28446-68-6

Usage

Chemical Properties

clear yellow liquid after melting

InChI:InChI=1/C10H9NO/c1-12-10-6-4-9(5-7-10)3-2-8-11/h2-7H,1H3/b3-2+

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 16640-68-9 cyanomethylene triphenylphosphorane 
• 18293-53-3 2-trimethylsilylacetonitrile 
• 2537-48-6 diethyl 1-cyanomethylphosphonate 
• 132017-31-3 C₁₄H₂₉BrNSb 
• 3319-15-1 rac-1-(4-methoxyphenyl)-ethanol 
• 68-12-2 N,N-dimethyl-formamide 
• 75-05-8 acetonitrile 
• 959-33-1 3-(4-methoxyphenyl)-1-phenylprop-2-en-1-one 
• 102423-74-5 2,6-diamino-4-(4-methoxyphenyl)-4H-thiopyran-3,5-dicarbonitrile 
• 696-62-8 para-iodoanisole 
• 107-13-1 acrylonitrile 
• 1089301-34-7 trans-2-<4-Methoxy-benzyliden>-2-cyan-essigsaeure 
• 590-17-0 cyanomethyl bromide 

Downstream Products

• 632-51-9 1,1,2,2-tetraphenylethylene 
• 94991-57-8 (E)-3-(4-Methoxy-phenyl)-acrylimidic acid ethyl ester 
• 100-09-4 4-methoxybenzoic acid 
• 66864-59-3 2,3-Dibromo-3-(4-methoxy-phenyl)-propionitrile 
• 107234-79-7 erythro-4-cyano-3-(4-methoxyphenyl)-2-phenylbutanoate d'ethyle 
• 59259-39-1 (+/-)-3endo-(4-methoxy-phenyl)-norborn-5-ene-2exo-carboxylic acid 
• 59259-39-1 (+/-)-3exo-(4-methoxy-phenyl)-norborn-5-ene-2endo-carboxylic acid 
• 94991-49-8 (E)-3-(4-Methoxyphenyl)propenthiosaeure-O-ethylester 
• 1199942-66-9 3-(3,4-dimethoxyphenyl)-3-(4-methoxyphenyl)propanenitrile 

Relevant academic research and scientific papers

Cu-catalyzed cyanomethylation of imines and α,β-alkenes with acetonitrile and its derivatives

We describe copper-catalyzed cyanomethylation of imines and α,β-alkenes with a methylnitrile source and provide an efficient route to synthesize arylacrylonitriles and β,γ-unsaturated nitriles. This method tolerates aliphatic and aromatic alkenes substituted with a variety of functional groups such as F, Cl, Br, Me, OMe,tert-Bu, NO2, NH2and CO2H with good to excellent yields (69-98%). These systems consist of inexpensive, simple copper catalyst and acetonitrile with its derivatives (α-bromo/α-iodo-acetonitrile) and are highly applicable in the industrial production of acrylonitriles.

Reactions of 3-arylpropenenitriles with arenes under superelectrophilic activation conditions: Hydroarylation of the carbon-carbon double bond followed by cyclization into 3-arylindanones

Reactions of 3-arylpropenenitriles [ArCH[dbnd]CHCN] with arenes [Ar'H] under the superelectrophilic activation conditions with Br?nsted superacid TfOH (CF3SO3H) or strong Lewis acid AlBr3 result, first, in the formation of products of hydroarylation of the carbon-carbon double bond, 3,3-diarylpropanenitriles [Ar(Ar’)CHCH2CN]. Reactions may go further in TfOH leading to 3-arylindanones, as products of intramolecular aromatic acylation by the electrophilically activated nitrile group. Intermediate cationic species, derived at the protonation of the starting 3-arylpropenenitriles onto the carbon of C[dbnd]C bond and the nitrile nitrogen, have been studied by DFT calculation. A plausible reaction mechanism including the formation of highly reactive dications [(Ar)HC+–CH2C+ = NH] has been proposed. The obtained 3,3-diarylpropanenitriles have been transformed into pharmaceutically valuable 5-(2,2-diarylethyl)-1H-tetrazoles [Ar(Ar’)CHCH2Tetr] and 3-diarylpropylamines [Ar(Ar’)CH(CH2)2NH2] by the reactions with NaN3 and LiAlH4 correspondingly.

