88-63-1

Usage

Uses

Used in Water Treatment Industry:
2,4-Diaminobenzenesulfonic acid is used as a reagent to enhance the chlorine resistance and water permeability of polyamide (PA) membranes. This improvement is crucial for the efficiency and longevity of water treatment systems, ensuring a continuous supply of clean water.
Used in Polymer Synthesis:
In the field of polymer chemistry, 2,4-Diaminobenzenesulfonic acid is utilized in the preparation of a series of sulfonated homoand random co-polyimides. These polymers exhibit unique properties, such as thermal stability and chemical resistance, which make them suitable for applications in aerospace, electronics, and other high-performance industries. The sulfonation of these polymers further enhances their solubility and processability, broadening their range of potential uses.

InChI:InChI=1/C6H8N2O3S/c7-4-1-2-6(5(8)3-4)12(9,10)11/h1-3H,7-8H2,(H,9,10,11)/p-1

Synthetic route

5-aminobenzothiazole (1123-93-9) → 2,4-Diaminobenzenesulfonic acid (88-63-1)

Conditions	Yield
With [RuCl(P(C6H5)3)2(O(C6H4)NCH(C4H3N))]; bromamine B; sodium hydroxide In water; acetonitrile at 39.84℃; for 4.41667h;	96%
With chloramine-B; sodium hydroxide; palladium dichloride In water; acetonitrile at 80℃; pH=12;	86%

m-phenylenediamine (108-45-2) → 2,4-Diaminobenzenesulfonic acid (88-63-1)

Conditions	Yield
With sulfur trioxide In 1,2-dichloro-ethane at 20 - 60℃; for 10h; Solvent; Temperature;	95.96%
With sulfuric acid at 160℃;
With sulfuric acid

2,4-dinitrobenzenesulfonic acid (89-02-1) → 2,4-Diaminobenzenesulfonic acid (88-63-1)

Conditions	Yield
Stage #1: 2,4-dinitrobenzenesulfonic acid With hydrogenchloride In water at 95 - 100℃; pH=2; Stage #2: In water pH=7; Product distribution / selectivity;	60%

meta-dinitrobenzene (99-65-0) + sodium hydrogensulfite → 2,4-Diaminobenzenesulfonic acid (88-63-1)

Conditions	Yield
large excess of NaHSO3;	10%
large excess of NaHSO3;	10%

3-nitroaniline-6-sulphonic acid (24311-40-8) → 2,4-Diaminobenzenesulfonic acid (88-63-1)

Conditions	Yield
With hydrogenchloride; tin
With hydrogenchloride; tin

4-amino-2-nitrobenzene sulfonic acid (712-24-3) → 2,4-Diaminobenzenesulfonic acid (88-63-1)

o-phenylenediamine dihydrochloride (615-28-1) → 2,4-Diaminobenzenesulfonic acid (88-63-1)

Conditions	Yield
With sulfuric acid at 170℃; im geschlossenen Rohr;

meta-dinitrobenzene (99-65-0) + aqueous NaHSO3-solution → 4-amino-2-nitrobenzene sulfonic acid (712-24-3) + 2,4-Diaminobenzenesulfonic acid (88-63-1)

Conditions	Yield
anschliessendes Behandeln mit H2SO4;

2,4-dinitrobenzenesulfonic acid (89-02-1) + acetic acid (64-19-7) + iron → 2,4-Diaminobenzenesulfonic acid (88-63-1)

hydrogenchloride (7647-01-0) + 2,4-dinitrobenzenesulfonic acid (89-02-1) + tin dichloride → 2,4-Diaminobenzenesulfonic acid (88-63-1)

2.4-dinitro-benzene-sulfonic acid-(1) → 2,4-Diaminobenzenesulfonic acid (88-63-1)

Conditions	Yield
With hydrogenchloride; tin(ll) chloride
With iron; acetic acid

sodium salt of/the/ 2.4-dinitro-benzene-sulfonic acid-(1) → 2,4-Diaminobenzenesulfonic acid (88-63-1)

