15446-39-6

Usage

Uses

Used in Polymer Industry:
N,N'-(azodi-4,1-phenylene)bisacetamide is used as a cross-linking agent for epoxy resins. Its application is crucial for enhancing the mechanical properties, thermal stability, and chemical resistance of the final polymer product. The cross-linking process improves the overall performance and durability of epoxy resins in various applications, such as adhesives, coatings, and composite materials.
Used in Optics and Photonics Industry:
In the field of optics and photonics, N,N'-(azodi-4,1-phenylene)bisacetamide is used as a key component in the synthesis of surface relief holographic materials. These materials have significant applications in the development of holographic data storage devices, optical sensors, and secure identification markers. The compound's role in creating surface relief holograms is essential for achieving the desired optical properties and performance of these advanced materials.

Upstream product

• 108-24-7 acetic anhydride 
• 538-41-0 4,4'-Diaminoazobenzene 
• 122-80-5 N-acetyl-p-phenylenediamine 
• 52578-66-2 p-(acetylamino)phenyl azide 
• 104-04-1 N-(4-Nitrophenyl)acetamide 
• 100-01-6 4-nitro-aniline 

Downstream Products

• 538-41-0 4,4'-Diaminoazobenzene 
• 106-50-3 1,4-phenylenediamine 
• 122-80-5 N-acetyl-p-phenylenediamine 
• 1373771-74-4 C₄₃H₆₉N₉O₁₁Si 
• 1373771-75-5 C₃₆H₅₆N₆O₉Si 
• 1373771-84-6 C₂₉H₄₃N₅O₇Si 
• 1373771-71-1 C₃₃H₄₈N₈O₇ 
• 1373771-72-2 C₂₆H₃₅N₅O₅ 

Relevant academic research and scientific papers

Time-resolved resonance raman and computational investigation of the influence of 4-acetamido and 4-N-methylacetamido substituents on the chemistry of phenylnitrene

A time-resolved resonance Raman (TR3) and computational investigation of the photochemistry of 4-acetamidophenyl azide and 4-N-methylacetamidophenyl azide in acetonitrile is presented. Photolysis of 4-acetamidophenyl azide appears to initially produce singlet 4-acetamidophenylnitrene which undergoes fast intersystem crossing (ISC) to form triplet 4-acetamidophenylnitrene. The latter species formally produces 4,4′-bisacetamidoazobenzene. RI-CC2/TZVP and TD-B3LYP/TZVP calculations predict the formation of the singlet nitrene from the photogenerated S 1 surface of the azide excited state. The triplet 4-acetamidophenylnitrene and 4,4′-bisacetamidoazobenzene species are both clearly observed on the nanosecond to microsecond time-scale in TR3 experiments. In contrast, only one species can be observed in analogous TR 3 experiments after photolysis of 4-N-methylacetamidophenyl azide in acetonitrile, and this species is tentatively assigned to the compound resulting from dimerization of a 1,2-didehydroazepine. The different photochemical reaction outcomes for the photolysis of 4-acetamidophenyl azide and 4-N-methylacetamidophenyl azide molecules indicate that the 4-acetamido group has a substantial influence on the ISC rate of the corresponding substituted singlet phenylnitrene, but the 4-N-methylacetamido group does not. CASSCF analyses predict that both singlet nitrenes have open-shell electronic configurations and concluded that the dissimilarity in the photochemistry is probably due to differential geometrical distortions between the states. We briefly discuss the probable implications of this intriguing substitution effect on the photochemistry of phenyl azides and the chemistry of the related nitrenes.

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.

The azo compound

A process for producing an azo compound (D) comprising a step of reacting more than one amino compound (A) represented by a formula (1) with an oxygen compound (B) in the presence of a metal component (C), wherein the oxygen compound (B) is at least one selected from a group consisting of hydrogen peroxide, an alkali metal salt of hydrogen peroxide, an alkaline earth metal salt of hydrogen peroxide, perborate, an alkali metal salt of perborate, perchloric acid, an alkali metal salt of perchloric acid, persulfuric acid, persulfate, and urea peroxide, the metal component (C) is at least one selected from the group consisting of a transition metal element and a compound containing the same, and the used amount of the metal component (C) relative to 1 mol of amino compound (A) is less than 0.1 mmol. In the formula, Q is a halogen atom, an alkyl group having 1 to 15 carbon atoms or the like, R is a halogen atom, alkyl group having 1 to 15 carbon atoms or the like. Q and R are different. m represents an integer of 0 to 5, and n represents an integer of 0 to 4. The total of m and n is less than 5.

