98-47-5

Usage

Uses

Used in Organic Synthesis:
3-Nitrobenzenesulfonic acid is used as an intermediate in the synthesis of various organic compounds, including dyes, pharmaceuticals, and agrochemicals. Its reactivity and functional groups make it a versatile building block for the development of new molecules with desired properties.
Used as a Protective Antireduction Agent:
The sodium salt of 3-nitrobenzenesulfonic acid serves as a protective antireduction agent in chemical reactions. It helps to prevent unwanted reduction reactions that could occur during the synthesis process, ensuring the desired product is obtained with minimal side reactions or impurities.
Used in Chemical Industries:
3-Nitrobenzenesulfonic acid is utilized in various chemical industries for the production of specialty chemicals, intermediates, and fine chemicals. Its unique chemical properties and reactivity make it suitable for a wide range of applications, from the synthesis of pharmaceuticals to the development of new materials with specific properties.

Safety Profile

A skin and severe eye irritant. Decomposes violently at about 200°. Mixture with sulfuric acid + sulfur trioxide may explode above 150°C. When heated to decomposition it emits toxic fumes of SOx and NOx. See also NITRO COMPOUNDS OF AROMATIC HYDROCARBONS and SULFONATES.

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

Upstream product

• 13257-95-9 3-nitrobenzenesulfinic acid 
• 23351-89-5 m-nitrodiphenyliodonium bromide 
• 98-95-3 nitrobenzene 
• 98-11-3 benzenesulfonic acid 
• 71-43-2 benzene 
• 67-56-1 methanol 
• 20443-61-2 m-Nitro-benzol-sulfonsaeure-allylester 
• 64-18-6 formic acid 
• 64-17-5 ethanol 
• 75-89-8 2,2,2-trifluoroethanol 
• 6209-71-8 m-nitrobenzenesulfonyl peroxide 
• 59263-05-7 3-nitro-benzenesulfonic acid-(methyl-nitro-amide) 
• 64-19-7 acetic acid 
• 84615-15-6 C₆H₅N₃O₆S 

Downstream Products

• 91-22-5 quinoline 
• 612-58-8 3-methylquinoline 
• 108011-34-3 3-nitro-benzenesulfonic acid-(4-bromo-phenacyl ester) 
• 27147-03-1 5-(phenylazo)salicylaldehyde 
• 52607-63-3 3‐methoxy‐5‐(phenyldiazenyl)salicylaldehyde 
• 116496-07-2 3-(3-sulfo-phenylazo)-benzoic acid 
• 64989-23-7 3,3'-azoxy-bis-benzenesulfonic acid 
• 121-73-3 3-Nitrochlorobenzene 
• 585-79-5 m-nitrobromobenzene 
• 117-61-3 4,4'-diamino-2,2'-biphenyldisulfonic acid 
• 28084-45-9 3,5-dinitro-benzenesulfonic acid 
• 1199-59-3 4-dimethylamino-o-tolualdehyde 
• 2835-04-3 5-amino-2-hydroxybenzenesulfonic acid 
• 4386-32-7 3,3'-hydrazo-bis-benzenesulfonic acid 

Relevant academic research and scientific papers

Effect of solvent on the kinetics of arylsulfonylation of N-alkylated anilines in a water-propan-2-ol system

The effect of the composition of a water-propan-2-ol solvent on the kinetics of arylsulfonylation of N-ethyl-, N-isopropyl-, and N-butylanilines with 3-nitrobenzenesulfonyl chloride at 298 K was studied. The reaction rate constant increases monotonically with an increase in the water fraction in the solvent from 5 to 30 wt.%. The apparent activation parameters of the reaction of N-butylaniline with 3-nitrobenzenesulfonyl chloride were calculated. No considerable changes in the activation parameters of the reaction were observed on going from pure propan-2-ol to a 10% aqueous solution, which indicates that the mechanism remains unchanged upon solvent change. Propan-2-ol with a water content of 5-30 wt.% can be used in the synthesis of arylsulfonylation products of the amines under study in 98-99% yield.

Solvent effect on the kinetics of arylsulfonation of benzhydrazide with 3-nitrobenzenesulfonyl chloride in aqueous-organic solutions

A comparative study is made of the solvent effect on the kinetics of arylsulfonation of benzhydrazide with 3-nitrobenzenesulfonyl chloride in aqueous-organic solutions (water-2-propanol, water-dioxane, water- tetrahydrofuran, and water-acetonitrile) at 298 K. The arylsulfonation product can be obtained in nearly theoretical yield at the initial reactant concentrations of 0.1 M in the water-dioxane, water-MeCN, and water-THF mixtures containing above 30 wt % water.

Reactivity of Benzamide toward Sulfonylation

Abstract: The ranges of variation of the rate constant (0.031– 0.153L·mol–1·s–1), energyof activation (21– 55 kJ/mol), and entropy of activation (88–191J·mol–1·K–1) for thereaction of benzamide with 3-nitrobenzenesulfonyl chloride in aqueous1,4-dioxane with a concentration of water of 15–40 wt % have been determined bystudying the reaction kinetics in the temperature range 298–313 K. The potentialenergy surface for the gas-phase reaction of benzamide with3-nitrobenzenesulfonyl chloride has been simulated at the DFT B3LYP/6-311G(d,p) level of theory; the results of quantum chemical simulationsuggest bimolecular nucleophilic substitution mechanism of this reaction.

