29418-31-3

Basic information

• Product Name: Bis(2,6-dimethylphenyl)diazene
• Synonyms: 2,2',6,6'-Tetramethylazobenzene;Bis(2,6-dimethylphenyl)diazene
• CAS NO: 29418-31-3
• Molecular Formula: C₁₆H₁₈N₂
• Molecular Weight: 0
• Mol File: 29418-31-3.mol

Chemical Properties

• Boiling Point: 386.5°C at 760 mmHg
• Flash Point: 180°C
• Appearance: /
• Density: 0.99g/cm³
• Vapor Pressure: 7.82E-06mmHg at 25°C
• Refractive Index: 1.553
• CAS DataBase Reference: Bis(2,6-dimethylphenyl)diazene(CAS DataBase Reference)
• NIST Chemistry Reference: Bis(2,6-dimethylphenyl)diazene(29418-31-3)
• EPA Substance Registry System: Bis(2,6-dimethylphenyl)diazene(29418-31-3)

Safety Data

• Hazardous Substances Data: 29418-31-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C16H18N2/c1-11-7-5-8-12(2)15(11)17-18-16-13(3)9-6-10-14(16)4/h5-10H,1-4H3/b18-17+

Upstream product

• 87-62-7 2,6-dimethylaniline 
• 3095-47-4 4-amino-3,5-dimethylbenzoic acid ethyl ester 
• 63615-06-5 2,2′,6,6′-(tetramethyldiphenyl)hydrazine 
• 2192-33-8 2,6-dimethylbenzenediazonium tetrafluoroborate 
• 81-20-9 2,6-dimethylnitrobenzene 
• 62-53-3 aniline 

Downstream Products

• 54827-17-7 3,3',5,5'-tetramethylbenzidine 

Relevant articles and documents

Versatile, concise and convenient process for the commercial scale preparation of highest pure 3,3'5,5'-Tetramethylbenzidine (TMB) and its salts, a chromogenic substrate used in staining procedures in immunohistochemistry and visualizing reagent in enzyme-linked immunosorbent assays

The present invention relates to a process for the preparation of 3,3′,5,5′-Tetramethylbenzidine represented by formula I, and processes for the preparation of intermediates used in the preparation of 3,3′,5,5′-Tetramethylbenzidine.

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.

A 3, 3 ', 5, 5' - tetramethyl benzidine and its hydrochloride synthesis method (by machine translation)

The present invention provides a synthetic 3, 3 ', 5, 5' - tetramethyl benzidine and its hydrochloride method, which belongs to the technical field of organic synthesis. In order to 2, 6 - dimethyl aniline as the raw material, first of all through the potassium permanganate oxidation of 2, 2 ', 6, 6' - tetramethyl azobenzene, then concentrated hydrochloric acid and zinc powder for the one-step method of 2, 2 ', 6, 6' - tetramethyl azobenzene reduction, rearrangement, and through processing and getting the 3, 3 ', 5, 5' - tetramethyl benzidine and its hydrochloride. In the present invention the used raw materials are cheap and easily obtained, operation process is simple and convenient, mild reaction conditions, higher yield. (by machine translation)

Aromatic amine oxidation process for preparing aromatic azobenzene method

The invention relates to a method for preparing an aromatic azo compound by utilizing aromatic amine oxidation. In the method, air or oxygen serves as an oxygen source, and under the effect of a catalyst, aromatic amine is oxidized into the aromatic azo compound. The method is high in oxidization efficiency and product yield; the air or the oxygen serves as the oxygen source, and the method is economical and environmentally friendly. The product and the catalyst can be separated easily, and the aftertreatment is simple. The catalyst is easy to reuse, and the method has very good application prospect.

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.

The palladium and copper contrast: A twist to products of different chemotypes and altered mechanistic pathways

A novel contrast in palladium and copper catalysis is revealed to form products of different chemotypes resulting in a phenazine to azoarene twist through an altered mechanistic pathway (from non-radical C-H activation mode of C-N coupling to radical N-N coupling) during the oxidative self-coupling of anilines catalysed by Pd-Ag and Cu-Ag nanoclusters.

Cathodic reduction of diazonium salts in aprotic medium

Cathodic reduction of diazonium salts in acetonitrile led to the formation of azobenzenes, in good to moderate yields, and diarylamines as minoritary products. The reactions were carried out at the second reduction potential of the diazonium salts, involving aryl anions in the formation of the products.

A simple and efficient method for the dehydrogenation of symmetric hydrazo compounds with NaNO2-Ac2O

Rapid oxidation of eighteen symmetric hydrazo compounds to corresponding azo compounds using NaNO2-acetic anhydride as a novel oxidizing agent under mild condition is reported for the first time.

A simple and efficient method for the dehydrogenation of symmetric hydrazo compounds with NaNo2/NaHSO4·H2O/SiO2

In this paper, 18 symmetric hydrazo compounds undergo rapid oxidation to corresponding azo compounds using NaNO2/NaHSO4·H2O/SiO2 as a novel oxidising agent under mild conditions for the first time.