88-63-1

Basic information

• Product Name: 2,4-Diaminobenzenesulfonic acid
• Synonyms: O-AMINOSULFANILIC ACID;3-Phenylenediamino-4-sulfonic acid;1,3-Phenylendiamin-4-sulfonsure;META PHENYLENE DIAMINE 4-SULFONIC ACID;3-AMINO-4-SULFOANILINE;2,4-DIAMINOBENZENESULFONIC ACID;2,4-DIAMINOBENZENESULPHONIC ACID;2,4-DIAMINO-1-SULFOBENZENE
• CAS NO: 88-63-1
• Molecular Formula: C₆H₈N₂O₃S
• Molecular Weight: 188.2
• EINECS: 201-846-5
• Product Categories: Intermediates of Dyes and Pigments;Organic acids;Organic Building Blocks;Sulfonic/Sulfinic Acids;Sulfur Compounds;Building Blocks;Chemical Synthesis;Organic Building Blocks;Sulfonic/Sulfinic Acids;Sulfur Compounds
• Mol File: 88-63-1.mol
• Article Data: 22

Chemical Properties

• Melting Point: 260-266 °C (dec.)
• Boiling Point: 500°C (estimate)
• Appearance: /
• Density: 1.366 (estimate)
• Vapor Pressure: 0Pa at 25℃
• Refractive Index: 1.6490 (estimate)
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly, Heated), Methanol (Slightly)
• PKA: 2.99±0.10(Predicted)
• Water Solubility: 1000g/L at 25℃
• BRN: 2694057
• CAS DataBase Reference: 2,4-Diaminobenzenesulfonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Diaminobenzenesulfonic acid(88-63-1)
• EPA Substance Registry System: 2,4-Diaminobenzenesulfonic acid(88-63-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/38-43-36/37/38
• Safety Statements: 26-36/39-37/39-36
• RIDADR: 1759
• WGK Germany: 2
• RTECS: DB5900000
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 88-63-1(Hazardous Substances Data)

Usage

Description

2,4-Diaminobenzenesulfonic acid, with the chemical formula C6H8N2O2S, is an organic compound that features two amino groups and a sulfonic acid group attached to a benzene ring. It is a white or slightly yellow crystalline solid and is soluble in water. 2,4-Diaminobenzenesulfonic acid is known for its chemical stability and reactivity, making it a versatile building block in various chemical and material applications.

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

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

Downstream Products

• 1443031-52-4 C₁₄H₁₆N₄O₆S₂ 
• 215674-61-6 C₂₂H₂₄N₆O₁₅S₅ 
• 77365-67-4 C₁₇H₁₇ClN₆O₉S₃ 
• 123848-64-6 4-amino-2-(N-methylamino)benzenesulfonic acid 
• 1038412-35-9 C₂₆H₂₁ClN₁₀O₁₃S₄ 
• 85946-21-0 C₁₇H₁₇ClN₆O₉S₃ 
• 53641-00-2 C₁₂H₁₂N₄O₆S₂ 
• 888854-35-1 C₁₄H₁₆N₄O₉S₃ 
• 192820-84-1 C₁₁H₁₃ClN₆O₆S₂ 
• 74758-53-5 C₁₇H₁₇FN₆O₉S₃ 
• 41602-30-6 C₉H₇Cl₂N₅O₃S 

Relevant articles and documents

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.

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.