80-82-0

Basic information

• Product Name: 2-NITROBENZENESULFONIC ACID
• Synonyms: O-NITROBENZENESULFONIC ACID;2-NITROBENZENESULFONATE ACID;2-NITROBENZENESULFONIC ACID;2-nitrobenzenesulphonic acid;2-NITROBENZENESULFONIC ACID HYDRATE;2-Nitrobenzenesulfonic Acid
• CAS NO: 80-82-0
• Molecular Formula: C₆H₅NO₅S
• Molecular Weight: 203.17
• EINECS: 201-311-6
• Product Categories: Intermediates of Dyes and Pigments
• Mol File: 80-82-0.mol
• Article Data: 12

Chemical Properties

• Appearance: /
• Density: 1.637
• Refractive Index: 1.612
• PKA: -1.43±0.18(Predicted)
• CAS DataBase Reference: 2-NITROBENZENESULFONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-NITROBENZENESULFONIC ACID(80-82-0)
• EPA Substance Registry System: 2-NITROBENZENESULFONIC ACID(80-82-0)

Safety Data

• Statements: 34-41
• Safety Statements: 26-36/37/39
• RIDADR: 2305
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 80-82-0(Hazardous Substances Data)

Usage

General Description

2-Nitrobenzenesulfonic acid is a chemical compound with the molecular formula C6H5NO6S. It is a yellow solid that is soluble in water, alcohol, and acetone. 2-NITROBENZENESULFONIC ACID is mainly used as an intermediate in the production of pharmaceuticals, dyes, and pigments. It is also used in the synthesis of various organic compounds and as a reagent in chemical reactions. 2-Nitrobenzenesulfonic acid is known for its strong acidic properties and is utilized in the manufacturing of sulfonated dyes and other sulfonated organic compounds. It is important to handle this chemical with caution, as exposure to it can cause irritation to the skin, eyes, and respiratory system.

InChI:InChI=1/C6H5NO5S/c8-7(9)5-3-1-2-4-6(5)13(10,11)12/h1-4H,(H,10,11,12)

Synthetic route

1-(o-nitrobenzenesulfonoyloxy)-2(1H)-quinolone → 2-nitrobenzenesulfonic acid (80-82-0) + 2-quinolone (59-31-4, 70254-42-1)

Conditions	Yield
In methanol; water Quantum yield; UV-irradiation; Photolysis;	A 85% B n/a

2-Nitrobenzenesulfonyl chloride (1694-92-4) → 2-nitrobenzenesulfonic acid (80-82-0)

Conditions	Yield
Stage #1: 2-Nitrobenzenesulfonyl chloride With N-ethyl-N,N-diisopropylamine; Wang resin In dichloromethane at 22℃; Stage #2: With trifluoroacetic acid In dichloromethane for 1h; Further stages.;	78%
With sulfuric acid at 25℃; Rate constant; Thermodynamic data; var. conc. of sulfuric acid; other reagent - H2O in dioxane;
With sodium hydrogencarbonate; sodium hydrogensulfite In water at 80℃; for 2h;

N-methyl-N-4'-ethoxycarbonylphenyl 2-nitrobenzenesulfenanilide (106411-90-9) → 2-nitrobenzenesulfonic acid (80-82-0)

Conditions	Yield
In acetonitrile Ambient temperature; electrolysis, electrolyte: 0.1 M NaOClO4, 1.55 V;	70.5%

bis(2-nitrophenyl)disulfide (1155-00-6) → 2-nitrobenzenesulfonic acid (80-82-0)

Conditions	Yield
With nitric acid
With nitric acid
With hydrogenchloride; sodium chlorate In water at 60 - 90℃;	4550 kg

benzenesulfonic acid (98-11-3) → 2-nitrobenzenesulfonic acid (80-82-0)

Conditions	Yield
Nitrierung;

benzenesulfonic acid (98-11-3) → 2-nitrobenzenesulfonic acid (80-82-0) + p-nitrobenzenesulfonic acid (138-42-1) + 3-Nitrobenzenesulfonic acid (98-47-5)

Conditions	Yield
With nitric acid

2-Nitro-benzenesulfonic acid allyl ester → 2-nitrobenzenesulfonic acid (80-82-0) + allyl alcohol (107-18-6)

Conditions	Yield
With water at 10 - 40℃; Rate constant; Thermodynamic data; Ea, ΔF(excit.), ΔH(excit.), -ΔS(excit.);

2-Nitro-benzenesulfonic acid prop-2-ynyl ester → 2-nitrobenzenesulfonic acid (80-82-0) + propargyl alcohol (107-19-7)

Conditions	Yield
With water at 30 - 60℃; Rate constant; Thermodynamic data; Ea, ΔF(excit.), ΔH(excit.), -ΔS(excit.);

n-propyl 2-nitrobenzenesulfonate → propan-1-ol (71-23-8) + 2-nitrobenzenesulfonic acid (80-82-0)

Conditions	Yield
With water at 40 - 70℃; Rate constant; Thermodynamic data; Ea, ΔF(excit.), ΔH(excit.), -ΔS(excit.);

