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Upstream product

• 121-69-7 N,N-dimethyl-aniline 
• 99-98-9 4-amino-N,N-dimethylaniline 
• 18523-44-9 p-(dimethylamino)phenyl azide 
• 100-23-2 N,N-Dimethyl-4-nitroaniline 
• 24564-52-1 4-(dimethylamino)benzenediazonium tetrafluoroborate 

Relevant academic research and scientific papers

1,2-Didehydroazepines from the Photolysis of Substituted Aryl Azides: Analysis of Their Chemical and Physical Properties by Time-Resolved Spectroscopic Methods

A series of substituted 1,2-didehydroazepines was prepared by photolysis of their precursor aryl azides.The chemical and physical properties of the didehydroazepines were probed by means of conventional chemical trapping experiments and by time-resolved spectroscopy with IR and UV detection.The didehydroazepines are formed from the azides with efficiencies that depend systematically on the nature of the substituent.In some cases, didehydroazepines are not formed at all.The didehydroazepines react relatively rapidly with starting aryl azide and with added amines.The rate of their reaction is largely controlled by the electronic properties of the substituent on the didehydroazepine.These results permit prediction of the reactivity of didehydroazepines from their structure.

Tuneable Copper Catalysed Transfer Hydrogenation of Nitrobenzenes to Aniline or Azo Derivatives

A highly versatile and flexible copper nanoparticle (Cu(0) NPs) catalytic system has been developed for the controlled and selective transfer hydrogenation of nitroarene. Interestingly, the final catalytic product is strongly dependent on the nature of the hydrogen donor source. The yield of nitrobenzene reduction to aniline increased from 20% to an almost quantitative yield over a range of alcohols, diols and aminoalcohols. In glycerol at 130 °C aniline was isolated in 93% yield. In ethanolamine, the reaction was conveniently performed at a lower temperature (55 °C) and gave selectively substituted azobenzene (92% yield). Experimental studies provide support for a reaction pathway in which the Cu(0) NPs catalysed transfer hydrogenation of nitrobenzene to aniline proceeds via the condensation route. The high chemoselectivity of both protocols has been proved in experiments on a panel of variously substituted nitroarenes. Enabling technologies, microwaves and ultrasound, used both separately and in combination, have successfully increased the reaction rate and reaction yield. (Figure presented.).

Method for highly stereoselective preparation of trans-aromatic tertiary amine azo compound

The invention provides a method for efficient and highly stereoselective preparation of an azo compound through para C-H bond selective activity of an organic aromatic tertiary amine. According to themethod, a Bronsted acid is adopted as a catalyst, an aromatic diazonium tetrafluoroboric acid compound and an organic aromatic tertiary amine compound are adopted as reaction substrates, and an organic solvent is put into a reaction system. The method has the advantages that the catalyst is cheap and easy to obtain, high in substrate applicability, gentle in reaction condition and safe and reliable; the selectivity of a target product is approximate to 100%, the E/Z selectivity of the target product is greater than 99:1, and relatively high yield is achieved; and by adopting the method, the defects that a conventional method for synthesizing different aromatic functional groups to replace organic aromatic tertiary amine azo compounds is harsh in reaction condition, poor in reaction selectivity, tedious in experiment step, low in yield, harmful to the environment since reagents harmful to the environment are used, and the like, can be overcome, and good industrial application prospectscan be achieved. The invention further provides an organic aromatic tertiary amine azo compound with different aryl substituted functional groups.

Continuous-flow oxidative homocouplings without auxiliary substances: Exploiting a solid base catalyst

The catalytic oxidative dimerization of aromatic amines and acetylenes is of outstanding synthetic importance among homocoupling reactions. Both transformations necessitate the use of extraneous bases and ligands, which contains significant disadvantages as concerns environmental impacts and process costs. We exploited the inherent basic character of a copper-containing layered double hydroxide to facilitate the catalytic homocouplings of alkynes and aniline derivatives without the need for any auxiliary substances. The reactions were studied in a continuous-flow system to achieve extended parameter spaces for chemical intensification, and also to avoid undesired reaction pathways by means of strategic control over the residence time. Valuable 1,4-disubstituted 1,3-diynes and diversely substituted aromatic azo compounds were achieved chemoselectively in excellent yields and in short process times even on preparative scales.

Oxidative dimerization of (hetero)aromatic amines utilizing t-BuOI leading to (hetero)aromatic azo compounds: Scope and mechanistic studies

A straightforward synthetic method of both symmetric and unsymmetric aromatic azo compounds through an efficient and cross-selective oxidative dimerization of aromatic amines using tert-butyl hypoiodite (t-BuOI) under metal-free and mild conditions has been developed. This method was also found applicable to the synthesis of heteroaromatic azo compounds. The spectroscopic study indicates the involvement of N,N-diiodoanilines in the oxidative reaction as the key intermediate.

Studies on UV/VIS Absorption Spectra of Azo Dyes. XV. An Analysis of the Absorption Spectra of 4,4'-Diaminoazobenzenes

In the visible absorption spectrum 4,4'-bis-diethylaminoazobenzene shows two absorption maxima (λmax = 426 nm and λmax = 477 nm) with high intensity.Quantum chemical calculations and examinations by peak separation of six 4-substituted azobenzenes and six 4'-substituted 4-diethylaminoazobenzenes (1a-k) indicate that the longest wavelenght band is due to a n-?* transition and the other band is due to a ?-?*-transition.This is verified using an inrement system for ?-?* absorption maxima.A linear relation is found between intensity ratios of the two bands and the HAMMETT-?-constants of the substituents.With increasing electron releasing tendency of the substituents the absorption intensity of the n-?*-band increases.