91-30-5

Usage

Uses

Used in Chemical Synthesis Industry:
4-Aminodiphenyamine-2-sulfonic acid is used as a building block for the synthesis of various dyes and pigments due to its chemical structure that facilitates the creation of a wide range of colored compounds.
Used in Organic Compounds Production:
It serves as a key intermediate in the production of other organic compounds, leveraging its reactive amine and sulfonic acid groups to form diverse chemical entities for different applications.
Given the potential toxicity to aquatic organisms, it is crucial that 4-Aminodiphenyamine-2-sulfonic acid is handled with care in industrial processes to prevent environmental contamination. This includes adhering to strict disposal protocols and ensuring that any release into aquatic systems is minimized or controlled.

InChI:InChI=1/C12H12N2O3S/c13-9-6-7-11(12(8-9)18(15,16)17)14-10-4-2-1-3-5-10/h1-8,14H,13H2,(H,15,16,17)

Synthetic route

p-nitrosodiphenylamine (156-10-5) → 4-aminodiphenylamine-2-sulfonic acid (91-30-5)

Conditions	Yield
With sodium sulfite
With sodium hydroxide; sodium sulfite Ansaeuern der Loesung;

2-anilino-5-nitro-benzenesulfonic acid (88-35-7) → 4-aminodiphenylamine-2-sulfonic acid (91-30-5)

Conditions	Yield
With hydrogenchloride; iron
With hydrogenchloride; iron

barium salt of/the/ 4-nitro-diphenylamine-sulfonic acid-(2) → 4-aminodiphenylamine-2-sulfonic acid (91-30-5)

Conditions	Yield
With barium dihydroxide; iron(II) sulfate

sodium salt of/the/ 4-nitro-diphenylamine-sulfonic acid-(2) → 4-aminodiphenylamine-2-sulfonic acid (91-30-5)

Conditions	Yield
With water; zinc
With water; zinc

aniline (62-53-3) → 4-aminodiphenylamine-2-sulfonic acid (91-30-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: glycerol; calcium carbonate / 180 - 185 °C 2: iron powder; hydrochloric acid View Scheme

4-hydroxy-1-methyl-2(1H)-quinolone (1677-46-9) + 4-aminodiphenylamine-2-sulfonic acid (91-30-5) → (E)-5-((4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinolin-yl)diazenyl)2(phenylamino)benzenesulfonic acid

Conditions	Yield
Stage #1: 4-aminodiphenylamine-2-sulfonic acid With sodium carbonate In water at 0 - 5℃; Stage #2: With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 0.833333h; Stage #3: 4-hydroxy-1-methyl-2(1H)-quinolone With sodium hydroxide at 0 - 5℃; for 4h; pH=6 - 7;	74.9%

4-aminodiphenylamine-2-sulfonic acid (91-30-5) → C24H18N4O6S2 + C24H20N4O6S2

Conditions	Yield
With recombinant CotA-laccase from Bacillus subtilis In methanol; aq. phosphate buffer at 37℃; for 24h; pH=6; Kinetics; Green chemistry; Enzymatic reaction;	A 70% B 27%

1-amino-4-bromo-2-(hydroxymethyl)anthraquinone (24094-46-0) + 4-aminodiphenylamine-2-sulfonic acid (91-30-5) → C27H21N3O6S

Conditions	Yield
With potassium acetate; copper diacetate at 95℃; for 0.583333h; Ullmann Condensation; Microwave irradiation;	57%

1-Amino-4-bromoanthraquinone-2-carboxylic acid (6363-90-2) + 4-aminodiphenylamine-2-sulfonic acid (91-30-5) → sodium 1-amino-4-[4-phenylamino-3-carboxyphenylamino]-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate (1052087-99-6)

Conditions	Yield
With copper at 120℃; for 0.0833333h; Ullmann reaction; aq. phosphate buffer; Microwave irradiation;	55%

1-amino-4-bromo-9,10-dioxoanthracene-2-sulphonic acid (116-81-4) + 4-aminodiphenylamine-2-sulfonic acid (91-30-5) → disodium 1-amino-4-[4-phenylamino-3-sulfophenylamino]-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate

Conditions	Yield
With copper at 120℃; for 0.0833333h; Ullmann reaction; aq. phosphate buffer; Microwave irradiation;	46%

1-amino-4-bromo-9,10-dioxo-9,10-dihydroanthracene-2-carbonitrile + 4-aminodiphenylamine-2-sulfonic acid (91-30-5) → C27H18N4O5S

Conditions	Yield
With potassium acetate; copper diacetate at 95℃; for 0.25h; Ullmann Condensation; Microwave irradiation;	44%

1-amino-2-methyl-4-bromoanthraquinone (81-50-5) + 4-aminodiphenylamine-2-sulfonic acid (91-30-5) → C27H21N3O5S (1052088-32-0)

Conditions	Yield
With potassium acetate; copper(II) acetate monohydrate; copper In methanol at 95℃; for 0.666667h; Ullmann Condensation; Microwave irradiation;	42%

1-amino-2, 4-dibromoanthraquinone (81-49-2) + 4-aminodiphenylamine-2-sulfonic acid (91-30-5) → C26H18BrN3O5S

Conditions	Yield
With potassium acetate; copper diacetate In pentan-1-ol at 95℃; for 0.0833333h; Ullmann Condensation; Microwave irradiation;	39%

