30926-02-4

Upstream product

• 917-64-6 methyl magnesium iodide 
• 60-29-7 diethyl ether 
• 99-99-0 1-methyl-4-nitrobenzene 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 540-23-8 p-toluidine hydrochloride 
• 2028-84-4 p-methylbenzenediazonium chloride 
• 67-66-3 chloroform 
• 112160-74-4 acetic acid-(2,4,N-trichloro-anilide) 
• 106-49-0 p-toluidine 
• 861367-03-5 3-p-tolyl-triazane-1,2-dicarboxylic acid diethyl ester 
• 108-88-3 toluene 
• 622-57-1 N-ethyl-p-tolylamine 
• 955-98-6 4,4'-Dimethyl-azoxybenzol 
• 100-51-6 benzyl alcohol 

Downstream Products

• 91-62-3 6-methylquinoline 
• 93731-15-8 1,2-di-p-tolyl-pyrazolidine 
• 637-47-8 1,2-di(p-tolyl)hydrazine 
• 14618-59-8 N-(tert-butoxycarbonyl)-4-methylaniline 
• 106-49-0 p-toluidine 
• 2759-55-9 N-p-tolylpropionamide 
• 103-89-9 4-Methylacetanilide 
• 108346-86-7 (2-((dimethylamino)methyl)phenyl)(2-((4-methylphenyl)azo)-5-methylphenyl)palladium 
• 108393-19-7 bis(2-((4-methylphenyl)azo)-5-methylphenyl)palladium 
• 1421276-54-1 2-(4-methylphenyl)-3-phenyl-5-methyl-2H-indazole 
• 1421276-37-0 C₂₁H₁₈N₂O 
• 1556645-87-4 C₆₂H₄₄N₂O₂ 
• 1556645-89-6 C₆₂H₄₄N₂O₂ 
• 1556645-93-2 C₆₂H₄₀⁽²⁾H₄N₂O₂ 

Relevant academic research and scientific papers

Monolayer alignment on azobenzene surfaces during UV light irradiation: Analysis of optical polarized absorption measurement results and theoretical treatment

The influence of the charge separation during the trans-cis conformational change on the surface of azobenzene 6Az10PVA monolayer on the polar liquid-crystal monolayer film, such as 4-n-pentyl- 4′ -cyanobiphenyl (5CB), is investigated. The effective anchoring energy (in the Rapini-Papolar form) is phenomenologically described in the framework of the molecular model, which takes into account the interaction between the surface polarization and surface electric field, for number of conformational states of the boundary surface. It is shown, using the experimental data for the voltage across the 6Az10PVA+5CB film, provided by the surface-potential technique, that the charge separation during the conformational changing, caused by the UV irradiation, may lead to changing of the surface alignment of liquid-crystalline molecules. The influence of the photoisomerization process on the orientational order parameter S2 (t) using the optical polarized absorption measurement is also investigated.

Supramolecular control of fluorescence through reversible encapsulation

The trans to cis isomerization of 4,4'-dimethylazobenzene by the nonchemical stimuli light and heat alters its guest binding properties, allowing control over encapsulation of a second guest. We show here how this remote control for reversible encapsulation can be used as a supramolecular fluorescence on/off switch. If trans-4-ethyl-4'-methylstilbene is used as the second guest its fluorescence is altered depending on whether it is free in solution or encapsulated. We demonstrate that the change in fluorescence is indeed a consequence of the controlled encapsulation state of the stilbene by correlation of fluorescence and1H NMR data.

Selective Encapsulation and Unusual Stabilization of cis-Isomers by a Spherical Polyaromatic Cavity

To explore new cavity functions, we herein employed cis-trans stereoisomers with a N=N, C=C, or C=N unit as guest indicators for a polyaromatic capsule. Thanks to the rigid, spherical cavity with a diameter of ～1 nm, azobenzene and stilbene derivatives ar

H2O2-mediated room temperature synthesis of 2-arylacetophenones from arylhydrazines and vinyl azides in water

An environmentally benign, cost-efficient and practical methodology for the room temperature synthesis of 2-arylacetophenones in water has been discovered. The facile and efficient transformation involves the oxidative radical addition of arylhydrazines with α-aryl vinyl azides in the presence of H2O2 (as a radical initiator) and PEG-800 (as a phase-transfer catalyst). From the viewpoint of green chemistry and organic synthesis, the present protocol is of great significance because of using cheap, non-toxic and readily available starting materials and reagents as well as amenability to gram-scale synthesis, which provides an attractive strategy to access 2-arylacetophenones.

