3096-63-7

Basic information

• Product Name: N-hydroxy-2,6-dimethylaniline
• Synonyms: benzenamine, N-hydroxy-2,6-dimethyl-; N-Hydroxy-2,6-dimethylaniline
• CAS NO: 3096-63-7
• Molecular Formula: C₈H₁₁NO
• Molecular Weight: 137.179
• Mol File: 3096-63-7.mol

Chemical Properties

• Boiling Point: 232.5°C at 760 mmHg
• Flash Point: 102.7°C
• Density: 1.12g/cm³
• Vapor Pressure: 0.0327mmHg at 25°C
• Refractive Index: 1.609
• CAS DataBase Reference: N-hydroxy-2,6-dimethylaniline(CAS DataBase Reference)
• NIST Chemistry Reference: N-hydroxy-2,6-dimethylaniline(3096-63-7)
• EPA Substance Registry System: N-hydroxy-2,6-dimethylaniline(3096-63-7)

Safety Data

• Hazardous Substances Data: 3096-63-7(Hazardous Substances Data)

Upstream product

• 81-20-9 2,6-dimethylnitrobenzene 
• 632-92-8 2,4-dimethyl-1,3,5-trinitrobenzene 

Downstream Products

• 72725-83-8 α-(p-Nitrophenyl)-N-(2,6-dimethylphenyl)nitrone 
• 107341-59-3 N-(2,6-Dimethylphenyl)propylidenamin-N-oxid 
• 3096-70-6 3,5-dimethyl-4-aminophenol 
• 24596-18-7 4-chloro-2,6-dimethylaniline 
• 24596-19-8 4-bromo-2,6-dimethylphenylamine 
• 87-62-7 2,6-dimethylaniline 
• 654-42-2 1,4-dihydroxy-2,6-dimethylbenzene 
• 129936-56-7 2,6,2',6'-tetramethyl-4,4'-oxy-di-aniline 
• 51284-70-9 1,2-bis(2,6-dimethylphenyl)diazene oxide 
• 19519-71-2 2,6-dimethylnitrosobenzene 
• 7722-84-1 dihydrogen peroxide 
• 34743-49-2 4-methoxy-2,6-dimethylaniline 
• 52662-14-3 ω-Ethylamino-N-hydroxy-2,6-dimethylacetanilid 
• 52662-13-2 ω-Diethylamino-N-hydroxy-2,6-dimethylacetanilid 

Relevant articles and documents

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1.Topical anesthesia with benzocaine or lidocaine occasionally causes methemoglobinemia, an uncommon but potentially fatal disorder where the blood has a reduced ability to transport oxygen. Previous in vitro studies using human whole blood have shown tha

Oxidation of 2,6-dimethylaniline by recombinant human cytochrome P450s and human liver microsomes

2,6-Dimethylaniline (2,6-DMA) is classified as a rodent nasal cavity carcinogen and a possible human carcinogen. The major metabolite of 2,6-DMA in rats and dogs is 4-amino-3,5-dimethylphenol (DMAP) but oxidization of the amino group to produce metabolite

Polystyrene stabilized iridium nanoparticles catalyzed chemo- and regio-selective semi-hydrogenation of nitroarenes to N-arylhydroxylamines

Polystyrene stabilized Iridium (Ir@PS) nanoparticles (NPs) as a heterogeneous catalyst have been developed and characterized by IR, UV–Vis, SEM, TEM, EDX and XRD studies. The prepared Ir@PS catalyst showed excellent reactivity for chemo- and regio-selective controlled-hydrogenation of functionalized nitroarenes to corresponding N-arylhydroxylamine using hydrazine hydrate as reducing source and environmentally benign polyethylene glycol (PEG-400) as green solvent. The present methodology was applied for vast substrate scope and found to be compatible with wide range of reducible functional groups. The reaction performed at 85 °C or ambient temperature and completed within 5–80 minutes. The catalyst can easily be filtered out from reaction mixture and reusable.

