825-85-4

Usage

Uses

Used in Polymer Industry:
N,N-Dimethyltoluidin-N-oxid is used as a catalyst for the polymerization of unsaturated polyester resins. It accelerates the curing process and improves the mechanical properties of the final product.
Used in Dye Production:
N,N-Dimethyltoluidin-N-oxid is used in the production of dyes due to its strong oxidizing properties, which help in the synthesis of various dye compounds.
Used in Pharmaceutical Industry:
N,N-Dimethyltoluidin-N-oxid is used in the synthesis of pharmaceuticals, where its oxidizing properties can be utilized for the production of specific drug compounds.
Used in Rubber Chemicals Production:
N,N-Dimethyltoluidin-N-oxid is used in the production of rubber chemicals, where it can act as an accelerator or a catalyst in the manufacturing process.
Safety Precautions:
N,N-Dimethyltoluidin-N-oxid is a clear, colorless to pale yellow liquid with a strong odor, and it is highly flammable and reactive with strong oxidizing agents. It should be handled with caution and stored in a cool, dry place away from heat and flame.

Upstream product

• 99-97-8 Dimethyl-p-toluidine 

Downstream Products

• 86254-05-9 2-(N-methylacetamido)-NN-dimethyl-p-toluidine 
• 99-97-8 Dimethyl-p-toluidine 
• 101-61-1 4,4'-methylene-bis(N,N-dimethylaniline) 
• 65163-86-2 4,4'-bis(dimethylaminobenzyl)ether 
• 1703-46-4 N,N-dimethyl-4-hydroxymethylaniline 
• 93300-74-4 [2,4-Bis-(4-dimethylamino-benzyl)-phenyl]-dimethyl-amine 
• 50-00-0 formaldehyd 
• 623-08-5 N-methyl-p-toluidine 
• 1137-79-7 N,N-dimethyl-4-biphenylamine 
• 46734-13-8 N,N-dimethyl-4-(phenylmethyl)benzenamine 
• 63113-40-6 Dimethyl-(2-methyl-biphenyl-4-yl)-amine 
• 63113-39-3 5-(N,N-dimethylamino)-2-methylbiphenyl 
• 36362-82-0 1,5-dimethyl-2,3-diphenyl-1H-indole 
• 1616786-45-8 ethyl (2-(N,N-dimethylamino)-5-methylphenyl)acetate 

Relevant academic research and scientific papers

Dimethylanilinic N-Oxides and Their Oxygen Surrogacy Role in the Formation of a Putative High-Valent Copper-Oxygen Species

The reaction of p-cyano-N,N-dimethylaniline N-oxide, an O-atom donor, with different copper(I) complexes (at room temperature and in acetone) indicates the formation via O-atom transfer of a high-valent copper oxyl species, CuII-O?, a putative key intermediate in the catalytic cycle of copper-containing monooxygenases. The formation of p-cyano-N-hydroxymethyl-N-methylaniline and p-cyano-N-methylaniline as the main products of the reaction highlight the capability of this species to hydroxylate strong C-H bonds (bond dissociation energy ～90 kcal/mol). A plausible mechanism for the reactivity of this catalytic system is proposed.

Oxido-alcoholato/thiolato-molybdenum(VI) complexes with a dithiolene ligand generated by oxygen atom transfer to the molybdenum(IV) complexes

Oxido-alcoholato- and oxido-thiolato-molybdenum(VI) complexes bearing two ene-1,2-dithiolate ligands (cyclohexene-1,2-dithiolate) are prepared as synthetic models of molybdenum(VI) reaction centers of dimethyl sulfoxide reductase family of molybdenum enzymes. These complexes are prepared by oxygen atom transfer from tertiary amine N-oxide (trimethylamine N-oxide and N,N-dimethylaniline N-oxide) to the five-coordinate alcoholato- and thiolato-molybdenum(IV) complexes, and are characterized by UV–vis, cold-spray-ionization mass, resonance Raman, and 1H NMR spectroscopies. The oxygen atom transfer reactions are studied kinetically at a low temperature (?40 °C) to demonstrate that the reactivity of the thiolato-molybdenum(IV) complex is higher than that of alcoholato-molybdenum(IV) complex by about 7 times, and that the oxygen atom transfer reactivity increases with increasing the electron withdrawing ability of the p-substituent of N,N-dimethylaniline N-oxide derivatives. Mechanistic details are discussed based on the reactivity studies.

