13050-56-1

Basic information

• Product Name: Benzenamine, 4-methoxy-N,N-bis(4-methoxyphenyl)-
• Synonyms: 4,4',4''-trimethoxytriphenylamine;tri-p-methoxytriphenylamine
• CAS NO: 13050-56-1
• Molecular Formula: C21H21NO3
• Molecular Weight: 335.403
• Mol File: 13050-56-1.mol

Chemical Properties

• CAS DataBase Reference: Benzenamine, 4-methoxy-N,N-bis(4-methoxyphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenamine, 4-methoxy-N,N-bis(4-methoxyphenyl)-(13050-56-1)
• EPA Substance Registry System: Benzenamine, 4-methoxy-N,N-bis(4-methoxyphenyl)-(13050-56-1)

Safety Data

• Hazardous Substances Data: 13050-56-1(Hazardous Substances Data)

Usage

Uses

Used in Polymer Production:
Benzenamine, 4-methoxy-N,N-bis(4-methoxyphenyl)is used as a crosslinking agent in the production of polymers, particularly in the manufacturing of epoxy resins and coatings. Its crosslinking properties contribute to the improved strength, durability, and thermal stability of these materials.
Used in Dye Industry:
Benzenamine, 4-methoxy-N,N-bis(4-methoxyphenyl)is used as a dye intermediate, playing a significant role in the development of various dyes for different applications.
Used in Pharmaceutical Synthesis:
Benzenamine, 4-methoxy-N,N-bis(4-methoxyphenyl)is used as a component in the synthesis of pharmaceuticals, contributing to the development of new drugs and therapeutic agents.
Used in Agrochemical Synthesis:
Benzenamine, 4-methoxy-N,N-bis(4-methoxyphenyl)is also utilized in the synthesis of agrochemicals, aiding in the development of effective products for agricultural applications.
It is important to handle Benzenamine, 4-methoxy-N,N-bis(4-methoxyphenyl)with proper safety precautions and storage measures due to its potential toxicity and environmental hazards.

Upstream product

• 696-62-8 para-iodoanisole 
• 101-70-2 bis(4-methoxyphenyl)amine 
• 4316-58-9 tri(p-bromophenyl)amine 
• 77-78-1 dimethyl sulfate 
• 104-94-9 4-methoxy-aniline 
• 67-56-1 methanol 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 623-12-1 4-chloromethoxybenzene 
• 603-36-1 triphenylantimony 
• 108-90-7 chlorobenzene 
• 108-86-1 bromobenzene 
• 13716-12-6 tri-tert-butyl phosphine 

Downstream Products

• 56525-76-9 3,6-dimethoxy-9-(4-methoxyphenyl)-carbazole 
• 32338-00-4 tris(2-bromo-4-methoxyphenyl)amine 
• 1050521-40-8 C₃₇H₂₇N₃O₇S₂ 
• 1259383-70-4 C₃₃H₅₇NO₆Si₆ 
• 221171-37-5 4-[bis(4-methoxyphenyl)amino]phenol 

Relevant articles and documents

Syntheses and Redox Properties of Di-, Tri-, Tetra-, and Pentaamines

A series of di-, tri-, tetra-, and pentaamines were synthesized as precursors for corresponding di-, tri-, tetra-, and penta(aminium radical-cations) by the aryl-N bond formation reaction between aryl iodides and in situ prepared copper amide in refluxing pyridine.Cyclic voltammograms of meta-connected derivatives consisted of irreversible waves which imply side reactions in addition to oxidation to aminium radical-cations.

Synthesis and oxidation of di-, tri-, tetra-, and pentaamines

A series of di-, tri-, tetra-, and pentaamines were synthesized as precursors of corresponding aminium radical-cations. Redox properties of these amines were studied by cyclic voltammetry and aminium radical-cations obtained by chemical oxidation of these amines were investigated by ESR and UV-VIS spectroscopy.

A green and mild procedure to selective synthesis of diarylamine via domino reaction of aryl halides and arginine catalyzed by magnetic-MOF

Efficient and selective direct synthesis of diarylamines from aryl halides and arginine as a nitrogen-donor reagent is reported. Arginine, which is an oral supplement, acts as a useful nitrogen source donor in the copper-catalyzed reaction. Fe3O4/Cu3(BTC)2, which was easily separated and recycled with a magnet, improved the rate and facilitation of the synthesis of diarylamines selectively. The introduction of a new and available N-source, simple magnetic separation process, normal atmospheric conditions, and excellent yields under mild reaction conditions are other important features of this work.

