39253-43-5

Usage

Uses

Used in Organic Synthesis:
N-(4-Methoxyphenyl)-4-methylbenzenamine is utilized as a building block in the field of organic synthesis. It serves as a key component for the creation of more complex chemical structures, contributing to the development of various chemical products.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, N-(4-Methoxyphenyl)-4-methylbenzenamine is used as an intermediate in the synthesis of certain drugs. Its unique structure allows for the formation of new compounds with potential therapeutic applications.
Used in Chemical Research:
N-(4-Methoxyphenyl)-4-methylbenzenamine is also employed in chemical research as a model compound for studying the properties and reactions of aromatic amines. This helps in understanding the behavior of similar compounds and their potential applications in various fields.

InChI:InChI=1/C14H15NO/c1-11-3-5-12(6-4-11)15-13-7-9-14(16-2)10-8-13/h3-10,15H,1-2H3

Upstream product

• 696-62-8 para-iodoanisole 
• 623-10-9 N-(4-methylphenyl)hydroxylamine 
• 100-66-3 methoxybenzene 
• 2101-86-2 p-methylazidobenzene 
• 623-12-1 4-chloromethoxybenzene 
• 106-49-0 p-toluidine 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 66107-29-7 4-methoxyphenyl triflate 
• 106-43-4 para-chlorotoluene 
• 104-94-9 4-methoxy-aniline 
• 106-38-7 para-bromotoluene 
• 384842-24-4 dicyclohexyl(1,1-diphenyl-1-propen-2-yl)phosphine 
• 5720-07-0 4-methoxyphenylboronic acid 
• 62-53-3 aniline 

Downstream Products

• 5257-08-9 3-methyl-6-hydroxycarbazol 
• 18440-54-5 N-(4-Methylphenyl)-1,4-benzoquinone monoimine 
• 59919-04-9 4-methoxy-N-methyl-N-(p-tolyl)aniline 
• 1378973-60-4 (E)-N-(1,3-diphenylallyl)-4-methoxy-N-p-tolylaniline 
• 1357929-84-0 C₈₁H₆₈N₄O₄ 
• 1357929-95-3 C₅₂H₇₂N₂O₆Si₆ 

Relevant academic research and scientific papers

Transition metals in organic synthesis, part 82.1 First total synthesis of methyl 6-methoxycarbazole-3-carboxylate, glycomaurrol, the anti-TB active micromeline, and the furo[2,3-c]carbazole alkaloid eustifoline-D

The palladium(0)-catalyzed animation followed by palladium(II)-catalyzed oxidative cyclization of the resulting diarylamine provides a short route to a series of 6-oxygenated carbazole alkaloids: glycozoline, 3-formyl-6- methoxycarbazole, methyl 6-methoxy

Cu(I)–N-heterocyclic carbene-catalyzed base free C–N bond formation of arylboronic acids with amines and azoles

A new N-heterocyclic carbene (NHC) precursor of imidazolium chloride and its corresponding Cu(I)–NHC complex 1 was synthesized. The complex 1 was found to be a highly effective catalyst for Chan-Evans-Lam coupling of arylboronic acid with amines and azoles (including imidazole, pyrazole and triazole), without addition of base at room temperature. Various substituents on three substrates can be tolerated, giving the desired coupling products in good to excellent yields (62–94%). The method is practical and offers an alternative to the corresponding copper-catalyzed Chan-Evans-Lam process for the construction of C–N bonds.

(DiMeIHeptCl)Pd: A Low-Load Catalyst for Solvent-Free (Melt) Amination

(DiMeIHeptCl)Pd, a hyper-branched N-aryl Pd NHC catalyst, has been shown to be efficient at performing amine arylation reactions in solvent-free ("melt") conditions. The highly lipophilic environment of the alkyl chains flanking the Pd center serves as lubricant to allow the complex to navigate through the paste-like environment of these mixtures. The protocol can be used on a multi-gram scale to make a variety of aniline derivatives, including substrates containing alcohol moieties.

Visible-Light- And PPh3-Mediated Direct C-N Coupling of Nitroarenes and Boronic Acids at Ambient Temperature

We present here a metal-free, visible-light- and triphenylphosphine-mediated intermolecular, reductive amination between nitroarenes and boronic acids at ambient temperature without any photocatalyst. Mechanistically, a slow reduction of nitroarenes to a nitroso and, finally, a nitrene intermediate occurs that leads to the amination product with concomitant 1,2-aryl/-alkyl migration from a boronate complex. A wide range of nitroarenes underwent C-N coupling with aryl-/alkylboronic acids providing high yields.

Electrochemical Reductive Arylation of Nitroarenes with Arylboronic Acids

The synthesis of diarylamine is extremely important in organic chemistry. Herein, a novel electrochemical reductive arylation of nitroarenes with arylboronic acids was developed. A variety of diarylamines were synthesized without the need for transition-metal catalysts. The reaction could be scaled up efficiently in a flow cell and several derivatization reactions were carried out smoothly. Cyclic voltammetry experiments and mechanism studies showed that acetonitrile, formic acid, and triethyl phosphite all played a role in promoting this reductive arylation transformation.

