63042-07-9

Upstream product

• 60-11-7 methyl yellow 
• 60-11-7 methyl yellow 

Downstream Products

• 99-98-9 4-amino-N,N-dimethylaniline 
• 62-53-3 aniline 
• 60-11-7 methyl yellow 

Relevant academic research and scientific papers

Transfer Hydrogenation of Azo Compounds with Ammonia Borane Using a Simple Acyclic Phosphite Precatalyst

Tris(quinolin-8-yl)phosphite, P(Oquin)3, promotes the dehydrogenation of H3N·BH3 (AB) and the transfer hydrogenation of azoarenes using ammonia borane (AB) as H2 source. The metal-free reduction of azoarenes proceeds under mild reaction conditions upon which several diphenylhydrazine derivatives are obtained in high yields. The reactivity of P(Oquin)3 toward AB was evaluated through NMR in situ tests. The rate of the reaction, activation parameters, deuterium kinetic isotope effect (DKIE) and linear-free energy relationship were investigated. Such mechanistic and kinetic studies suggest that P(Oquin)3 is a precatalyst and that AB is likely involved in more than one stage of the reaction pathway. Furthermore, the kinetic data indicate that the reaction proceeds through an ordered transition state, possibly associative.

Tuning the reduction power of supported gold nanoparticle photocatalysts for selective reductions by manipulating the wavelength of visible light irradiation

Gold nanoparticles supported on CeO2 were found to be efficient photocatalysts for three selective reductions of organic compounds at ambient temperatures, under irradiation of visible light; their reduction ability can be tuned by manipulating the irradiation wavelength.

Structure requirements for anaerobe processing of azo compounds: Implications for prodrug design

This Letter generalizes the metabolism of the azo class of compounds by Clostridium perfringens, an anaerobe found in the human colon. A recently reported 5-aminosalicylic acid-based prednisolone prodrug was shown to release the drug when incubated with the bacteria, while the para-aminobenzoic acid (PABA) based analogue did not. Instead, it showed a new HPLC peak with a relatively close retention time to the parent which was identified by LCMS as the partially reduced hydrazine product. This Letter investigates azoreduction across a panel of substrates with varying degrees of electronic and steric similarity to the PABA-based compound. Azo compounds with an electron donating group on the azo-containing aromatic ring showed immediate disproportionation to their parent amines without any detection of hydrazine intermediates by HPLC. Compounds containing only electron withdrawing groups are partially and reversibly reduced to produce a stable detectable hydrazine. They do not disproportionate to their parent amines, but regenerate the parent azo compound. This incomplete reduction is relevant to the design of azo-based prodrugs and the toxicology of azo-based dyes.

Square Wave Voltammetry for Two-Step Surface Reductions

Strongly adsorbed species on an electrode surface are used to create a stable, redox-modified surface. Square wave voltammetry is then used to degrade the surface electrochemically, as evidenced by the resulting voltammetric response. This process can be mathematically modeled as a quasi-reversible surface reaction coupled with a first-order irreversible surface reaction of the product. This is the simplest possible model that can explain a two-step surface reduction. Exemplary calculations for square wave voltammetry show a wide variety of peak shapes depending on rate constants and square wave amplitude. The reduction of Dimethyl Yellow (4-(dimethylamino)azobenzene) adsorbed on mercury is accurately described by this model. Characteristic parameters of the overall surface process are obtained from voltammograms by using the two-step model with nonlinear least-squares analysis (COOL). For Dimethyl Yellow in Britton - Robinson buffer (pH 6.00) at a surface concentration of 17.3 pmol cm-2, these parameters are as follows: standard potential, E10 = -0.397 ± 0.001 V vs SCE; transfer coefficient for the first step, α1 = 0.43 ± 0.02; rate constant for the first step, k10 = 103 ± 8 s-1; transfer coefficient for the second step, α2 = 0.11 ± 0.04; and rate constant for the second step, k20 (referenced to E10) = 11.1 ± 1.7 s-1. Uncertainties are 95% confidence intervals derived from a pool of 11 voltammograms collected at different square wave amplitudes (ESW = 0-100 mV).

AN EFFECT TRIFLUOROMETHYL GROUP ON PHOTOSENSITIZING BEHAVIOR OF BENZOPHENONE DERIVATIVES

2,2'-Bis(trifluoromethyl)benzophenone acted as an efficient and stable photosensitizer in energy transfer and hydrogen transfer reactions.