783-08-4

Usage

InChI:InChI=1/C14H13NO/c1-16-14-9-7-13(8-10-14)15-11-12-5-3-2-4-6-12/h2-11H,1H3/b15-11+

Upstream product

• 100-52-7 benzaldehyde 
• 104-94-9 4-methoxy-aniline 
• 588-53-4 4-benzylidenamino-phenol 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 19064-76-7 N-benzylidene-4-methoxyaniline oxide 
• 17377-95-6 benzyl(4-methoxyphenyl)amine 
• 2211-66-7 N-phenyl(methylidene)cyclohexanamine 
• 110788-30-2 C₂₅H₂₂AsNO 
• 123-11-5 4-methoxy-benzaldehyde 
• 62-53-3 aniline 
• 57527-55-6 (E)-N-benzylidenebutan-1-amine 
• 27845-53-0 (E)-N-cyclohexyl-1-phenylmethanimine 
• 101960-60-5 [(Z)-4-Methoxy-phenylimino]-phenyl-acetic acid 

Downstream Products

• 24870-10-8 maleic acid mono(4-methoxyphenyl)amide 
• 56264-82-5 acetoxy-(N-acetyl-p-anisidino)-phenyl-methane 
• 420133-77-3 2,3,6-trichloro-4-methoxy-aniline 
• 60566-20-3 N-(4-methoxyphenyl)-N'-(4-methoxyphenyl)benzamidine 
• 100-52-7 benzaldehyde 
• 51527-45-8 (±)-trans-1-(4-methoxyphenyl)-3,4-diphenylazetidin-2-one 
• 6709-42-8 N-(4-methoxyphenyl)-1,1-diphenylmethylamine 
• 32795-58-7 2-phenyl-6-methoxyquinoline-4-carboxylic acid 
• 116028-06-9 1-(4-methoxy-phenyl)-3,3,4-triphenyl-azetidin-2-one 
• 17377-95-6 benzyl(4-methoxyphenyl)amine 
• 6725-34-4 thiobenzaldehyde 
• 98861-13-3 8-methoxy-9b-methyl-4-phenyl-2,3,3a,4,5,9b-hexahydro-furo[3,2-c]quinoline 
• 34798-63-5 3-(4-methoxy-phenyl)-5-naphthalen-2-yloxymethyl-2-phenyl-oxazolidine 
• 34798-59-9 3-(4-methoxy-phenyl)-5-phenoxymethyl-2-phenyl-oxazolidine 

Relevant academic research and scientific papers

Controlling Proton-Coupled Electron Transfer in Bioinspired Artificial Photosynthetic Relays

Bioinspired constructs consisting of benzimidazole-phenol moieties bearing N-phenylimines as proton-accepting substituents have been designed to mimic the H-bond network associated with the TyrZ-His190 redox relay in photosystem II. These compo

Cobalt-Catalyzed Deoxygenative Hydroboration of Nitro Compounds and Applications to One-Pot Synthesis of Aldimines and Amides

The commercially available and bench-stable Co(acac)2 ligated with bis[(2-diphenylphosphino)phenyl] ether (dpephos) was employed for selective room temperature hydroboration of nitro compounds with HBPin (TOF up to 4615 h?1), tolerating halide, hydroxy, amino, ether, ester, lactone, amide and heteroaromatic functionalities. These reactions offered a direct access to a variety of N-borylamines RN(H)BPin, which were in situ treated with aldehydes and carboxylic acids to produce a series of aldimines and secondary carboxamides without the need for dehydrating and/or coupling reagents. Combination of these transformations in a sequential one-pot manner allowed for direct and selective synthesis of aldimines and secondary carboxamides from readily available and inexpensive nitro compounds.

Method for preparing asymmetric imine or asymmetric secondary amine compound through photocatalysis

The invention relates to a method for preparing asymmetric imine or asymmetric secondary amine compounds through photocatalysis. According to the method, under the conditions of illumination and inert gas, different types of photocatalysts supported by cocatalysts are selected, so that an aromatic alcohol compound and an aromatic amino compound can react to obtain the asymmetric imine compound or the asymmetric secondary amine compound. The method can be used for replacing the existing mature organic synthesis process, is mild in condition and high in selectivity, has universality and is suitable for industrial production.

Photocatalytic one-pot multidirectional N-alkylation over Pt/D-TiO2/Ti3C2: Ti3C2-based short-range directional charge transmission

Visible-light-induced one-pot, multistep, and chemoselectivity adjustable reactions highlight the economical, sustainable, and green process. Herein, we report Pt nanoparticles dispersed on S and N co-doped titanium dioxide/titanium carbide (MXene) (3%Pt/

Redox-Neutral Imination of Alcohol with Azide: A Sustainable Alternative to the Staudinger/Aza-Wittig Reaction

The traditional Staudinger/aza-Wittig reaction represents one of the most powerful tools for imine formation. However, for this multistep procedure, the sacrificial phosphine has to be used, resulting in difficulties in the purification process and waste disposal at the same time. Here, we report a redox-neutral azide-alcohol imination methodology enabled by a base-metal nickel PN3 pincer catalyst. The one-step, waste-free, and high atom-economical features highlight its advantages further. Moreover, mechanistic insight suggests a non-metal-ligand cooperation pathway based on the observation of an intermediate and density functional theory calculations.

