6852-54-6

Usage

Uses

Used in Pharmaceutical and Agrochemical Synthesis:
Benzylidene(ethyl)amine is utilized as a building block in the synthesis of various pharmaceuticals and agrochemicals, contributing to the development of new drugs and agricultural products.
Used in Coordination Chemistry:
In the field of coordination chemistry, benzylidene(ethyl)amine serves as a ligand for the study and application of transition metal complexes, playing a crucial role in understanding their properties and potential uses.
Used in Research and Industrial Settings:
benzylidene(ethyl)amine is a valuable resource in research and industrial applications, where it is employed for the development and production of various chemical products, ensuring that safety protocols are strictly followed during its handling and production.

InChI:InChI=1/C9H11N/c1-2-10-8-9-6-4-3-5-7-9/h3-8H,2H2,1H3

Upstream product

• 100-52-7 benzaldehyde 
• 75-04-7 ethylamine 
• 110079-23-7 BnNEtCl 
• 917-64-6 methyl magnesium iodide 
• 124316-00-3 1-<<(Triphenylphosphoranylidene)amino>methyl>benzotriazole 
• 861521-90-6 3,4-dioxo-5-phenyl-valeronitrile 
• 100-46-9 benzylamine 
• 19961-27-4 N-isopropylethylamine 
• 773837-37-9 sodium cyanide 
• 14321-27-8 N-ethylbenzylamine 
• 79-24-3 Nitroethane 
• 100-51-6 benzyl alcohol 
• 64-17-5 ethanol 
• 107-95-9 3-amino propanoic acid 

Downstream Products

• 72961-53-6 ethyl-(1-phenyl-pentyl)-amine 
• 73418-67-4 N-ethyl-5-methyl-2,4-dinitro-aniline 
• 87876-92-4 N-(1-phenylpropyl)-N-ethylamine 
• 53693-47-3 N-benzhydrylethanamine 
• 119-65-3 isoquinoline 
• 39203-76-4 N-ethylbenzothioamide 
• 60509-63-9 meso-N,N'-diethyl-bibenzyl-α,α'-diyldiamine 
• 14321-27-8 N-ethylbenzylamine 
• 100-47-0 benzonitrile 
• 721458-19-1 3-ethyl-2-phenyl-thiazolidin-4-one 
• 102010-12-8 3-ethylamino-2,3-diphenyl-propionic acid ethyl ester 
• 23252-24-6 6-(4-chloro-phenyl)-3-ethyl-2-phenyl-2,3-dihydro-[1,3,5]oxadiazin-4-one 
• 49770-21-0 Ethyl-(2-methyl-1-phenyl-but-3-ynyl)-amine 
• 56930-94-0 C₁₂H₁₉NSi 

Relevant academic research and scientific papers

Metal- and oxidant-free electrochemically promoted oxidative coupling of amines

The selective oxidation of amines into imines is a priority research topic in organic synthesis and has attracted much attention over the past few decades. However, the oxidation of amines generally suffers from the drawback of transition-metal, even noble-metal catalysts. Thus, the strategy of metal- and oxidant-free selective synthesis of imines is highly desirable yet largely unmet. This paper unravels a metal-free and external oxidant-free electrochemical strategy for the oxidative coupling methodology of amines. This general transformation is compatible with various functional amines and led to functionalized imines in moderate to satisfactory yields.

Discovery of tert-amine-based RORγt agonists

The nuclear receptor retinoic acid receptor-related orphan receptor gamma-t (RORγt) is a transcription factor regulating Th17 cell differentiation and proliferation from naive CD4+ T cells. Since Th17 cells have demonstrated the antitumor efficacy by eliciting remarkable activation of CD8+ T cells, RORγt agonists could be applied as potential small molecule therapeutics for cancer immunotherapy. Based on the previously reported RORγt agonist 1 and its resolved co-crystal structure, a series of new tertiary amines were designed, synthesized and biologically evaluated, yielding optimal moieties with improved chemical properties and biological responses. The combination of these optimal moieties resulted in identification of novel RORγt agonists such as 8b with further elevated RORγt agonism responses at a target-based level as well as in cell-based assays, which provided some structural knowledge for further optimization of RORγt agonists as small molecule therapeutics for cancer immunotherapy.