Preparation method of secondary aromatic amine

The invention provides a method for preparing secondary aromatic amine by performing a palladium-catalyzed C-N coupling reaction on (pseudo)aryl halide and (pseudo)heterocyclic aryl halide and primary(heterocyclic)aromatic amine. The method is characterized in that an alkali for promoting the reaction is an alkali metal carboxylate or an alkali metal bicarbonate.

Copper complexes of 1,4-diazabutadiene ligands: Tuning of metal oxidation state and, application in catalytic C-C and C-N bond formation

Reaction of 1,4-diazabutadiene (p-RC6H4N = C(H)(H)C = NC6H4R-p; R = OCH3, CH3, H and Cl; abbreviated as L-R) with CuCl2·2H2O in methanol at ambient temperature (25 °C) affords a group of doubly chloro-bridged dicopper complexes of type [{CuI(L-R)Cl}2], designated as 1-R. Similar reaction carried out in acetonitrile furnishes a family of doubly chloro-bridged dicopper complexes of type [{CuII(L-R)Cl2}2], designated as 2-R. Molecular structures of 1-OCH3 and 2-OCH3 have been determined by X-ray crystallography. While copper(I) is having a nearly tetrahedral N2Cl2 coordination sphere in 1-OCH3, the N2Cl3 coordination sphere around copper(II) is distorted square pyramidal in nature in 2-OCH3. Isolated 2-R complexes, on dissolution in methanol, are found to undergo facile reduction of the metal center to generate the corresponding 1-R complexes. The 1-R and 2-R complexes show intense absorptions in the visible and ultraviolet regions. Cyclic voltammetry on the 1-R and 2-R complexes shows both metal-centered and ligand centered redox responses. The 1-R complexes are found to efficiently catalyze C-N cross-coupling reactions between arylboronic acids and aryl amines; while the 2-R complexes display notable catalytic efficiency for nitroaldol reactions.

Synthesis and characterization of new square planar heteroleptic cationic complexes [Ni(ii) β-oxodithioester-dppe]+; Their use as a catalyst for Chan-Lam coupling

Novel heteroleptic [Ni(ii) β-oxodithioester-dppe]+PF6- complexes (β-oxodithioester = methyl-3-hydroxy-3-benzyl-2-propenedithioate L1 1, methyl-3-hydroxy-3-(p-methoxyphenyl)-2-propenedithioate L2 2, methyl-3-hydroxy-3-(naphthyl)-2-propenedithioate L3 3, methyl-3-hydroxy-3-(p-chlorophenyl)-2-propenedithioate L4 4, methyl-3-hydroxy-3-(p-bromophenyl)-2-propenedithioate L5 5 and methyl-3-hydroxy-3-(p-cyanophenyl)-2-propenedithioate L6 6) have been synthesized and characterized by elemental (C, H, N) analysis, ESI-MS, IR, UV-visible, 1H, 13C{1H}, 31P{1H} and 19F{1H} NMR spectroscopy. The distorted square planar structures of the isomorphous cationic complexes 2, 3, 4 and 5 have been determined by X-ray crystallography. The catalytic activities of 1-6 were investigated for the Chan-Lam coupling reaction involving arylboronic acids and amines to afford N-arylated products in good to excellent yields under mild conditions with 1 mol% catalyst loading. This catalytic protocol offers significant functional group tolerance, and is endowed with a broad substrate scope. This journal is

Activator-Promoted Aryl Halide-Dependent Chemoselective Buchwald-Hartwig and Suzuki-Miyaura Type Cross-Coupling Reactions

Herein, we report the development of aryl halide-dependent chemoselective reactions, viz., the Buchwald-Hartwig type coupling reaction of an aryl iodide with an arylboronic acid and an aryl amine in the presence of a heterogeneous and reusable nickel catalyst and the Suzuki-Miyaura type coupling of an aryl chloride under similar conditions. Control experiments revealed that the presence of stoichiometric amounts of the phenylboronic acid/ester and aryl amine are essential for both reactions. NMR and XAFS studies suggested the formation of a boron-amine "ate"complex.

Continuous Synthesis of Aryl Amines from Phenols Utilizing Integrated Packed-Bed Flow Systems

Aryl amines are important pharmaceutical intermediates among other numerous applications. Herein, an environmentally benign route and novel approach to aryl amine synthesis using dehydrative amination of phenols with amines and styrene under continuous-flow conditions was developed. Inexpensive and readily available phenols were efficiently converted into the corresponding aryl amines, with small amounts of easily removable co-products (i.e., H2O and alkanes), in multistep continuous-flow reactors in the presence of heterogeneous Pd catalysts. The high product selectivity and functional-group tolerance of this method allowed aryl amines with diverse functional groups to be selectively obtained in high yields over a continuous operation time of one week.