Iron-Catalyzed Hydrogen Transfer Reduction of Nitroarenes with Alcohols: Synthesis of Imines and Aza Heterocycles

A straightforward and selective reduction of nitroarenes with various alcohols was efficiently developed using an iron catalyst via a hydrogen transfer methodology. This protocol led specifically to imines in 30-91% yields, with a good functional group tolerance. Noticeably, starting from o-nitroaniline derivatives, in the presence of alcohols, benzimidazoles can be obtained in 64-72% yields when the reaction was performed with an additional oxidant, DDQ, and quinoxalines were prepared from 1,2-diols in 28-96% yields. This methodology, unprecedented at iron for imines, also provides a sustainable alternative for the preparation of quinoxalines and benzimidazoles.

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.

Efficient Imine Formation by Oxidative Coupling at Low Temperature Catalyzed by High-Surface-Area Mesoporous CeO2 with Exceptional Redox Property

High-surface-area mesoporous CeO2 (hsmCeO2) was prepared by a facile organic-template-induced homogeneous precipitation process and showed excellent catalytic activity in imine synthesis in the absence of base from primary alcohols and amines in air atmosphere at low temperature. For comparison, ordinary CeO2 and hsmCeO2 after different thermal treatments were also investigated. XRD, N2 physisorption, UV-Raman, H2 temperature-programmed reduction, O2 temperature-programmed desorption, EPR spectroscopy, and X-ray photoelectron spectroscopy were used to unravel the structural and redox properties. The hsmCeO2 calcined at 400 °C shows the highest specific surface area (158 m2 g?1), the highest fraction of surface coordinatively unsaturated Ce3+ ions (18.2 %), and the highest concentration of reactive oxygen vacancies (2.4×1015 spins g?1). In the model reaction of oxidative coupling of benzyl alcohol and aniline, such an exceptional redox property of the hsmCeO2 catalyst can boost benzylideneaniline formation (2.75 and 5.55 mmol (Formula presented.) h?1 based on >99 % yield at 60 and 80 °C, respectively) in air with no base additives. It can also work effectively at a temperature of 30 °C and in gram-scale synthesis. These are among the best results for all benchmark ceria catalysts in the literature. Moreover, the hsmCeO2 catalyst shows a wide scope towards primary alcohols and amines with good to excellent yield of imines. The influence of reaction parameters, the reusability of the catalyst, and the reaction mechanism were investigated.

Highly efficient and selective one-pot tandem imine synthesis via amine-alcohol cross-coupling reaction catalysed by chromium-based MIL-101 supported Au nanoparticles

One-pot tandem synthesis of imines from alcohols and amines is regarded as an effective, economic and green approach under mild conditions. In this work, Au nanoparticles (NPs) dispersed on MIL-101 (Au/MIL-101) were demonstrated as highly active and selective bifunctional heterogeneous catalyst for production of various imine derivatives with excellent yields, via amine-alcohol cross-coupling reaction at 343 K in an open flask under an Ar atmosphere. Various physicochemical techniques, including inductively coupled plasma optical emission spectroscopy (ICP-OES), powder X-ray diffraction (P-XRD), X-ray photoelectron spectroscopy (XPS) transmission electron microscopy (TEM) and N2 adsorption-desorption, were used to characterize of the Au/MIL-101 catalyst. The obtained bifunctional catalyst is highly active and selective towards one-pot imine formation and exhibited the highest TOF (30.15-51.47 h?1) among all the ever-reported MOF-supported Au catalysts. The reaction mechanism of the imine formation from alcohol and amine over Au/MIL-101 catalyst was proposed. Mechanism experiment results demonstrate that Au NPs highly effective in activating oxidation of benzyl alcohol to benzaldehyde while the Lewis acid sites on MIL-101 catalyzed the second condensation step without interfering with the oxidation step. As a result, the excellent catalytic performance of Au/MIL-101 can be ascribed to the synergistic effect between Au NPs with Lewis acid sites in MIL-101.

Functional POM-catalyst for selective oxidative dehydrogenative couplings under aerobic conditions

Development of selective and efficient reusable catalytic systems for sustainable chemical production under benign conditions is attractive and received much attention. Herein, we report a rod-shaped octadecyl trimethylammonium functionalized Keggin-type polyoxometalate [PMO12O40] hybrids (OTA-POM) as an efficient heterogeneous catalyst for selective oxidative dehydrogenative couplings under aerobic conditions without any additive or external base. The catalyst recovery and subsequent five successive recyclability studies of hybrid POM confirms the heterogeneous nature of present catalytic system.