13021-15-3

Usage

Uses

Used in Pharmaceutical Industry:
N,N,2,4,6-Pentamethylaniline is used as a synthetic intermediate for the production of pharmaceutical compounds. It is involved in the synthesis of benzyl 2-amino-2-deoxy-α-D-glucoand -mannopyranoside hydrochloride, which are important building blocks for the development of new drugs.
Used in Organic Synthesis:
N,N,2,4,6-Pentamethylaniline is used as a reagent in the condensation of dimeric 3,4,6-tri-O-acetyl-2-deoxy-2-nitroso-α-D-glucopyranosyl chloride with benzyl alcohol to yield an oximino glycoside. This reaction is an important step in the synthesis of complex organic molecules, which can be further modified for various applications.

InChI:InChI=1/C11H17N/c1-8-6-9(2)11(12(4)5)10(3)7-8/h6-7H,1-5H3

Upstream product

• 50-00-0 formaldehyd 
• 603-71-4 nitromesitylene 
• 77-78-1 dimethyl sulfate 
• 88-05-1 2,4,6-trimethylaniline 
• 74-88-4 methyl iodide 
• 7647-01-0 hydrogenchloride 
• 64-19-7 acetic acid 
• 124-38-9 carbon dioxide 
• 64-18-6 formic acid 
• 32884-91-6 N,N-dimethyl-O-tosylhydroxylamine 
• 108-67-8 1,3,5-trimethyl-benzene 
• 40751-99-3 N-oxyde de dimethylmesidine 

Downstream Products

• 155671-06-0 2,4,6,N-tetramethyl-N-nitroso-aniline 
• 40751-99-3 N-oxyde de dimethylmesidine 
• 86893-66-5 2-{[Methyl-(2,4,6-trimethyl-phenyl)-amino]-methyl}-cyclohexanone 
• 86893-71-2 C₂₃H₃₃NO₂ 
• 1783-02-4 2,4,6-trimethyl-4-nitrocyclohexa-2,5-dien-1-one 
• 76641-15-1 C₁₁H₁₇N₂O₂⁽¹⁺⁾*F₆P^(1-) 
• 76641-14-0 Dimethyl-(2,4,6-trimethyl-4-nitro-cyclohexa-2,5-dienylidene)-ammonium 
• 86893-68-7 2-{[Methyl-(2,4,6-trimethyl-phenyl)-amino]-methyl}-cyclopentanone 
• 86893-72-3 C₂₁H₂₉NO₂ 
• 250650-88-5 dimethyl-(2,4,6-trimethyl-3-nitro-phenyl)-amine 
• 527-60-6 Mesitol 
• 2819-86-5 pentamethylphenol 
• 488-71-1 2,3,4,6-tetramethylaniline 
• 88-05-1 2,4,6-trimethylaniline 

Relevant academic research and scientific papers

Aminomethylation of Aryl Bromides by Nickel-Catalyzed Electrochemical Redox Neutral Cross Coupling

We develop an electrochemical nickel-catalyzed aminomethylation of aryl bromides under mild conditions. The convergent paired electrolysis makes full use of anode and cathode processes, free of a terminal oxidant, a sacrificial anode, a metal reductant, and a prefunctionalized radical precursor. In addition, this method exhibits wide functional group tolerance (63 examples), including some sensitive substituents and aromatic heterocycles. This redox neutral cross coupling provides a more environmentally friendly and synthetic practical protocol for forging C(sp2)–C(sp3) bonds.

A Metal-Free Direct Arene C?H Amination

The synthesis of aryl amines via the formation of a C?N bond is an essential tool for the preparation of functional materials, active pharmaceutical ingredients and bioactive products. Usually, this chemical connection is only possible by transition metal-catalyzed reactions, photochemistry or electrochemistry. Here, we report a metal-free arene C?H amination using hydroxylamine derivatives under benign conditions. A charge transfer interaction between the aminating reagents TsONHR and the arene substrates enables the chemoselective amination of the arene, even in the presence of various functional groups. Oxygen was crucial for an effective conversion and its accelerating role for the electron transfer step was proven experimentally. In addition, this was rationalized by a theoretical study which indicated the involvement of a dioxygen-bridged complex with a “Sandwich-like” arrangement of the aromatic starting materials and the aminating agents at the dioxygen molecule. (Figure presented.).

Selective formylation or methylation of amines using carbon dioxide catalysed by a rhodium perimidine-based NHC complex

Carbon dioxide can play a vital role as a sustainable feedstock for chemical synthesis. To be viable, the employed protocol should be as mild as possible. Herein we report a methodology to incorporate CO2 into primary, secondary, aromatic or alkyl amines catalysed by a Rh(i) complex bearing a perimidine-based NHC/phosphine pincer ligand. The periminide-based ligand belongs to a class of 6-membered NHC ligand accessed through chelate-assisted double C-H activation. N-Formylation and -methylation of amines were performed using a balloon of CO2, and phenylsilane as the reducing agent. Product selectivity between formylated and methylated products was tuned by changing the solvent, reaction temperature and the quantity of phenylsilane used. Medium to excellent conversions, as well as tolerance to a range of functional groups, were achieved. Stoichiometric reactions with reactants employed in catalysis and time course studies suggested that formylation and methylation reactions of interest begin with hydrosilylation of CO2 followed by reaction with amine substrates.

