15818-64-1

Usage

Uses

Used in Pharmaceutical Industry:
N-[(4-methylphenyl)methyl]aniline serves as a crucial intermediate in the synthesis of pharmaceuticals, contributing to the development of new medications that address a range of health conditions. Its chemical properties make it a valuable component in the creation of active pharmaceutical ingredients.
Used in Agrochemical Industry:
In the agrochemical sector, N-[(4-methylphenyl)methyl]aniline is utilized as an intermediate in the production of various agrochemicals, including pesticides and herbicides. Its role in these applications is essential for enhancing crop protection and agricultural productivity.
Used in Dye and Pigment Production:
N-[(4-methylphenyl)methyl]aniline also finds application in the manufacturing of dyes and pigments, where it is used to produce a wide array of colors for use in various industries, such as textiles, plastics, and printing inks. Its versatility in color production is a testament to its importance in these industries.
Given the compound's slight toxicity and potential for environmental harm, it is imperative that it is handled with care to minimize risks to both human health and the environment. Proper safety measures and disposal methods should be strictly adhered to in all applications of N-[(4-methylphenyl)methyl]aniline.

InChI:InChI=1/C14H15N/c1-12-7-9-13(10-8-12)11-15-14-5-3-2-4-6-14/h2-10,15H,11H2,1H3

Upstream product

• 2362-77-8 (4-methylbenzylidene)phenylamine 
• 104-87-0 4-methyl-benzaldehyde 
• 62-53-3 aniline 
• 104-81-4 4-Methylbenzyl bromide 
• 75366-05-1 3-methylbicyclo<4.1.0>hepta-1,3,5-triene 
• 33542-68-6 N-Phenyl-N-p-methylbenzylformamid 
• 1613-98-5 (E)-N-phenyl-1-(p-tolyl)methanimine 
• 589-18-4 4-Methylbenzyl alcohol 
• 617-86-7 triethylsilane 
• 97-93-8 triethylaluminum 
• 762-72-1 allyl-trimethyl-silane 
• 100-52-7 benzaldehyde 
• 108-90-7 chlorobenzene 
• 104-84-7 para-methylbenzylamine 

Downstream Products

• 2362-77-8 (4-methylbenzylidene)phenylamine 
• 104-87-0 4-methyl-benzaldehyde 
• 6833-18-7 4-methyl-N-phenylbenzamide 
• 99-94-5 p-Toluic acid 
• 108-88-3 toluene 
• 71-43-2 benzene 
• 890-29-9 (1H-indol-3-yl)(4-methylphenyl)methanone 
• 1415355-54-2 4-(4-fluorophenyl)-2-p-tolylquinoline 
• 676442-24-3 4-(4-tolyl)-2-(4-tolyl)quinoline 
• 1236-89-1 2-(4-methylphenyl)-4-phenylquinoline 
• 111978-56-4 N-benzyl-N-(4-methylbenzyl)aniline 
• 1438900-54-9 N⁴,N^4'-dibenzyl-N⁴,N^4'-bis(4-methylbenzyl)-[1,1'-biphenyl]-4,4'-diamine 
• 18818-41-2 2-(4-methylphenyl)-4(3H)-quinazolinone 
• 1618670-79-3 N-(4-methylbenzyl)-N-(3-phenylprop-2-ynyl)aniline 

Relevant academic research and scientific papers

Palladium(II) acetate-catalyzed reduction of imines to the corresponding amines by triethylsilane

Reduction of a variety of imine compounds with triethylsilane in the presence of catalytic amounts of palladium(II) acetate in ethanol resulted in the formation of the corresponding amines in excellent yields after short reaction times. Copyright

Complexes of Pd(II), 6-C6H6Ru(II), and 5-CpRh(III) with Chalcogenated Schiff Bases of Anthracene-9-carbaldehyde and Base-Free Catalytic Transfer Hydrogenation of Aldehydes/Ketones and N-Alkylation of Amines

