99-97-8

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

• 64-17-5 ethanol 
• 99-99-0 1-methyl-4-nitrobenzene 
• 512-56-1 trimethyl phosphite 
• 106-49-0 p-toluidine 
• 67-56-1 methanol 
• 74-83-9 methyl bromide 
• 77-78-1 dimethyl sulfate 
• 71-43-2 benzene 
• 74-88-4 methyl iodide 
• 100-10-7 4-dimethylamino-benzaldehyde 
• 119-61-9 benzophenone 
• 87066-90-8 2-dimethylamino-5-methyl-benzyl alcohol 
• 865-47-4 potassium tert-butylate 
• 825-85-4 N,N-dimethyl-p-toluidine N-oxide 

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 
• 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 
• 857727-39-0 N-cyanomethyl-N,N-dimethyl-p-toluidinium 
• 2739-04-0 N-methyl-N-(4-methylphenyl)formamide 
• 23970-61-8 3--N,N-dimethyl-p-toluidine 

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.

CO2-tuned highly selective reduction of formamides to the corresponding methylamines

We herein describe an efficient, CO2-tuned and highly selective C-O bond cleavage of N-methylated formanilides. With easy-to-handle and commercially available NaBH4 as the reductant, a variety of formanilides could be turned into the desired tertiary amines in moderate to excellent yields. The role of CO2 has been investigated in detail, and the mechanism is proposed on the basis of experiments.

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.

Mesoionic N-heterocyclic olefin catalysed reductive functionalization of CO2for consecutiveN-methylation of amines

A mesoionic N-heterocyclic olefin (mNHO) was introduced as a metal-free catalyst for the reductive functionalization of CO2leading to consecutive doubleN-methylation of primary amines in the presence of 9-borabicyclo[3.3.1]nonane (9-BBN). A wide range of secondary amines and primary amines were successfully methylated under mild conditions. The catalyst sustained over six successive cycles ofN-methylation of secondary amines without compromising its activity, which encouraged us to check its efficacy towards doubleN-methylation of primary amines. Moreover, this method was utilized for the synthesis of two commercially available drug molecules. A detailed mechanistic cycle was proposed by performing a series of control reactions along with the successful characterisation of active catalytic intermediates either by single-crystal X-ray study or by NMR spectroscopic studies in association with DFT calculations.

Alcohol promoted N -methylation of anilines with CO2/H2over a cobalt catalyst under mild conditions

N-Methylation of amines with CO2/H2 to N-methylamines over non-noble metal catalysts is very interesting but remains challenging. Herein, we present an alcohol (e.g., ethanol) promoted strategy for the N-methylation of anilines with CO2/H2 with high efficiency under mild conditions (e.g., 125 °C), which is achieved over a cobalt catalytic system composed of Co(OAc)2·4H2O, triphos and Sn(OTf)2. This catalytic system has a broad substrate scope and is tolerant toward a wide range of anilines and N-methyl anilines, and a series of N,N-dimethyl anilines were obtained in high yields. Mechanism investigation indicates that the alcohol solvent shifts the equilibrium of CO2 hydrogenation by forming an alkyl formate, which further reacts with the amine to produce N-formamide, and Sn(OTf)2 promotes the deoxygenative hydrogenation of N-formamides to afford N-methylamines. This is the first example of the N-methylation of amines with CO2/H2 over a cobalt catalytic system, which shows comparable performance to the reported Ru catalysts and may have promising applications.

Borane-Trimethylamine Complex as a Reducing Agent for Selective Methylation and Formylation of Amines with CO2

We report herein that a borane-trimethylamine complex worked as an efficient reducing agent for the selective methylation and formylation of amines with 1 atm CO2 under metal-free conditions. 6-Amino-2-picoline serves as a highly efficient catalyst for the methylation of various secondary amines, whereas in its absence, the formylation of primary and secondary amines was achieved in high yield with high chemoselectivity. Mechanistic studies suggest that the 6-amino-2-picoline-borane catalytic system operates like an intramolecular frustrated Lewis pair to activate CO2.

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.