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.

Tunable Synthesis of α-Amino Boronic Esters from Available Aldehydes and Amines through Sequential One-Pot Dehydration and Copper-Catalyzed Borylacylation

Copper-catalyzed multicomponent borylacylation of imines with acid chlorides and bis(pinacolato)diboron was developed for the preparation of synthetically useful and pharmacologically relevant α-amino boronic acid derivatives. Starting from a range of acid chlorides and imines with aryl, heteroaryl, and alkyl substituents, most of these ligand-free reactions proceeded smoothly at room temperature in moderate to good yields. Furthermore, a facile and convenient one-pot, multistep access to the direct synthesis of α-amino boronic acid derivatives from available aldehydes and amines was also developed.

Efficient Co-Catalyzed Double Hydroboration of Nitriles: Application to One-Pot Conversion of Nitriles to Aldimines

The commercially available and bench-stable Co(acac)2/dpephos system is employed as a precatalyst for selective and efficient room temperature hydroboration of organic nitriles with HBPin to produce a series of N,N-diborylamines [RN(BPin)2], which react in situ with aldehydes to give aldimines. Formation of aldimines from N,N-diborylamines does not require a dehydrating agent, is applicable to a wide range of N,N-diborylamine and aldehyde substrates and is highly chemoselective, being unaffected by various common functional groups, such as alkenes, alkynes, secondary amines, ketones, esters, amides, carboxylic acids, pyridines, nitriles, and nitro compounds. The overall transformation represents a synthetically valuable approach to aldimines from nitriles and can be performed in a sequential one-pot manner, tolerating ester, lactone, carboxamide and unactivated alkene functionalities.

Selective Synthesis of Secondary and Tertiary Amines by Reductive N-Alkylation of Nitriles and N-Alkylation of Amines and Ammonium Formate Catalyzed by Ruthenium Complex

A new ruthenium catalytic system for the syntheses of secondary and tertiary amines via reductive N-alkylation of nitriles and N-alkylation of primary amines is proposed. Isomeric complexes 8 catalyze transfer hydrogenation and N-alkylation of nitriles in ethanol to give secondary amines. Unsymmetrical secondary amines can be produced by N-alkylation of primary amines with alcohols via the borrowing hydrogen methodology. Aliphatic amines were obtained with excellent yields, while only moderate conversions were observed for anilines. Based on kinetic and mechanistic studies, it is suggested that the rate determining step is the hydrogenation of intermediate imine to amine. Finally, ammonium formate was applied as the amination reagent for alcohols in the presence of ruthenium catalyst 8. Secondary amines were obtained from primary alcohols within 24 hours at 100 °C, and tertiary amines can be produced after prolonged heating. Secondary alcohols can only be converted to secondary amines with moderate yield. Based on mechanistic studies, the process is suggested to proceed through an ammonium alkoxy carbonate intermediate, where carbonate acts as an efficient leaving group.

The preparation and photocatalytic activity of Ag-Pd/g-C3N4 for the coupling reaction between benzyl alcohol and aniline

