4340-77-6

Usage

Uses

Used in Organic Synthesis:
1-(4-Chlorophenyl)-2-phenyldiazene is utilized as a reagent in organic synthesis for the creation of a variety of chemical compounds. Its presence in reactions can facilitate the formation of desired products, making it a valuable component in the synthesis process.
Used in Chemical Reactions:
As a reagent, 1-(4-Chlorophenyl)-2-phenyldiazene is used in chemical reactions to alter the structure or properties of other compounds. Its reactivity with certain functional groups can lead to the formation of new chemical entities with specific applications.
Used in Synthesis of Azo Dyes:
1-(4-Chlorophenyl)-2-phenyldiazene is employed in the synthesis of azo dyes, which are a class of compounds known for their vibrant colors and used extensively in the dyeing and coloring of fabrics, plastics, and other materials.
Used in Pharmaceutical and Materials Science:
Due to its unique properties, 1-(4-Chlorophenyl)-2-phenyldiazene may have potential applications in the pharmaceutical industry for the development of new drugs. Additionally, its reactivity and structural characteristics could be harnessed in materials science for the creation of novel materials with specific properties.

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

• 1227476-15-4 Azobenzene 
• 7446-70-0 aluminium trichloride 
• 20972-43-4 trans-azoxybenzene 
• 36968-72-6 4-phenylazo-benzenediazonium; chloride 
• 7647-01-0 hydrogenchloride 
• 861367-73-9 1,4-diacetyl-1,2,3,4-tetraphenyl-tetrazane 
• 71-43-2 benzene 
• 106-47-8 4-chloro-aniline 
• 62-53-3 aniline 
• 586-96-9 Nitrosobenzene 
• 108-94-1 cyclohexanone 
• 1073-69-4 N-4-chlorophenylhydrazine 
• 1602-00-2 bis-(4-chloro-phenyl)-diazene 
• 932-98-9 1-chloro-4-nitroso-benzene 

Downstream Products

• 13065-93-5 4-amino-4'-chlorodiphenylamine 
• 68406-47-3 4-chloro-N₂-phenylbenzene-1,2-diamine 
• 860766-43-4 2,3,5-trichloro-N¹-(4-chloro-phenyl)-p-phenylenediamine 
• 7466-26-4 (4-bromo-phenyl)-(4-chloro-phenyl)-diazene 
• 106-47-8 4-chloro-aniline 
• 29808-86-4 (4-chloro-phenyl)-(4-nitro-phenyl)-diazene 
• 2491-66-9 4-(4-chloro-phenylazo)-benzenesulfonic acid 
• 1602-00-2 bis-(4-chloro-phenyl)-diazene 
• 949-88-2 1-(4-chlorophenyl)-2-phenylhydrazine 
• 85046-92-0 N,N'-Dibenzyl-N'-(4-chloro-phenyl)-N-phenyl-hydrazine 
• 21737-17-7 2-(4-chloro-phenylazo)-phenol 
• 2703-27-7 4-chloro-4'-hydroxyazobenzene 
• 144499-67-2 4-chloro-2'-heptafluoropropylazobenzene 
• 144499-66-1 4-chloro-4'-heptafluoropropylazobenzene 

Relevant academic research and scientific papers

Bifunctional Cs?Au/Co3O4 (Basic and Redox)-Catalyzed Oxidative Synthesis of Aromatic Azo Compounds from Anilines

An eco-friendly alkali-promoted (Cs?Au/Co3O4) catalyst, with redox and basic properties for the oxidative dehydrogenative coupling of anilines to symmetrical and unsymmetrical aromatic azo compounds, was developed. We realized a base additive- and molecular O2 oxidant-free process (using air), with reasonable reusability of the catalyst achieved under milder reaction conditions. Notably, the enhanced catalytic activity was also linked to the increased basic site concentration, low reduction temperatures, and the effect of lattice oxygen on the nanomaterials. The increased basic strength of the cation-promoted catalyst improved the electron density of the active Au species, resulting in higher yields of the desired aromatic azo compounds.

Manganese Catalyzed Hydrogenation of Azo (N=N) Bonds to Amines

We report the first example of homogeneously catalyzed hydrogenation of the N=N bond of azo compounds using a complex of an earth-abundant-metal. The hydrogenation reaction is catalyzed by a manganese pincer complex, proceeds under mild conditions, and yields amines, which makes this methodology a sustainable alternative route for the conversion of azo compounds. A plausible mechanism involving metal-ligand cooperation and hydrazine intermediacy is proposed based on mechanistic studies. (Figure presented.).

