29418-36-8

Upstream product

• 95-64-7 4-amino-o-xylene 
• 67666-03-9 1,2-bis(3,4-dimethylphenyl)hydrazine 
• 99-51-4 4-nitro-o-xylene 
• 104-94-9 4-methoxy-aniline 
• 67666-02-8 (Z)-1,2-bis(3,4-dimethylphenyl)diazene 1-oxide 

Downstream Products

• 67666-03-9 1,2-bis(3,4-dimethylphenyl)hydrazine 
• 1584667-93-5 (E)-N-(2-((3,4-dimethylphenyl)diazenyl)-4,5-dimethylphenyl)-4-methylbenzenesulfonamide 
• 3171-45-7 4,5-dimethyl-1,2-phenylenediamine 

Relevant academic research and scientific papers

Catalytic Polymerization of Aniline and Its Derivatives by Using Copper(II) Salts and Oxygen. New Type of Polyaniline with Branched Structure

The catalytic polymerization of aniline and its derivatives was performed by stirring the solution of the corresponding monomer and copper(II) salts (50/5, mmol/mmol) in acetonitrile and water (1/1, v/v) under oxygen at room temperature for 24 h.Among copper salts, CuBr2 and CuCl2 are more active than the others.In each case the copper salts do not work as a stoichiometrical oxidant but work as a catalyst, which can be proved on the basis of turn-over-frequency.The polymers isolated were characteristic of polyaniline with an Emeraldine structure, although a small amount of branched structures were by-produced by an addition reaction at ortho-position.Thus, heat treatment of the polymer at 284 deg C results in partial decomposition to produce the stable polymer and aniline.Although the resulting polymer had an Emeraldine type structure, a strong doping effect on its electroconductivity was not observed, probably because of the amorphous morphology.The UV-vis spectra of the reaction solution have suggested that the catalytic polymerization of aniline proceeds through the formation of the copper(II) complex of aniline.

Synthesis of novel 1,2-diarylpyrazolidin-3-one–based compounds and their evaluation as broad spectrum antibacterial agents

There is a continuous need to develop new antibacterial agents with non-traditional mechanisms to combat the nonstop emerging resistance to most of the antibiotics used in clinical settings. We identified novel pyrazolidinone derivatives as antibacterial hits in an in-house library screening and synthesized several derivatives in order to improve the potency and increase the polarity of the discovered hit compounds. The oxime derivative 24 exhibited promising antibacterial activity against E. coli TolC, B. subtilis and S. aureus with MIC values of 4, 10 and 20 μg/mL, respectively. The new lead compound 24 was found to exhibit a weak dual inhibitory activity against both the E. coli MurA and MurB enzymes with IC50 values of 88.1 and 79.5 μM, respectively, which could partially explain its antibacterial effect. A comparison with the previously reported, structurally related pyrazolidinediones suggested that the oxime functionality at position 4 enhanced the activity against MurA and recovered the activity against the MurB enzyme. Compound 24 can serve as a lead for further development of novel and safe antibiotics with potential broad spectrum activity.

Synthesis of 2 - fluoro aniline compounds of the method

The invention discloses a method for synthesizing 2 - fluoro aniline compounds of the method, the method is: shown in formula Ia aniline compound of formula Ib α and β shown aniline compound as raw materials, through coupling reaction shown [...] azobenzene compound II, then the type II shown azobenzene compound with a palladium catalyst, fluorination reagent, additive, organic solvent, in the 30 - 150 °C temperature closed agitating the fluorination reaction, [...] compound of formula III, type III compounds are shown in the reaction under the action of a reducing [...] shown IV 2 - fluoro aniline compounds; this invention synthetic 2 - fluoro aniline compounds substrate wide adaptability, mild reaction conditions, the operation is simple, fluorinated and good selectivity, [...] aniline compounds is prepared by many drug molecule is an important intermediate and starting material, wide application prospects.

Transition Metal-Free Oxidative Coupling of Primary Amines in Polyethylene Glycol at Room Temperature: Synthesis of Imines, Azobenzenes, Benzothiazoles, and Disulfides

A transition metal-free protocol has been developed for the oxidative coupling of primary amines to imines and azobenzenes, thiols to disulfides, and 2-aminothiophenols to benzothiazoles, offering excellent yields. The advantageous features of the present environmentally benign methodology include the usage of biocompatible and green reaction conditions such as, solvent, room temperature reactions and transition metal-free approach. Moreover, it offers a broader substrate scope.