The condensation of 2-(phenylsulfanyl)ethylamine and 2-(phenylselenyl)ethylamine with anthracene-9-carbaldehyde resulted in Schiff bases [PhS(CH2)2C-N-9-C14H9](L1) and [PhSe(CH2)2C-N-9-C14H9] (L2), respectively. Na2[PdCl4] treatment of L1/L2 in acetone-water mixture for 3 h at room temperature gave palladacycle [PdCl(C-, N, S/Se)] (1/2; L1/L2-H = (C-, N, S)/(C-, N, Se)). The reaction of [(6-C6H6)RuCl(μ-Cl)]2 with L1/L2 in methanol for 8 h at room temperature (followed by addition of NH4PF6) afforded half-sandwich complex [(6-C6H6)Ru(L)Cl][PF6], 3/4: (L = L1/L2 - (N, E) ligand). The reaction of [(5-Cp)RhCl(μ-Cl)]2 with L1 /L2 in the presence of CH3COONa at 50 °C (followed by treatment with NH4PF6) resulted in [(5-Cp)Rh(L-H)][PF6], 5/6: (L = L1/L2). On carrying out the reaction of [(5-Cp)RhCl(μ-Cl)]2 with these ligands at room temperature and in the absence of CH3COONa, complex [(5-Cp)Rh(L)Cl][PF6], 7/8 (L = L1/L2 - (N, E) ligand), was formed. Complexes 1-8 were authenticated with 1H, 13C{1H}, and 77Se{1H} NMR spectroscopy, high-resolution mass spectrometry, elemental analyses, and single-crystal X-ray diffraction. The moisture- And air-insensitive complexes of Pd(II) (1, 2), Ru(II) (3, 4) and Rh(III) (5-8) were thermally stable. Palladium and rhodium (under base-free condition) species efficiently catalyzed transfer hydrogenation (propan-2-ol as H-source). At room temperature conversion was 90% in TH catalyzed with 0.2 mol % of 2. N-Alkylation of aniline with benzyl alcohol under base-free condition was promoted by 3-8. The 7 was most efficient for the two base-free catalytic reactions. For TH optimum loading of 1-2 and 5-8 as catalyst is 0.05-0.2 and 0.2-0.5 mol % respectively. The optimum temperatures are 80 and 100 °C for TH and N-alkylation, respectively. The optimum loading of 3-8 for N-alkylation is 0.5 mol %. Mercury poisoning test supported homogeneous pathway for the two catalytic reactions. The rhodacycles probably gave real catalytic species by losing a Cp? group.

Reusable Co-nanoparticles for general and selectiveN-alkylation of amines and ammonia with alcohols

A general cobalt-catalyzedN-alkylation of amines with alcohols by borrowing hydrogen methodology to prepare different kinds of amines is reported. The optimal catalyst for this transformation is prepared by pyrolysis of a specific templated material, which is generatedin situby mixing cobalt salts, nitrogen ligands and colloidal silica, and subsequent removal of silica. Applying this novel Co-nanoparticle-based material, >100 primary, secondary, and tertiary amines includingN-methylamines and selected drug molecules were conveniently prepared starting from inexpensive and easily accessible alcohols and amines or ammonia.

Cobalt encapsulated in N?doped graphene sheet for one-pot reductive amination to synthesize secondary amines

To develop an efficient base-metal reductive amination catalyst for synthesis of secondary amines is still a major challenge. In this study, an efficient N-doped graphene sheet-coated cobalt catalyst (Co@CN-800) was developed through a simple pyrolysis process, which could gave 99.5 % yield of N-benzylaniline by one-pot reductive amination of nitrobenzene with benzaldehyde during at least 5 cycles. Catalyst characterization and control experiments confirmed that the robust catalytic performance of the catalyst is probably due to the synergy effect of in situ generated Co-Nx encapsulated in N?doped graphene layer and appropriate meso-pore structure. Additionally, The substrate adaptability of the catalyst was proved since a variety of corresponding secondary amines were smoothly obtained under relatively mild conditions, which makes the secondary amine synthesis strategy based on Co@CN-800 shows excellent application prospect.

Tungsten-Catalyzed Direct N-Alkylation of Anilines with Alcohols

The implementation of non-noble metals mediated chemistry is a major goal in homogeneous catalysis. Borrowing hydrogen/hydrogen autotransfer (BH/HA) reaction, as a straightforward and sustainable synthetic method, has attracted considerable attention in the development of non-noble metal catalysts. Herein, we report a tungsten-catalyzed N-alkylation reaction of anilines with primary alcohols via BH/HA. This phosphine-free W(phen)(CO)4 (phen=1,10-phenthroline) system was demonstrated as a practical and easily accessible in-situ catalysis for a broad range of amines and alcohols (up to 49 examples, including 16 previously undisclosed products). Notably, this tungsten system can tolerate numerous functional groups, especially the challenging substrates with sterically hindered substituents, or heteroatoms. Mechanistic insights based on experimental and computational studies are also provided.

