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Usage

Uses

Used in Dental Restorative Materials:
N,N-DIMETHYL-P-TOLUIDINE is used as an amine accelerator for the polymerization of dental methacrylic restorative materials. It enhances the setting process and improves the mechanical properties of the final restoration.
Used in Polymer and Resin Industries:
N,N-DIMETHYL-P-TOLUIDINE is used as a polymerization catalyst for polyesters, acrylate, and epoxy resins. Its catalytic properties enable the efficient production of these materials, which are widely used in coatings, adhesives, and composites.
Used in Dental Cement Hardening:
N,N-DIMETHYL-P-TOLUIDINE serves as a hardener for dental cements, promoting the rapid setting and hardening of these materials to ensure a strong and durable bond in dental applications.
Used in Adhesives:
N,N-DIMETHYL-P-TOLUIDINE is used in the formulation of adhesives, where its ability to accelerate polymerization contributes to the development of strong, quick-setting adhesives for various applications.
Used in Photographic Chemicals:
N,N-DIMETHYL-P-TOLUIDINE acts as an intermediate in the production of photographic chemicals, playing a crucial role in the development of film and other imaging materials.
Used in Industrial Glues:
N,N-DIMETHYL-P-TOLUIDINE is utilized in the formulation of industrial glues, where its polymerization properties contribute to the creation of strong, durable adhesives for a variety of substrates.
Used in Artificial Fingernail Preparations:
N,N-DIMETHYL-P-TOLUIDINE is used in the production of artificial fingernail preparations, where its ability to accelerate polymerization helps in creating strong, long-lasting nail enhancements.
Used in Colorants and Pharmaceuticals:
N,N-DIMETHYL-P-TOLUIDINE serves as an intermediate in the synthesis of colorants and pharmaceuticals, contributing to the development of a wide range of products across these industries.
Used in the Synthesis of Tetrahydroquinolines:
N,N-DIMETHYL-P-TOLUIDINE reacts with vinyl ether in the presence of copper(II) chloride to produce tetrahydroquinolines, which are valuable compounds in various chemical applications.
Used to Accelerate Polymerization of Ethyl Methacrylate:
N,N-DIMETHYL-P-TOLUIDINE is used to accelerate the polymerization of ethyl methacrylate, enhancing the efficiency and speed of the polymerization process for various applications.

Synthesis Reference(s)

Synthetic Communications, 19, p. 3051, 1989 DOI: 10.1080/00397918908052700Tetrahedron Letters, 8, p. 1849, 1967

Reactivity Profile

N,N-DIMETHYL-P-TOLUIDINE neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. May generate hydrogen, a flammable gas, in combination with strong reducing agents such as hydrides.

Purification Methods

Reflux for 3hours with 2 molar equivalents of Ac2O, then fractionally distil it under reduced pressure. Alternatively, dry it over BaO, distil and store it over KOH. The picrate has m 128o (from EtOH). Methods described for N,N-dimethylaniline are applicable here. [Beilstein 12 H 902, 12 III 2026, 12 IV 1874.]

InChI:InChI=1/C9H13N/c1-8-4-6-9(7-5-8)10(2)3/h4-7H,1-3H3

Upstream product

• 67-56-1 methanol 
• 90263-57-3 p-Toluidine hydroiodide 
• 67614-05-5 4-methylaniline hydrobromide 
• 64-17-5 ethanol 
• 99-99-0 1-methyl-4-nitrobenzene 
• 15257-27-9 bis-(4-dimethylamino-benzylidene)-p-phenylenediamine 
• 141-52-6 sodium ethanolate 
• 6140-15-4 trimethyl-p-tolylammonium iodide 
• 70789-29-6 tri-N-methyl-p-toluidinium; trimethyl-p-tolyl-ammonium hydroxide 
• 93687-12-8 tri-N-methyl-p-toluidinium; bromide 
• 98-04-4 phenyltrimethylammonium iodide 
• 512-56-1 trimethyl phosphite 
• 106-49-0 p-toluidine 
• 74-83-9 methyl bromide 

Downstream Products

• 937-24-6 N-methyl-N-nitroso-p-toluidine 
• 52262-63-2 4,N,N-trimethyl-2-nitroaniline 
• 612-03-3 4-(N-methylacetamido)toluene 
• 97788-15-3 N-benzyl-N,N-dimethyl-p-methylanilinium bromide 
• 116235-73-5 N-benzyl-N,N-dimethyl-p-toluidinium; chloride 
• 23667-06-3 2-bromo-4-methyl-N,N-dimethylaniline 
• 70577-99-0 tri-N-methyl-p-toluidinium; methyl sulfate 
• 54675-16-0 5-methyl-2-methylaminobenzoic acid 
• 87066-90-8 2-dimethylamino-5-methyl-benzyl alcohol 
• 64794-20-3 2,2′-methylenebis(N,N,4-trimethylaniline) 
• 32111-89-0 methyl-p-tolyl-carbamonitrile 
• 93687-12-8 tri-N-methyl-p-toluidinium; bromide 

Relevant academic research and scientific papers

Additive-free selective methylation of secondary amines with formic acid over a Pd/In2O3 catalyst

Formic acid is used as the sole carbon and hydrogen source in the methylation of aromatic and aliphatic amines to methylamines. The reaction proceeds via a formylation/transfer hydrogenation pathway over a solid Pd/In2O3 catalyst without the need for any additive.