Stilbene type compound as well as synthesis method and application thereof

The invention discloses a stilbene type compound as well as a synthesis method and application thereof, wherein the synthesis method comprises the steps: taking an intermediate 2 and an intermediate 4 as initiators, sequentially carrying out Wittig reaction, reduction reaction, amino protection reaction, condensation reaction, deprotection reaction and amidation reaction, and then refining to obtain the stilbene type compound. The synthesis process is high in controllability, used reagents are low in price, and the method is simple and easy to industrialize. The stilbene type compound can be used as a medicine for resisting tumors and viruses and treating fungal infection and cardiovascular and cerebrovascular diseases.

Reactivity of 2-Sulfobenzoic Acid Imide and Benzenesulfonamide in Arenesulfonylation

Experimental study of the kinetics of the reactions of 2-sulfobenzoic acid imide (saccharin) and benzenesulfonamide with 3-nitrobenzenesulfonyl chloride in a 1,4-dioxane-water mixture (80:20 by weight) in the temperature range 298–318 K has shown that both compounds are low reactive (k298 = 1.66 × 10?4 and 3.37 × 10?3 L mol?1 s?1, respectively). The activation barriers to these reactions exceed 50 kJ/mol. Aqueous dioxane can be recommended as a solvent for the preparation of N-(benzenesulfonyl)-3-nitrobenzenesulfonamide in up to 87% yield.

Sulfonation method of aromatic hydrocarbons with low electron cloud density

The invention discloses a sulfonation method of aromatic hydrocarbons with a low electron cloud density. The sulfonation method comprises following steps: (1) in a solvent, taking metal sulfate as a catalyst, mixing chlorosulfonic acid and an aromatic hydrocarbon substrate according to a mole ratio of 1.2-1.5:1, and carrying out sulfonation reactions for 1 to 5 hours, wherein the aromatic hydrocarbon substrate is aromatic hydrocarbons with a low electron cloud density and the solvent is an inert reagent; and (2) subjecting the reaction product obtained in the step (1) to reduced pressure distillation to remove the solvent, after reduced pressure distillation, pouring residues into ice water, adjusting the pH to 0.9-1.1, filtering, and drying the filter cakes to obtain a sulfonation product. The provided sulfonation method has a high yield and reduces the discharge of waste acids.

Regioselective Sulfonation of Aromatic Compounds over 1,3-Disulfonic Acid Imidazolium Chloride under Aqueous Media

1,3-Disulfonic acid imidazolium chloride ([Dsim]Cl), as a Bronsted acidic ionic liquid, is introduced for the sulfonation of aromatic compounds by in situ generation of sulfuric acid at 50 °C under mild conditions and in aqueous medium.

Nucleophilic Substitution Reactions of 2,4-Dinitrophenyl X-Substituted-Benzenesulfonates and Y-Substituted-Phenyl 4-Nitrobenzenesulfonates with Azide Ion: Regioselectivity and Reaction Mechanism

The second-order rate constants for reactions of 2,4-dinitrophenyl X-substituted-benzenesulfonates (4a-4f) and Y-substituted-phenyl-4-nitrobenzenesulfonates (5a-5f) with N3- ion have been measured spectrophotometrically. The reactions of 4a-4f proceed through S-O and C-O bond fission pathways competitively. Fraction of the S-O bond fission decreases rapidly as the substituent X in the benzenesulfonyl moiety changes from an electron-withdrawing group to an electron-donating group. The Hammett plots for reactions of 4a-4f are linear with ρX=1.87 and 0.56 for the S-O and C-O bond fission, respectively. The fact that the substituent X is further away from the reaction site of the C-O bond fission than that of the S-O bond fission is one reason for the smaller ρX value. The nature of the reaction mechanism (i.e., a stepwise mechanism in which expulsion of the leaving group occurs after the rate-determining step) is also responsible for the smaller ρX value obtained from the C-O bond fission. The Bronsted-type plot for the reactions of 5a-5f is linear with βlg=-0.63, which is typical for reactions reported previously to proceed through a concerted mechanism. Effects of substituents X and Y on regioselectivity and reaction mechanism are discussed in detail.

Clean-chemistry sulfonation of aromatics

A solution of TFAA/H2SO4 is an atom-efficient liquid-phase system for rapid sulfonation of aromatic structures; H2SO4 is consumed stoichiometrically and the spent trifluoroacetic anhydride (TFAA) is readily recovered as trifluoroacetic acid (TFA) which can be recycled to TFAA.

Kinetics of arylsulfonation of aminobenzoic acids with m-and p-nitrobenzenesulfonyl chlorides in the system water-2-propanol

The concentrations of the uncharged and anionic forms of m-and p-aminobenzoic acids participating in arylsulfonation of the acids with m-and p-nitrobenzenesulfonyl chlorides in the system water-2-propanol at 298 K at various water contents and pHs were estimated. The resulting data were used to estimate the rate constants for the reactions of the above forms with nitrobenzenesulfonyl chlorides, based on experimental kinetic data.