96-67-3

Basic information

• Product Name: 2-Amino-4-nitrophenol-6-sulfonic acid
• Synonyms: 6-amino-4-nitro-1-phenol-2-sulfonic acid;4-NITRO-2-AMINOPHENOL-6-SULFONIC ACID;3-AMINO-2-HYDROXY-5-NITROBENZENESULFONIC ACID;2-HYDROXY-5-NITROMETANILIC ACID;2-AMINO-4-NITROPHENOL-6-SULFONIC ACID;2-hydroxy-5-nitro-metanilicaci;3-amino-2-hydroxy-5-nitro-benzenesulfonicaci;3-Amino-2-hydroxy-5-nitrobenzenesulfonic Acid Monohydrate
• CAS NO: 96-67-3
• Molecular Formula: C₆H₆N₂O₆S
• Molecular Weight: 234.19
• EINECS: 202-523-1
• Product Categories: Intermediates of Dyes and Pigments;Organic acids
• Mol File: 96-67-3.mol
• Article Data: 6

Chemical Properties

• Melting Point: 285°C
• Boiling Point: 453.78℃
• Appearance: /solid
• Density: 1.608 (estimate)
• Vapor Pressure: 0Pa at 25℃
• Refractive Index: 1.6490 (estimate)
• Storage Temp.: 2-8°C
• PKA: -1.79±0.50(Predicted)
• Water Solubility: 0.1-0.5 g/100 mL at 21.5 ºC
• CAS DataBase Reference: 2-Amino-4-nitrophenol-6-sulfonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-4-nitrophenol-6-sulfonic acid(96-67-3)
• EPA Substance Registry System: 2-Amino-4-nitrophenol-6-sulfonic acid(96-67-3)

Safety Data

• RTECS: OY2357500
• Hazardous Substances Data: 96-67-3(Hazardous Substances Data)

Usage

Reactivity Profile

2-Amino-4-nitrophenol-6-sulfonic acid may react with strong oxidizers and mineral acids . May react with bases.

Fire Hazard

Flash point data for 2-Amino-4-nitrophenol-6-sulfonic acid is not available; however, 2-Amino-4-nitrophenol-6-sulfonic acid is probably combustible.

InChI:InChI=1/C6H6N2O6S/c7-4-1-3(8(10)11)2-5(6(4)9)15(12,13)14/h1-2,9H,7H2,(H,12,13,14)

Synthetic route

3-amino-2-hydroxy-benzenesulfonic acid (80-79-5) → 2-hydroxy-3-amino-5-nitrobenzenesulfonic acid (96-67-3)

Conditions	Yield
With sulfuric acid; nitric acid at -5℃;

dipotassium salt of/the/ 4.6-dinitro-phenol-sulfonic acid-(2) → 2-hydroxy-3-amino-5-nitrobenzenesulfonic acid (96-67-3)

Conditions	Yield
With sulfuralkali man scheidet die freie Saeure mit verd. Mineralsaeure ab;

3-amino-2-hydroxy-benzenesulfonic acid (80-79-5) + HNO3+H2SO4 → 2-hydroxy-3-amino-5-nitrobenzenesulfonic acid (96-67-3)

Conditions	Yield
at -5℃;

2-hydroxy-3-nitro-benzenesulfonic acid (861338-29-6) → 2-hydroxy-3-amino-5-nitrobenzenesulfonic acid (96-67-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: tin; hydrochloric acid 2: HNO3+H2SO4 / -5 °C View Scheme

5-amino-2-hydroxy-3-nitro-benzenesulfonic acid (6362-52-3) → 2-hydroxy-3-amino-5-nitrobenzenesulfonic acid (96-67-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: durch Diazotieren und Behandeln mit Kupferpulver 2: tin; hydrochloric acid 3: HNO3+H2SO4 / -5 °C View Scheme

