613-43-4

Basic information

• Product Name: 2,2'-Diethoxyazobenzene
• Synonyms: 2,2'-Azophenetole;2,2'-Diethoxyazobenzene
• CAS NO: 613-43-4
• Molecular Formula: C₁₆H₁₈N₂O₂
• Molecular Weight: 270.32632
• Mol File: 613-43-4.mol
• Article Data: 5

Chemical Properties

• Melting Point: 131°C
• Boiling Point: 413.44°C (rough estimate)
• Appearance: /
• Density: 1.0807 (rough estimate)
• Refractive Index: 1.6240 (estimate)
• CAS DataBase Reference: 2,2'-Diethoxyazobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-Diethoxyazobenzene(613-43-4)
• EPA Substance Registry System: 2,2'-Diethoxyazobenzene(613-43-4)

Safety Data

• Hazardous Substances Data: 613-43-4(Hazardous Substances Data)

Upstream product

• 610-67-3 1-ethoxy-2-nitrobenzene 
• 88-73-3 2-Chloronitrobenzene 
• 1033-71-2 2,2'-diethoxyhydrazobenzene 
• 94-70-2 ortho-phenitidine 

Downstream Products

• 6264-77-3 4,4'-diamino-3,3'-diethoxybiphenyl 
• 136-79-8 2-Amino-4-nitroethoxybenzen 
• 1033-71-2 2,2'-diethoxyhydrazobenzene 

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.

Facile synthesis of azo compounds from aromatic nitro compounds using magnesium and triethylammonium formate

Magnesium/triethylammonium formate is a convenient reagent for the reduction of aromatic nitro compounds to corresponding symmetrically substituted azo compounds. Various azo compounds containing additional reducible substituents, including halogen, nitrile, acid, phenol, ester, and methoxy functions, have been synthesized in a single step by the use of this reagent. The conversion is reasonably fast, clean, high yielding, and occurs at room temperature in methanol.

Lack of linear free energy relationship: Tungsten(VI) catalyzed perborate oxidation of anilines

Operation of linear free energy relationships in tungsten(VI) catalyzed perborate oxidation was studied with 29 para-, meta- and ortho-substituted anilines. The activation parameters were calculated from k*( = rate/[substrate]2) at 35, 40, 45, 50 and 55 °C using the Erying relationship by the method of least squares. The oxidation is not isoentropic; in an isoentropic series only enthalpy of activation determines the reactivity and the isokinetic temperature is at infinity. At the isokinetic temperature all the compounds of the reaction series react at equal rate, the variation of substituent at this temperature has no influence on the free energy of activation.