In this study, the carrier g-C3N4 was prepared by melamine, and the Ag-Pd/g-C3N4 catalyst was synthesized by the NaBH4 reduction method. Different characterization techniques, including SEM, TEM, XRD, UV–vis DRS, XPS, photoluminescence spectra (PL) and BET, were employed to investigate the morphology and optical properties of the as-prepared samples. The Ag-Pd/g-C3N4 catalyst was used for the synthesis of imine from a benzyl alcohol and aniline. The results show that when the total loading of Ag and Pd is 2 wt%, and the mass ratio of Ag and Pd is 1:1, the activity of the catalyst is the highest (The highest conversion of aniline is 86.7% and the product selectivity is >99%.). The reaction is optimized by changing the type of solvent, the type and amount of base, the type of catalyst, and the amount of reactants. The optimal reaction conditions are 6 ml of n-hexane, 1.4 mmol of Cs2CO3, 50 mg of the Ag-Pd/g-C3N4 (2 wt%, 1:1), and 2:1 mol ratio of benzyl alcohol and aniline. Under optimal reaction conditions, alcohol derivatives and amine derivatives were investigated to determine the suitable range of the catalyst for alcohols and amines. Then, the effects of different light intensities and wavelengths on the reaction were explored. Additionally, the catalyst's recycling ability was tested, and it was found to be relatively stable. The effect of reactive groups on the mechanism shows that the reaction is mainly achieved by the synergy between h+, e? and ·O2?.

A visible-light-responsive metal-organic framework for highly efficient and selective photocatalytic oxidation of amines and reduction of nitroaromatics

Photocatalysis is a green synthetic method for organics transformation. We present here the synthesis of a novel visible-light-responsive metal-organic framework and its photocatalytic application. The prepared MOF is highly efficient for the self-coupling of primary amines and oxidative dehydrogenation of secondary amines to selectively produce imines assisted by the green and economic oxidant of molecular oxygen. Studies reveal that both energy transfer and electron transfer from the photoexcited MOF to molecular oxygen are important for amine oxidation, where the highly reactive species of superoxide radicals and singlet oxygen together account for the high catalytic performance. The photogenerated electrons of the MOF have also been utilized for the reduction of aromatic nitroarenes. Results show that they are highly selective for the reduction of nitroarenes to produce anilines in the presence of hydrazine hydrate. The work demonstrates the enormous potential of photoactive MOFs for converting organic substrates into valuable chemicals.

Synthesis and evaluation of Zn(II) dithiocarbamate complexes as potential antibacterial, antibiofilm, and antitumor agents

Four complexes having the formula [Zn(L)2] [L1 = (C18H20NS2 –), N-(4-isopropyl-benzyl)-(benzyl)-dithiocarbamate], [L2 = (C10H12NS2 –), N-(benzyl)-(ethyl)-dithiocarbamate], [L3 = (C19H22ONS2 –), N-(4-isopropyl-benzyl)-(4-methoxy-benzyl)-dithiocarbamate], and [L4 = (C16H16NS2 –), N-(benzyl)-(4-methyl-benzyl)-dithiocarbamate] have been contemplated, synthesized, and characterized by elemental analysis and IR, 1H, 13C NMR and UV–visible absorption spectra. All Zn(II) complexes have similar geometry and coordination number. Complex A2 (with ligand L2) crystallizes in triclinic system with space group P-1 having distorted square pyramidal geometry which was stabilized by weak C–H···π and C–H···S intramolecular interactions. The antibacterial, antibiofilm, and antitumor activities of the complexes have been screened and A2 and A3 showed their prominence. Interestingly, both A2 and A3 showed more killing potential against multi-drug resistant gram-positive isolates with MIC indices of 16 μg mL?1 and 16 μg mL?1, respectively, against both MRSA and MSSA, while the antitumor agent A3 showed its prominence with GI50 and LC50 41.15 and 133.73 μg mL?1, respectively.

Method for synthesizing imine by catalytic oxidation of asymmetric secondary amine in presence of visible light

The invention belongs to the technical field of chemical engineering and pharmaceutical industry, and particularly relates to a method for synthesizing imine by catalytic oxidation of asymmetric secondary amine in the presence of visible light. With aza-metalloporphyrin containing sulfur as a visible light catalyst, 1,8-diazabicycloundecene-7-alkene as an auxiliary agent, and oxygen as an oxidant,asymmetric secondary amine is subjected to catalytic oxidation under irradiation of visible light of lambda being larger than or equal to 420nm, so as to obtain the oxidation product imine. A new andefficient imine production way is provided.