Photosensitive and Photoswitchable TRPA1 Agonists Optically Control Pain through Channel Desensitization

Transient receptor potential ankyrin 1 (TRPA1) channel, as a nonselective ligand-gated cation channel robustly in dorsal root ganglion sensory neurons, is implicated in sensing noxious stimuli and nociceptive signaling. However, small-molecule tools targeting TRPA1 lack temporal and spatial resolution, limiting their use for validation of TRPA1 as a therapeutic target for pain. In our previous work, we found that 4,4′-(diazene-1,2-diyl)dianiline (AB1) is a photoswitchable TRPA1 agonist, but the poor water solubility and activity hinder its further development. Here, we report a series of specific and potent azobenzene-derived photoswitchable TRPA1 agonists (series 1 and 2) that enable optical control of the TRPA1 channel. Two representative compounds 1g and 2c can alleviate capsaicin-induced pain in the cheek model of mice through channel desensitization but not in TRPA1 knockout mice. Taken together, our findings demonstrate that photoswitchable TRPA1 agonists can be used as pharmacological tools for study of pain signaling.

Hydrogen peroxide based oxidation of hydrazines using HBr catalyst

Azo compounds (RN = NR′) are an important class of organic molecules that find wide application in organic synthesis. Herein, we report an efficient, practical and metal-free oxidation of hydrazines (RNH-NHR’) to azo compounds using 5 mol% HBr and hydrogen peroxide as terminal oxidant. This new method has been demonstrated by 40 examples with excellent yields. In addition, we showcased two examples of the one-pot sequential reactions involving our hydrazine oxidation/hydrolysis/Heck reaction or Cu-catalyzed N-arylation with aryl boronic acid. The distinct advantages of this protocol include metal-free catalysis, waste prevention, and easy operation.

Synthesis of Unsymmetrical Azoxyarenes via Copper-Catalyzed Aerobic Oxidative Dehydrogenative Coupling of Anilines with Nitrosoarenes

A copper-catalyzed oxidative dehydrogenative coupling of nitrosobenzenes with anilines for the synthesis of unsymmetrical azoxybenzenes was developed. This approach uses O2 as the oxidant. The reaction products are diverse unsymmetrical azoxybe

Method for preparing asymmetric azobenzene and azobenzene oxide compounds through photocatalysis

The invention relates to a method for preparing asymmetric azobenzene and azobenzene oxide compounds through photocatalysis. Through a photocatalyst, an aromatic nitro compound reacts with an aromaticamino compound under the conditions of illumination and inert gas to obtain an asymmetric azobenzene compound represented by a formula I and an asymmetric azoxybenzene compound represented by a formula II; the method can be used for replacing a conventional mature organic synthesis process, has the advantages of mild conditions, high selectivity and universality, and is suitable for industrial production.

Nitrate promoted mild and versatile Pd-catalysed C(sp2)-H oxidation with carboxylic acids

A nitrate-promoted Pd-catalysed mild cross-dehydrogenative C(sp2)-H bond oxidation of oximes or azobenzenes with diverse carboxylic acids has been developed. In contrast to the previous catalytic systems, this protocol features mild conditions (close to room temperature for most cases) and a broad substrate scope (up to 64 examples), thus constituting a versatile method to directly prepare diverse O-aryl esters. Moreover, the superiority of the nitrate additive in this mild transformation was further determined by experimental and computational evidence.

TEMPO catalyzed oxidative dehydrogenation of hydrazobenzenes to azobenzenes

A metal-free direct oxidative dehydrogenation approach for the synthesis of azobenzenes from hydrazobenzenes has been developed by using TEMPO as an organocatalyst for the first time. The reaction proceeded in open air under mild reaction conditions. A wide range of hydrazobenzenes readily undergo dehydrogenation to give the corresponding azobenzenes in excellent yields.

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.

Synthesis of Unsymmetrical Aromatic Azoxy Compounds by Silver-Mediated Oxidative Coupling of Aromatic Amines with Nitrosoarenes

A silver(I) oxide-mediated synthesis of unsymmetrical aromatic azoxy compounds has been successfully achieved, wherein oxidative coupling reactions between aromatic amines and nitrosoarenes take place in ethanol under air. This reaction has very high economic value because silver(I) oxide is the only oxidant required and no other additive is needed. The resulted silver particles can be easily recovered, while the only other byproduct is water. This new procedure is compatible with various functional groups and proceeds under mild reaction conditions.