18265-00-4

Usage

Uses

Used in Research and Laboratory Applications:
(E)-1-(3-chlorophenyl)-2-phenyldiazene is used as a reagent for organic synthesis, facilitating the creation of various organic compounds in research and laboratory settings. Its unique chemical structure allows for specific reactions and transformations that are valuable in the development of new chemical entities.
Used in Precursor Synthesis:
In the field of organic chemistry, (E)-1-(3-chlorophenyl)-2-phenyldiazene is used as a precursor for the preparation of other organic compounds. Its role as a starting material is crucial in the synthesis of complex molecules and contributes to the advancement of chemical research.
Used in Chemical Industry:
(E)-1-(3-chlorophenyl)-2-phenyldiazene may also find applications in the chemical industry, where it could be employed in the production of dyes, pharmaceuticals, or other specialty chemicals. Its bright yellow color and solubility properties make it a candidate for use in specific industrial processes.

Upstream product

• 121-73-3 3-Nitrochlorobenzene 
• 103-84-4 Acetanilid 
• 98-95-3 nitrobenzene 
• 62-53-3 aniline 
• 1227476-15-4 Azobenzene 
• 586-96-9 Nitrosobenzene 
• 108-42-9 3-chloro-aniline 

Downstream Products

• 62858-14-4 (3-chloro-phenyl)-(4-nitro-phenyl)-diazene 
• 37790-14-0 (E)-1-(3-chlorophenyl)-2-phenyldiazene 
• 949-73-5 1-(3-chlorophenyl)-2-phenylhydrazine 

Relevant academic research and scientific papers

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.

Deoxygenative coupling of nitroarenes for the synthesis of aromatic azo compounds with CO using supported gold catalysts

A facile and efficient catalytic system based on a mesostructured ceria-supported gold (Au/meso-CeO2) catalyst was developed for the synthesis of various aromatic azo compounds by the reductive coupling of the corresponding nitroaromatics, using CO as the sole deoxygenative reagent, under additive-free and mild reaction conditions.

Gold-catalyzed direct hydrogenative coupling of nitroarenes to synthesize aromatic azo compounds

The azo linkage is a prominent chemical motif which has found numerous applications in materials science, pharmaceuticals, and agrochemicals. Described herein is a sustainable heterogeneous-gold-catalyzed synthesis of azo arenes. Available nitroarenes are deoxygenated and linked selectively by the formation of N-N bonds using molecular H2 without any external additives. As a result of a unique and remarkable synergy between the metal and support, a facile surface-mediated condensation of nitroso and hydroxylamine intermediates is enabled, and the desired transformation proceeds in a highly selective manner under mild reaction conditions. The protocol tolerates a large variety of functional groups and offers a general and versatile method for the environmentally friendly synthesis of symmetric or asymmetric aromatic azo compounds.

Indirect Electrochemical Reduction of Some Peroxide Derivatives

Indirect reduction of derivatives of tert-butyl hydroperoxide by means of aromatic radical anions in DMF results in the formation of tert-butoxy radicals, which abstract a hydrogen atom from DMF.The N,N-dimethylaminocarbonyl radical may couple with the radical anion or be reduced by it; from this competition the reduction potential of the N,N-dimethylaminocarbonyl radical is estimated to be -1.62 V (SCE).

A novel synthesis of unsymmetrical azo aromatics inaccessible by diazo-coupling reaction

A novel synthesis of unsymmetrical azo aromatics inaccessible by diazo-coupling reaction is reported. The synthesis involved the reaction of acetanilides with nitroarenes under moderate reaction conditions. A reaction pathway via a nitrosoarene intermediate involving elimination of the elements of the acetate anion, is proposed.

Kinetics of the Chlorination of Azobenzene and Comparison with Azoxybenzene

The activating effect of the phenylazo substituent in electrophilic substitution has been examined.The rates and partial rate factors for chlorination of azobenzene with molecular chlorine and protonated chlorine acetate have been determined relative to benzene.Whereas the chlorine acetate reaction proceeds readily (relative rate 4900) there is virtually no activation to chlorination by molecular chlorine.Complexes between azobenzene and bromine were, however, isolated and characterized.Their formation implies that during molecular halogenation reactions the electrop hile is essentially unavailable.The relative chlorination rates for azobenzene and azoxybenzene have also been established: the phenylazo group is more activating towards protonated chlorine acetate whereas azoxybenzene (which does not complex with halogens) is the more reactive with molecular chlorine.The chlorination results confirm the versatility of the phenylazo group which is the first substituent for which kinetic data have been obtained quantifying activation of aromatic electrophilic, radical and nucleophilic substitution.

Aryliminodimagnesium Reagents. IV. The Independent Preparation of Unsymmetrically Substituted Azoxyarene Isomers and Their Deoxygenation

By use of the condensation reaction of aryliminodimagnesium reagents (ArN(MgBr)2) with nitroarenes, six symmetrical and eight unsymmetrical azoxyarenes including four pairs of isomers were prepared in 40-80percent yields.The deoxygenation reaction of the azoxyarenes by treating with five molar equivalents of p-MeOC6H4N(MgBr)2 at 55 deg C in tetrahydrofuran was also studied, and the reactivity of deoxygenation was correlated to the shift of the electronic absorption maximum of azoxyarene.