2-Nitro-benzenesulfonic acid isobutyl ester → 2-methyl-propan-1-ol (78-83-1) + 2-nitrobenzenesulfonic acid (80-82-0)

Conditions	Yield
With water at 40 - 70℃; Rate constant; Thermodynamic data; Ea, ΔF(excit.), ΔH(excit.), -ΔS(excit.);

<2-nitro-phenyl>-phenyl-iodonium-bromide → 2-nitrobenzenesulfonic acid (80-82-0)

Conditions	Yield
With water; sodium sulfite

benzenesulfonic acid (98-11-3) → 2-nitrobenzenesulfonic acid (80-82-0) + m and p compound

Conditions	Yield
With nitric acid

benzene (71-43-2) → 2-nitrobenzenesulfonic acid (80-82-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid 2: Nitrierung View Scheme

o-(2-nitrobenzenesulfonoxy) acetanilide (924057-07-8) → 2-nitrobenzenesulfonic acid (80-82-0) + 2-(acetylamino)phenol (614-80-2)

Conditions	Yield
With water In methanol for 1.25h; UV-irradiation;	A 90 %Spectr. B n/a

o-(2-nitrobenzenesulfonoxy) benzanilide (1309926-95-1) → 2-nitrobenzenesulfonic acid (80-82-0) + N-(2-hydroxyphenyl)benzamide (3743-70-2)

Conditions	Yield
With water In methanol for 0.75h; UV-irradiation;	A 95 %Spectr. B n/a

C14H12N2O6S → 2-nitrobenzenesulfonic acid (80-82-0) + 2-(acetylamino)phenol (614-80-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: dichloromethane / 20 °C 2: water / methanol / 1.25 h / UV-irradiation View Scheme

C19H14N2O6S → 2-nitrobenzenesulfonic acid (80-82-0) + N-(2-hydroxyphenyl)benzamide (3743-70-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: dichloromethane / 12 h / 20 °C 2: water / methanol / 0.75 h / UV-irradiation View Scheme

1-hydroxycarbostyril (58-57-1) + 2-Nitrobenzenesulfonyl chloride (1694-92-4) → 2-nitrobenzenesulfonic acid (80-82-0) + 2-quinolone (59-31-4, 70254-42-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 20 °C 2: water; methanol / UV-irradiation; Photolysis View Scheme

2-Chloronitrobenzene (88-73-3) → 2-nitrobenzenesulfonic acid (80-82-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium disulfide / water / 60 - 90 °C / Large scale 2: hydrogenchloride; sodium chlorate / water / 60 - 90 °C View Scheme
With hydrogenchloride; sulfuric acid; nitric acid under 75.0075 Torr; for 0.5h; Inert atmosphere;

C6H5NO5S*C12H23N → 2-nitrobenzenesulfonic acid (80-82-0)

Conditions	Yield
With sodium hydroxide In water Large scale;	1653 kg

2-nitrobenzenesulfonic acid (80-82-0) → 2-amino-1-benzenesulfonic acid (88-21-1)

Conditions	Yield
With hydrogen at 120℃; under 30003 - 37503.8 Torr; for 0.75h; Reflux;	97%
With Raney nickel at 90 - 120℃; under 6000.6 - 9750.98 Torr;	4200 kg

2-nitrobenzenesulfonic acid (80-82-0) → o-nitrobenzenesulfonyl azide (6655-31-8)

Conditions	Yield
With sodium azide; trichloroacetonitrile; triphenylphosphine In acetonitrile at 20℃; for 0.5h;	93%
With sodium azide; trichloroisocyanuric acid; triphenylphosphine In tetrahydrofuran at 20℃;

2-nitrobenzenesulfonic acid (80-82-0) + ethanolamine (141-43-5) → 2-[(2-nitrophenyl)amino]ethanol (4926-55-0)

Conditions	Yield
In dimethyl sulfoxide at 150℃; for 12h; Green chemistry;	74%

(phenylthio)acetonitrile (5219-61-4) + 2-nitrobenzenesulfonic acid (80-82-0) → 2-nitro-5-cyanomethylbenzenesulfonic acid (127204-86-8) + 2-nitro-3-cyanomethylbenzenesulfonic acid (127204-87-9)

Conditions	Yield
With hydrogenchloride; potassium tert-butylate 1.) DMF, 30 deg C, 45, min, 2.) DMF, ether, 40 deg C; Yield given. Multistep reaction. Yields of byproduct given;

chloromethyl phenyl sulfone (7205-98-3) + 2-nitrobenzenesulfonic acid (80-82-0) → 2-nitro-3-phenylsulfonylmethylbenzenesulfonic acid (127204-85-7) + 2-nitro-5-phenylsulfonylmethylbenzenesulfonic acid (127204-84-6)

Conditions	Yield
With hydrogenchloride; potassium tert-butylate 1.) DMF, 30 deg C, 45, min, 2.) DMF, ether, 40 deg C; Yield given. Multistep reaction. Yields of byproduct given;

tetradecylamine (2016-42-4) + 2-nitrobenzenesulfonic acid (80-82-0) → Tetradecylammonium o-nitrobenzenesulfonate

