1562-94-3

Basic information

• Product Name: 4,4'-AZOXYANISOLE
• Synonyms: 1,2-Bis(4-methoxyphenyl)diazene 1-oxide;4,4’-dimethoxy-azoxybenzen;4-azoxyanisole;azoxyanisole;Azoxybenzene, 4,4'-dimethoxy-;Azoxy-bis(4-methoxybenzene);benzene,4,4’-dimethoxyazoxy-;bis(4-methoxyphenyl)-diazen1-oxide
• CAS NO: 1562-94-3
• Molecular Formula: C₁₄H₁₄N₂O₃
• Molecular Weight: 258.27
• EINECS: 216-348-3
• Product Categories: Aromatic Ethers;Azoxybenzenes (Liquid Crystals);Liquid Crystals & Related Compounds;Functional Materials
• Mol File: 1562-94-3.mol
• Article Data: 77

Chemical Properties

• Melting Point: 132 °C
• Boiling Point: 401.53°C (rough estimate)
• Flash Point: 206.6°C
• Appearance: /
• Density: 1.14
• Refractive Index: 1.6419 (estimate)
• Storage Temp.: -20°C
• BRN: 752723
• CAS DataBase Reference: 4,4'-AZOXYANISOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-AZOXYANISOLE(1562-94-3)
• EPA Substance Registry System: 4,4'-AZOXYANISOLE(1562-94-3)

Safety Data

• Hazard Codes: Xn-F
• Statements: 20/21/22-11
• Safety Statements: 36/37/39-26-22-16-24/25
• WGK Germany: 3
• RTECS: HM2966500
• Hazardous Substances Data: 1562-94-3(Hazardous Substances Data)

Usage

Chemical Properties

bright yellow crystalline powder

General Description

Yellow monoclinic needles (in alcohol) or bright yellow crystals.

Air & Water Reactions

Dust may form an explosive mixture in air. Insoluble in water.

Reactivity Profile

4,4'-AZOXYANISOLE is incompatible with strong oxidizing agents and strong reducing agents.

Fire Hazard

Flash point data for 4,4'-AZOXYANISOLE are not available; however, 4,4'-AZOXYANISOLE is probably combustible.

Upstream product

• 100-17-4 para-methoxynitrobenzene 
• 302-01-2 hydrazine 
• 67-56-1 methanol 
• 100-00-5 4-chlorobenzonitrile 
• 104-94-9 4-methoxy-aniline 
• 1516-21-8 4-methoxynitrosobenzene 
• 14548-16-4 Dimethyl-(1-phenyl-vinyl)-amine 
• 80466-34-8 2,4-hexadienal 
• 201230-82-2 carbon monoxide 
• 124-41-4 sodium methylate 
• 100-29-8 1-ethoxy-4-nitrobenzene 
• 4546-20-7 p-methoxyphenylhydroxylamine 
• 542-11-0 aniline hydrobromide 
• 100-25-4 para-dinitrobenzene 

Downstream Products

• 7647-01-0 hydrogenchloride 
• 75-60-5 Dimethylarsinic acid 
• 104-94-9 4-methoxy-aniline 
• 501-58-6 bis(4-methoxyphenyl)diazene 
• 1078-28-0 6-methoxyquinaldine 
• 120455-06-3 5-methoxy-2-(4-methoxyphenyl)-2H-indazole 
• 1456728-84-9 2-(2-benzoyl-4-methoxyphenyl)-1-(4-methoxyphenyl)-2-oxohydrazin-2-ium-1-ide 
• 501-58-6 (E)-1,2-bis(4-methoxyphenyl)diazene 
• 1586777-38-9 C₁₉H₂₀N₂O₅ 
• 1586777-32-3 C₁₇H₁₄F₂N₂O₃ 

Relevant articles and documents

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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.

Light-Promoted C–N Coupling of Aryl Halides with Nitroarenes

A photochemical C–N coupling of aryl halides with nitroarenes is demonstrated for the first time. Catalyzed by a NiII complex in the absence of any external photosensitizer, readily available nitroarenes undergo coupling with a variety of aryl halides, providing a step-economic extension to the widely used Buchwald–Hartwig C–N coupling reaction. The method tolerates coupling partners with steric-congestion and functional groups sensitive to bases and nucleophiles. Mechanistic studies suggest that the reaction proceeds via the addition of an aryl radical, generated from a NiI/NiIII cycle, to a nitrosoarene intermediate.