825-85-4

Basic information

• Product Name: N,N-Dimethyltoluidin-N-oxid
• Synonyms: N,N-Dimethyltoluidin-N-oxid;Benzenamine, N,N,4-trimethyl-, N-oxide;Benzenamine,N,N,4-trimethyl-,N-oxide;N,N-dimethyl-p-toluidine-N-oxide;4-Methyl-N,N-dimethylaniline N-oxide;N,N,4-Trimethylaniline N-oxide;N,N,4-Trimethylbenzenamine N-oxide;N,N-Dimethyl-4-toluidine N-oxide
• CAS NO: 825-85-4
• Molecular Formula: C₉H₁₃NO
• Molecular Weight: 151.21
• Mol File: 825-85-4.mol
• Article Data: 15

Chemical Properties

• Melting Point: 137℃
• Appearance: /
• CAS DataBase Reference: N,N-Dimethyltoluidin-N-oxid(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-Dimethyltoluidin-N-oxid(825-85-4)
• EPA Substance Registry System: N,N-Dimethyltoluidin-N-oxid(825-85-4)

Safety Data

• Hazardous Substances Data: 825-85-4(Hazardous Substances Data)

Usage

General Description

N,N-Dimethyltoluidin-N-oxid, also known as DMTDNO, is a chemical compound with the molecular formula C9H13NO. It is a powerful oxidizing agent that is commonly used as a catalyst in the polymerization of unsaturated polyester resins. DMTDNO is also used in the production of dyes, pharmaceuticals, and rubber chemicals. It is a clear, colorless to pale yellow liquid with a strong odor, and it is highly flammable and reactive with strong oxidizing agents. DMTDNO 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

• 102439-20-3 2-(N,N-dimethylamino)-5-methylphenol 
• 13541-33-8 4-N,N-dimethylaminobenzyl methyl ether 
• 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 

Relevant articles and documents

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.

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.

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.