621-90-9

Usage

Uses

Used in Textile Industry:
4-(METHYLAMINO)AZOBENZENE is used as a dye for textiles, providing vibrant yellow hues to fabrics. Its colorfastness and stability make it a popular choice in this application.
Used in Plastics and Rubber Industry:
In the plastics and rubber industry, 4-(METHYLAMINO)AZOBENZENE is used as a colorant to impart yellow shades to these materials, enhancing their visual appeal and appearance.
Used in Organic Synthesis:
4-(METHYLAMINO)AZOBENZENE is utilized as a reagent in organic synthesis, contributing to the creation of various chemical compounds and products. Its unique structure allows it to participate in a range of chemical reactions, making it valuable in the synthesis of other dyes and organic compounds.

InChI:InChI=1/C13H13N3/c1-14-11-7-9-13(10-8-11)16-15-12-5-3-2-4-6-12/h2-10,14H,1H3/b16-15+

Upstream product

• 74-83-9 methyl bromide 
• 60-09-3 aniline yellow 
• 74-88-4 methyl iodide 
• 100-34-5 benzene diazonium chloride 
• 100-61-8 N-methylaniline 
• 2747-31-1 4-(phenylazo)-N,N-dimethylaniline amino oxide 
• 297766-64-4 1,3-Diphenyltriazen 
• 2684-02-8 benzenediazonium 
• 7722-84-1 dihydrogen peroxide 
• 60-11-7 methyl yellow 
• 75-65-0 tert-butyl alcohol 
• 13921-67-0 4-(phenyl-ONN-azoxy)-N,N-dimethylaniline amino oxide 

Downstream Products

• 4845-14-1 formic acid-(N-methyl-4-phenylazo-anilide) 
• 103276-87-5 4-[4-(4,4'-bis-dimethylamino-benzhydryl)-phenylazo]-N-methyl-aniline 
• 60-11-7 methyl yellow 
• 122119-23-7 tri-O-acetyl-1-(N-methyl-4-phenylazo-anilino)-1-deoxy-β-D-glucopyranuronic acid methyl ester 
• 2350-78-9 trans-N,N,N-trimethyl-4-(phenylazo)benzenammonium iodide 

Relevant academic research and scientific papers

Clay catalysed facile rearrangement of diazoaminobenzene to p-aminoazobenzene

Rearrangement of diazoaminobenzene in the presence of acidic cation-exchanged K10-montmorillonite gives exclusively p-aminoazobenzene at room temperature within three hours.

ELECTROCHEMICAL AND CHEMICAL OXIDATION OF SOME AZO DYES

The oxidation potential of representative azo dyes, viz. a series of N,N-dialkylaminoazo dyes 1 and of tautomeric azonaphthols (2 and 5) has been determined.Anodic oxidation and chemical oxidation have been carried out for some of the dyes.The results are rationalized as involving a single intermediate, the radical cation of the dyes, and its evolution along two main pathways, viz. a) deprotonation whenever possible (from the α position of the N-alkyl group in aminoazo dyes, leading ultimately to N-dealkylation; fromthe naphthols to eventually yield a C-C-coupled dimer) and b) heterolytic cleavage to an aryl radical and a diazonium cation, the latter trapped under favourable conditions to yield a bisazodye.

Photochemical Decomposition of 4-Arylazo- and 4-Arylazoxy-N,N-dialkylaniline N-Oxides

The 4-aryl-N,N-dialkylaniline N-oxides (1a-c) decompose on u.v. irradiation in aprotic solvents, undergoing deoxygenation as well as intramolecular hydrogen abstraction, to give amides and dealkylated products.The latter process is more important for the diethyl derivative (1b) (photoCope elimination).Visible irradiation is ineffective.The 4-arylazoxy-N,N-dialkylaniline N-oxides (2a-d) undergo photochemical deoxygenation from the amino group (major process) as well as from the azo group.The mechanism of these photoprocesses is discussed in general and in relation to the possible involvement of these N-oxide derivatives in photofading of the related azo dyes.