Conditions	Yield
With hydrogenchloride; iron

3-nitro-aniline (99-09-2) + p-tert-octylphenoxy polyoxyethanol (TX-100) → 2,4-Diaminobenzenesulfonic acid (88-63-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid / 1 h / 160 °C 2: Sn; conc. HCl View Scheme

3-nitro-aniline (99-09-2) → 2,4-Diaminobenzenesulfonic acid (88-63-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: fuming sulfuric acid / 160 °C 2: tin; hydrochloric acid View Scheme

3-aminobenzenesulfonic acid (121-47-1) → 2,4-Diaminobenzenesulfonic acid (88-63-1)

1,3,5-trichloro-2,4,6-triazine (108-77-0) + 4-amino-2-(N-methylamino)benzenesulfonic acid (123848-64-6) + 3-(3-methylimidazol-1-ylium)-4-methyl-6-hydroxypyrid-2-one hydrochloride → 2,4-Diaminobenzenesulfonic acid (88-63-1)

Conditions	Yield
With sodium hydrogencarbonate; hydrogenchloride In ice-water

1-chloro-2,4-dinitro-benzene (97-00-7) → 2,4-Diaminobenzenesulfonic acid (88-63-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: ethanol; water; sodium sulfite View Scheme

1,3,5-trichloro-2,4,6-triazine (108-77-0) + 2,4-Diaminobenzenesulfonic acid (88-63-1) + Na(1+)*C23H20N3O8S2(1-) + p-toluidine (106-49-0) → C38H28ClN10O11S3(3-)*3Na(1+)

Conditions	Yield
Stage #1: 1,3,5-trichloro-2,4,6-triazine; Na(1+)*C23H20N3O8S2(1-) at 0 - 5℃; for 4h; pH=4 - 6.5; Stage #2: 2,4-Diaminobenzenesulfonic acid at 5 - 30℃; pH=2.5 - 3.5; Stage #3: p-toluidine Further stages;	86.29%

1,3,5-trichloro-2,4,6-triazine (108-77-0) + 2,4-Diaminobenzenesulfonic acid (88-63-1) + Na(1+)*C23H20N3O8S2(1-) + aniline (62-53-3) → C38H28ClN10O11S3(3-)*3Na(1+)

Conditions	Yield
Stage #1: 1,3,5-trichloro-2,4,6-triazine; Na(1+)*C23H20N3O8S2(1-) at 0 - 5℃; for 4h; pH=4 - 6.5; Stage #2: 2,4-Diaminobenzenesulfonic acid at 5 - 30℃; pH=2.5 - 3.5; Stage #3: aniline Further stages;	85.02%

1,3,5-trichloro-2,4,6-triazine (108-77-0) + 2,4-Diaminobenzenesulfonic acid (88-63-1) + Na(1+)*C23H20N3O8S2(1-) + 4-aminobenzene sulfonic acid (121-57-3) → C38H27ClN10O14S4(4-)*4Na(1+)

Conditions	Yield
Stage #1: 1,3,5-trichloro-2,4,6-triazine; Na(1+)*C23H20N3O8S2(1-) at 0 - 5℃; for 4h; pH=4 - 4.5; Stage #2: 2,4-Diaminobenzenesulfonic acid at 5 - 30℃; pH=2.5 - 3.5; Stage #3: 4-aminobenzene sulfonic acid Further stages;	84.67%

2-(p-aminophenylsulfonyl)ethyl hydrogen sulfate (2494-89-5) + 1,3,5-trichloro-2,4,6-triazine (108-77-0) + 2,4-Diaminobenzenesulfonic acid (88-63-1) + Na(1+)*C23H20N3O8S2(1-) → C40H31ClN10O17S5(4-)*4Na(1+)

