6141-95-3

Usage

InChI:InChI=1/C12H9ClN2/c13-10-6-8-12(9-7-10)15-14-11-4-2-1-3-5-11/h1-9H

Upstream product

• 60-09-3 4-Aminoazobenzene 
• 64-17-5 ethanol 
• 6530-97-8 cis-(4-chloro-phenyl)-phenyl-diazene 
• 873-77-8 (4-chlorphenyl)magnesium bromide 
• 106-47-8 4-chloro-aniline 
• 62-53-3 aniline 
• 98-95-3 nitrobenzene 
• 932-98-9 1-chloro-4-nitroso-benzene 
• 586-96-9 Nitrosobenzene 
• 100-00-5 4-chlorobenzonitrile 
• 4340-77-6 4-chloroazobenzene 
• 949-88-2 1-(4-chlorophenyl)-2-phenylhydrazine 
• 100-58-3 phenylmagnesium bromide 
• 861367-73-9 1,4-diacetyl-1,2,3,4-tetraphenyl-tetrazane 

Downstream Products

• 6530-97-8 cis-(4-chloro-phenyl)-phenyl-diazene 
• 949-88-2 1-(4-chlorophenyl)-2-phenylhydrazine 
• 97870-46-7 1-(4-chlorophenyl)-2-propylbenzimidazole 
• 1602-00-2 bis-(4-chloro-phenyl)-diazene 
• 1447966-68-8 (E)-1-(2-bromophenyl)-2-(4-chlorophenyl)diazene 
• 1374253-89-0 (E)-1-(4-chlorophenyl)-2-(2-iodophenyl)diazene 
• 3933-77-5 2-(4-chlorophenyl)-2H-benzo[d][1,2,3]triazole 
• 118416-54-9 5-chloro-2-phenyl-2H-benzo[d][1,2,3]triazole 

Relevant academic research and scientific papers

Zr(OH)4-Catalyzed Controllable Selective Oxidation of Anilines to Azoxybenzenes, Azobenzenes and Nitrosobenzenes

The selective oxidation of aniline to metastable and valuable azoxybenzene, azobenzene or nitrosobenzene has important practical significance in organic synthesis. However, uncontrollable selectivity and laborious synthesis of the expensive required catalysts severely hinders the uptake of these reactions in industrial settings. Herein, we have pioneered the discovery of Zr(OH)4 as an efficient heterogeneous catalyst capable of the selective oxidation of aniline, using either peroxide or O2 as oxidant, to selectively obtain various azoxybenzenes, symmetric/unsymmetric azobenzenes, as well as nitrosobenzenes, by simply regulating the reaction solvent, without the need for additives. Mechanistic experiments and DFT calculations demonstrate that the activation of H2O2 and O2 is primarily achieved by the bridging hydroxyl and terminal hydroxyl groups of Zr(OH)4, respectively. The present work provides an economical and environmentally friendly strategy for the selective oxidation of aniline in industrial applications.

Design of phase-transition molecular solar thermal energy storage compounds: compact molecules with high energy densities

A series of compact azobenzene derivatives were investigated as phase-transition molecular solar thermal energy storage compounds that exhibit maximum energy storage densities around 300 J g?1. The relative size and polarity of the functional g

Chemoselective Hydrogenation of Nitroarenes Using an Air-Stable Base-Metal Catalyst

The reduction of nitroarenes to anilines as well as azobenzenes to hydrazobenzenes using a single base-metal catalyst is reported. The hydrogenation reactions are performed with an air-and moisture-stable manganese catalyst and proceed under relatively mild reaction conditions. The transformation tolerates a broad range of functional groups, affording aniline derivatives and hydrazobenzenes in high yields. Mechanistic studies suggest that the reaction proceeds via a bifunctional activation involving metal-ligand cooperative catalysis.

Oxidative dehydrogenation of hydrazines and diarylamines using a polyoxomolybdate-based iron catalyst

We report an efficient method for the oxidative dehydrogenation of hydrazines and diarylamines in aqueous ethanol using Anderson-type polyoxomolybdate-based iron(iii) as a catalyst and hydrogen peroxide as an oxidant. A series of azo compounds and tetraarylhydrazines were obtained in moderate to excellent yields. The reaction conditions and substrate scopes are complementary or superior to those of more established protocols. In addition, the catalyst shows good stability and reusability in water. The preliminary mechanistic studies suggest that a radical process is involved in the reaction.

