1749-08-2

Basic information

• Product Name: N-(4-METHOXYBENZYLIDENE)-4-METHOXYANILINE
• Synonyms: (E)-4-Methoxy-N-(4-Methoxybenzylidene)aniline;N-(4-Methoxybenzylidene)-4-methoxyaniline 97%;N-(p-Methoxybenzylidene)-p-anisidine;4-METHOXY-N-(4-METHOXYBENZYLIDENE)ANILINE;N-(4-METHOXYBENZYLIDENE)-4-METHOXYANILINE;N-(4-METHOXYBENZYLIDENE)-4-ANISIDINE;4-Methoxy-N-(4-methoxybenzylidene)aniline, N-(4-Methoxybenzylidene)-4-anisidine;(4-methoxybenzylidene)-(4-methoxyphenyl)amine
• CAS NO: 1749-08-2
• Molecular Formula: C₁₅H₁₅NO₂
• Molecular Weight: 241.29
• Mol File: 1749-08-2.mol

Chemical Properties

• Melting Point: 146-150 °C(lit.)
• Boiling Point: 389.5°C at 760 mmHg
• Flash Point: 153.2°C
• Appearance: /
• Density: 1.03g/cm³
• Vapor Pressure: 6.38E-06mmHg at 25°C
• Refractive Index: 1.53
• PKA: 4.51±0.50(Predicted)
• CAS DataBase Reference: N-(4-METHOXYBENZYLIDENE)-4-METHOXYANILINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-METHOXYBENZYLIDENE)-4-METHOXYANILINE(1749-08-2)
• EPA Substance Registry System: N-(4-METHOXYBENZYLIDENE)-4-METHOXYANILINE(1749-08-2)

Safety Data

• Hazard Codes: Xi
• Statements: 37/38-41-43
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 1749-08-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
N-(4-Methoxybenzylidene)-4-methoxyaniline serves as a key building block in organic synthesis, facilitating the creation of a variety of complex organic molecules. Its structural features make it a versatile component in the formation of new chemical entities.
Used in Dye and Pigment Production:
N-(4-METHOXYBENZYLIDENE)-4-METHOXYANILINE is utilized in the production of dyes and pigments, capitalizing on its chemical properties to yield colorants for various applications, including textiles, plastics, and printing inks.
Used in Pharmaceutical Industry:
N-(4-Methoxybenzylidene)-4-methoxyaniline is employed in the pharmaceutical industry as an intermediate for the synthesis of drugs. Its unique structure contributes to the development of new medicinal compounds with potential therapeutic applications.
Used in Medicinal Chemistry Research:
In the realm of medicinal chemistry, this compound is used for the development of new drugs, leveraging its wide range of biological activities. Its potential to interact with biological targets makes it a valuable tool in the discovery and design of novel pharmaceuticals.
Safety Precautions:
It is crucial to handle N-(4-Methoxybenzylidene)-4-methoxyaniline with appropriate safety measures due to its potential health hazards. Proper protective equipment and adherence to safety protocols are essential when working with this compound to minimize risks to human health and the environment.

InChI:InChI=1/C15H15NO2/c1-17-14-7-3-12(4-8-14)11-16-13-5-9-15(18-2)10-6-13/h3-11H,1-2H3/b16-11+

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 104-94-9 4-methoxy-aniline 
• 6552-63-2 4'-chloro-4-methoxy-chalcone 
• 14429-14-2 N-(4-methoxybenzyl)-4-methoxyaniline 
• 56644-00-9 N-(4-methoxybenzylidene)cyclohexylamine 
• 105-45-3 acetoacetic acid methyl ester 
• 5416-93-3 4-Methoxyphenyl isocyanate 
• 100-17-4 para-methoxynitrobenzene 
• 105-13-5 4-Methoxybenzyl alcohol 
• 123-08-0 4-hydroxy-benzaldehyde 
• 100-52-7 benzaldehyde 
• 62-53-3 aniline 
• 103-82-2 phenylacetic acid 
• 599-67-7 1,1-diphenylethanol 