Conditions	Yield
Stage #1: 1,3,5-trichloro-2,4,6-triazine; Na(1+)*C23H20N3O8S2(1-) at 0 - 5℃; for 4h; pH=4 - 6.5; Stage #2: 2,4-Diaminobenzenesulfonic acid at 5 - 30℃; pH=2.5 - 3.5; Stage #3: 2-(p-aminophenylsulfonyl)ethyl hydrogen sulfate Further stages;	82.14%

3-(β-chloroethylsulfonyl)-methyl-benzoyl chloride (81922-32-9) + 2,4-Diaminobenzenesulfonic acid (88-63-1) → sodium salt of 3-[3'-(β-chloroethylsulfonyl-methyl)-benzoylamino]-aniline-4-sulfonic acid

Conditions	Yield
In diethylene glycol dimethyl ether	82%

2-(p-aminophenylsulfonyl)ethyl hydrogen sulfate (2494-89-5) + 1,3,5-trichloro-2,4,6-triazine (108-77-0) + 2-amino-1-benzenesulfonic acid (88-21-1) + 2,4-Diaminobenzenesulfonic acid (88-63-1) + H-acid → C43H26ClN12O26S8(7-)*7Na(1+)

Conditions	Yield
Stage #1: 1,3,5-trichloro-2,4,6-triazine; H-acid With sodium carbonate; sodium hydroxide In water at 0 - 5℃; for 4.6h; pH=4.5 - 6; Stage #2: 2-amino-1-benzenesulfonic acid With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 2.6h; Stage #3: 2-(p-aminophenylsulfonyl)ethyl hydrogen sulfate; 2,4-Diaminobenzenesulfonic acid Further stages;	78.5%

2-(p-aminophenylsulfonyl)ethyl hydrogen sulfate (2494-89-5) + 1,3,5-trichloro-2,4,6-triazine (108-77-0) + 2-amino-1-benzenesulfonic acid (88-21-1) + 1-hydroxy-6-amino-3-naphthalenesulfonic acid (87-02-5) + 4-amino-5-hydroxy-2,7-naphthalenedisulfonic acid (90-20-0) + 2,4-Diaminobenzenesulfonic acid (88-63-1) → C43H27ClN12O23S7(6-)*6Na(1+)

Conditions	Yield
Stage #1: 1,3,5-trichloro-2,4,6-triazine; 7-amino-4-hydroxy-2-naphthalenesulfonic acid With sodium hydroxide In water at 0 - 5℃; pH=5.6 - 6.5; Stage #2: With sodium carbonate In water at 3 - 5℃; for 5h; Stage #3: 2-(p-aminophenylsulfonyl)ethyl hydrogen sulfate; 2-amino-1-benzenesulfonic acid; 4-amino-5-hydroxy-2,7-naphthalenedisulfonic acid; 2,4-Diaminobenzenesulfonic acid Further stages;	77.1%

4-chloro-3-nitrophenyl hydroxyethyl sulfone + 2,4-Diaminobenzenesulfonic acid (88-63-1) → 4-(3-amino-4-sulfophenyl)-amino-3-nitrophenyl hydroxyethyl sulfone

Conditions	Yield
With sodium hydroxide In water	73.5%

1H-indene-1,3(2H)-dione (606-23-5) + 2,4-Diaminobenzenesulfonic acid (88-63-1) → 2,4-bis[(3-oxoinden-1-yl)amino]benzenesulfonic acid (1352954-39-2)

Conditions	Yield
In ethanol for 8h; Reflux;	66%

2,4-Diaminobenzenesulfonic acid (88-63-1) + sodium 1-amino-4-bromoanthraquinone-2-sulfonate (6258-06-6) → disodium 1-amino-4-(3-amino-4-sulfophenylamino)-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate

Conditions	Yield
With sodium carbonate; copper(l) chloride; sodium sulfite In water at 20℃; for 8h; Ullmann coupling;	49%

N-(eicosanoyloxy)succinimide (69888-87-5) + 2,4-Diaminobenzenesulfonic acid (88-63-1) → C26H46N2O4S

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 2h;	20.7%

2,4-Diaminobenzenesulfonic acid (88-63-1) + 1-Bromooctadecane (112-89-0) → C42H80N2O3S