Dirhodium-Catalyzed Chemo-and Site-Selective C-H Amidation of N, N-Dialkylanilines

A method for dirhodium-catalyzed C(sp 3)-H amidation of N, N-dimethylanilines was developed. Chemoselective C(sp 3)-H amidation of N-methyl group proceeded exclusively in the presence of C(sp 2)-H bonds of the electron-rich aromatic ring. Site-selective C(sp 3)-H amidation proceeded exclusively at the N-methyl group of N-methyl-N-Alkylaniline derivatives with secondary, tertiary, and benzylic C(sp 3)-H bonds α to a nitrogen atom.

Preparation method of N-alkylated derivative of primary amine compound

The invention relates to a preparation method of an N-alkylated derivative of a primary amine compound. The method comprises the following steps: uniformly mixing a primary amine compound, an alcohol compound and a catalyst in a reactor, and heating to react for a period of time to generate an N-alkylated substituted tertiary amine compound; wherein the catalyst is a copper-cobalt bimetallic catalyst, and the carrier of the catalyst is Al2O3. According to the method, alcohol is adopted as an alkylating reagent and is low in price and easy to obtain, a byproduct is water, no pollution is caused to the environment, and the overall reaction atom economy is high; the catalyst is simple in preparation method, low in cost, high in reaction activity and good in structural stability; meanwhile, by using the copper-cobalt bimetallic catalyst, the use of strong base additives can be avoided, and the requirement on reaction equipment is low; and the reaction post-treatment is convenient, and the catalyst can be recycled and is environment-friendly.

Photochemical Reaction of N,N-Dimethylanilines with N-Substituted Maleimides Utilizing Benzaldehyde as the Photoinitiator

Photoorganocatalysis constitutes a powerful domain of photochemistry and organic synthesis. The scaffold of pyrrolo[3,4-c]quinolinoles exhibits interesting and potent inhibition against various enzymes, making them really promising pharmaceutical targets. Herein, we describe a photochemical methodology for the reaction of N,N-dimethylanilines with N-substituted maleimides, utilizing benzaldehyde as the photoinitiator. A variety of substituted N,N-dimethylanilines and N-substituted maleimides were converted into the corresponding adducts in moderate to high yields.

Metal-Free Deoxygenation of Amine N-Oxides: Synthetic and Mechanistic Studies

We report herein an unprecedented combination of light and P(III)/P(V) redox cycling for the efficient deoxygenation of aromatic amine N-oxides. Moreover, we discovered that a large variety of aliphatic amine N-oxides can easily be deoxygenated by using only phenylsilane. These practically simple approaches proceed well under metal-free conditions, tolerate many functionalities and are highly chemoselective. Combined experimental and computational studies enabled a deep understanding of factors controlling the reactivity of both aromatic and aliphatic amine N-oxides.

Metal-Organic Framework-Confined Single-Site Base-Metal Catalyst for Chemoselective Hydrodeoxygenation of Carbonyls and Alcohols

Chemoselective deoxygenation of carbonyls and alcohols using hydrogen by heterogeneous base-metal catalysts is crucial for the sustainable production of fine chemicals and biofuels. We report an aluminum metal-organic framework (DUT-5) node support cobalt(II) hydride, which is a highly chemoselective and recyclable heterogeneous catalyst for deoxygenation of a range of aromatic and aliphatic ketones, aldehydes, and primary and secondary alcohols, including biomass-derived substrates under 1 bar H2. The single-site cobalt catalyst (DUT-5-CoH) was easily prepared by postsynthetic metalation of the secondary building units (SBUs) of DUT-5 with CoCl2 followed by the reaction of NaEt3BH. X-ray photoelectron spectroscopy and X-ray absorption near-edge spectroscopy (XANES) indicated the presence of CoII and AlIII centers in DUT-5-CoH and DUT-5-Co after catalysis. The coordination environment of the cobalt center of DUT-5-Co before and after catalysis was established by extended X-ray fine structure spectroscopy (EXAFS) and density functional theory. The kinetic and computational data suggest reversible carbonyl coordination to cobalt preceding the turnover-limiting step, which involves 1,2-insertion of the coordinated carbonyl into the cobalt-hydride bond. The unique coordination environment of the cobalt ion ligated by oxo-nodes within the porous framework and the rate independency on the pressure of H2 allow the deoxygenation reactions chemoselectively under ambient hydrogen pressure.