Downstream Products

• 41226-83-9 2-(4-chloro-phenyl)-3,4-bis-(4-methoxy-phenyl)-oxazolidine-5,5-dicarbonitrile 
• 66172-23-4 4,5-bis-(4-methoxy-phenyl)-2,6-bis-(2,2,2-trifluoro-1-trifluoromethyl-ethylidene)-[1,3,5]dithiazinane 
• 16552-12-8 α-Cyan-4-methoxy-zimtsaeure-p-anisidid 
• 1834-75-9 4-methoxy-N-(1-(4-methoxyphenyl)-2-phenylethyl)aniline 
• 63384-90-7 2,3-bis-(4-methoxy-phenyl)-6-trichloromethyl-2,3-dihydro-[1,3,5]oxadiazin-4-one 
• 77894-51-0 trans-4-hydroxy-2,3-bis(4-methoxyphenyl)-3,4-dihydro-1(2H)-isoquinolone 
• 77894-51-0 cis-4-hydroxy-2,3-bis(4-methoxyphenyl)-3,4-dihydro-1(2H)-isoquinolone 
• 133702-04-2 3-(4-Methoxy-phenyl)-2-[(E)-2-(4-methoxy-phenyl)-vinyl]-3H-benzo[g]quinazolin-4-one 
• 91118-90-0 3-(4-Methoxy-phenyl)-2-[(E)-2-(4-methoxy-phenyl)-vinyl]-3H-pyrido[2,3-h]quinazolin-4-one 
• 109388-01-4 1,4-bis(4-methoxyphenyl)-3-vinylazetidin-2-one 
• 127896-43-9 4-[4-Hydroxy-1,2-bis-(4-methoxy-phenyl)-5-oxo-2,5-dihydro-1H-pyrrol-3-yl]-2,4-dioxo-butyric acid ethyl ester 
• 121411-11-8 (4-Methoxy-phenyl)-[(R)-1-(4-methoxy-phenyl)-2-((R)-toluene-4-sulfinyl)-ethyl]-amine 
• 121411-12-9 (4-Methoxy-phenyl)-[(S)-1-(4-methoxy-phenyl)-2-((R)-toluene-4-sulfinyl)-ethyl]-amine 
• 86451-28-7 1,2-Bis-(4-methoxy-phenyl)-aziridine 

Relevant articles and documents

Photoimmobilized Ni Clusters Boost Photodehydrogenative Coupling of Amines to Imines via Enhanced Hydrogen Evolution Kinetics

Imines are important precursors for pharmaceutical, agricultural, and synthetic chemistry. The state-of-art synthesis of imines via condensation of amines with aldehydes or ketones often uses homogeneous catalysts and dehydrating agents to promote the elimination of water, which requires huge manpower input for the late-stage purification process and is usually environmentally unfriendly. Photocatalytic synthesis of imines from amines oxidation via the release of hydrogen (H2) is of great promise due to the mild reaction characteristics; however, the efficiency of such a reaction lags due to the missing designed photocatalyst owing to the ambiguous reaction mechanism. Here, we demonstrate that by constructing in situ photoimmobilized Ni clusters on the CdS photocatalyst, the generation of imines is dramatically improved with the rapid release of molecular H2 under visible light illumination. Mechanistic investigation reveals that the adsorption of photogenerated hydrogen atoms during the dehydrogenation of amines is significantly weakened on Ni clusters, thus resulting in fast C-N coupling kinetics for the generation of imines. The photocatalyst presents stable performance with high efficiency. A remarkably apparent quantum efficiency (AQE) of ?44% is realized under 420 nm irradiation for the conversion of 4-methoxybenzylamine within six consecutive runs. Furthermore, a series of primary and secondary amines bearing different functional groups (i.e., heterocyclic, aliphatic, N-heterocycles) that are synthetically challenging by the condensation process can be selectively converted to the corresponding imines, featuring its application prospect.

Probing binding and cellular activity of pyrrolidinone and piperidinone small molecules targeting the urokinase receptor

The urokinase receptor (uPAR) is a cell-surface protein that is part of an intricate web of transient and tight protein interactions that promote cancer cell invasion and metastasis. Here, we evaluate the binding and biological activity of a new class of

Studies towards synthesis and Lewis acid catalysed functionalization of 3-(4′-substitutedphenylthio)-azetidin-2-ones

Abstract: Medicinal chemistry of heterocycles especially β-lactams have been an important discovery in today’s mankind. β-Lactam nucleus is structural feature and core of the biological activity of one of most successful classes of therapeutics to date ch

A novel water-dispersible and magnetically recyclable nickel nanoparticles for the one-pot reduction-Schiff base condensation of nitroarenes in pure water

In this work, a heterogeneous nanocatalyst called Ni-Fe3O4@Pectin~PPA ~ Piconal was first synthesized, which was investigated as a bifunctional catalyst containing nickel functional groups. On the other hand, this Ni-Fe3O4@Pectin~PPA ~ Piconal catalyst in aqueous solvents shows a very effective performance at ambient temperature for the nitroarene reduction reaction with sodium borohydride, for which NaBH4 is considered as a reducing agent. This is a novelty magnetic catalyst that was approved by various methods, including Fourier-transform infrared spectroscopy (FT-IR), X-ray powder diffraction (XRD), Dynamic light scattering (DLS), Transmission electron microscopy (TEM), vibrating sample magnetometer (VSM), Inductively coupled plasma (ICP), Energy-dispersive X-ray spectroscopy (EDX), and Field emission scanning electron microscopy (FESEM) analyses. From the satisfactory results obtained from the reduction of nitrogen, this catalytic system is used for a one-pot protocol containing a reduction-Schiff base concentration of diverse nitroarenes. It was corroborated with the heterogeneous catalytic experiments on the one-pot tandem synthesis of imines from nitroarenes and aldehydes. Finally, the novel Ni-Fe3O4@Pectin~PPA ~ Piconal catalyst could function as a more economically desirable and environmentally amicable in the catalysis field. The favorable products are acquired in good to high performance in the attendance of Ni-Fe3O4@Pectin~PPA ~ Piconal as a bifunctional catalyst. This catalyst can be recycled up to six steps without losing a sharp drop.

