584-90-7

Basic information

• Product Name: 2,2'-azotoluene
• Synonyms: 2,2'-azotoluene;1,2-Bis(2-methylphenyl)diazene;Bis(2-methylphenyl)diazene
• CAS NO: 584-90-7
• Molecular Formula: C₁₄H₁₄N₂
• Molecular Weight: 0
• Mol File: 584-90-7.mol
• Article Data: 127

Chemical Properties

• Melting Point: 55.5°C
• Boiling Point: 339.81°C (rough estimate)
• Flash Point: 155.9°C
• Appearance: /
• Density: 1.0215
• Vapor Pressure: 0.000111mmHg at 25°C
• Refractive Index: 1.6180 (estimate)
• CAS DataBase Reference: 2,2'-azotoluene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-azotoluene(584-90-7)
• EPA Substance Registry System: 2,2'-azotoluene(584-90-7)

Safety Data

• Hazardous Substances Data: 584-90-7(Hazardous Substances Data)

Usage

General Description

2,2'-Azotoluene, also known as 4-methyl-4'-nitrodiphenylamine, is an organic compound with the chemical formula C15H14N2O2. It is a yellow crystalline solid that is commonly used as a precursor in the production of dyes and pigments. 2,2'-Azotoluene is classified as a hazardous substance and can cause irritation to the skin, eyes, and respiratory system upon contact or inhalation. It is also considered to be potentially carcinogenic and mutagenic. Due to its toxicity, proper safety precautions and handling procedures must be followed when working with this compound.

InChI:InChI=1/C14H14N2/c1-11-7-3-5-9-13(11)15-16-14-10-6-4-8-12(14)2/h3-10H,1-2H3/b16-15+

Upstream product

• 917-64-6 methyl magnesium iodide 
• 60-29-7 diethyl ether 
• 88-72-2 1-methyl-2-nitrobenzene 
• 17333-74-3 2-methylbenzene diazonium 
• 925-90-6 ethylmagnesium bromide 
• 67-66-3 chloroform 
• 112160-74-4 acetic acid-(2,4,N-trichloro-anilide) 
• 95-53-4 o-toluidine 
• 64-17-5 ethanol 
• 617-22-1 2,2'-dimethylhydrazobenzene 
• 956-31-0 N,N'-Di-o-tolyl-diazene N-oxide 
• 15182-74-8 2-Methylsulfinylanilin 
• 611-22-3 N-(o-tolyl)hydroxylamine 
• 623-11-0 1-methyl-4-nitrosobenzene 

Downstream Products

• 617-22-1 2,2'-dimethylhydrazobenzene 
• 956-31-0 N,N'-Di-o-tolyl-diazene N-oxide 
• 14983-92-7 methyl N-(2-methylphenyl)carbamate 
• 614-68-6 2-tolyl isocyanate 
• 119-93-7 o-tolidin 
• 95-53-4 o-toluidine 
• 1440356-48-8 C₂₄H₃₂N₂ 
• 107922-57-6 4-methyl-2-(o-tolyl)-2H-benzo[d][1,2,3]triazole 
• 611-32-5 8-methylquinoline 
• 584-70-3 N-benzoyl-2-methylaniline 

Relevant articles and documents

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.

Electrosynthesis of Azobenzenes Directly from Nitrobenzenes

The electrochemical reduction strategy of nitrobenzenes is developed. The chemistry occurs under ambient conditions. The protocol uses inert electrodes and the solvent, DMSO, plays a dual role as a reducing agent. Its synthetic value has been demonstrated by the highly efficient synthesis of symmetric, unsymmetric and cyclic azo compounds.

Chemoselective electrochemical reduction of nitroarenes with gaseous ammonia

Valuable aromatic nitrogen compounds can be synthesized by reduction of nitroarenes. Herein, we report electrochemical reduction of nitroarenes by a protocol that uses inert graphite felt as electrodes and ammonia as a reductant. Depending on the cell voltage and the solvent, the protocol can be used to obtain aromatic azoxy, azo, and hydrazo compounds, as well as aniline derivatives with high chemoselectivities. The protocol can be readily scaled up to >10 g with no decrease in yield, demonstrating its potential synthetic utility. A stepwise cathodic reduction pathway was proposed to account for the generations of products in turn.