13665-50-4

Basic information

• Product Name: Diazene, bis(2,4-dichlorophenyl)-
• CAS NO: 13665-50-4
• Molecular Formula: C12H6Cl4N2
• Molecular Weight: 320.005
• Mol File: 13665-50-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Diazene, bis(2,4-dichlorophenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Diazene, bis(2,4-dichlorophenyl)-(13665-50-4)
• EPA Substance Registry System: Diazene, bis(2,4-dichlorophenyl)-(13665-50-4)

Safety Data

• Hazardous Substances Data: 13665-50-4(Hazardous Substances Data)

Upstream product

• 554-00-7 2,4-Dichloroaniline 
• 7647-01-0 hydrogenchloride 
• 1025698-05-8 2,2'-dinitro-azobenzene-4,4'-disulfonic acid 

Downstream Products

• 73626-13-8 2,2',4,4'-tetrachloroazoxybenzene 
• 554-00-7 2,4-Dichloroaniline 

Relevant articles and documents

Conversion of anilines into azobenzenes in acetic acid with perborate and Mo(VI): correlation of reactivities

Azobenzenes are extensively used to dye textiles and leather and by tuning the substituent in the ring, vivid colours are obtained. Here, we report preparation of a large number of azobenzenes in good yield from commercially available anilines using sodium perborate (SPB) and catalytic amount of Na2MoO4 under mild conditions. Glacial acetic acid is the solvent of choice and the aniline to azobenzene conversion is zero, first and first orders with respect to SPB, Na2MoO4 and aniline, respectively. Based on the kinetic orders, UV–visible spectra and cyclic voltammograms, the conversion mechanism has been suggested. The reaction rates of about 50 anilines at 20–50?°C and their energy and entropy of activation conform to the isokinetic or Exner relationship and compensation effect, respectively. However, the reaction rates, deduced by the so far adopted method, fail to comply with the Hammett correlation. The specific reaction rates of molecular anilines, obtained through a modified calculation, conform to the Hammett relationship. Thus, this work presents a convenient inexpensive non-hazardous method of preparation of a larger number of azobenzenes, and shows the requirement of modification in obtaining the true reaction rates of anilines in acetic acid and the validity of Hammett relationship in the conversion process, indicating operation of a common mechanism.

OXIDATION OF AROMATIC AMINES WITH CHROMYL CHLORIDE - I OXYDATION OF AROMATIC PRIMARY AMINES

The oxidation of aromatic primary amines with chromyl chloride in carbon tetrachloride or chloroform, results in the formation of intermediate solid adducts (Etard adducts) which, on hydrolysis, give azobenzenes(1), 1,4-benzoquinones(2), anilino-1,4-benzoquinones(3), 1,4-benzoquinone anils(4) and anilino-1,4-benzoquinone anils(5) in yields which depend on the position, nature and degree of substitution of the ring.