Renewable waste rice husk grafted oxo-vanadium catalyst for oxidation of tertiary amines to N-oxides

Low cost renewable waste rice husks (RH) have been used as a support for grafting of an oxo-vanadium Schiff base via covalent attachment for the oxidation of tertiary amines to N-oxide. The synthesis of the desired RH grafted oxo-vanadium complex involves prior functionalization of the RH support with amino-propyltrimethoxysilane (APTMS) followed by its reaction with salicylaldehyde to get an RH-functionalized Schiff base which subsequently reacted with vanadyl sulphate to get the targeted oxo-vanadium catalyst. The synthesized catalyst was found to be an efficient heterogeneous catalyst and afforded an excellent yield of corresponding N-oxides via oxidation of tertiary amines with hydrogen peroxide as an oxidant. Furthermore, the synthesized catalyst was found to be quite stable and showed consistent activity for five runs without any loss in activity.

A lipase-glucose oxidase system for the efficient oxidation of: N -heteroaromatic compounds and tertiary amines

In this work, a lipase-glucose oxidase system has been designed and proven to be an efficient system for the oxidation of N-heteroaromatic compounds and tertiary amines. This dual-enzyme system not only displays environmental friendliness, but also demonstrates its huge potential in industrial applications.

Oxovanadium(IV)-salen ion catalyzed H2O2 oxidation of tertiary amines to n-oxides- critical role of acetate ion as external axial ligand

The oxovanadium(IV)-salen ion catalyzed H2O2 oxidation of N,N-dimethylaniline forms N-oxide as the product of the reaction. The reaction follows Michaelis-Menten kinetics and the rate of the reaction is accelerated by electron donating groups present in the substrate as well as in the salen ligand. This peculiar substituent effect is accounted for in terms of rate determining bond formation between peroxo bond of the oxidant and the N-atom of the substrate in the transition state. Trichloroacetic acid (TCA) shifts the λmax value of the oxidant to the red region and catalyzes reaction enormously. The cleavage of N￡O bond by vanadium complex leads to moderate yield of the product. But the percentage yield of the product becomes excellent in the presence of TCA.

Catalytic N-oxidation of tertiary amines on RuO2NPs anchored graphene nanoplatelets

Ultrafine ruthenium oxide nanoparticles (RuO2NPs) with an average diameter of 1.3 nm were anchored on graphene nanoplatelets (GNPs) using a Ru(acac)3 precursor by a very simple dry synthesis method. The resultant material (GNPs-RuO2NPs) was used as a heterogeneous catalyst for the N-oxidation of tertiary amines for the first time. The transmission electron microscopy (TEM) images of the GNPs-RuO2NPs showed the excellent attachment of RuO2NPs on GNPs. The loading of Ru in GNPs-RuO2NPs was 2.68 wt%, as confirmed by scanning electron microscope-energy dispersive spectroscopy (SEM-EDS). The X-ray photoelectron spectrum (XPS) and the X-ray diffraction pattern (XRD) of GNPs-RuO 2NPs revealed that the chemical state of Ru on GNPs was +4. After the optimization of reaction conditions for N-oxidation of triethylamine, the scope of the reaction was extended to various aliphatic, alicyclic and aromatic tertiary amines. The GNPs-RuO2NPs showed excellent catalytic activity in terms of yields even at a very low amount of Ru catalyst (0.13 mol%). The GNPs-RuO2NPs was heterogeneous in nature, chemically as well as physically, very stable and could be reused up to 5 times. The Royal Society of Chemistry 2014.