Silver/manganese dioxide nanorod catalyzed hydrogen-borrowing reactions and tert-butyl ester synthesis

Silver/manganese dioxide (Ag@MnO2) nanorods are synthesized and characterized by scanning electron microscopy, transmission electron microscopy, energy dispersive X-ray spectroscopy, X-ray powder diffraction, and X-ray photoelectron spectroscopy. It was discovered that Ag@MnO2 nanorods can realize hydrogen-borrowing reactions in high yields and are also effective for the synthesis of tert-butyl esters from aryl cyanides and tert-butyl hydroperoxide in a short period of time. Mechanistic experiments revealed that this catalytic system acts as a Lewis acid in hydrogen-borrowing reactions, while the synthesis of tert-butyl esters occurs through a radical pathway. This is the first report on the excellent catalytic activity of Ag@MnO2 nanorods as a catalyst.

Ruthenium(ii) complexes with N-heterocyclic carbene-phosphine ligands for theN-alkylation of amines with alcohols

Metal hydride complexes are key intermediates forN-alkylation of amines with alcohols by the borrowing hydrogen/hydrogen autotransfer (BH/HA) strategy. Reactivity tuning of metal hydride complexes could adjust the dehydrogenation of alcohols and the hydrogenation of imines. Herein we report ruthenium(ii) complexes with hetero-bidentate N-heterocyclic carbene (NHC)-phosphine ligands, which realize smart pathway selection in theN-alkylated reactionviareactivity tuning of [Ru-H] species by hetero-bidentate ligands. In particular, complex6cbwith a phenyl wingtip group and BArF?counter anion, is shown to be one of the most efficient pre-catalysts for this transformation (temperature is as low as 70 °C, neat conditions and catalyst loading is as low as 0.25 mol%). A large variety of (hetero)aromatic amines and primary alcohols were efficiently converted into mono-N-alkylated amines in good to excellent isolated yields. Notably, aliphatic amines, challenging methanol and diamines could also be transformed into the desired products. Detailed control experiments and density functional theory (DFT) calculations provide insights to understand the mechanism and the smart pathway selectionvia[Ru-H] species in this process.

Effect of the ancillary ligand in N-heterocyclic carbene iridium(III) catalyzed N-alkylation of amines with alcohols

A series of air-stable N-heterocyclic carbene (NHC) Ir(III) complexes (Ir1-6), bearing various combinations of chlorine, pyridine and NHC ligands, were assayed for the N-alkylation of amines with alcohols. It was found that Ir3, with two monodentate 1,3-bis-methyl-imidazolylidene (IMe) ligands, emerged as the most active complex. A large variety of amines and primary alcohols were efficiently converted into mono-N-alkylated amines in 53–96% yields. As a special highlight, for the challenging MeOH, selective N-monomethylation could be achieved using KOH as a base under an air atmosphere. Moreover, this catalytic system was successfully applied to the gram-scale synthesis of some valuable compounds.

Enhanced Hydride Donation Achieved Molybdenum Catalyzed Direct N-Alkylation of Anilines or Nitroarenes with Alcohols: From Computational Design to Experiment

An example of homogeneous Mo-catalyzed direct N-alkylation of anilines or nitroarenes with alcohols is presented. The DFT aimed design suggested the easily accessible bis-NHC-Mo(0) complex features a strong hydride-donating ability, achieving effective N-alkylation of anilines or challenging nitroarenes with alcohols. The enhanced hydride-donating strategy should be useful in designing highly active systems for borrowing hydrogen transformations.

Nickel?Copper bimetallic mesoporous nanoparticles: As an efficient heterogeneous catalyst for N-alkylation of amines with alcohols

A bimetallic catalyst (Ni/Cu-MCM-41) is prepared via co-condensation method. The latter is characterized by Fourier transform infrared (FT-IR), X-ray powder diffraction (XRD), scanning electron microscopy (SEM), energy dispersive X-ray spectroscopy (EDX), diffuse reflectance spectroscopy (DRS), and nitrogen adsorption–desorption analysis. Catalytic performance of Ni/Cu-MCM-41 is probed in N-alkylation of amines with alcohols through a hydrogen autotransfer process. Noteworthy, this catalytic system appears very efficient for synthesis of a range of secondary and tertiary amines in good to excellent isolated yields. Moreover, the catalyst is successfully recovered and reused four times without notable decrease in its activity.