767-71-5

Usage

Uses

Used in Dye and Pigment Production:
N,2,6-trimethylaniline is used as an intermediate for the production of dyes and pigments, contributing to the coloration and stability of these substances in various applications.
Used in Pharmaceutical Synthesis:
N,2,6-trimethylaniline is used as a chemical intermediate in the synthesis of various pharmaceuticals, playing a crucial role in the development of new medications.
Used in Agrochemical Production:
N,2,6-trimethylaniline is utilized as an intermediate in the synthesis of agrochemicals, aiding in the creation of products that protect crops and enhance agricultural yields.
Used in Rubber Chemical and Antioxidant Manufacturing:
N,2,6-trimethylaniline is employed as a chemical intermediate in the manufacture of rubber chemicals and antioxidants, which are essential for improving the durability and performance of rubber products.
Safety Note:
N,2,6-trimethylaniline is considered to be harmful if swallowed, inhaled, or absorbed through the skin, and it is classified as a hazardous substance. Therefore, proper safety measures should be taken when handling this chemical.

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

Upstream product

• 98-04-4 phenyltrimethylammonium iodide 
• 77-78-1 dimethyl sulfate 
• 87-62-7 2,6-dimethylaniline 
• 74-88-4 methyl iodide 
• 607-92-1 2,6-dimethylformanilide 
• 35203-02-2 2,6-dimethyl-N-methylene benzamine 
• 616-38-6 carbonic acid dimethyl ester 
• 769-06-2 N,N,2,6-tetramethylaniline 
• 53782-79-9 (E)-4-(pent-3-en-2-yl)morpholine 
• 107-02-8 acrolein 
• 27237-52-1 N-methyl-N-2,6-dimethylphenylcarbamoylchloride 
• 333-27-7 methyl trifluoromethanesulfonate 
• 124-38-9 carbon dioxide 
• 156267-16-2 benzyl N-(2,6-dimethylphenyl)carbamate 

Downstream Products

• 111438-57-4 N,N'-bis-(2,6-dimethyl-phenyl)-N,N'-dimethyl-butanediyldiamine 
• 769-06-2 N,N,2,6-tetramethylaniline 
• 132984-55-5 (+/-)-trans-2-(2,6,N-Trimethyl-anilino)-cyclohexanol 
• 18835-47-7 N-(2,6-dimethylphenyl)-N-methylacetamide 
• 123103-29-7 succinic acid bis-(2,6,N-trimethyl-anilide) 
• 101581-78-6 2,6,N-trimethyl-N-phenethyl-aniline 
• 100319-52-6 N-(3-bromo-propyl)-2,6,N-trimethyl-aniline 
• 100452-08-2 N-(4-chloro-butyl)-2,6,N-trimethyl-aniline 
• 113651-87-9 N,N'-bis-(2,6-dimethyl-phenyl)-N,N'-dimethyl-but-2-ynediyldiamine 
• 35517-66-9 N-(2,6-Dimethylphenyl)-N-methylformamide 
• 830-52-4 [N-methyl-N-(2,6-dimethylphenyl)aminocarbonylmethyl]chloride 
• 83843-13-4 1-[N-methyl-N-(2,6-dimethylphenyl)-amino]-2-propanol 
• 67358-21-8 1,7-dimethylindolin-2-one 
• 156136-68-4 1,7-Dimethyl-1,3-dihydro-indole-2-thione 

Relevant academic research and scientific papers

Low-Temperature Intramolecular [4+2] Cycloaddition of Allenes with Arenes for the Synthesis of Diene Ligands

The intramolecular [4+2] cycloaddition between arenes and allenes first reported by Himbert gives rapid access to rigid polycyclic scaffolds. Herein, we report a one-pot oxyalkynylation/cycloaddition reaction proceeding under mild conditions (23–90 °C) an

N-heterocyclic carbene copper(i) catalysed N-methylation of amines using CO2

The N-methylation of amines using CO2 and PhSiH3 as source of CH3 was efficiently performed using a N-heterocyclic carbene copper(i) complex. The methodology was found compatible with aromatic and aliphatic primary and secondary amines. Synthetic and computational studies have been carried out to support the proposed reaction mechanism for this transformation.

Selective monomethylation of primary amines with simple electrophiles

Direct monomethylation of primary amines with methyl triflate was achieved with high selectivity (up to 96%). The key point of this single methyl transfer stems from the use of HFIP as the solvent that interferes with amines and avoids overmethylation.

INDAZOLEPROPIONIC ACID AMIDE COMPOUND

Disclosed is a compound which is useful in preventing and treating cardiac arrhythmia such as atrial fibrillation. A compound represented by formula (1) or a pharmaceutically acceptable salt of the same. In formula (1), ring X represents benzene or pyridine; R1 represents an optionally substituted alkyl group; R2 represents an optionally substituted aryl group, an optionally substituted heterocyclic group, an optionally substituted arylalkyl group or an optionally substituted heterocyclic group-substituted alkyl group; R3, R4, R5, R6, R7, R8 and R9 represent each hydrogen or an alkyl group, provided that R3 and R5 may be bonded to each other to form, together with the carbon atom adjacent thereto, a cycloalkyl group; and m represents 0 or 1.

