123155-78-2

Upstream product

• 104-94-9 4-methoxy-aniline 
• 104-15-4 toluene-4-sulfonic acid 
• 14034-69-6 Toluene-4-sulfonic acid; compound with 4-methoxy-phenylamine 

Downstream Products

• 696-62-8 para-iodoanisole 
• 21130-91-6 triethoxy(4-methoxyphenyl)silane 
• 1234713-32-6 [2-(4-methoxyphenyl)-1H-indol-3-yl]acetic acid methyl ester 
• 106833-44-7 (E)-3-(4-methoxyphenyl)pent-2-enedioic acid 
• 3901-07-3 3-(4-methoxy-phenyl)acrylic acid methyl ester 
• 13411-91-1 1-(4-methoxyphenylazo)naphthalen-2-ol 

Relevant academic research and scientific papers

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.

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.

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.