2-hydroxy-3-amino-5-nitrobenzenesulfonic acid (96-67-3) + 1-phenylbutan-1,3-dione (93-91-4) → 1-phenyl-2-(2-hydroxy-3-sulfo-5-nitrophenylhydrazo)butane-1,3-dione

Conditions	Yield
Stage #1: 2-hydroxy-3-amino-5-nitrobenzenesulfonic acid With hydrogenchloride; sodium hydroxide; sodium nitrite In water at 0 - 5℃; Japp-Klingemann reaction; Stage #2: 1-phenylbutan-1,3-dione With sodium acetate In ethanol; water Japp-Klingemann reaction; Cooling with ice;	76%

BARBITURIC ACID (67-52-7) + 2-hydroxy-3-amino-5-nitrobenzenesulfonic acid (96-67-3) → 2-hydroxy-5-nitro-3-(2-(2,4,6-trioxotetrahydro-pyrimidin-5(2H)-ylidene)hydrazinyl)benzene sulfonic acid (1389396-43-3)

Conditions	Yield
Stage #1: 2-hydroxy-3-amino-5-nitrobenzenesulfonic acid With hydrogenchloride; sodium hydroxide; sodium nitrite In water at -0.16℃; Stage #2: BARBITURIC ACID In water at -0.16℃; for 1h;	65%

2-hydroxy-3-amino-5-nitrobenzenesulfonic acid (96-67-3) → 3,5-diamino-2-hydroxy-benzenesulfonic acid (13066-93-8)

Conditions	Yield
With hydrogenchloride; tin

2-hydroxy-3-amino-5-nitrobenzenesulfonic acid (96-67-3) + p-(methylsulfonamido)aniline (53250-82-1) + recorcinol (108-46-3) → 2-amino-5-nitro-benzenesulfonic acid (96-75-3)

Conditions	Yield
With sodium nitrite In hydrogenchloride; water

2-hydroxy-3-amino-5-nitrobenzenesulfonic acid (96-67-3) + dimedone (126-81-8) → 3-(2-(4,4-dimethyl-2,6-dioxocyclohexylidene)hydrazinyl)-2-hydroxy-5-nitrobenzenesulfonic acid (1417721-45-9)

Conditions	Yield
Stage #1: 2-hydroxy-3-amino-5-nitrobenzenesulfonic acid With hydrogenchloride; sodium hydroxide; sodium nitrite In water at 4.84℃; for 1h; Cooling with ice; Stage #2: dimedone With sodium acetate In ethanol at -0.16℃; for 1h; Cooling with ice;

2-hydroxy-3-amino-5-nitrobenzenesulfonic acid (96-67-3) → C6H3N3O6S*K(1+)*Cl(1-)

Conditions	Yield
Stage #1: 2-hydroxy-3-amino-5-nitrobenzenesulfonic acid With potassium hydroxide In water Stage #2: With hydrogenchloride; sodium nitrite In water at 0℃; for 1h; Cooling with ice;

2-hydroxy-3-amino-5-nitrobenzenesulfonic acid (96-67-3) → C6H5N3O6S

Conditions	Yield
With hydrogenchloride; sodium nitrite In water at 0℃; for 1h;

Upstream product

• 6362-52-3 5-amino-2-hydroxy-3-nitro-benzenesulfonic acid 
• 861338-29-6 2-hydroxy-3-nitro-benzenesulfonic acid 
• 80-79-5 3-amino-2-hydroxy-benzenesulfonic acid 

Downstream Products

• 96-75-3 2-amino-5-nitro-benzenesulfonic acid 
• 1389396-43-3 2-hydroxy-5-nitro-3-(2-(2,4,6-trioxotetrahydro-pyrimidin-5(2H)-ylidene)hydrazinyl)benzene sulfonic acid 
• 13066-93-8 3,5-diamino-2-hydroxy-benzenesulfonic acid 
• 1417721-45-9 3-(2-(4,4-dimethyl-2,6-dioxocyclohexylidene)hydrazinyl)-2-hydroxy-5-nitrobenzenesulfonic acid 

Relevant articles and documents

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