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 
• 104-87-0 4-methyl-benzaldehyde 
• 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 
• 1613-98-5 (E)-N-phenyl-1-(p-tolyl)methanimine 
• 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 

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 
• 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 
• 1618670-79-3 N-(4-methylbenzyl)-N-(3-phenylprop-2-ynyl)aniline 
• 24667-94-5 2-(4-methylphenyl)quinoline 
• 64101-91-3 2-(4-methylphenyl)-2-(phenylamino)acetonitrile 

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.

BF3·Et2O as a metal-free catalyst for direct reductive amination of aldehydes with amines using formic acid as a reductant

A versatile metal- and base-free direct reductive amination of aldehydes with amines using formic acid as a reductant under the catalysis of inexpensive BF3·Et2O has been developed. A wide range of primary and secondary amines and diversely substituted aldehydes are compatible with this transformation, allowing facile access to various secondary and tertiary amines in high yields with wide functional group tolerance. Moreover, the method is convenient for the late-stage functionalization of bioactive compounds and preparation of commercialized drug molecules and biologically relevant N-heterocycles. The procedure has the advantages of simple operation and workup and easy scale-up, and does not require dry conditions, an inert atmosphere or a water scavenger. Mechanistic studies reveal the involvement of imine activation by BF3and hydride transfer from formic acid.

A simple method for the reduction of Schiff bases using biosynthesized nickel oxide nanoparticles

An innovative and simple approach for the reduction of aldimines to the corresponding secondary amines was described using biosynthesized nickel oxide nanoparticles as heterogeneous catalyst and ammonium formate as the hydrogen donor. This catalytic trans

Hydrosilylation and Mukaiyama aldol-type reaction of quinolines and hydrosilylation of imines catalyzed by a mesoionic carbene-stabilized borenium ion

Aldimines and ketimines containing electron-donating and electron-withdrawing groups can be hydrosilylated with borenium catalysts at as low as 1 mol% catalyst loading at room temperature, providing the corresponding secondary amines in excellent yields. Reactions with 2-phenylquinoline gave the 1,4-hydrosilylquinoline product selectively which can be further functionalized in a one-pot synthesis to give unique γ-amino alcohol derivatives. Control experiments suggest that the borenium ion catalyzes both the hydrosilylation and subsequent addition to the aldehyde.

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.