588-52-3

Basic information

• Product Name: 4,4'-DIETHOXYAZOBENZENE
• Synonyms: 4,4’-azodi-phenetol;4,4’-azophenetole;4,4’-diethoxy-azobenzen;bis(4-ethoxyphenyl)-diazen;bis(4-ethoxyphenyl)diazene;bis-p-ethoxyazobenzene;Diazene, bis(4-ethoxyphenyl)-;4,4'-DIETHOXYAZOBENZENE
• CAS NO: 588-52-3
• Molecular Formula: C₁₆H₁₈N₂O₂
• Molecular Weight: 270.33
• Product Categories: Aromatic Hydrocarbons (substituted) & Derivatives
• Mol File: 588-52-3.mol
• Article Data: 30

Chemical Properties

• Melting Point: 162°C
• Boiling Point: 413.44°C (rough estimate)
• Flash Point: 162.5°C
• Appearance: /
• Density: 1.0807 (rough estimate)
• Refractive Index: 1.6240 (estimate)
• CAS DataBase Reference: 4,4'-DIETHOXYAZOBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-DIETHOXYAZOBENZENE(588-52-3)
• EPA Substance Registry System: 4,4'-DIETHOXYAZOBENZENE(588-52-3)

Safety Data

• Statements: 20/21/22
• Safety Statements: 26-36/37/39
• RTECS: HM2966300
• TSCA: Yes
• Hazardous Substances Data: 588-52-3(Hazardous Substances Data)

Usage

General Description

4,4'-diethoxyazobenzene is an organic compound belonging to the azobenzene family, and it is commonly used as a dye intermediate. It is a red powder with a molecular formula of C14H16N2O2 and a molecular weight of 244.29 g/mol. It is insoluble in water but soluble in organic solvents such as ethanol and acetone. 4,4'-diethoxyazobenzene is known for its use in the synthesis of azo dyes and pigments, as well as in the production of pharmaceuticals, agricultural chemicals, and photographic materials. It has also been studied for its potential applications in organic electronics and materials science. However, it is important to handle this chemical with care, as it may be harmful if ingested, inhaled, or in contact with the skin.

Upstream product

• 74-96-4 ethyl bromide 
• 2496-26-6 4-ethoxy-4'-hydroxyazobenzene 
• 19262-82-9 4-ethoxybenzenediazonium 
• 4792-83-0 4,4'-diethoxyazoxybenzene 
• 38793-99-6 4-ethoxy-benzenediazonium; chloride 
• 58285-73-7 4-[(4-ethoxy-phenylimino)-methyl]-2-methoxy-phenol 
• 15484-91-0 N-benzylidene-4-ethoxyaniline 
• 22988-79-0 N-(4-ethoxy-benzylidene)-p-phenetidine 
• 156-43-4 4-Ethoxyaniline 
• 75-03-6 ethyl iodide 
• 350-46-9 4-Fluoronitrobenzene 
• 108-95-2 phenol 
• 1034-25-9 4,4'-diethoxyhydrazobenzene 
• 100-29-8 1-ethoxy-4-nitrobenzene 

Downstream Products

• 1034-25-9 4,4'-diethoxyhydrazobenzene 
• 156-43-4 4-Ethoxyaniline 
• 2050-16-0 4,4'-dihydroxyazobenzene 
• 75-00-3 chloroethane 
• 610-54-8 2,4-dinitro-1-ethoxybenzene 
• 59255-66-2 N-(tert-butoxycarbonyl)-4-ethoxyaniline 

Relevant articles and documents

Correlation studies in the oxidation of Vanillin Schiff bases by acid bromate - A kinetic and semi-empirical approach

Kinetics and mechanistic aspects of oxidation of Vanillin Schiff bases (obtained from Vanillin and p-substituted anilines) by bromate in acid medium has been studied at 313 ?K. The reaction exhibited first order in [bromate] and less than unity order each in [Vanillin Schiff base] and [acid]. The increase in the rate of reaction with decrease in dielectric constant of the medium is observed with all the studied substrates. The reaction failed to induce the polymerization of acrylonitrile. Electron withdrawing substituents in the aniline ring moiety of Vanillin Schiff base accelerate the rate of oxidation to a large extent and electron releasing substituents retard the rate. The order of reactivity is found to be p-nitro ?> ?p-bromo ?> ?p-chloro ?> ?–H ?> ?p-fluoro ?> ?p-methyl ?> ?p-methoxy ?> ?p-ethoxy and the sensitivity of the substrates towards the reaction rate is further supported by the semi-empirical calculation of electronic properties and global descriptors of the substrates (Vanillin Schiff bases) with different substituents in the aniline ring moiety. The observed trend in the reactivity of the substrates was correlated with the calculated descriptors like electronegativity, chemical potential, electrophilicity index, chemical hardness and frontier molecular orbitals. The linear free-energy relationship is characterized by a straight line in the Hammett's plot of log k versus σ. The ρ values are positive and increase with increase in temperature. From the Exner and Arrhenius plots, the isokinetic relationship is discussed. Oxidation products identified are p-substituted azobenzene and vanillic acid. Based on the experimental observations, a plausible mechanism is proposed and rate law is derived.

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.

Application of Silicon-Initiated Water Splitting for the Reduction of Organic Substrates

The use of water as a donor for hydrogen suitable for the reduction of several important classes of organic compounds is described. It is found that the reductive water splitting can be promoted by several metalloids among which silicon shows the best efficiency. The developed methodologies were applied for the reduction of nitro compounds, N-oxides, sulfoxides, alkenes, alkynes, hydrodehalogenation as well as for the gram-scale synthesis of several substrates of industrial importance.