Facile, mild and convenient preparation and characterization of some novel schiff base ligands from synthetic diamines and salicylaldehyde

Some novel Schiff base ligands have been prepared through condensation of salicylaldehyde with synthetic various primary diamines under mild reaction conditions. The used aromatic diamines were synthesized in good yields starting from low-cost commercially available materials. In these reactions, the Schiff base products have been afforded with excellent yields and appropriate reaction times. The structure of these ligands has been characterized by IR, 1H NMR and 13C NMR techniques.

Laccase-catalysed homocoupling of primary aromatic amines towards the biosynthesis of dyes

Coloured disubstituted benzoquinonimine trimeric structures are obtained as main reaction products of the oxidation of p-electron donor pri-mary aromatic amines using two different laccases, CotA-laccase from Baccilus subtilus and TvL from Trametes versicolor. These orange-red to purple products, presenting high molar extinction coeffi-cients, presumably result from oxidative homocou-pling reactions, through the formation of N-C bonds at positions 2 and 5, of the laccase oxidised inter-mediate as showed in the proposed oxidative path-way. The product of 1,4-phenylenediamine is shown to be the trimer known as Bandrowski's base which has an established role in hair and fur dyeing. Our results also show that the occurrence and/or rates of oxidation of aromatic amines are strongly dependent on the presence of p-electron releasing substituents in the aromatic ring and are independent on the properties of the enzyme used. Overall our data con-tribute for (i) understanding key features of laccase reactivity with p-substituted aromatic amines and (ii) establishing enzymatic processes that lead to the syn-thesis of coloured bio-products under mild condi-tions with potential impact in the cosmetic and dye industries.

Dynamic photo-control of kinesin on a photoisomerizable monolayer - Hydrolysis rate of ATP and motility of microtubules depending on the terminal group

The reversibly and repeatedly altered gliding motility of microtubules driven by kinesin on the photoresponsive monolayer surface is studied. It was confirmed that an azobenzene monolayer surface needs to have free amino terminal groups for the successful dynamic control of the motility of microtubule. The surface of the azobenzene monolayer with terminal amino groups can dynamically control the ATP hydrolysis activity of kinesin which resulted in the change in motility of the microtubules.

Correlation analysis of reactivity in the oxidation of anilines by nicotinium dichromate in nonaqueous media

The kinetics of oxidation of 15 para- and meta-substituted anilines by nicotinium dichromate (NDC) in different organic solvent media in the presence of p-toluenesulfonic acid (TsOH) has been investigated. The rate of the reaction is zero order with respect to substrate, first order in NDC, and is found to increase with increase in [TsOH]. The various thermodynamic parameters for the oxidation have been reported and discussed along with the validity of the isokinetic relationship. The specific rate of oxidizing species-anilines reaction (k2) correlates with Hammett's substituent constants affording negative reaction constants. The effect of paraand meta-substituents on the oxidation rates confirms to Swain et al.'s substituent constants F and R. both with negative reaction constants. The rate data failed to correlate with macroscopic solvent parameters such as εr, and E TN while showing satisfactory correlation with Kamlet-Taft's solvatochromic parameters (α. β. and π*).

Effect of preferential solvation on the kinetics and thermodynamics of oxidation of anilines by nicotinium dichromate

The nicotinium dichromate (NDC) oxidation of anilines, in varying mole fractions of benzene/2-methylpropan-2-ol mixtures, in the presence of p-toluenesulfonic acid (TsOH) is first order in NDC and TsOH and zero order with respect to anilines in the concentration range investigated. The NDC oxidation of 15 meta- and para-substituted anilines complies with the isokinetic relationship but not to any of the linear free energy relationships. The activation free energy data failed to correlate with macroscopic solvent parameters such as εΓ and ENT. Correlation of ΔG# with Kamlet-Taft solvatochromic parameters (α, β, π*) suggests that the specific solute-solvent-solvent interactions play a major role in governing the reactivity.

Mechanism and reactivity in perborate oxidation of anilines in acetic acid

Perborate but not percarbonate in acetic acid generates peracetic acid on standing and the peracetic acid oxidation of anilines is fast. The oxidation with a fresh solution of perborate in acetic acid is smooth and second order but the specific oxidation rate increases with increasing [perborate]0 or [boric acid]. Perborate on dissolution affords hydrogen peroxide and a borate; the latter assists the former in the oxidation. The oxidation rates of anilines under identical conditions do not conform to any of the linear free energy relationships but the reaction rates of molecular anilines do. Perborate oxidation proceeds via two reaction paths but the overall oxidation rates of molecular anilines conform to structure reactivity relationships; the transition states do not differ significantly. Analysis of the oxidation rates of perborate and percarbonate reveals that while perborate oxidation is faster than percarbonate it is at least as selective as the latter.

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.