Selective Oxidation of Anilines to Azobenzenes and Azoxybenzenes by a Molecular Mo Oxide Catalyst

Aromatic azo compounds, which play an important role in pharmaceutical and industrial applications, still face great challenges in synthesis. Herein, we report a molybdenum oxide compound, [N(C4H9)4]2[Mo6O19] (1), catalyzed selective oxidation of anilines with hydrogen peroxide as green oxidant. The oxidation of anilines can be realized in a fully selectively fashion to afford various symmetric/asymmetric azobenzene and azoxybenzene compounds, respectively, by changing additive and solvent, avoiding the use of stoichiometric metal oxidants. Preliminary mechanistic investigations suggest the intermediacy of highly active reactive and elusive Mo imido complexes.

Trichloroisocyanuric Acid Mediated Oxidative Dehydrogenation of Hydrazines: A Practical Chemical Oxidation to Access Azo Compounds

A highly efficient, metal-free, chemical oxidation of hydrazines has been implemented using environmentally friendly TCCA as oxidant. This benign protocol provides straightforward access to a wide range of azo compounds in THF in excellent yield. Altogether, 35 azo compounds were obtained in this way and scale-up preparations were performed. Additionally, a plausible mechanism was also proposed. Step-economical process, mild reaction conditions, operational simplicity, high reaction efficiency, and easy scale-up highlight the practicality of this methodology.

Electrochemical dehydrogenation of hydrazines to azo compounds

A strategy for the electrochemical dehydrogenation of hydrazine compounds is disclosed under ambient conditions. This protocol proceeded smoothly in ethanol by employing electrons as clean oxidants. Its synthetic value is well demonstrated by the highly efficient synthesis of symmetric and unsymmetric azo compounds. It is an environmentally friendly transformation and the present protocol was effective on a large scale.

Easily Accessible, Highly Potent, Photocontrolled Modulators of Bacterial Communication

External control of bacterial communication—quorum sensing—allows for the regulation of a multitude of biological processes. Herein, we describe the development of a new synthetic methodology, as well as the characterization, photoisomerization, and biological evaluation of a privileged series of novel photoswitchable quorum-sensing agonists and antagonists. The presented method allows for the rapid and convenient synthesis of previously unknown photoswitchable agonists with up to 70% quorum-sensing induction and inhibitors reaching up to 40% inhibition, which significantly extends the level of photocontrol over bacterial communication achieved before. Remarkably, for the lead photoswitchable agonist, a >700-fold difference in activity was observed between the irradiated and non-irradiated forms, which allows for antagonism-to-agonism switching upon exposure to light, showing levels of control unprecedented in photopharmacology. Finally, utilizing this system, we were able to regulate toxin production in Pseudomonas aeruginosa with light. Photopharmacology is an emerging approach aimed at the regulation of biological function with light. Herein, the application of molecular photoswitches allows for the reversible switching between two distinct structural states of bioactive compounds. Bacterial communication (quorum sensing) is an interesting target for photopharmacology, from the perspective of both clinical and basic research, because of its implications for pathogenicity of bacteria and complex biological mechanism of action. By the novel synthesis and application of photoswitchable modulators, we were able to reversibly control bacterial communication with light. Remarkably, one of our lead compounds allows the control of bacterial communication with very high selectivity, switching from a quorum-sensing inhibitor to a quorum-sensing activator upon irradiation with light, which was further exemplified by the control of quorum-sensing-regulated toxin production in Pseudomonas aeruginosa. By applying the photopharmacological approach, bacterial communication can be controlled with light through the application of photoswitchable modulators. Interestingly, one of the lead photoswitchable modulators of bacterial communication, presented herein, shows a remarkable (>700-fold) difference in activity between the non-irradiated and irradiated states. The photoresponsive quorum-sensing modulators can be used to control toxin production in Pseudomonas aeruginosa and have a promising outlook as next-generation research tools.

Dehydrogenation of the NH?NH Bond Triggered by Potassium tert-Butoxide in Liquid Ammonia

A novel strategy for the dehydrogenation of the NH?NH bond is disclosed using potassium tert-butoxide (tBuOK) in liquid ammonia (NH3) under air at room temperature. Its synthetic value is well demonstrated by the highly efficient synthesis of aromatic azo compounds (up to 100 % yield, 3 min), heterocyclic azo compounds, and dehydrazination of phenylhydrazine. The broad application of this strategy and its benefit to chemical biology is proved by a novel, convenient, one-pot synthesis of aliphatic diazirines, which are important photoreactive agents for photoaffinity labeling.

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.