6319-23-9

Basic information

• Product Name: (E)-bis(3-methoxyphenyl)diazene
• Synonyms: 3,3'-DIMETHOXYAZOBENZENE
• CAS NO: 6319-23-9
• Molecular Formula: C₁₄H₁₄N₂O₂
• Molecular Weight: 242.2732
• Mol File: 6319-23-9.mol
• Article Data: 48

Chemical Properties

• Boiling Point: 394.3°C at 760 mmHg
• Flash Point: 155.5°C
• Density: 1.09g/cm³
• Vapor Pressure: 4.56E-06mmHg at 25°C
• Refractive Index: 1.548
• CAS DataBase Reference: (E)-bis(3-methoxyphenyl)diazene(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-bis(3-methoxyphenyl)diazene(6319-23-9)
• EPA Substance Registry System: (E)-bis(3-methoxyphenyl)diazene(6319-23-9)

Safety Data

• Hazardous Substances Data: 6319-23-9(Hazardous Substances Data)

Usage

General Description

(E)-bis(3-methoxyphenyl)diazene is a chemical compound with the formula C14H14N2O2. It is a diazene molecule with two 3-methoxyphenyl groups attached to the nitrogen atoms in a trans configuration. Diazene compounds are known for their ability to undergo dimerization, and (E)-bis(3-methoxyphenyl)diazene is no exception. It is used in organic synthesis as a precursor to various types of nitrogen-containing compounds and has potential applications in material science and pharmaceutical research. However, it is important to handle (E)-bis(3-methoxyphenyl)diazene with care as diazene compounds are known to be toxic and can undergo decomposition under certain conditions.

Upstream product

• 99-99-0 1-methyl-4-nitrobenzene 
• 536-90-3 m-Anisidine 
• 555-03-3 3-nitroanisole 
• 106-47-8 4-chloro-aniline 
• 589-16-2 4-aminoethylbenzene 
• 13556-81-5 bis-(3-methoxy-phenyl)-diazene-N-oxide 
• 5344-78-5 4-bromo-3-nitroanizole 
• 3866-16-8 3-methoxyphenyl azide 
• 1027-32-3 3,3'-bis(methoxy)diphenyl hydrazine 

Downstream Products

• 1027-32-3 3,3'-bis(methoxy)diphenyl hydrazine 
• 1581291-36-2 (E)-(4-methoxy-2-((3-methoxyphenyl)diazenyl)phenyl)(phenyl)methanone 
• 19490-87-0 7-methoxy-2-methylquinoline 

Relevant articles and documents

Photocatalytic oxidative coupling of arylamines for the synthesis of azoaromatics and the role of O2 in the mechanism

The photocatalytic oxidative coupling of aryl amines to selectively synthesize azoaromatic compounds has been realized. Multiple different photocatalysts can be used to perform the general reaction; however, Ir(dF-CF3-ppy)2(dtbpy)+, where dF-CF3-ppy is 2-(2,4-difluorophenyl)-5-(trifluoromethyl)-pyridine and dtpby is 4,4′-tert-butyl-2,2′-bipyridine, showed the greatest range of reactivity with various amine substrates. Both electron-rich and -deficient amines can be coupled with yields up to 95% under an ambient air atmosphere. Oxygen was deemed to be essential for the reaction and is utilized in the regeneration of the photocatalyst. Fluorescence quenching and radical trap experiments indicate an amine radical coupling mechanism that proceeds through a hydrazoaromatic intermediate before further oxidation occurs to form the desired azoaromatic products.

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.

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.