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.

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

Bi(I)-Catalyzed Transfer-Hydrogenation with Ammonia-Borane

A catalytic transfer-hydrogenation utilizing a well-defined Bi(I) complex as catalyst and ammonia-borane as transfer agent has been developed. This transformation represents a unique example of low-valent pnictogen catalysis cycling between oxidation states I and III, and proved useful for the hydrogenation of azoarenes and the partial reduction of nitroarenes. Interestingly, the bismuthinidene catalyst performs well in the presence of low-valent transition-metal sensitive functional groups and presents orthogonal reactivity compared to analogous phosphorus-based catalysis. Mechanistic investigations suggest the intermediacy of an elusive bismuthine species, which is proposed to be responsible for the hydrogenation and the formation of hydrogen.

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

PROCESS FOR PREPARING SUBSTITUTED N-PHENYLHYDROXYLAMINES

The present invention relates to a process for the preparation of 2-[[[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy]methyl] phenyl]-hydroxylamine from the correspondingly substituted nitrobenzene compound.

NMR Study of the Monomer-Dimer Equilibria of Dimethylnitrosobenzenes in Solution. Identification of Mixed Azodioxy Dimeric Species

The monomer-dimer equilibria of 2,6- and 3,5-dimethylnitrosobenzenes in CDCl3 solution were investigated by 1H and/or 13C NMR spectroscopy.The mixed systems nitrosobenzene + 2,6-dimethylnitrosobenzene and 2,6-dimethylnitrosobenzene + 3,5-dimethylnitrosobenzene were also studied, and mixed azodioxy dimers were identified.In all systems exchange occurs exclusively between dimer and monomer species, rates and activation energies being calculated from time-dependent 1H 1D spectra and/or 1H 2D-EXSY spectra measured at different temperatures. KEY WORDS 1H NMR 13C NMR 2,6-Dimethylnitrosobenzene 3,5-Dimethylnitrosobenzene Monomer-dimer equilibria Mixed azodioxy dimers

Substituent Effects on Solvent Dependence of the Bandshape of Charge-Transfer Transitions in N-Pyridinium Phenolates

The solvatochromic absorption bands for "betaine-1", "betaine-22", and "betaine-29" (2,4,6-triphenyl-N-(4-hydroxyphenyl)-, 2,4,6-triphenyl-N-(2,6-dimethyl-4-hydroxyphenyl)- and 2,4,6-triphenyl-N-(3,5-dodecamethylene-4-hydroxyphenyl)pyridinium ions, respectively) in a range of polar, apolar, protic, aprotic solvents have been investigated.The bands can be accurately fitted by a single harmonic high-frequency mode Franck-Condon envelope of Gaussian solvent-broadened sub-bands.Multiphonon band analysis including both molecular modes and the solvent dynamics indicates that the solvent broadening for betaine-29 in polar solvents correlates well with εo-1 - εs-1, εo being the optical and εs the static dielectric constant, not only for aprotic solvents but also for normal alcohols.This is different from the behavior of 2,4,6-triphenyl-N-(3,5-di-tert-butyl-4-hydroxyphenyl)pyridinium ion ("betaine-26") for which the high-frequency solvent vibrational spectral part was previously found to be important.Bands for apolar solvents are independent of the solvent and are much wider than what corresponds to a structureless dielectric medium, pointing to other than purely electrostatic coupling mechanisms.Both the molecular frequencies and coordinate displacements are largely independent of the solvent, emphasizing their molecular character, and the frequency value of about 1600 cm-1 suggests that C-O or C-N stretching is involved.Spectral data for "betaine-1" and "betaine-22" could also be obtained for alcohol solvents and chloroform.The C-O/C-N mode at 1600 cm-1 can also be identified for these compounds.In addition, the band features suggest that coupling both to O-H stretching modes and to less isotope sensitive solvent modes is important.