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 40℃;	6.1%

bromoundecane (693-67-4) + 2,4-Diaminobenzenesulfonic acid (88-63-1) → C28H52N2O3S

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 40℃;	4.3%

N-succinimidyl laurate (14565-47-0) + 2,4-Diaminobenzenesulfonic acid (88-63-1) → C18H30N2O4S

Conditions	Yield
In aq. phosphate buffer; N,N-dimethyl-formamide at 20℃; for 3h; pH=9.5;	2.1%

N-(eicosanoyloxy)succinimide (69888-87-5) + 2,4-Diaminobenzenesulfonic acid (88-63-1) → C46H84N2O5S

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 2h;	0.84%

N-succinimidyl laurate (14565-47-0) + 2,4-Diaminobenzenesulfonic acid (88-63-1) → C30H52N2O5S

Conditions	Yield
In aq. phosphate buffer; N,N-dimethyl-formamide at 20℃; for 3h; pH=9.5;	0.65%

4-methyleneoxetan-2-one (674-82-8) + 2,4-Diaminobenzenesulfonic acid (88-63-1) → 7-amino-2-hydroxy-4-methyl-quinoline-6-sulfonic acid (101872-02-0)

Conditions	Yield
With water Erhitzen des Reaktionsgemisches mit wss. HCl;

2,4-Diaminobenzenesulfonic acid (88-63-1) + 4-acetoxy-3-nitro-benzoyl chloride → 2-amino-4-(4-hydroxy-3-nitro-benzoylamino)-benzenesulfonic acid

Conditions	Yield
With sodium acetate; sodium carbonate

2,4-Diaminobenzenesulfonic acid (88-63-1) + 4-ethoxycarbonyloxy-3-nitro-benzoyl chloride (861377-45-9) → 2-amino-4-(4-hydroxy-3-nitro-benzoylamino)-benzenesulfonic acid

Conditions	Yield
With sodium acetate; sodium carbonate

2,4-Diaminobenzenesulfonic acid (88-63-1) + acetic anhydride (108-24-7) → 2-amino-4-acetylaminobenzene sulfonic acid (88-64-2)

Conditions	Yield
With alkali at 50℃;

2,4-Diaminobenzenesulfonic acid (88-63-1) + 1-chloro-2,4-dinitro-benzene (97-00-7) → 2-amino-4-(2,4-dinitro-anilino)-benzenesulfonic acid

Conditions	Yield
With ethanol; sodium acetate

2,4-Diaminobenzenesulfonic acid (88-63-1) + p-acetylaminobenzenesulfonyl chloride (121-60-8) → 2,4-bis-sulfanilylamino-benzenesulfonic acid (62707-58-8)

Conditions	Yield
With sodium hydroxide; sodium carbonate Erwaermen des Reaktionsprodukts mit wss. Natronlauge;

1-amino-4-bromo-9,10-dioxoanthracene-2-sulphonic acid (116-81-4) + 2,4-Diaminobenzenesulfonic acid (88-63-1) → 1-aminoanthraquinone-2-sulfonic acid (83-62-5) + 1-amino-4-hydroxy-9,10-dioxo-9,10-dihydroanthracene-2-sulfonic acid (24929-02-0) + 1-amino-4-(3-amino-4-sulfophenylamino)anthraquinone-2-sulfonic acid (128-99-4)

Conditions	Yield
bronze powder; copper(l) iodide In water at 40℃; Mechanism; Rate constant; various pH, various electrolyte concentrations, various Cu(1+) concentrations;
bronze powder; copper(l) iodide In water at 40℃; Mechanism; Rate constant; various pH, various electrolyte concentrations, various Cu(1+) concentrations;

