3096-62-6

Upstream product

• 83-41-0 2,3-dimethylnitrobenzene 

Downstream Products

• 83-41-0 2,3-dimethylnitrobenzene 
• 19618-11-2 bis-(2,3-dimethyl-phenyl)-diazene-N-oxide 
• 227008-56-2 1,2-dimethyl-3-nitrosobenzene 
• 3096-69-3 4-amino-2,3-dimethylphenol 
• 87-59-2 2,3-Dimethylaniline 
• 17075-25-1 1,4-dimethyl-2-nitrosobenzene 
• 29418-34-6 bis-(2,3-dimethyl-phenyl)-diazene 
• 107418-14-4 bis(2,3-dimethyl)phenylhydrazine 
• 59478-05-6 3,3-dimethyl-1-(2,3-dimethylphenyl)triazene-1-oxide 
• 69891-38-9 N-(2,3-dimethylphenyl)-N-hydroxycinnamamide 

Relevant academic research and scientific papers

Redox-Neutral Selenium-Catalysed Isomerisation of para-Hydroxamic Acids into para-Aminophenols

A selenium-catalysed para-hydroxylation of N-aryl-hydroxamic acids is reported. Mechanistically, the reaction comprises an N?O bond cleavage and consecutive selenium-induced [2,3]-rearrangement to deliver para-hydroxyaniline derivatives. The mechanism is studied through both 18O-crossover experiments as well as quantum chemical calculations. This redox-neutral transformation provides an unconventional synthetic approach to para-aminophenols.

Selective Photoinduced Reduction of Nitroarenes to N-Arylhydroxylamines

We report the selective photoinduced reduction of nitroarenes to N-arylhydroxylamines. The present methodology facilitates this transformation in the absence of catalyst or additives and uses only light and methylhydrazine. This noncatalytic photoinduced transformation proceeds with a broad scope, excellent functional-group tolerance, and high yields. The potential of this protocol reflects on the selective and straightforward conversion of two general antibiotics, azomycin and chloramphenicol, to the bioactive hydroxylamine species.

Synthesis of meta-substituted anilines via copper-catalyzed [1,3]-methoxy rearrangement

meta-Substituted anilines were efficiently synthesized via copper-catalyzed [1,3]-methoxy rearrangement of N-methoxyanilines followed by Michael addition of nucleophiles to the in situ generated ortho-quinol imine. The present reaction exhibits excellent

A general and scalable synthesis of polysubstituted indoles

A consecutive 2-step synthesis of N-unprotected polysubstituted indoles bearing an electron-withdrawing group at the C-3 position from readily available nitroarenes is reported. The protocol is based on the [3,3]-sigmatropic rearrangement of N-oxyenamines generated by the DABCO-catalyzed reaction of N-arylhydroxylamines and conjugated terminal alkynes, and delivers indoles endowed with a wide array of substitution patterns and topologies.

Regioselective installation of fluorosulfate (-OSO2F) functionality into aromatic C(sp2)-H bonds for the construction of: Para-amino-arylfluorosulfates

The construction of para-amino-arylfluorosulfates was achieved through installation of fluorosulfate (-OSO2F) functionality into aromatic C(sp2)-H bonds by the reaction of N-arylhydroxylamine with sulfuryl fluoride (SO2Fs

Synthesis, characterization, and conformational analysis of DNA adducts from methylated anilines present in tobacco smoke

The ability of a series of aromatic amines present in tobacco smoke (2-, 3-, and 4-methylaniline, 2,3- and 2,4-dimethylaniline) to bind to DNA has been investigated by reacting N-(acyloxy)arylamines with dG, dG nucleotides, and DNA. The predominant products from reactions with dG and the nucleotides were characterized as N-(deoxyguanosin-8-yl)arylamines by spectroscopic and HPLC methods. HPLC and spectroscopic analyses of the modified DNA indicated the same adducts. Analyses of the 1H and 13C NMR spectra suggested that the adducts containing a methyl substituent ortho to the arylamine nitrogen had a higher percentage of syn conformers. This observation was supported by theoretical simulation studies that indicated substantial percentages of low energy syn conformers, increasing with the substitution pattern in the order para meta ortho ortho,para ortho,meta. The results demonstrate that, although single-ring arylamines are considered weak carcinogens, their electrophilic N-acetoxy derivatives, which are plausible metabolic intermediates, react with DNA to yield covalent adducts structurally identical to those derived from carcinogenic polyarylamines, such as 2- aminofluorene and 4-aminobiphenyl. Furthermore, the conformational perturbation induced in DNA by the formation of the monoarylamine-DNA adducts, especially those with an ortho substituent, may contribute to the biological activities of these compounds.

Kinetics and Mechanism of the Bamberger Rearrangement. Part 4. Rearrangement of Sterically Hindered Phenylhydroxylamines to 4-Aminophenols in Aqueous Sulphuric Acid Solution

The rates of the Bamberger rearrangement of sterically hindered phenylhydroxylamines have been determined in aqueous sulphuric acid solution and the substituent effects (in particular, the steric effects) are discussed.The rate constants for phenylhydroxylamines with 2-substituents (Me, Cl, I) satisfied the Taft equation: log krel = ρ*?* - δES with ρ*-1.93 and δ-1.16.The result shows that steric hindrance of the substituents, in addition to the electron-donating effect, has an accelerating effect on the rates of the Bamberger rearrangement.The rate constants for 3-substituted 2-methylphenylhydroxylamines were generally greater than those for 5-substituted 2-methylphenylhydroxylamines.The difference was attributed to the 'buttressing effect' of neighbouring 3-substituents.This is the first example of steric acceleration of the Bamberger rearrangement.