10386-93-3

Usage

Uses

Used in Chemical Synthesis:
N-cyclohexyl-4-methylaniline is used as an intermediate in the synthesis of various organic compounds, including dyes, pigments, and pharmaceuticals. Its unique structure allows it to serve as a building block for the creation of a wide range of products that have different applications across industries.
Used in Corrosion Inhibition:
In the oil and gas industry, N-cyclohexyl-4-methylaniline is utilized as a corrosion inhibitor. Its properties enable it to protect metal surfaces from corrosion, which is crucial for maintaining the integrity and longevity of pipelines and other equipment used in these sectors.
Used in Pharmaceutical Development:
Due to its chemical structure, N-cyclohexyl-4-methylaniline is also used in the development of pharmaceuticals. It can be a component in the synthesis of drugs that target specific biological pathways or serve as active pharmaceutical ingredients themselves.
Used in Dye and Pigment Production:
N-cyclohexyl-4-methylaniline is employed in the production of dyes and pigments, where its chemical properties contribute to the color and stability of these products. This makes it valuable in industries such as textiles, plastics, and printing inks, where colorants are essential for product quality and performance.

Upstream product

• 108-94-1 cyclohexanone 
• 106-49-0 p-toluidine 
• 108-85-0 1-bromocyclohexane 
• 5720-05-8 4-methylphenylboronic acid 
• 108-91-8 cyclohexylamine 
• 352-32-9 p-fluorotoluene 
• 3899-96-5 4-methylphenyl tosylate 
• 99-99-0 1-methyl-4-nitrobenzene 
• 108-95-2 phenol 
• 106-44-5 p-cresol 
• 98-89-5 Cyclohexanecarboxylic acid 
• 17797-15-8 1-(p-Tolyl)-cyclohexylamin 
• 106-48-9 4-chloro-phenol 
• 106-41-2 4-bromo-phenol 

Downstream Products

• 1451061-04-3 1-cyclohexyl-5-methylindoline-2,3-dione 
• 865288-85-3 N-cyclohexyl-2-iodo-4-methylaniline 
• 87261-67-4 2-[(N-cyclohexyl-4-methylanilino)methyl]-4,5-dihydro-1H-imidazole 

Relevant academic research and scientific papers

Efficient protocol for reductive amination of aldehydes and ketones with sodium borohydride in an ionic liquid/H2O system

The imines were generated in situ from carbonyl compounds and amines, which undergo smooth reduction with sodium borohydride in an ionic liquid/H 2O solvent system. The reaction conditions were very mild and neutral to afford the corresponding highly functionalized amines in excellent yields. Copyright Taylor & Francis Group, LLC.

Glycerol ingrained copper: An efficient recyclable catalyst for the N-arylation of amines with aryl halides

A copper-catalyzed coupling reaction of aryl halides with various aromatic and cyclic amines by using glycerol as a green recyclable solvent has been developed efficiently. The glycerol embedded copper catalyst could readily be separated from the reaction mixture and reused for several runs without any loss in catalytic efficiency.

USE OF HEXAMETHYLPHOSPHORAMIDE (HMPA) IN THE ALKYLATION OF AROMATIC AMINES

The convenience of using HMPA as solvent in the mono and dialkylation of anilines was demonstrated through the study of the reaction of p-toluidine with alkyl halides, tosylates and epoxides.

Buchwald-Hartwig amination using Pd(i) dimer precatalysts supported by biaryl phosphine ligands

We report the synthesis of air-stable Pd(i) dimer complexes featuring biaryl phosphine ligands. Catalytic experiments suggest that these complexes are competent precatalysts that can mediate cross-coupling amination reactions between aryl halides with bot

Nickel(II) complex covalently anchored on core shell structured SiO2@Fe3O4 nanoparticles: A robust and magnetically retrievable catalyst for direct one-pot reductive amination of ketones