Upstream product

• 24311-40-8 3-nitroaniline-6-sulphonic acid 
• 712-24-3 4-amino-2-nitrobenzene sulfonic acid 
• 615-28-1 o-phenylenediamine dihydrochloride 
• 108-45-2 m-phenylenediamine 
• 99-65-0 meta-dinitrobenzene 
• 89-02-1 2,4-dinitrobenzenesulfonic acid 
• 64-19-7 acetic acid 
• 7647-01-0 hydrogenchloride 
• 121-47-1 3-aminobenzenesulfonic acid 
• 108-77-0 1,3,5-trichloro-2,4,6-triazine 
• 123848-64-6 4-amino-2-(N-methylamino)benzenesulfonic acid 
• 1123-93-9 5-aminobenzothiazole 
• 97-00-7 1-chloro-2,4-dinitro-benzene 
• 99-09-2 3-nitro-aniline 

Downstream Products

• 88-64-2 2-amino-4-acetylaminobenzene sulfonic acid 
• 62707-58-8 2,4-bis-sulfanilylamino-benzenesulfonic acid 
• 83-62-5 1-aminoanthraquinone-2-sulfonic acid 
• 24929-02-0 1-amino-4-hydroxy-9,10-dioxo-9,10-dihydroanthracene-2-sulfonic acid 
• 128-99-4 1-amino-4-(3-amino-4-sulfophenylamino)anthraquinone-2-sulfonic acid 
• 77365-67-4 C₁₇H₁₇ClN₆O₉S₃ 
• 41602-30-6 C₉H₇Cl₂N₅O₃S 
• 74758-53-5 C₁₇H₁₇FN₆O₉S₃ 
• 192820-84-1 C₁₁H₁₃ClN₆O₆S₂ 
• 888854-35-1 C₁₄H₁₆N₄O₉S₃ 
• 53641-00-2 C₁₂H₁₂N₄O₆S₂ 
• 85946-21-0 C₁₇H₁₇ClN₆O₉S₃ 
• 1038412-35-9 C₂₆H₂₁ClN₁₀O₁₃S₄ 

Relevant academic research and scientific papers

Method for preparing 2,4-diaminobenzenesulfonic acid

The invention relates to a method for preparing 2,4-diaminobenzenesulfonic acid. The method comprises the following steps: (1) adding m-phenylenediamine and an organic solvent to a vessel equipped with a thermometer and a stirring device, and dissolving at room temperature; a feed ratio of m-phenylenediamine to the organic solvent is 1g to (5 to20mL); (2) slowly adding sulfur trioxide to the solution in (1) under stirring, and raising the temperature to 20 to 100 DEG C, and reacting for 2.5 swung dash 60h; wherein the molar ratio of m-phenylenediamine to sulfur trioxide is 1:(1.0-3.0); (3) filtering and drying the reaction solution in (2) to obtain 2,4-diaminobenzenesulfonate acid. The method for preparing 2,4-diaminobenzenesulfonic acid has the advantages of mild conditions, simple process, low cost, recyclability of organic reagents, no waste acid formation, high product purity and high yield and the like.

The efficient palladium-catalyzed selective t synthesis of benzenesulfonic acids

Palladium-catalyzed synthetic methodology has been developed for the synthesis of 2-aminobenzenesulfonic acids from benzothiazoles in good to excellent yields using chloramine-B in alkaline (pH 12) acetonitrile/water (1:1) at 80C.

SUSTAINABLE CHEMICAL PROCESS FOR REDUCTION OF NITRO COMPOUNDS (R-NO2) OR NITROSO COMPOUNDS (R-NO) CONTAINING SULPHONIC OR CARBOXYLIC GROUP INTO CORRESPONDING AMINO COMPOUNDS (R-NH2) WITH INHERENT RECYCLE OF ALL ACIDIC STREAMS GENERATED IN SYNTHESIS

The process of the present invention creates a sustainable and closed water loop allowing inherent recycles of all liquid streams generated in the process. The liquid streams generated during the process of the invention are inherently recycled completely, making the process of the present invention a zero liquid discharge process which is environmentally friendly and sustainable. This invention further relates to a sustainable chemical process of reduction of R- NO2 or R-NO into corresponding R-NH2 that produces environmentally friendly R-NH2 in good yields and selectivity with large of mother liquor recycle. The process has a wide scope in that it can be applied to a number of molecules.