Method for realizing N-alkylation by using alcohols as carbon source under photocatalysis

The invention discloses a method for realizing N-alkylation by using alcohols as a carbon source under photocatalysis, and belongs to the technical field of catalytic synthesis. Alcohol, a substrate raw material and a catalyst are placed in a reaction device, ultraviolet and/or visible light irradiation is carried out in an inert atmosphere, after the irradiation is finished, solid-liquid separation is carried out to remove the catalyst, and an N-alkylation product can be obtained through extraction, distillation and purification, wherein the substrate raw material comprises any one of an amine compound, an aromatic nitro compound or an aromatic nitrile compound, the alcohol comprises any one or more of soluble primary alcohols, and the catalyst is metal oxide/titanium dioxide or metal sulfide/titanium dioxide. The method is simple and easy to operate, can be used for efficient photocatalysis one-pot multi-step hydrogenation N-alkylation reaction, and is mild in reaction condition, high in chemical selectivity of N-alkylamine, good in catalyst stability and easy to recycle.

Additive-freeN-methylation of amines with methanol over supported iridium catalyst

An efficient and versatile zinc oxide-supported iridium (Ir/ZnO) catalyst was developed to catalyze the additive-freeN-methylation of amines with methanol. Mechanistic studies suggested that the high catalytic reactivity is rooted in the small sizes (1.4 nm) of Ir nanoparticles and the high ratio (93%) of oxidized iridium species (IrOx, Ir3+and Ir4+) on the catalyst. Moreover, the delicate cooperation between the IrOxand ZnO support also promoted its high reactivity. The selectivity of this catalyticN-methylation was controllable between dimethylation and monomethylation by carefully tuning the catalyst loading and reaction solvent. Specifically, neat methanol with high catalyst loading (2 mol% Ir) favored the formation ofN,N-dimethylated amine, while the mesitylene/methanol mixture with low catalyst loading (0.5 mol% Ir) was prone to producing mono-N-methylated amines. An environmentally benign continuous flow system with a recycled mode was also developed for the efficient production ofN-methylated amines. With optimal flow rates and amine concentrations, a variety ofN-methylamines were produced with good to excellent yields in this Ir/ZnO-based flow system, providing a starting point for the clean and efficient production ofN-methylamines with this cost-effective chemical process.

Visible-Light-Induced C(sp2)-C(sp3) Cross-Dehydrogenative-Coupling Reaction of N-Heterocycles with N-Alkyl- N-methylanilines under Mild Conditions

Disclosed herein is a cross-dehydrogenative-coupling reaction of N-heterocycles including 1,2,4-triazine-3,5(2H, 4H)-diones and quinoxaline-2(1H)-ones with N-methylanilines to form C(sp2)-C(sp3) under visible-light illumination and ambient air at room temperature. In this process, easily available Ru(bpy)3Cl2·6H2O serves as the catalyst, and air acts as the green oxidant. This method features high atom economy, environmental friendliness, and convenient operation and provides an efficient and practical access to aminomethyl-substituted N-heterocycles with extensive functional group compatibility in 40-86% yields.

Simple RuCl3-catalyzed N-Methylation of Amines and Transfer Hydrogenation of Nitroarenes using Methanol

Methanol is a potential hydrogen source and C1 synthon, which finds interesting applications in both chemical synthesis and energy technologies. The effective utilization of this simple alcohol in organic synthesis is of central importance and attracts scientific interest. Herein, we report a clean and cost-competitive method with the use of methanol as both C1 synthon and H2 source for selective N-methylation of amines by employing relatively cheap RuCl3.xH2O as a ligand-free catalyst. This readily available catalyst tolerates various amines comprising electron-deficient and electron-donating groups and allows them to transform into corresponding N-methylated products in moderate to excellent yields. In addition, few marketed pharmaceutical agents (e. g., venlafaxine and imipramine) were also successfully synthesized via late-stage functionalization from readily available feedstock chemicals, highlighting synthetic value of this advanced N-methylation reaction. Using this platform, we also attempted tandem reactions with selected nitroarenes to convert them into corresponding N-methylated amines using MeOH under H2-free conditions including transfer hydrogenation of nitroarenes-to-anilines and prepared drug molecules (e. g., benzocaine and butamben) as well as key pharmaceutical intermediates. We further enable one-shot selective and green syntheses of 1-methylbenzimidazole using ortho-phenylenediamine (OPDA) and methanol as coupling partners.