Metal-free functionalization of N, N-dialkylanilines via temporary oxidation to N, N-dialkylaniline N-oxides and group transfer

A simple set of protocols for the controlled elaboration of anilines is reported allowing access to a diverse array of aminophenols, aminoarylsulfonates, alkylated anilines, and aminoanilines in 29-95% yield in a single laboratory operation from easily isolable, bench-stable N,N-dialkylaniline N-oxides. The introduction of new C-O, C-C, and C-N bonds on the aromatic ring is made possible by a temporary increase in oxidation level and excision of a weak N-O bond.

Mild and rapid hydroxylation of aryl/heteroaryl boronic acids and boronate esters with N-oxides

Aryl and heteroaryl boronic acids and boronate esters are rapidly, often within minutes, transformed into the corresponding phenols by N-oxides in an open flask at ambient temperature. This transformation has broad compatibility with a variety of functional groups.

Biomimetic oxidation reactions of a naked manganese(V)-Oxo porphyrin complex

The intrinsic reactivity of a manganese(V)-oxo porphyrin complex, a typically fleeting intermediate in catalytic oxidation reactions in solution, has been elucidated in a study focused on its gas-phase ion-chemistry. The naked high-valent MnV-oxo porphyrin intermediate 1 ([(tpfpp)Mn VO]+; tpfpp=meso-tetrakis(pentafluorophenyl)porphinato dianion), has been obtained by controlled treatment of [(tpfpp)Mn III]Cl (2-Cl) with iodosylbenzene in methanol, delivered in the gas phase by electrospray ionization and assayed by FT-ICR mass spectrometry. A direct kinetic study of the reaction with selected substrates, each containing a heteroatom X (X=S, N, P) including amines, sulfides, and phosphites, was thus performed. Ionic products arising from electron transfer (ET), hydride transfer (HT), oxygen-atom transfer (OAT), and formal addition (Add) may be observed, with a predominance of two-electron processes, whereas the product of hydrogen-atom transfer (HAT), [(tpfpp)MnIVOH]+, is never detected. A thermochemical threshold for the formation of the product radical cation allows an evaluation of the electron-transfer ability of a Mn V-oxo complex, yielding a lower limit of 7.85 eV for the ionization energy of gaseous [(tpfpp)MnIVO]. Linear free-energy analyses of the reactions of para-substituted N,N-dimethylanilines and thioanisoles indicate that a considerable amount of positive charge is developed on the heteroatom in the oxidation transition state. Substrates endowed with different heteroatoms, but similar ionization energy display a comparable reaction efficiency, consistent with a mechanism initiated by ET. For the first time, the kinetic acidity of putative hydroxo intermediates playing a role in catalytic oxidations, [(tpfpp)FeIVOH]+ and [(tpfpp)Mn IVOH]+, has been investigated with selected reference bases, revealing a comparatively higher basicity for the ferryl, [(tpfpp)Fe IVO], with respect to the manganyl, [(tpfpp)MnIVO], unit. Finally, the neat association reaction of 2 has been studied with various ligands showing that harder ligands are more strongly bound.

Probing the reactivity of oxomanganese-salen complexes: An electrospray tandem mass spectrometric study of highly reactive intermediates

Electrospray ionization in combination with tandem mass spectrometric techniques has been employed to study the formation of oxomanganese-salen complexes upon oxidation of [MnIII(salen)]+ cations as well as the properties and reactions of the oxidized species in the gas phase. Two species could be characterized as the principal oxidation products: the oxomanganese(V) complex, [Mn=O(salen)]+, which is the actual oxygen-transfer agent in epoxidation reactions, and the dinuclear, μ-oxo bridged [L(salen)Mn-Q-Mn-(salen)L]2+ with two terminal ligands L; the latter acts as a reservoir species. The effects of various substituents in the 5-and 5′-positions, respectively, of the salen ligand on the reactivity of the epoxidation catalyst were determined quantitatively from CID (collision-induced dissociation) experiments and B3LYP density functional calculations. Accordingly, the effect of axial donor ligands on the reactivity of the epoxidation catalyst was studied. Electron-withdrawing substitutents on the salen ligand and additional axial ligands decrease the stability and thus enhance the reactivity of the Mn=O moiety, while electron-donating salen substituents have a strong stabilizing effect. WILEY-VCH Verlag GmbH, 2001.