1947-33-7

Basic information

• Product Name: 4-nitrobenzenediazonium toluene-4-sulphonate
• Synonyms: 4-nitrobenzenediazonium toluene-4-sulphonate;Einecs 217-749-6
• CAS NO: 1947-33-7
• Molecular Formula: C₆H₄N₃O₂*C₇H₇O₃S
• Molecular Weight: 321.30854
• EINECS: 217-749-6
• Mol File: 1947-33-7.mol
• Article Data: 8

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• CAS DataBase Reference: 4-nitrobenzenediazonium toluene-4-sulphonate(CAS DataBase Reference)
• NIST Chemistry Reference: 4-nitrobenzenediazonium toluene-4-sulphonate(1947-33-7)
• EPA Substance Registry System: 4-nitrobenzenediazonium toluene-4-sulphonate(1947-33-7)

Safety Data

• Hazardous Substances Data: 1947-33-7(Hazardous Substances Data)

Usage

Uses

Used in Organic Chemistry:
4-Nitrobenzenediazonium toluene-4-sulphonate is used as a diazonium salt for the synthesis of new organic compounds. Its ability to form carbon-carbon and carbon-nitrogen bonds makes it a valuable intermediate in organic synthesis.
Used in Dye Production:
In the dye industry, 4-Nitrobenzenediazonium toluene-4-sulphonate is used as a precursor in the production of various dyes. Its reactivity allows for the creation of a wide range of colored compounds.
Used in Pharmaceutical Industry:
4-Nitrobenzenediazonium toluene-4-sulphonate is used as a chemical intermediate in the synthesis of pharmaceuticals. Its versatility in forming different types of chemical bonds contributes to the development of new drug molecules.
Used in Industrial Chemical Production:
4-Nitrobenzenediazonium toluene-4-sulphonate is also utilized in the production of other industrial chemicals, where its reactivity and ability to form new bonds are advantageous for creating a variety of chemical products.
Safety Note:
It is crucial to handle 4-Nitrobenzenediazonium toluene-4-sulphonate with care due to its high reactivity. Proper safety measures should be implemented to prevent hazardous situations during its use in various applications.

InChI:InChI=1/C7H8O3S.C6H4N3O2/c1-6-2-4-7(5-3-6)11(8,9)10;7-8-5-1-3-6(4-2-5)9(10)11/h2-5H,1H3,(H,8,9,10);1-4H/q;+1/p-1

Upstream product

• 14034-64-1 4-nitro-aniline; toluene-4-sulfonate 
• 104-15-4 toluene-4-sulfonic acid 
• 100-01-6 4-nitro-aniline 

Downstream Products

• 636-98-6 p-nitrobenzene iodide 
• 1153-45-3 4-nitrophenyl 4-methylbenzenesulfonate 
• 2765-24-4 4'-nitro-2-phenylnaphthalene 
• 92-93-3 1-phenyl-4-nitrobenzene 
• 2765-23-3 1-(4-nitrophenyl)naphthalene 
• 924868-84-8 4'-nitro-[1,10-biphenyl]-2-carbaldehyde 
• 2143-90-0 4-methoxy-4'-nitrobiphenyl 
• 637-57-0 p-nitrocinnamic acid methyl ester 
• 586-78-7 para-nitrophenyl bromide 
• 100-25-4 para-dinitrobenzene 
• 1694-20-8 trans-4-nitrostilbene 
• 52010-83-0 1-((4-nitrophenyl)diazenyl)piperidine 

Relevant articles and documents

A convenient approach to arenediazonium tosylates

Herein we present a mild, simple and environmentally friendly diazotization protocol of aromatic and heteroaromatic anilines into stable diazonium salts that surpass previously reported procedures. The reaction proceeds with tert-butyl nitrite in the presence of an equimolar amount or small excesses of p-toluenesulfonic acid in ethyl acetate, at room temperature. o-Phenylenediamines yield benzotriazolium tosylates. The resulting diazonium tosylates proved to be bench stable over a long period of time. In selected examples, diazonium salts were let to react with activated aromatic compounds including 2-naphthol and aniline derivatives into the corresponding azo dyes.