A robust and efficient core shell structured magnetically retrievable nickel nanocatalytic system was fabricated via the covalent immobilization of 2-acetyl furan on the surface of an amine functionalized silica coated magnetic nanosupport followed by its metallation with nickel acetate. The newly synthesized magnetic silica based organic-inorganic hybrid nanocatalyst (Ni-ACF@Am-SiO2@Fe3O4) was systematically affirmed using several physico-chemical characterization tools such as FT-IR, XRD, VSM, SEM, TEM, EDS, ED-XRF and AAS. Thereafter, the catalytic performance of this Ni-ACF@Am-SiO2@Fe3O4 nanocatalyst was investigated in the one-pot reductive amination of ketones using NaBH4 as the reductant under neat conditions. The developed core shell magnetic silica based nickel nanocatalyst successfully afforded a structurally diverse range of secondary amines with high turnover frequency (TOF) and excellent conversion percentage. Additionally, it was found that this catalyst could not only be retrieved from the reaction vessel within a fraction of seconds using an external magnet but also be recycled for multiple runs without any discernible loss in its activity that rendered this protocol superior to all the previously established methodologies for the one-pot synthesis of substituted amines. Besides, some of the other fascinating features of this methodology that made it a potential candidate for addressing various economic and environmental concerns were ambient reaction conditions, broad substrate scope, simple workup procedure, shorter reaction time and cost effectiveness.

A new efficient palladium catalyst for the amination of aryl chlorides

A highly active catalyst for the Buchwald-Hartwig amination has been developed. The new catalyst, a combination of a dimethylaminomethyl ferrocene palladacycle and bis(2-nor-bornyl)phosphine shows high activity and broad scope for the coupling of non- or deactivated aryl chlorides with primary and secondary amines as well as (hindered) anilines.

Catalytic Amination of Phenols with Amines

Given the wide prevalence and ready availability of both phenols and amines, aniline synthesis through direct coupling between these starting materials would be extremely attractive. Herein, we describe a rhodium-catalyzed amination of phenols, which provides concise access to diverse anilines, with water as the sole byproduct. The arenophilic rhodium catalyst facilitates the inherently difficult keto–enol tautomerization of phenols by means of π-coordination, allowing for the subsequent dehydrative condensation with amines. We demonstrate the generality of this redox-neutral catalysis by carrying out reactions of a large array of phenols with various electronic properties and a wide variety of primary and secondary amines. Several examples of late-stage functionalization of structurally complex bioactive molecules, including pharmaceuticals, further illustrate the potential broad utility of the method.

Porous polymeric ligand promoted copper-catalyzed C-N coupling of (hetero)aryl chlorides under visible-light irradiation

A porous polymeric ligand (PPL) has been synthesized and complexed with copper to generate a heterogeneous catalyst (Cu@PPL) that has facilitated the efficient C-N coupling with various (hetero)aryl chlorides under mild conditions of visible-light irradiation at 80 °C (58 examples, up to 99% yields). This method could be applied to both aqueous ammonia and substituted amines, and is compatible to a variety of functional groups and heterocycles, as well as allows tandem C-N couplings with conjunctive dihalides. Furthermore, the heterogeneous characteristic of Cu@PPL has enabled a straightforward catalyst separation in multiple times of recycling with negligible catalytic efficiency loss by simple filtration, affording reaction mixtures containing less than 1 ppm of Cu residue. [Figure not available: see fulltext.]

Visible-Light-Enabled Direct Decarboxylative N-Alkylation

The development of efficient and selective C?N bond-forming reactions from abundant feedstock chemicals remains a central theme in organic chemistry owing to the key roles of amines in synthesis, drug discovery, and materials science. Herein, we present a dual catalytic system for the N-alkylation of diverse aromatic carbocyclic and heterocyclic amines directly with carboxylic acids, by-passing their preactivation as redox-active esters. The reaction, which is enabled by visible-light-driven, acridine-catalyzed decarboxylation, provides access to N-alkylated secondary and tertiary anilines and N-heterocycles. Additional examples, including double alkylation, the installation of metabolically robust deuterated methyl groups, and tandem ring formation, further demonstrate the potential of the direct decarboxylative alkylation (DDA) reaction.

Oxalic amide ligands, and uses thereof in copper-catalyzed coupling reaction of aryl halides

The present invention provides oxalic amide ligands and uses thereof in copper-catalyzed coupling reaction of aryl halides. Specifically, the present invention provides a use of a compound represented by formula I, wherein definitions of each group are described in the specification. The compound represented by formula I can be used as a ligand in copper-catalyzed coupling reaction of aryl halides for the formation of C—N, C—O and C—S bonds.