2396-60-3

Basic information

• Product Name: 4-METHOXYAZOBENZENE
• Synonyms: (4-methoxyphenyl)-phenyl-diazene;4-Methoxyazobenzene,97%;PARA-METHOXYAZOBENZENE;METHOXYAZOBENZENE;4-METHOXYAZOBENZENE 97%;p-METHOXYAZOBENZENE extrapure AR;1-(4-Methoxyphenyl)-2-phenyldiazene;4-(Benzeneazo)anisole
• CAS NO: 2396-60-3
• Molecular Formula: C₁₃H₁₂N₂O
• Molecular Weight: 212.25
• EINECS: 219-250-9
• Mol File: 2396-60-3.mol

Chemical Properties

• Melting Point: 54-56 °C
• Boiling Point: 340 °C
• Flash Point: 150.8°C
• Appearance: /
• Density: 1.1200
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.6920 (estimate)
• BRN: 958054
• CAS DataBase Reference: 4-METHOXYAZOBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-METHOXYAZOBENZENE(2396-60-3)
• EPA Substance Registry System: 4-METHOXYAZOBENZENE(2396-60-3)

Safety Data

• Statements: 36/37/38
• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 2396-60-3(Hazardous Substances Data)

Usage

Purification Methods

Crystallise 4-methoxyazobenzene from EtOH. [Beilstein 16 IV 162.]

InChI:InChI=1/C13H12N2O/c1-16-13-9-7-12(8-10-13)15-14-11-5-3-2-4-6-11/h2-10H,1H3

Upstream product

• 104-94-9 4-methoxy-aniline 
• 586-96-9 Nitrosobenzene 
• 100-66-3 methoxybenzene 
• 62-53-3 aniline 
• 77-78-1 dimethyl sulfate 
• 1689-82-3 4-hydroxyazobenzene 
• 501-58-6 bis(4-methoxyphenyl)diazene 
• 108-94-1 cyclohexanone 
• 3471-32-7 4-Methoxyphenylhydrazine 
• 100-17-4 para-methoxynitrobenzene 
• 98-95-3 nitrobenzene 
• 953-12-8 1-(4-methoxyphenyl)-2-phenylhydrazine 
• 865-33-8 potassium methanolate 
• 60-11-7 methyl yellow 

Downstream Products

• 85545-85-3 3-acetoxy-4-methoxyazobenzene 
• 17478-75-0 N'-(4-methoxy-phenyl)-N-phenyl-diazene-N-oxide 
• 104-94-9 4-methoxy-aniline 
• 62-53-3 aniline 
• 501-58-6 bis(4-methoxyphenyl)diazene 
• 85046-90-8 N,N'-Dibenzyl-N'-(4-methoxy-phenyl)-N-phenyl-hydrazine 
• 942-01-8 1,2,3,4-tetrahydrocarbazole 
• 13070-45-6 6-Methoxy-1,2,3,4-tetrahydrocarbazole 
• 74152-89-9 2-(4-methoxyphenyl)-1,2-dihydro-3H-indazol-3-one 
• 21650-49-7 (E)-1-(4-methoxyphenyl)-2-phenyldiazene 

Relevant articles and documents

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.).

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.

Substitution of a nitro group by diazonium salts in σH-Adducts of carbanions to mono-nitrobenzenes. Formation of substituted azobenzenes and indazoles

σH-Adducts formed at low temperature from nitrobenzene derivatives and carbanions stabilized by cyano, alkoxycarbonyl or sulfonyl groups react with benzenediazonium salts as nucleophiles, forming a new C–N bond preferentially at carbon atom bearing the nitro group. The so-formed intermediates eliminate HNO2 molecule under action of base, yielding substituted azobenzenes. Adducts of secondary carbanions, stabilized by cyano or sulfonyl groups to the ortho positions of nitrobenzenes, cyclize in situ to substituted indazoles. Some ortho σH-adducts of 1-chloroethyl phenyl sulfone carbanion add diazonium cations at meta position to the nitro group. In this case, the subsequent elimination of HCl leads to azo compounds retaining the nitro group in its original position.

Method for preparing azobenzene and azobenzene compound by electro-catalysis

The invention relates to a method for preparing azobenzene and azoxybenzene compounds through electrocatalysis. Under the conditions of room temperature and inert gas, an aromatic nitro compound is reduced and coupled with an aromatic amino compound to be oxidized through electro-catalysis, and an azoxybenzene compound is obtained. The method has the advantages of mild conditions, high efficiencyand selectivity, and high universality, and can realize the synthesis of asymmetric azobenzene and azoxybenzene compounds.

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.

Visible-light-promoted oxidative dehydrogenation of hydrazobenzenes and transfer hydrogenation of azobenzenes

Azo compounds are widely used in the pharmaceutical and chemical industries. Here, we report the use of a non-metal photo-redox catalyst, Eosin Y, to synthesize azo compounds from hydrazine derivatives. The use of visible-light with air as the oxidant makes this process sustainable and practical. Moreover, the visible-light-driven, photo-redox-catalyzed transfer hydrogenation of azobenzenes is compatible with a series of hydrogen donors such as phenyl hydrazine and cyclic amines. Compared with traditional (thermal/transition-metal) methods, our process avoids the issue of over-reduction to aniline, which extends the applicability of photo-redox catalysis and confirms it as a useful tool for synthetic organic chemistry.

Synthetic method for aromatic azo compound based on cyclohexanone aromatization

The invention provides a synthetic method for an aromatic azo compound based on cyclohexanone aromatization, and belongs to the technical field of organic chemistry. The method provided by the invention comprises the step of using iodine and DMSO to promote a cyclohexanone compound and arylhydrazine to condensation and dehydrogenation aromatization, and generating the aromatic azo compound. The synthetic method provided by the invention is capable of conveniently synthesizing the asymmetrical aromatic azo compound, and moderate in condition, wide in substrate applicability, simple and convenient in operation, lower in cost, high in product purity, convenient for separation and purification, and is suitable for large-scale preparation without using acid and transition metal.

Photocatalyzed oxidative dehydrogenation of hydrazobenzenes to azobenzenes

Visible light mediated oxidative dehydrogenation of hydrazobenzenes under an ambient atmosphere using an organic dye as a photocatalyst was reported for the first time. The reaction provides an environmentally benign method for the preparation of azobenzenes in excellent yields with good functional group tolerance.

T BuOK-triggered bond formation reactions

Recently, inexpensive and readily available tBuOK has seen widespread use in transition-metal-free reactions. Herein, we report the use of tBuOK for S-S, S-Se, NN and CN bond formations, which significantly extends the scope of tBuOK in chemical synthesis. Compared with traditional methods, we have realized mild and general methods for disulfide, azobenzenes imine etc. synthesis.

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.