3588-91-8

Basic information

• Product Name: 4,4'-Bis(diethylamino)azobenzene
• Synonyms: 4,4'-Azobis(N,N-diethylbenzenamine);4,4'-Bis(diethylamino)azobenzene
• CAS NO: 3588-91-8
• Molecular Formula: C₂₀H₂₈N₄
• Molecular Weight: 0
• Mol File: 3588-91-8.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4,4'-Bis(diethylamino)azobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-Bis(diethylamino)azobenzene(3588-91-8)
• EPA Substance Registry System: 4,4'-Bis(diethylamino)azobenzene(3588-91-8)

Safety Data

• Hazardous Substances Data: 3588-91-8(Hazardous Substances Data)

Usage

Purification Methods

Purify the azobenzene by column chromatography on alumina, elute with, and crystallise it from, toluene, [Albini et al. J Chem Soc Perkin Trans 2 1393 1982, Flamigni & Monti J Phys Chem 8 9 3702 1985]. The deoxycholate (1:4) complex has m 194-194o (from EtOH). [Beilstein 16 H 341, 16 I 311, 16 III 342, 16 IV 455.]

Upstream product

• 60-29-7 diethyl ether 
• 64-17-5 ethanol 
• 120-22-9 N,N-diethyl-4-nitrosoaniline 
• 100-63-0 phenylhydrazine 
• 29812-35-9 N,N-Diethyl-p-benzochinondiimin 
• 93-05-0 N,N-diethylaniline 
• 91-66-7 N,N-diethylaniline 
• 2198-58-5 N,N-diethyl-p-phenylenediamine hydrochloride 
• 98-95-3 nitrobenzene 

Downstream Products

• 2216-15-1 1-diethylamino-4-nitrobenzene 
• 837-64-9 N,N-diethyl-2,4-dinitroaniline 
• 18996-77-5 N,N,N',N'-tetraethyl-1,4-benzenediamine 
• 93-05-0 N,N-diethylaniline 
• 55042-35-8 N,N-diethyl-N,N',N',N'-tetramethyl-N,N'-p-phenylene-di-ammonium; iodide 

Relevant articles and documents

Unprecedented intermolecular aldol-type condensation involving CH-acid and the nitro group

The first evidence that α-acylnitrone is an intermediate in the base-promoted reaction of 4-nitro-N,N-diethylaniline with acetophenone to give an enaminoketone was obtained.

Synthesis of Azobenzene Dyes Mediated by CotA Laccase

An eco-friendly protocol for the synthesis of azobenzene dyes by oxidative coupling of primary aromatic amines is reported. As efficient biocatalytic systems, CotA laccase and CotA laccase/ABTS (2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonic acid)) enable the oxidation of various substituted anilines, in aqueous medium, ambient atmosphere and under mild reaction conditions of pH and temperature. A series of azobenzene dyes were prepared in good to excellent yields in an one-pot reaction. A mechanistic proposal for the formation of the azo derivatives is presented. Our strategy offers an alternative approach for the direct synthesis of azobenzene dyes, avoiding the harsh conditions generally required for most of the traditional synthetic methods.

Chemoselective reductive coupling of nitroarenes with magnesium in methanol via single electron transfer

A chemoselective reductive coupling of nitroarenes using magnesium in methanol has been reported at ambient temperature. While the cyano, formyl, methoxycarbonyl, methyl, methoxy, phenyl, amino, and chloro groups are unaffected, iodo and bromo groups undergo dehalogenation but in a slower reaction than the coupling of nitro group. The coupling is believed to be proceeding via SET from Mg to nitroarenes.