2050-48-8 4,4'-dibromodiphenyl sulfone 
• 75853-45-1 4,4'-sulfonylbis(1-bromo-2-nitrobenzene) 
• 108-86-1 bromobenzene 

Downstream Products

• 1099749-17-3 C₂₈H₁₈Cl₂N₆O₆S 
• 1099749-18-4 C₂₈H₁₈N₈O₈S 
• 1099749-19-5 C₂₈H₁₈Cl₂N₆O₄S 
• 1099749-20-8 C₂₈H₁₆Cl₂N₈O₈S 
• 1099749-21-9 C₂₈H₁₈Br₂N₆O₄S 
• 1099749-22-0 C₂₆H₂₀N₆O₆S₃ 
• 1099749-23-1 C₂₈H₂₀N₆O₄S 
• 1099749-24-2 C₃₀H₂₂Cl₂N₆O₆S 
• 1099749-25-3 C₂₈H₁₆Cl₄N₆O₄S 
• 1099749-26-4 C₂₈H₁₈I₂N₆O₄S 
• 1099749-28-6 C₃₀H₂₀Cl₄N₆O₆S 
• 1099749-31-1 C₃₀H₂₄N₆O₆S 
• 68575-20-2 2,2'-diphenyl-5,5'-sulfonyldibenzimidazole 

Relevant articles and documents

Synthesis and characterization of polybenzimidazoles derived from tetraaminodiphenylsulfone for high temperature gas separation membranes

Abstract A series of polybenzimidazoles containing sulfonyl groups were synthesized in Eaton's reagent for high temperature H2/CO2 separation membranes. The key monomer, 3,3′,4,4′-tetraaminodiphenylsulfone, was prepared via a novel and economical synthetic route starting from 4,4′-dichlorodiphenylsulfone. These polybenzimidazoles with sulfonyl moieties had enhanced solubilities in dipolar aprotic solvents relative to the commercial Celazole that is prepared from diaminobenzidine. Thermal gravimetric analysis showed that the materials were stable at elevated temperatures with 5% weight loss values of at least 485 °C in either air or N2. Glass transition temperatures of three polybenzimidazoles in this series were ascertained by dynamic mechanical analysis to be 438-480 °C. These sulfonyl-containing polybenzimidazoles exhibited excellent gas separation properties for H2/CO2. Polymers from tetraaminodiphenylsulfone and either terephthalic or isophthalic acid crossed Robeson's upper bound for H2/CO2.

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.

Synthesis and anthelmintic activity of 2,2'-disubstituted 5,5'-dibenzimidazolylsulfides and sulfones

A number of substituted diphenylsulfides and sulfones (4-11) and 2,2'-disubstituted-5,5'-dibenzimidazolyl sulfides and sulphones (12-19) have been synthesized starting from 5-chloro-2-nitroacetanilide (3) and 4,4'-dichlorodiphenyl sulfone (9), respectively. Among the compounds tested against Ancylostoma ceylanicum in hamsters and Hymenolepis nana in rats and mice, 14, 15, 18 and 19 removed 100% of the worms at an oral dose of 25 mg/kg x 1 to 250 mg/kg x 3. Some of the compounds were tested for their blood schizontocidal activity against Plasmodium berghei in mice but none showed any activity up to an oral dose of 10 mg/kg given for 6 days.