Dye-sensitized electron transfer from TiO2 to oxidized triphenylamines that follows first-order kinetics

Two sensitizers, [Ru(bpy)2(dcb)]2+ (RuC) and [Ru(bpy)2(dpb)]2+ (RuP), where bpy is 2,2′-bipyridine, dcb is 4,4′-dicarboxylic acid-2,2′-bipyridine and dpb is 4,4′-diphosphonic acid-2,2′-bipyridine, were anchored to mesoporous TiO2 thin films and utilized to sensitize the reaction of TiO2 electrons with oxidized triphenylamines, TiO2(e-) + TPA+ → TiO2 + TPA, to visible light in CH3CN electrolytes. A family of four symmetrically substituted triphenylamines (TPAs) with formal Eo(TPA+/0) reduction potentials that spanned a 0.5 eV range was investigated. Surprisingly, the reaction followed first-order kinetics for two TPAs that provided the largest thermodynamic driving force. Such first-order reactivity indicates a strong Coulombic interaction between TPA+ and TiO2 that enables the injected electron to tunnel back in one concerted step. The kinetics for the other TPA derivatives were non-exponential and were modelled with the Kohlrausch-William-Watts (KWW) function. A Perrin-like reaction sphere model is proposed to rationalize the kinetic data. The activation energies were the same for all of the TPAs, within experimental error. The average rate constants were found to increase with the thermodynamic driving force, consistent with electron transfer in the Marcus normal region.

Arylation of aniline and amines by Pd-(N-Heterocyclic carbene) complexes

Aminoarenes constitute valuable building blocks in organic synthesis and an essential skeleton ubiquitously found in ligands, agrochemicals, and pharmaceuticals. This synopsis presents recent amination methods using nitrogen-heteroatom bonds as a powerful and versatile platform to rapidly synthesize diverse aminoarenes, with transition-metal catalyzed arene C-H amination. The Buchwald-Hartwig amination has been investigated theoretically and experimentally to examine the scope of possible bases under different reaction conditions. We report examples of the palladium NHC (N-heterocyclic carbene) catalyzed amination of aryl halides with anilines and amines in the presence of dimethoxyethane solvent and potassium tertiary-butoxide as a base.

Method for producing hydroxytriarylamine (by machine translation)

PROBLEM TO BE SOLVED: To economically provide arylamines such as triarylamine. SOLUTION: An arylamine compound represented by formula (1) and an aryl compound having a leaving group represented by formula (2): X-Ar2-X1, are subjected to an arylamination reaction in the presence of a basic group, an alkaline metal salt and/or an alkaline earth metal salt, and an iron catalyst to thereby obtain arylamines such as triarylamines. In formula (1), Ar and Ar1are identical or different, and denote a substituted or non-substituted aryl group, and may be ring-condensed; and a denotes 1 or 2. In formula (2), X and X1are identical or different, and denote at least one leaving group selected from the group consisting of H or Br, I, CMs (mesylate), OTf (triflate) and OTs (tosylate), provided that X and X1are not simultaneously H, and have at least one leaving group; and Ar2denotes a substituted or non-substituted aryl group. COPYRIGHT: (C)2012,JPO&INPIT

Redox-controlled fluorescence modulation (electrofluorochromism) in triphenylamine derivatives

The study of the chemical and electrochemical fluorescence switching properties of a family of substituted triphenylamine derivatives is reported. First of all, the synthesis of a family of six compounds is described. They are characterized by electrochemistry, UV-vis and fluorescence spectroscopy and spectroelectrochemistry. Theoretical calculations were performed in order to corroborate the experimental results. While these compounds emit blue to green light under UV irradiation with a large quantum yield (37%) in the case of one molecule, the fluorescence intensity is quenched upon oxidation. The fluorescence behavior can be switched between the strong fluorescent (neutral) state and the non-fluorescent (oxidized) state with a high contrast (around 1500 for the fluorescence intensity for one of these molecules). Furthermore, the chromatic contrast of three of these molecules reaches 70% that can be important for further applications. This journal is the Partner Organisations 2014.

A visible-light-mediated synthesis of carbazoles

The photosynthetic preparation of N-aryl- and N-alkyl-bearing carbazoles utilizes continuous flow, visible light, and an in situ formed Cu-based sensitizer (see picture). The method is mild and efficient, and allows the straightforward synthesis of a variety of carbazoles with different substituents, heterocycles, and complex carbon architectures. Copyright

A reusable polymer supported copper(I) complex for the C-N bond cross-coupling reaction

The Ullmann coupling of amines with aryl iodide as well as arylboronic acids and N(H)-heterocycles with arylboronic acids has been carried out efficiently using PS-LCu(I) catalyst. The copper complex has been prepared and characterized by using scanning electron microscope (SEM), elemental analysis, atomic absorption spectroscopy (AAS), Thermo gravimetric analysis and spectrometric methods like Fourier transform infrared spectroscopy (FTIR). The effects of various parameters such as temperature, solvent and base on the reaction system were studied. The reusability experiments show that the catalyst can be used five times without much loss in the catalytic activity.

Siloxane-triarylamine hybrids: Discrete room temperature liquid triarylamines via the Piers-Rubinsztajn reaction

A series of room temperature liquid siloxane-triarylamine hybrids were synthesized using the Piers-Rubinsztajn reaction. These materials displayed well behaved electrochemical oxidation and low Tg's and were free-flowing liquids. The interaction between the Lewis acidic tris(pentafluorophenyl)borane catalyst and the Lewis basic starting triarylamine substrate was also investigated by steady state UV-vis spectroscopy and 19F NMR.