Iron(II)-Catalyzed Aerobic Biomimetic Oxidation of Amines using a Hybrid Hydroquinone/Cobalt Catalyst as Electron Transfer Mediator

Herein we report the first FeII-catalyzed aerobic biomimetic oxidation of amines. This oxidation reaction involves several electron transfer steps and is inspired by biological oxidation in the respiratory chain. The electron transfer from the amine to molecular oxygen is aided by two coupled catalytic redox systems, which lower the energy barrier and improve the selectivity of the oxidation reaction. An iron hydrogen transfer complex was utilized as the substrate-selective dehydrogenation catalyst along with a bifunctional hydroquinone/cobalt Schiff base complex as a hybrid electron transfer mediator. Various primary and secondary amines were oxidized in air to their corresponding aldimines or ketimines in good to excellent yield.

Azetidinimines as a novel series of non-covalent broad-spectrum inhibitors of β-lactamases with submicromolar activities against carbapenemases KPC-2 (class A), NDM-1 (class B) and OXA-48 (class D)

The occurrence of resistances in Gram negative bacteria is steadily increasing to reach extremely worrying levels and one of the main causes of resistance is the massive spread of very efficient β-lactamases which render most β-lactam antibiotics useless. Herein, we report the development of a series of imino-analogues of β-lactams (namely azetidinimines) as efficient non-covalent inhibitors of β-lactamases. Despite the structural and mechanistic differences between serine-β-lactamases KPC-2 and OXA-48 and metallo-β-lactamase NDM-1, all three enzymes can be inhibited at a submicromolar level by compound 7dfm, which can also repotentiate imipenem against a resistant strain of Escherichia coli expressing NDM-1. We show that 7dfm can efficiently inhibit not only the three main clinically-relevant carbapenemases of Ambler classes A (KPC-2), B (NDM-1) and D (OXA-48) with Ki's below 0.3 μM, but also the cephalosporinase CMY-2 (class C, 86% inhibition at 10 μM). Our results pave the way for the development of a new structurally original family of non-covalent broad-spectrum inhibitors of β-lactamases.

Au(I) Catalyzed Synthesis of Densely Substituted Pyrazolines and Dihydropyridines via Sequential Aza-Enyne Metathesis/6π-Electrocyclization

A gold(I) autotandem catalysis protocol is reported for the de novo synthesis of densely substituted pyrazolines and dihydropyridines from the corresponding imine derivatives in a highly regioselective fashion via a one-pot aza-enyne metathesis/6π-electrocyclization sequence. The substituents on the nitrogen atom of the imine perfectly control the reaction pathways from the pivotal 1-azabutadiene intermediate; thus, carbazates were converted into pyrazolines via 6π-electrocyclization of α,β-unsaturated hydrazones, while aryl imines provided dihydropyridines via 6π-electrocyclization of 3-azahexatrienes.

A highly stereoselective oxidation and an easy one pot elimination methodology for 3-allyl-3-phenylthio-β-lactams

A novel, facile, highly efficient and stereoselective protocol for the synthesis of cis-3-allyl-3-phenylsulfinyl-β-lactams and 3-allylidene-β-lactams from cis-3-allyl-3-phenylthio-β-lactams using Selectfluor both as an oxidizing agent and as an eliminating agent with temperature as a control parameter over the reaction outcome has been reported. The methodology is able to conquer the earlier reported shortcomings of long reaction time (24–90 hrs.) and lack of control over product ratio. The synthesized compounds will serve as important synthons for compounds of enhanced biological activity and potency.

Carbon monoxide-driven osmium catalyzed reductive amination harvesting WGSR power

Herein, we present the first example of Os-catalyzed efficient reductive amination under water-gas shift reaction conditions. The developed catalytic systems are formedin situin aqueous solutions, employ as small as 0.0625 mol% osmium and are capable of delivering reductive amination products for a broad range of aliphatic and aromatic carbonyl compounds and amines. The scope of the reaction, active catalytic systems, possible limitations of the method and DFT-supported mechanistic considerations are discussed in detail in the manuscript.

Tandem imine formationviaauto-hydrogen transfer from alcohols to nitro compounds catalyzed by a nanomagnetically recyclable copper catalyst under solvent-free conditions

A direct imination reaction was developed by tandem reaction of alcohols and nitro compounds in the presence of Cu-isatin Schiff base-γ-Fe2O3as a nanomagnetically recyclable catalyst under solvent-free conditions. By this method, various imines were prepared in good to high yields from one-pot reaction of various alcohols (primary aromatic and aliphatic) and nitro compounds (aromatic and aliphatic)viaan auto-hydrogen transfer reaction. Use of an inexpensive and easily reusable catalyst, without requiring any additives or excess amounts of benzyl alcohol as the reaction solvent are the other advantages of this method. This catalytic system has the merits of cost effectiveness, environmental benignity, excellent recyclability and good reproducibility.