1-amino-2-methyl-4-bromoanthraquinone (81-50-5) + 4-aminodiphenylamine-2-sulfonic acid (91-30-5) → sodium 1-amino-2-methyl-4-[4-phenylamino-3-sulfophenylamino]-9,10-dioxo-9,10-dihydroanthracene (1052088-02-4)

Conditions	Yield
With copper at 120℃; for 0.0833333h; Ullmann reaction; aq. phosphate buffer; Microwave irradiation;	30%

2,4,6-trinitrochlorobenzene (88-88-0) + 4-aminodiphenylamine-2-sulfonic acid (91-30-5) → 2-anilino-5-(2,4,6-trinitro-anilino)-benzenesulfonic acid

Conditions	Yield
With water; sodium acetate

2,4-dichloro-1,5-dinitrobenzene (3698-83-7) + 4-aminodiphenylamine-2-sulfonic acid (91-30-5) → 6,6'-dianilino-3,3'-(4,6-dinitro-m-phenylenediamino)-bis-benzenesulfonic acid

Conditions	Yield
With ethanol; sodium carbonate

4-aminodiphenylamine-2-sulfonic acid (91-30-5) + 2,6-dichloro-3,5-dinitrotoluene (51676-76-7) → 6,6'-dianilino-3,3'-(2-methyl-4,6-dinitro-m-phenylenediamino)-bis-benzenesulfonic acid

Conditions	Yield
With copper(I) sulfate; sodium carbonate; copper(II) sulfate

4-aminodiphenylamine-2-sulfonic acid (91-30-5) → 4-anilino-3-sulfo-benzenediazonium-betaine (46988-73-2)

Conditions	Yield
Diazotization;
Diazotization;

4-aminodiphenylamine-2-sulfonic acid (91-30-5) → N-phenylphenylene-1,4-diamine (101-54-2)

Conditions	Yield
With sulfuric acid
With hydrogenchloride; tin(ll) chloride

4-aminodiphenylamine-2-sulfonic acid (91-30-5) + 1-chloro-4,7-dinitro-10H-acridin-9-one (857612-92-1) → 2-anilino-5-(4,7-dinitro-9-oxo-9,10-dihydro-acridin-1-ylamino)-benzenesulfonic acid

Conditions	Yield
With sodium acetate; nitrobenzene

4-aminodiphenylamine-2-sulfonic acid (91-30-5) + 2-naphthol-6-sulfonic acid (93-01-6) → 6-(4-anilino-3-sulfo-anilino)-naphthalene-2-sulfonic acid

Conditions	Yield
nach dem Sulfit-Verfahren;

4-aminodiphenylamine-2-sulfonic acid (91-30-5) + potassium-salt of/the/ 4-chloro-3,5-dinitro-benzenesulfonic acid-(1) → 6-anilino-3',5'-dinitro-3,4'-imino-bis-benzenesulfonic acid

Conditions	Yield
With water; sodium acetate

sulfuric acid (7664-93-9) + 4-aminodiphenylamine-2-sulfonic acid (91-30-5) → N-phenylphenylene-1,4-diamine (101-54-2)

hydrogenchloride (7647-01-0) + 4-aminodiphenylamine-2-sulfonic acid (91-30-5) + tin dichloride → N-phenylphenylene-1,4-diamine (101-54-2)

4-aminodiphenylamine-2-sulfonic acid (91-30-5) + 4-(4,6-dichloro-[1,3,5]triazin-2-ylamino)-5-hydroxy-naphthalene-2,7-disulfonic acid (7538-88-7) → C25H17Cl2N7O10S3

Conditions	Yield
Stage #1: 4-aminodiphenylamine-2-sulfonic acid With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 2h; Stage #2: 4-(4,6-dichloro-[1,3,5]triazin-2-ylamino)-5-hydroxy-naphthalene-2,7-disulfonic acid With sodium carbonate In water at 5 - 15℃; for 2h; pH=6.5 - 7;	74.2 g

Upstream product

• 156-10-5 p-nitrosodiphenylamine 
• 88-35-7 2-anilino-5-nitro-benzenesulfonic acid 
• 62-53-3 aniline 

Downstream Products

• 46988-73-2 4-anilino-3-sulfo-benzenediazonium-betaine 
• 101-54-2 N-phenylphenylene-1,4-diamine 
• 1052088-02-4 sodium 1-amino-2-methyl-4-[4-phenylamino-3-sulfophenylamino]-9,10-dioxo-9,10-dihydroanthracene 
• 1052087-99-6 sodium 1-amino-4-[4-phenylamino-3-carboxyphenylamino]-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate 
• 1052088-32-0 C₂₇H₂₁N₃O₅S 

Relevant academic research and scientific papers

Light-sensitive polycondensation product containing diazonium and dialdehyde groups, and light-sensitive recording material prepared therewith

A light-sensitive diazonium group-containing polycondensation product of a diazonium salt corresponding to the general formula STR1 wherein R1, R2, and R3 denote hydrogen atoms, halogen atoms, alkyl groups having 1 to 3 carbon atoms or alkoxy groups having 1 to 6 carbon atoms, and X denotes the anion of the diazonium salt, and an aldehyde selected from the group consisting of dialdehydes, acetals of dialdehyde hydrates, and esters of dialdehyde hydrates, a process for producing such a light-sensitive polycondensation product and a light-sensitive recording material comprising a layer support and a light-sensitive layer containing such a light-sensitive polycondensation product.