613-39-8

Usage

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 14, p. 535, 1977 DOI: 10.1002/jhet.5570140340The Journal of Organic Chemistry, 52, p. 1673, 1987 DOI: 10.1021/jo00385a006Tetrahedron Letters, 27, p. 377, 1986 DOI: 10.1016/S0040-4039(00)84023-X

InChI:InChI=1/C16H18N2/c1-3-7-15(8-4-1)17-11-13-18(14-12-17)16-9-5-2-6-10-16/h1-10H,11-14H2

Upstream product

• 142-04-1 aniline hydrochloride 
• 3976-10-1 4-phenyl-morpholine; hydrochloride 
• 1005-66-9 N-(β-bromoethyl)aniline hydrobromide 
• 108-24-7 acetic anhydride 
• 150-61-8 N,N'-diphenylethylenediamine 
• 107-21-1 ethylene glycol 
• 106-93-4 ethylene dibromide 
• 62-53-3 aniline 
• 64-17-5 ethanol 
• 127-09-3 sodium acetate 
• 100-61-8 N-methylaniline 
• 79-11-8 chloroacetic acid 
• 762-50-5 1-chloro-2-fluoroethane 
• 80-41-1 2-chloroethyl tosylate 

Downstream Products

• 59281-86-6 N-(2-anilino-ethyl)-acetanilide 
• 728938-28-1 N,N'-dinitro-N,N'-dipicryl-ethylenediamine 
• 123183-90-4 4-Phenyl-1-(p-nitroazobenzenyl)piperazine 
• 10159-39-4 4,4’-(1,4-piperazinediyl)bisbenzaldehyde 
• 187800-49-3 (N,N'-diphenylpiperazine)(1,3-η(3)-propenyl)palladiumtrifluoromethanesulfonate 
• 1426255-14-2 5,5'-((piperazine-1,4-diylbis(1,4-phenylene))bis(diazene-1,2-diyl))bis(2-acetamidobenzenesulfonic acid) 
• 65018-25-9 1,4-bis-(4-bromo-phenyl)-piperazine 
• 1422043-19-3 C₂₆H₃₄N₂Si₂ 
• 1422043-08-0 C₂₀H₁₈N₂ 
• 728-24-5 1,3-diphenyl-2-imidazolidone 
• 858850-94-9 1,4-diphenyl-piperazine-2,3-dione 
• 4963-30-8 di-(4-nitrosophenyl)-N,N-piperazine 

Relevant academic research and scientific papers

Reaction of Carbon Dioxide with 1-Phenylaziridine Catalyzed by Organo-antimony and -tin Compounds

The reactions of carbon dioxide (CO2) with 1-phenylaziridine (1) to afford 3-phenyl-2-oxazolidone (2) were carried out in the presence of organo-antimony and -tin compounds as catalysts.Tetraphenylstibonium bromide (Ph4SbBr) and triphenyltin bromide (Ph3SnBr) were found to be active catalysts.The use of a polar aprotic solvent, such as a HMPA, provided optimal reaction conditions.

Functionalization of superparamagnetic Fe3O4@SiO2 nanoparticles with a Cu(II) binuclear Schiff base complex as an efficient and reusable nanomagnetic catalyst for N-arylation of α-amino acids and nitrogen-containing heterocycles with aryl halides

Fe3O4@SiO2 nanoparticles was functionalized with a binuclear Schiff base Cu(II)-complex (Fe3O4@SiO2/Schiff base-Cu(II) NPs) and used as an effective magnetic hetereogeneous nanocatalyst for the N-arylation of α-amino acids and nitrogen-containig heterocycles. The catalyst, Fe3O4@SiO2/Schiff base-Cu(II) NPs, was characterized by Fourier transform infrared (FTIR) and ultraviolet-visible (UV-vis) analyses step by step. Size, morphology, and size distribution of the nanocatalyst were studied by transmission electron microscopy (TEM), scanning electron microscopy (SEM), and dynamic light scatterings (DLS) analyses, respectively. The structure of Fe3O4 nanoparticles was checked by X-ray diffraction (XRD) technique. Furthermore, the magnetic properties of the nanocatalyst were investigated by vibrating sample magnetometer (VSM) analysis. Loading content as well as leaching amounts of copper supported by the catalyst was measured by inductive coupled plasma (ICP) analysis. Also, thermal studies of the nanocatalyst was studied by thermal gravimetric analysis (TGA) instrument. X-ray photoelectron spectroscopy (XPS) analysis of the catalyst revealed that the copper sites are in +2 oxidation state. The Fe3O4@SiO2/Schiff base-Cu(II) complex was found to be an effective catalyst for C–N cross-coupling reactions, which high to excellent yields were achieved for α-amino acids as well as N-hetereocyclic compounds. Easy recoverability of the catalyst by an external magnet, reusability up to eight runs without significant loss of activity, and its well stability during the reaction are among the other highlights of this catalyst.