Conditions	Yield
In methanol

hexadecylamine (143-27-1) + 2-nitrobenzenesulfonic acid (80-82-0) → Hexadecylamine; compound with 2-nitro-benzenesulfonic acid

Conditions	Yield
In methanol

1-pentadecylamine (2570-26-5) + 2-nitrobenzenesulfonic acid (80-82-0) → Pentadecylammonium o-nitrobenzenesulfonate

Conditions	Yield
In methanol

1-heptadecanamine (4200-95-7) + 2-nitrobenzenesulfonic acid (80-82-0) → Heptadecylamine; compound with 2-nitro-benzenesulfonic acid

Conditions	Yield
In methanol

2-nitrobenzenesulfonic acid (80-82-0) + 1-aminooctadecane (124-30-1) → Octadecylammonium o-nitrobenzenesulfonate

Conditions	Yield
In methanol

2-nitrobenzenesulfonic acid (80-82-0) + KOH → ammonia (7664-41-7) + oxalic acid (144-62-7)

2-nitrobenzenesulfonic acid (80-82-0) + tin oxide → azoxy compound + azo compound

2-nitrobenzenesulfonic acid (80-82-0) + ammonium sulfide → o-amino-benzenesulfonic acid

hydrogenchloride (7647-01-0) + 2-nitrobenzenesulfonic acid (80-82-0) + tin dichloride → o-amino-benzenesulfonic acid

Upstream product

• 1155-00-6 bis(2-nitrophenyl)disulfide 
• 98-11-3 benzenesulfonic acid 
• 1694-92-4 2-Nitrobenzenesulfonyl chloride 
• 106411-90-9 N-methyl-N-4'-ethoxycarbonylphenyl 2-nitrobenzenesulfenanilide 
• 71-43-2 benzene 
• 924057-07-8 o-(2-nitrobenzenesulfonoxy) acetanilide 
• 1309926-95-1 o-(2-nitrobenzenesulfonoxy) benzanilide 
• 58-57-1 1-hydroxycarbostyril 
• 88-73-3 2-Chloronitrobenzene 

Downstream Products

• 127204-86-8 2-nitro-5-cyanomethylbenzenesulfonic acid 
• 127204-87-9 2-nitro-3-cyanomethylbenzenesulfonic acid 
• 88-21-1 2-amino-1-benzenesulfonic acid 
• 4926-55-0 2-[(2-nitrophenyl)amino]ethanol 
• 6655-31-8 o-nitrobenzenesulfonyl azide 
• 121-47-1 3-aminobenzenesulfonic acid 
• 770698-49-2 2'-propylsulfonyl-2-(anilinomethyl)imidazoline 
• 76697-58-0 2-Aminophenyl-propyl-sulfon 
• 76697-43-3 2-propylsulfonyl nitrobenzene 
• 127204-85-7 2-nitro-3-phenylsulfonylmethylbenzenesulfonic acid 
• 127204-84-6 2-nitro-5-phenylsulfonylmethylbenzenesulfonic acid 

Relevant articles and documents

Aryl sulfonic acid ammonium salt compound, preparation method and application thereof (by machine translation)

The invention discloses a aryl sulfonic acid ammonium salt compound, preparation method and application thereof, the main process expressed as follows: formula (I) indicated by the aryl sulfonic acid compound crude product as raw material, in the solvent with the structural formula (II) shown in mixed organic amine, to form the structural formula (III) as shown by a aryl sulfonic acid ammonium salt; the resulting structural formula (III) aryl sulfonic acid ammonium salt shown by the alkali soluble acid or directly to obtain the acid of formula (I) shown in the purification of compounds such as aryl sulfonic acid. The invention is primarily embodied in the [...]: through the low quality aryl sulfonic acid compound refining, effectively reduces the content of harmful impurities, improve the quality of the aryl sulfonic acid compound, reducing the pressure of the downstream use, the process is stable. (by machine translation)

Development of 1-Hydroxy-2(1H)-quinolone-Based Photoacid Generators and Photoresponsive Polymer Surfaces

A new class of carboxylate and sulfonate esters of 1-hydroxy-2(1H)- quinolone has been demonstrated as nonionic photoacid generators (PAGs). Irradiation of carboxylates and sulfonates of 1-hydroxy-2(1H)-quinolone by UV light (γ≥310 nm) resulted in homolysis of weak N-O bond leading to efficient generation of carboxylic and sulfonic acids, respectively. The mechanism for the homolytic N-O bond cleavage was supported by time-dependent DFT calculations. Photoresponsive 1-(p-styrenesulfonyloxy)-2-quinolone-methyl methacrylate (SSQL-MMA) and 1-(p-styrenesulfonyloxy)-2-quinolone-lauryl acrylate (SSQL-LA) copolymers were synthesized from PAG monomer 1-(p-styrenesulfonyloxy) -2-quinolone, and subsequently controlled surface wettability was demonstrated for the above-mentioned photoresponsive polymers. Copyright