Expedient Synthesis of N-Methyl- and N-Alkylamines by Reductive Amination using Reusable Cobalt Oxide Nanoparticles

N-Methyl- and N-alkylamines represent important fine and bulk chemicals that are extensively used in both academic research and industrial production. Notably, these structural motifs are found in a large number of life-science molecules and play vital roles in regulating their activities. Therefore, the development of convenient and cost-effective methods for the synthesis and functionalization of amines by using earth-abundant metal-based catalysts is of scientific interest. In this regard, herein we report an expedient reductive amination process for the selective synthesis of N-methylated and N-alkylated amines by using nitrogen-doped, graphene-activated nanoscale Co3O4-based catalysts. Starting from inexpensive and easily accessible nitroarenes or amines and aqueous formaldehyde or aldehydes in the presence of formic acid, this cost-efficient reductive amination protocol allows the synthesis of various N-methyl- and N-alkylamines, amino acid derivatives, and existing drug molecules.

Diverse catalytic reactivity of a dearomatized PN3P?-nickel hydride pincer complex towards CO2 reduction

A dearomatized PN3P?-nickel hydride complex has been prepared using an oxidative addition process. The first nickel-catalyzed hydrosilylation of CO2 to methanol has been achieved, with unprecedented turnover numbers. Selective methylation and formylation of amines with CO2 were demonstrated by such a PN3P?-nickel hydride complex, highlighting its versatile functions in CO2 reduction.

Preparation method by using amine and imine nitrogen methylation and application thereof

The invention discloses a preparation method by using amine and imine nitrogen methylation and application thereof. The preparation method comprises the following steps: A, adding an active carbon loaded platinum catalyst into a Schlenk tube, and after vacuumizing to replace argon, adding a solvent; B, under protection of argon, separately adding phenylsilane, an initial raw material and formic acid; C, stirring the whole reaction system at a certain temperature to react; and D, after reaction, adding ethyl acetate into the system to dilute, stopping the reaction by using a sodium hydroxide aqueous solution, performing extraction with ethyl acetate, separating out an organic phase, drying and filtering the organic phase, and performing rotatable evaporation to remove the solvent. Column chromatography is performed on residues by using ethyl acetate/petroleum ether mixed solvent to obtain a target product, wherein the ethyl acetate and petroleum ether are different in proportion. According to the application of the method in isotope labeled drug synthesis, the dosage of a catalyst is extremely low, the cost is quite low, and the method is suitable for large-scaled production, can be suitable for amine and imine with different substituents, and suitable for realizing methylation conveniently on nitrogen atoms in a natural product structure to prepare drug molecules.

Methylation of aromatic amines and imines using formic acid over a heterogeneous Pt/C catalyst

We describe here a commercially available Pt/C catalyst capable of catalyzing the methylation of anilines and aromatic imines with formic acid in the presence of a hydrosilane reductant. Both primary aniline and secondary aniline can be methylated. The advantage of this newly described method includes operational simplicity, high TON, ready availability of the catalyst, and also good functional group compatibility.

Synthesis and characterization of 2-[Mes(Me)NCH2]C6H4Br and 2-[Mes{(O)CH}NCH2]C6H4Br - Precursors for novel one pendant arm ligands

A new secondary amine 2-(MesNHCH2)C6H4Br (2) was synthesized starting from imine 2-(MesN=CH)C6H4Br (1) and NaBH4. Reaction of 2 with paraformaldehyde and HC(O)OH gave almost quantitatively 2-[Mes(Me)NCH2]C6H4Br (3), while treatment of 2 with paraformaldehyde and CH3C(O)OH resulted in 3 as a major product besides a minor amount of the unexpected 2-[Mes{(O)CH}NCH2]C6H4Br (4) compound. The compounds were characterized by multinuclear NMR and IR spectroscopy, mass spectrometry and the molecular structure of 4 was established by single-crystal X-ray diffraction.

Boron-Catalyzed N-Alkylation of Amines using Carboxylic Acids

A boron-based catalyst was found to catalyze the straightforward alkylation of amines with readily available carboxylic acids in the presence of silane as the reducing agent. Various types of primary and secondary amines can be smoothly alkylated with good selectivity and good functional-group compatibility. This metal-free amine alkylation was successfully applied to the synthesis of three commercial medicinal compounds, Butenafine, Cinacalcet. and Piribedil, in a one-pot manner without using any metal catalysts.

METHOD FOR THE METHYLATION OF NITROGEN-CONTAINING ORGANIC COMPOUNDS

A method for the methylation of amines, amides and imines comprises the step of reacting these compounds with CO2 and H2 in the presence of a Ruthenium-phosphine complex.