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 
• 104-82-5 4-Methylbenzyl chloride 
• 62-53-3 aniline 
• 104-81-4 4-Methylbenzyl bromide 
• 75366-05-1 3-methylbicyclo<4.1.0>hepta-1,3,5-triene 
• 15935-96-3 2-Amino-1,8-naphthyridine-3-carboxamide 
• 33542-68-6 N-Phenyl-N-p-methylbenzylformamid 
• 2437-33-4 4-chlorobenzolsulfonsaeure-phenylester 
• 104-84-7 para-methylbenzylamine 
• 640-60-8 toluene-4-sulfonic acid phenyl ester 
• 4358-63-8 phenyl benzenesulfonate 
• 32337-46-5 Phenyl p-nitrobenzenesulphonate 
• 1613-98-5 (E)-N-phenyl-1-(p-tolyl)methanimine 
• 589-18-4 4-Methylbenzyl alcohol 

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 
• 59852-99-2 dimethyl (4-methylphenyl)(N-phenylamino)methylphosphonate 

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.

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.

Reductive Alkylation of Azides and Nitroarenes with Alcohols: A Selective Route to Mono- And Dialkylated Amines

Herein, we demonstrated an efficient protocol for reductive alkylation of azides/nitro compounds via a borrowing hydrogen (BH) method. By following this protocol, selective mono- and dialkylated amines were obtained under mild and solvent-free conditions. A series of control experiments and deuterium-labeling experiments were performed to understand this catalytic process. Mechanistic studies suggested that the Ir(III)-H was the active intermediate in this reaction. KIE study revealed that the breaking of the C-H bond of alcohol might be the rate-limiting step. Notably, this solvent-free strategy disclosed a high TON of around 5600. Based on kinetic studies and control experiments, a metal-ligand cooperative mechanism was proposed.

Ru(II)-NHC catalysed N-Alkylation of amines with alcohols under solvent-free conditions

The reaction of [RuCl2(p-cymene)]2 with in situ prepared Ag-N-heterocyclic carbene (NHC) complexes yields a series of [RuCl2(p-cymene)(NHC)] complexes (2). All of the complexes have been characterised by elemental analysis, and 1H NMR and 13C NMR spectroscopies. These complexes have been tested for the N-alkylation of aromatic amines with arylmethyl alcohols under neat conditions in the presence of KOtBu at 120 °C. Compounds (2) are stable and have high catalytic/selective activity for the N-alkylation reactions of primary amines to afford secondary amines.

Half-sandwich Ru(ii) arene complexes bearing benzimidazole ligands for theN-alkylation reaction of aniline with alcohols in a solvent-free medium

In this article, the directN-alkylation reactions of amines with alcohol derivatives using the borrowing hydrogen methodology have been investigated. For this purpose, a new series of half-sandwich ruthenium(ii) complexes bearing N-coordinated benzimidazole complexes have been synthesized and fully characterized by FT-IR,1H NMR and13C NMR spectroscopies. Additionally, the structures of the complexes2a-2ehave been characterized by X-ray crystallography. All new complexes were investigated for their catalytic activities in the alkylation reaction of amines with alcohol derivatives. It was found that alkylation reactions in a solvent-free medium are efficient and selective.

Amino-functionalized zirconium and cerium MOFs: Catalysts for visible light induced aerobic oxidation of benzylic alcohols and microwaves assisted N-Alkylation of amines

Herein we report that mixed zirconium-cerium-MOFs with amino-functionalized linkers (2-amino-1,4-benzenedicarboxylate, BDC-NH2, and 4-aminonaphthalene-2,6-dicarboxylate, NDC-NH2) act as effective non-noble-metal-based heterogeneous c

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.