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

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

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

Downstream Products

• 18996-77-5 N,N,N',N'-tetraethyl-1,4-benzenediamine 
• 837-64-9 N,N-diethyl-2,4-dinitroaniline 
• 2216-15-1 1-diethylamino-4-nitrobenzene 
• 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.

Gold(I)-Catalyzed Oxidative 1,4-Additions of 3-En-1-ynamide with Nitrones via Carbon- versus Nitrogen-Addition Chemoselectivity

This work reports gold-catalyzed 1,4-oxofunctionalizations of 3-en-1-ynamides with nitrones, yielding two distinct E-configured products. We obtained 1,4-oxoarylation products from 3-en-1-ynamides bearing C(4)-electron-donating substituents and 1,4-oxoamination products from those analogues bearing C(4)-aryl substituents. We propose that if vinylgold carbenes are stable, imines undergo a para-arylation on these gold carbenes. If vinylgold carbenes are highly electron-deficient, this N-attack is irreversible to enable 1,4-oxoaminations.

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.

Thermodynamic and Electrochemical oxidation of some diamine derivatives: Experimental and theoretical investigation

Electrochemical oxidation of some diamine derivatives (1H+-4H+) has been investigated both experimentally and theoretically. Experimental results were obtained using cyclic voltammetry and controlled potential coulometry and the theoretical results were calculated at DFT (B3LYP and BP86) levels of theory and 6-311+G (p,d) basis set. The calculated result indicates that oxidation potential of 1H+-4H+is directly dependent on theΔGtotand species with more positive oxidation potential (EpA1) have largerΔGtotvalues. Also in this paper electrochemical oxidations of N,N-diethyl-p-phenylenediamine (3) were studied in the absence and in the presence of some nucleophiles. Mechanistic study of the electrochemical oxidation of 3 indicates that its electrochemical oxidation proceed in the thermodynamically favored direction.

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.

STUDIES ON ORGANOPHOSPHORUS COMPOUNDS XXXII Reactions of 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide with compounds containing the N=O function

Reactions of 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide, 1, with a series of substrates having a semipolar bond have been studied.C-Nitroso compounds react to give azoxy compounds or azo compounds, whereas N,N-dimethyl-p-nitrosoaniline furnishes p-dimethylamino-N-thiosulfinyl-aniline, 6, and benzofurazan-1-oxide produces 2,1,3-benzothiadiazole.N-nitroso compounds react with 1 to give phosphorous heterocycles in which the N-nitroso function is destroyed.Elimination of HNO from certain N-nitroso compounds has also been observed.Nitrones and N-oxides react with 1 to form the corresponding deoxygenated products.In the case of quinoline-N-oxide, small amounts of quinoline-2-thione could be isolated in addition to the deoxygenated product.Mechanistic considerations are presented.