106273-53-4

Upstream product

• 14034-57-2 anilinium p-tolylsulfonate 
• 104-15-4 toluene-4-sulfonic acid 
• 62-53-3 aniline 

Downstream Products

• 780-69-8 triethoxyphenylsilane 
• 103-26-4 Methyl cinnamate 
• 92-52-4 biphenyl 
• 88990-48-1 3-(4-iodophenyl)-1,5-diphenylformazan 
• 4567-05-9 (2-phenyl-1H-indol-3-yl)acetic acid methyl ester 
• 1350637-99-8 methyl 2-(2-phenyl-1-methyl-1H-indol-3-yl)acetate 
• 451-40-1 phenyl benzyl ketone 
• 7265-22-7 1,5,1',5'-tetraphenyl-3,3'-p-phenylene-di-formazan 
• 1610724-59-8 (E)-3-phenylpent-2-enedioic acid 

Relevant academic research and scientific papers

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.

Hypervalent Iodine(III)-Catalyzed Balz–Schiemann Fluorination under Mild Conditions

An unprecedented hypervalent iodine(III) catalyzed Balz–Schiemann reaction is described. In the presence of a hypervalent iodine compound, the fluorination reaction proceeds under mild conditions (25–60 °C), and features a wide substrate scope and good functional-group compatibility.

2,5-Disubstituted Pyrazolo[4,3-c]cinnolin-3-ones

Complementary strategies to 2,5-disubstituted pyrazolo[4,3-c]cinnolin-3-ones are reported herein, providing late stage substituent introduction at either the 2- or the 5-position. Treating a readily prepared 4-thiocinnoline ester with substituted hydrazines afforded late stage access to the 2-position, while late stage substituent introduction at the 5-position was achieved via two different strategies: alkylation of 4-hydrazonopyrazol-3-ones, followed by a ring-closing intramolecular SNAr tactic and direct reaction of 5-(2-fluorophenyl)-2,4-dihydro-3H-pyrazol-3-ones with aryl diazonium salts, followed by cyclization. The strategies described herein provide practical and general methods to prepare 2,5-disubstituted pyrazolo[4,3-c]cinnolin-3-ones.

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.

No carrier-added nucleophilic aromatic radiofluorination using solid phase supported arenediazonium sulfonates and 1-(aryldiazenyl)piperazines

This Letter concerns the investigation of a solid phase based method for no carrier-added nucleophilic [18F]fluorination of aromatic compounds via de-diazofluorination. Initial screening of reaction conditions was conducted using soluble analog

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.