Palladium-catalyzed amidation by chemoselective C(sp3)-H activation: Concise route to oxindoles using a carbamoyl chloride precursor

Quite select: A new strategy was developed for the synthesis of various oxindoles from carbamoyl chlorides. Under the optimum reaction conditions, with Ad2PBu as a ligand, tBuCONHOH as an additive, and a CO atmosphere, selective C(sp3/sup

Half-titanocence anilide complexes Cp′TiCl2[N(2,6-R 12C6H3)R2]: Synthesis, structures and catalytic properties for ethylene polymerization and copolymerization with 1-hexene

A number of new half-sandwich titanium(IV) complexes of the type [Cp′TiCl2{N(2,6-R12C6H 3)R2}] [R1 = iPr (1, 2, 4), Me (3, 5); R 2 = Me (1, 3, 4, 5), Bn (2); Cp′ = Cp

Substituent effects on aromatic stacking interactions

Synthetic supramolecular zipper complexes have been used to quantify substituent effects on the free energies of aromatic stacking interactions. The conformational properties of the complexes have been characterised using NMR spectroscopy in CDCl3, and by comparison with the solid state structures of model compounds. The structural similarity of the complexes makes it possible to apply the double mutant cycle method to evaluate the magnitudes of 24 different aromatic stacking interactions. The major trends in the interaction energy can be rationalised using a simple model based on electrostatic interactions between the π-faces of the two aromatic rings. However, electrostatic interactions between the substituents of one ring and the π-face of the other make an additional contribution, due to the slight offset in the stacking geometry. This property makes aromatic stacking interactions particularly sensitive to changes in orientation as well as the nature and location of substituents. This journal is The Royal Society of Chemistry.

Selective mono-N-methylation of primary aromatic amines by dimethyl carbonate over faujasite X- and Y-type zeolites

The reaction of dimethyl carbonate (DMC) with different primary aromatic amines has been investigated under batch conditions (autoclave) in the presence of Y- and X-type zeolites. Operating at 120-150°C, highly selective mono-N-methylations are observed for anilines even when they are deactivated by either electronic effects or steric hindrance (G-C6H4NH2, G = p-NO2,p-CN, o-CO2CH3 and 2,6-dimethylaniline); typical selectivities for the formation of the corresponding mono-N-methyl derivatives [ArNH(CH3)] are in the range 92-98%, at a substrate conversion of 72-93%. A synergic effect between the reactivity of DMC (acting both as a methylating and as a reversible methoxycarbonylating agent) and the dual acid-base properties of zeolites is considered to be responsible for the unusually high selectivity observed; accordingly, a reaction mechanism is discussed, involving carbamates (ArNHCO2CH3) and N-methyl-carbamates [ArN(CH3)CO2CH3] as intermediates. The reaction is an example of a synthesis with low environmental impact: it couples the use of a non-toxic methylating agent (DMC, in place of the highly toxic methyl halides or dimethyl sulfate) with eco-friendly catalysts (zeolites) in a waste-free process.

Tyrosine kinase inhibitors. 3. Structure-activity relationships for inhibition of protein tyrosine kinases by nuclear-substituted derivatives of 2,2'-dithiobis(1-methyl-N-phenyl-1H-indole-3-carboxamide)

A series of indole-substituted 2,2'-dithiobis(1-methyl-N-phenyl-1H- indole-3-carboxamides) were prepared and evaluated for their ability to inhibit the tyrosine kinase activity of both the epidermal growth factor receptor (EGFR) and the nonreceptor pp60(v-src) tyrosine kinase. The compounds were synthesized by conversion of appropriate 1-methyloxindoles to 1-methyl-2-indolinethiones with P2S5 followed by subsequent reaction with NaH and phenyl isocyanate and oxidative dimerization of the resulting 2,3- dihydro-N-phenyl-2-thioxo-1H-indole-3-carboxamides. The parent compound and many of the substituted analogues were moderately potent inhibitors of both kinase enzymes, but no clear relationships were seen between substitution on the indole ring and inhibitory activity. While 4-substituted compounds were generally inactive, 5-substituted derivatives with electron-withdrawing groups showed inhibitory activity. However, none of the substituted compounds showed significantly better activity than the unsubstituted parent compound. There was generally a good correlation between activity against the EGFR and pp60(v-src) kinases, but several compounds did show some specificity (>20- fold) of inhibition; 5-Cl and 5-Br derivatives preferentially inhibited pp60(v-src), while the 5-CF3 compound preferentially inhibited EGFR. Selected compounds from the series were found to inhibit the growth of Swiss 3T3 fibroblasts with IC50s in the range 2-25 μM, the most active being 4- substituted derivatives. The compounds inhibited bFGF-mediated protein tyrosine phosphorylation in intact cells more effectively than EGFR- or PDGF- mediated phosphorylation.