Development of an efficient ruthenium catalyzed synthetic process and mechanism for the facile conversion of benzothiazoles to orthanilic acids

Ruthenium-Schiff base complex catalyzed efficient protocol has been developed for the synthesis of orthanilic acids from benzothiazoles in good to excellent yields using N-haloamines. Hexa-coordinated ruthenium complex with Schiff base and triphenylphosphine ligands has been prepared and its catalytic function was invented for the synthesis of orthanilic acids. The synthetic process utilizes our efficient method for the selective and preferential oxidation of thiazole ring of benzothiazoles using N-haloamines without effecting phenyl ring. The detailed catalytic, mechanistic and kinetic investigations have been made for the synthetic reactions. Solvent isotope studies have been made in H2O-D2O and the reactions were carried out at different temperatures. Under the identical set of conditions, the kinetics of catalyzed reactions has been compared with uncatalyzed reactions and found that the catalyzed reactions are 9-11 folds faster. The catalytic constants (KC) have been calculated for each N-haloamine at different temperatures and the values of activation parameters with respect to the catalyst have been evaluated. Spectroscopic evidence for the formation of 1:1 complex between N-haloamine and ruthenium has been obtained. The observed results have been explained by a plausible mechanism and the related rate law has been deduced.

One step hair coloring compositions using salts

A hair coloring composition comprising the following two compositions which are mixed just prior to application to the hair: (a) a composition comprising a water-soluble peroxygen oxidizing agent; and (b) a composition comprising one or more oxidative hair coloring agents selected from the group consisting of an aromatic diamine, an amino phenol, a naphthol, a polyhydric phenol, a catechol and mixtures thereof; wherein the composition comprising one or more oxidative hair coloring agents further comprises al least one water soluble carbonate releasing salts; and optionally a water soluble ammonium salt, is described.

Surprises in a 'simple' system: 2,4-Diaminobenzenesulfonic acid

The search for the polymorphic forms of 2,4-diaminobenzenesulfonic acid (DBSA), known to exist since 1880, has revealed a surprisingly rich solid-state system for such a simple molecule. A monohydrate, a dimoiric hydrate, an anhydrate and two polymorphic forms of the hydrochloride of this material have thus far been prepared. Their characterization by microscopic and thermal methods, FT-IR spectroscopy, and single-crystal structure determination are described.

Transition metal complexes as dye forming catalysts in hair coloring compositions

A hair coloring composition comprising a first composition which comprises: (a) a dye forming transition metal salt or complex; which is first applied to the hair; and a second composition which comprises the following two compositions which are mixed just prior to application to the hair: (a) a composition comprising a water-soluble peroxygen oxidizing agent; and (b) a composition comprising one or more oxidative hair coloring agents selected from the group consisting of an aromatic diamine, an aminophenol, a polyhydric phenol a catechol and mixtures thereof.

5-chloro-4-fluoropyrimidinyl substituted diazopyridone

Dyestuffs of the formula STR1 wherein D represents the radical of a diazo component; R represents hydrogen, an optionally substituted alkyl radical, a cycloaliphatic hydrocarbon radical, an optionally substituted phenyl radical, or a hetaryl radical; represents H, Cl, Br, CH3, CH2 SO3 H, CH(CH3)--SO3 H, CONH2, CN, COCH3, SO3 H, STR2 Y represents hydrogen, hydroxyl, an optionally substituted alkyl radical, an optionally substituted phenyl or benzyl radical, or carboxyl; and Z represents a fiber-reactive radical of the formula STR3 are suitable for dyeing fiber materials containing OH and amide groups and produce dyeings and prints with good fastness properties.

Reactive dyestuffs

Reactive dyestuffs of the formula STR1 in which the substituents have the meanings given in the description are highly suitable for the dyeing and printing of cellulose materials and nitrogen-containing materials. They produce dyeings and prints having good wet and light fastness properties.