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

• 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 
• 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 
• 74-87-3 methylene chloride 

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.

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.

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.

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.

Simplified preparation of a graphene-co-shelled Ni/NiO@C nano-catalyst and its application in theN-dimethylation synthesis of amines under mild conditions

The development of Earth-abundant, reusable and non-toxic heterogeneous catalysts to be applied in the pharmaceutical industry for bio-active relevant compound synthesis remains an important goal of general chemical research.N-methylated compounds, as one of the most essential bioactive compounds, have been widely used in the fine and bulk chemical industries for the production of high-value chemicals. Herein, an environmentally friendly and simplified method for the preparation of graphene encapsulated Ni/NiO nanoalloy catalysts (Ni/NiO@C) was developed for the first time, for the highly selective synthesis ofN-methylated compounds using various functional amines and aldehydes under easy to handle, and industrially applicable conditions. A large number of primary and secondary amines (more than 70 examples) could be converted to the correspondingN,N-dimethylamines with the participation of different functional aldehydes, with an average yield of over 95%. A gram-scale synthesis also demonstrated a similar yield when compared with the benchmark test. In addition, it was further proved that the catalyst could easily be recycled because of its intrinsic magnetism and reused up to 10 times without losing its activity and selectivity. Also, for the first time, the tandem synthesis ofN,N-dimethylamine products in a one-pot process, using only a single earth-abundant metal catalyst, whose activity and selectivity were more than 99% and 94%, respectively, for all tested substrates, was developed. Overall, the advantages of this newly developed method include operational simplicity, high stability, easy recyclability, cost-effectiveness of the catalyst, and good functional group compatibility for the synthesis ofN-methylation products as well as the industrially applicable tandem synthesis process.

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.