Conversion of anilines into azobenzenes in acetic acid with perborate and Mo(VI): correlation of reactivities

Azobenzenes are extensively used to dye textiles and leather and by tuning the substituent in the ring, vivid colours are obtained. Here, we report preparation of a large number of azobenzenes in good yield from commercially available anilines using sodium perborate (SPB) and catalytic amount of Na2MoO4 under mild conditions. Glacial acetic acid is the solvent of choice and the aniline to azobenzene conversion is zero, first and first orders with respect to SPB, Na2MoO4 and aniline, respectively. Based on the kinetic orders, UV–visible spectra and cyclic voltammograms, the conversion mechanism has been suggested. The reaction rates of about 50 anilines at 20–50?°C and their energy and entropy of activation conform to the isokinetic or Exner relationship and compensation effect, respectively. However, the reaction rates, deduced by the so far adopted method, fail to comply with the Hammett correlation. The specific reaction rates of molecular anilines, obtained through a modified calculation, conform to the Hammett relationship. Thus, this work presents a convenient inexpensive non-hazardous method of preparation of a larger number of azobenzenes, and shows the requirement of modification in obtaining the true reaction rates of anilines in acetic acid and the validity of Hammett relationship in the conversion process, indicating operation of a common mechanism.

Efficient Solar-Driven Hydrogen Transfer by Bismuth-Based Photocatalyst with Engineered Basic Sites

Photocatalytic organic conversions involving a hydrogen transfer (HT) step have attracted much attention, but the efficiency and selectivity under visible light irradiation still needs to be significantly enhanced. Here we have developed a noble metal-free, basic-site engineered bismuth oxybromide [Bi24O31Br10(OH)] that can accelerate the photocatalytic HT step in both reduction and oxidation reactions, i.e., nitrobenzene to azo/azoxybenzene, quinones to quinols, thiones to thiols, and alcohols to ketones under visible light irradiation and ambient conditions. Remarkably, quantum efficiencies of 42% and 32% for the nitrobenzene reduction can be reached under 410 and 450 nm irradiation, respectively. The Bi24O31Br10(OH) photocatalyst also exhibits excellent performance in up-scaling and stability under visible light and even solar irradiation, revealing economic potential for industrial applications.

Palladium-catalyzed cyclizative carbonylation of azobenzenes toward 3H-Indazol-3-ones using formic acid as CO source

A palladium-catalyzed cyclizative carbonylation of azobenzenes has been developed to access 1-acyl 2-aryl 3H-indazol-3-ones in moderate to good yields with good functional compatibility. This procedure proceeded with the sequential ortho-C–H carbonylation and cyclization, where formic acid served as the CO source. The practicability of this transformation was further increased by the employment of facilely available azobenzenes derivatives as one-handled starting materials.

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.

Convenient Electrocatalytic Synthesis of Azobenzenes from Nitroaromatic Derivatives Using SmI2

The synthesis of azobenzenes has been a long-standing challenge. Their current preparation at a preparative or industrial scale requires stoichiometric amounts of environmentally unfriendly reactants. Herein, we demonstrate that the catalytic use of electrogenerated samarium diiodide (SmI2) could promote, in one-step synthesis, the reduction of nitrobenzenes into azobenzenes in high yields under mild reaction conditions. This catalytic procedure contains many elements satisfying a sustainable chemical process for the preparation of one of the most widely wanted family of chemical compounds. The easy synthetic procedure, and the absence of precious metals, bases, and nonhazardous substances, already makes our catalytic procedure a serious alternative to currently available methods. This is a promising method for the efficient synthesis of both symmetrical and asymmetrical azo compounds with a high functional group tolerance.

First use of p-tert-butylcalix[4]arene-tetra-O-acetate as a nanoreactor having tunable selectivity towards cross azo-compounds by trapping silver ions

p-tert-Butylcalix[4]arene-tetra-O-acetate was established for the first time as a member of the nanoreactor series, even without having any -OH group. The nano range distribution of this nanoreactor was ascertained by DLS, SEM and TEM studies. The capability of this cavitand towards hosting amines in a competitive manner generates a new green pathway for cross coupling of aromatic amines to give the corresponding azo-compounds. In this context, using p-tert-butylcalix[4]arene-tetra-O-acetate as a nanoreactor and silver nitrate as a catalyst, we got the cross azo-compound in good to excellent yields in the eco-friendly solvent water. This green methodology is also applicable for the synthesis of respective homo-compounds.