Synthesis of Symmetric Binuclear 5,6-Dihydro-1,2,4,5-tetrazinium Perchlorates

Abstract: A series of 3,3′-(1,4-phenylene)bis(1-4-R-phenyl)-5-phenyl-5,6-dihydro-1,2,4,5-tetrazinium) perchlorates (R = H, Me, Cl, OMe, CN, NO2) were obtained as a result of a three-stage synthesis from terephthalic aldehyde. The synthesis of tetrazinium salts was carried out by reaction of the corresponding formazans with formalin in the presence of perchloric acid in dioxane. Formazans and tetrazinium perchlorates were isolated in individual state and characterized by elemental analysis, IR, UV, 1H, and 13C NMR spectroscopy data. The process of electrochemical reduction of tetrazinium perchlorates was studied using the method of cyclic voltammetry (CV). It has been shown that these compounds are perspective precursors of symmetric biradical systems based on verdazyl radicals.

[3+2]-Cycloaddition of α-Diazocarbonyl Compounds with Arenediazonium Salts Catalyzed by Silver Nitrate Delivers 2,5-Disubstituted Tetrazoles

[3+2]-Cycloaddition of arenediazonium salts with diazo compounds (earlier exemplified only for trimethylsilyldiazomethane and 2,2,2-trifluorodiazoethane) has been developed to include a wide range of readily available α-diazocarbonyl compounds. The resulting 2-aryl-5-acyl-2 H -tetrazoles are of high value in medicinal chemistry.

Flexible Entry into 3-Arylpent-2-enedioic Acids via Heck-Matsuda Arylation of Dimethyl Glutaconate with Arenediazonium Tosylates

For the preparation of compound libraries of Michael acceptors with tunable reactivity toward nuclophilic selenocysteine residue of thioredoxin reductase, a range of 3-arylglutaconic acids were required. The existing methods at the time had limited scope or involved several steps. A hitherto undescribed protocol for direct palladium(II) acetate-catalyzed arylation of glutaconic acid dimethyl ester at position 3 has been developed with a diverse set of arenediazonium tosylates followed by hydrolysis. This generally good-yielding two-step sequence displayed a propensity to deliver E -configured coupling products while compounds mostly featured in the literature were predominantly Z -configured. The possibility for preparing a library of 4-arylpyridine-2,6(1 H,3 H)-diones has been exemplified.

Changes in major charge transport by molecular spatial orientation in graphene channel field effect transistors

Changes in major charge transport of graphene channel transistors in terms of the spatial orientation of adsorbed functional molecules were demonstrated. In contrast to the horizontally (physically) bound molecules, the vertically (chemically) bound molecules did not change major charge carriers of graphene channels, revealing the molecular orientation-dependent doping effects.

Rhodium(I)-catalyzed synthesis of aryltriethoxysilanes from arenediazonium tosylate salts with triethoxysilane

An efficient method for the preparation of aryltriethoxy-silanes from arenediazonium tosylate salts has been developed, which expands the substrates of rhodium-catalyzed silylation from iodides, bromides, and triflates to diazonium salts. A new method for hydrodediazoniation has also been explored.

Unusually stable, versatile, and pure arenediazonium tosylates: Their preparation, structures, and synthetic applicability

(Graph Presented) A new, simple, and effective method for the diazotization of a wide range of arylamines has been developed by using a polymer-supported diazotization agent in the presence of p-toluenesulfonic acid. Various pure arenediazonium tosylates with unusual stabilities can be easily prepared by this method. As a result, these salts are useful and versatile substrates for subsequent transformations, such as halogenation and Heck-type reactions. The unusual stabilities of arenediazonium tosylates are also preliminarily discussed with their X-ray structures.

Iodination of aryl amines in a water-paste form via stable aryl diazonium tosylates

The diazotization of aryl amines at room temperature in paste form with NaNO2, p-TsOH and a small amount of water, followed by treatment with KI provides a new, simple, and effective route for the preparation of various aryl iodides. The water-paste and strong acid-free reaction conditions are environmentally friendly and compatible with acid-sensitive functional groups.