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.

Selective Reduction of Nitroarenes to Arylamines by the Cooperative Action of Methylhydrazine and a Tris(N-heterocyclic thioamidate) Cobalt(III) Complex

We report an efficient catalytic protocol that chemoselectively reduces nitroarenes to arylamines, by using methylhydrazine as a reducing agent in combination with the easily synthesized and robust catalyst tris(N-heterocyclic thioamidate) Co(III) complex [Co(κS,N-tfmp2S)3], tfmp2S = 4-(trifluoromethyl)-pyrimidine-2-thiolate. A series of arylamines and heterocyclic amines were formed in excellent yields and chemoselectivity. High conversion yields of nitroarenes into the corresponding amines were observed by using polar protic solvents, such as MeOH and iPrOH. Among several hydrogen donors that were examined, methylhydrazine demonstrated the best performance. Preliminary mechanistic investigations, supported by UV-vis and NMR spectroscopy, cyclic voltammetry, and high-resolution mass spectrometry, suggest a cooperative action of methylhydrazine and [Co(κS,N-tfmp2S)3] via a coordination activation pathway that leads to the formation of a reduced cobalt species, responsible for the catalytic transformation. In general, the corresponding N-arylhydroxylamines were identified as the sole intermediates. Nevertheless, the corresponding nitrosoarenes can also be formed as intermediates, which, however, are rapidly transformed into the desired arylamines in the presence of methylhydrazine through a noncatalytic path. On the basis of the observed high chemoselectivity and yields, and the fast and clean reaction processes, the present catalytic system [Co(κS,N-tfmp2S)3]/MeNHNH2 shows promise for the efficient synthesis of aromatic amines that could find various industrial applications.

Manganese Catalyzed Hydrogenation of Azo (N=N) Bonds to Amines

We report the first example of homogeneously catalyzed hydrogenation of the N=N bond of azo compounds using a complex of an earth-abundant-metal. The hydrogenation reaction is catalyzed by a manganese pincer complex, proceeds under mild conditions, and yields amines, which makes this methodology a sustainable alternative route for the conversion of azo compounds. A plausible mechanism involving metal-ligand cooperation and hydrazine intermediacy is proposed based on mechanistic studies. (Figure presented.).

Photocatalytic oxidative coupling of arylamines for the synthesis of azoaromatics and the role of O2 in the mechanism

The photocatalytic oxidative coupling of aryl amines to selectively synthesize azoaromatic compounds has been realized. Multiple different photocatalysts can be used to perform the general reaction; however, Ir(dF-CF3-ppy)2(dtbpy)+, where dF-CF3-ppy is 2-(2,4-difluorophenyl)-5-(trifluoromethyl)-pyridine and dtpby is 4,4′-tert-butyl-2,2′-bipyridine, showed the greatest range of reactivity with various amine substrates. Both electron-rich and -deficient amines can be coupled with yields up to 95% under an ambient air atmosphere. Oxygen was deemed to be essential for the reaction and is utilized in the regeneration of the photocatalyst. Fluorescence quenching and radical trap experiments indicate an amine radical coupling mechanism that proceeds through a hydrazoaromatic intermediate before further oxidation occurs to form the desired azoaromatic products.

Single crystal MnOOH nanotubes for selective oxidative coupling of anilines to aromatic azo compounds

Catalytic synthesis of aromatic azo compounds by oxidative coupling of anilines using molecular oxygen represents a facile, green and valuable process; however, such an economical process suffers from poor catalytic activity and selectivity. Herein, novel single crystal MnOOH nanotubes with abundant Mn3+sites and high oxygen defects were successfully synthesized. The catalyst exhibited high selectivity for oxidative coupling of anilines, achieving complete transformation into aromatic azo compounds under mild conditions, even at room temperature.

Metal- and oxidant-free electrochemically promoted oxidative coupling of amines

The selective oxidation of amines into imines is a priority research topic in organic synthesis and has attracted much attention over the past few decades. However, the oxidation of amines generally suffers from the drawback of transition-metal, even noble-metal catalysts. Thus, the strategy of metal- and oxidant-free selective synthesis of imines is highly desirable yet largely unmet. This paper unravels a metal-free and external oxidant-free electrochemical strategy for the oxidative coupling methodology of amines. This general transformation is compatible with various functional amines and led to functionalized imines in moderate to satisfactory yields.