Nickel-Catalyzed Amination of Aryl Chlorides with Amides

A nickel-catalyzed amination of aryl chlorides with diverse amides via C-N bond cleavage has been realized under mild conditions. A broad substrate scope with excellent functional group tolerance at a low catalyst loading makes the protocol powerful for synthesizing various aromatic amines. The aryl chlorides could selectively couple to the amino fragments rather than the carbonyl moieties of amides. Our protocol complements the conventional amination of aryl chlorides and expands the usage of inactive amides.

Catalyst-free photodecarbonylation ofortho-amino benzaldehyde

It is almost a consensus that decarbonylation of the aldehyde group (-CHO) needs to not only be mediated by transition metal catalysts, but also requires severe reaction conditions (high temperature and long reaction time). In this work, inspired by the “conformational-selectivity-based” design strategy, we broke this consensus and discovered a catalyst-free photodecarbonylation of the aldehyde group. It revealed that decarbonylation can be easily achieved with visible light irradiation by introducing a tertiary amine into theortho-position of the aldehyde group. A diverse array of tertiary amines is tolerated by our photodecarbonylation under mild conditions. Furthermore, the (QM) computations of the mechanism and the experiments on well-designed special substrates revealed that our photodecarbonylation depends on the conformational specificity of the aldehyde group and tertiary amine, and occurs through an unusual [1,4]-H shift and a subsequent [1,3]-H shift.

Photo-induced dealdehyding method

The invention provides a photo-induced dealdehyding method, and belongs to the technical field of organic synthesis. The photo-induced dealdehyding method comprises the following steps that a mixtureof a compound shown in the formula I and a solvent are reacted under an inert gas atmosphere and visible light irradiation, a dealdehyding product is obtained, and no photocatalyst is used in the whole process; wherein the structural formula of the formula I shown in the specification, R is a functional group and is selected from hydrogen, methyl, methoxyl, cyano, chlorine, bromine or fluorine. According to the photo-induced dealdehyding method, in the inert gas atmosphere, the compound shown in the formula (I) can be excited to generate carbon-oxygen bond homogeneous cracking through visiblelight irradiation, then free radical migration and double bond displacement are conducted, finally carbon monoxide is removed, aldehyde group removal is completed, no photocatalyst is needed in the whole process, operation is easy and convenient, and conditions are mild.

Ligand complex of copper (II) supported on superparamagnetic Fe3O4?SiO2 nanoparticles: an efficient and magnetically separable catalyst for N-arylation of nitrogen-containing heterocycles with aryl halides

In this study, we introduce the ligand complex of copper (II) supported on superparamagnetic Fe3O4?SiO2 nanoparticles as a highly intriguing magnetic catalyst in N-arylation of nitrogen heterocycles with aryl halides. The present methodology offers several advantages such as; low catalyst loading, the use of magnetically recoverable and reusable catalyst, high to excellent yields without using any external ligands or additives, short reaction times and simplicity of operation. Also, the magnetic catalyst could be easily separated from the final product by an external magnet and reused up to seven times without any significant loss of activity. Therefore, this separation strategy with negligible leaching makes Fe3O4?SiO2/ligand/Cu(II) an economical catalyst to perform this transformation.

Compound and color filter

PROBLEM TO BE SOLVED: To provide a triarylmethane compound having high contrast and excellent color tone and a color filter containing the compound. SOLUTION: The present invention provides a triarylmethane compound represented by formula 2 and a color filter containing a compound represented by the compound as a coloring material. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT

Copper-catalyzed, ceric ammonium nitrate mediated N-arylation of amines

Cu-Catalyzed, ligand- and base-free cross-coupling of aryl boronic acids with primary and secondary amines has been reported. This ‘Chan-Evans-Lam' reaction has revealed that at room temperature, with a catalytic amount of copper(ii) acetate and ceric ammonium nitrate (CAN) as an oxidant, N-arylation can result in an effective C-N bond formation. This air stable, practical, robust protocol enables tolerance towards a variety of functional groups on both boronic acid and amine partners.

Robust Buchwald-Hartwig amination enabled by ball-milling

An operationally simple mechanochemical method for the Pd catalysed Buchwald-Hartwig amination of arylhalides with secondary amines has been developed using a Pd PEPPSI catalyst system. The system is demonstrated on 30 substrates and applied in the context of a target synthesis. Furthermore, the performance of the reaction under aerobic conditions has been probed under traditional solution and mechanochemical conditions, the observations are discussed herein.

Practical Catalytic Cleavage of C(sp3)?C(sp3) Bonds in Amines

The selective cleavage of thermodynamically stable C(sp3)?C(sp3) single bonds is rare compared to their ubiquitous formation. Herein, we describe a general methodology for such transformations using homogeneous copper-based catalysts in the presence of air. The utility of this novel methodology is demonstrated for Cα?Cβ bond scission in >70 amines with excellent functional group tolerance. This transformation establishes tertiary amines as a general synthon for amides and provides valuable possibilities for their scalable functionalization in, for example, natural products and bioactive molecules.