Design, synthesis and biological evaluation of 8-(2-amino-1-hydroxyethyl)-6-hydroxy-1,4-benzoxazine-3(4H)-one derivatives as potent β2-adrenoceptor agonists

A series of β2-adrenoceptor agonists with an 8-(2-amino-1-hydroxyethyl)-6-hydroxy-1,4-benzoxazine-3(4H)-one moiety is presented. The stimulatory effects of the compounds on human β2-adrenoceptor and β1-adrenoceptor were characterized by a cell-based assay. Their smooth muscle relaxant activities were tested on isolated guinea pig trachea. Most of the compounds were found to be potent and selective agonists of the β2-adrenoceptor. One of the compounds, (R)-18c, possessed a strong β2-adrenoceptor agonistic effect with an EC50 value of 24 pM. It produced a full and potent airway smooth muscle relaxant effect same as olodaterol. Its onset of action was 3.5 min and its duration of action was more than 12 h in an in vitro guinea pig trachea model of bronchodilation. These results suggest that (R)-18c is a potential candidate for long-acting β2-AR agonists.

Magnetic MCM-41 nanoparticles as a support for the immobilization of a palladium organometallic catalyst and its application in C-C coupling reactions

In this study, the surface of magnetic MCM-41 nanoparticles (MCM-41/Fe3O4) was modified by 3-Aminopropyltriethoxysilane (APTES) and further, 1-methyl imidazole was anchored on their surface using cyanuric chloride as a linker. Then, Pd2+ ions were immobilized on the surface of the modified MCM-41/Fe3O4 (Pd-imi-CC@MCM-41/Fe3O4), and its application was studied as a magnetically recyclable nanocatalyst in carbon-carbon coupling reactions between a wide range of aryl halides and butyl acrylate, methyl acrylate, acrylonitrile, phenylboronic acid, or 3,4-difluorophenylboronic acid under the conditions of a phosphine-free ligand and an air atmosphere. This catalyst has the advantages of both the Fe3O4 nanoparticles and mesoporous MCM-41. The structure of the catalyst was characterized via TEM, SEM, EDS, WDX, N2 adsorption-desorption isotherm, XRD, TGA, FT-IR, and AAS. Also, the recovered catalyst was characterized via SEM, AAS and FT-IR. All the products from the carbon-carbon coupling reaction were obtained with excellent yields and high TON and TOF values, which indicate the high efficiency and activity of this catalyst. The selectivity of this catalyst was studied with various aryl halides bearing different functional groups. Furthermore, the heterogeneity and stability of Pd-imi-CC@MCM-41/Fe3O4 was studied via AAS, and leaching and poisoning tests. According to the results, this heterogeneous catalyst can be reused several times.

Visible light-induced direct conversion of aldehydes into nitriles in aqueous medium using Co@g-C3N4 as photocatalyst

Unprecedented Co@g-C3N4 catalyzed visible light driven efficient conversion of a variety of aldehydes into corresponding nitriles is reported. Operational simplicity, excellent yield of pure products (87–94%), ambient reaction condition, using aqueous methanol as solvent, visible-light photocatalysis are the salient features of envisaged methodology for direct conversion of aldehydes into nitriles. Furthermore, reusability of Co@g-C3N4 was checked up to five runs and it was noticed that there was no substantial change in morphology as well as the catalytic efficiency of catalyst.

Polymer-supported palladium: A hybrid system for multifunctional catalytic application

Polymer-supported palladium was synthesized by applying a single-step wet chemical synthesis route and the resultant composite material was characterized by means of various techniques. Infrared and UV–visible spectra provided information on the chemical structure of the polymer. Microscopy techniques showed the general morphology of the polymer. The oxidation state of palladium was determined using the X-ray photoelectron spectroscopy method. The synthesized material was applied as a heterogeneous catalyst for the Heck coupling reaction and also as an electrocatalyst for the oxidation of cysteine.

An efficient class of bis-NHC salts: Applications in Pd-catalyzed reactions under mild reaction conditions

This study describes an efficient class of bis-N-heterocyclic carbene (bis-NHC) salts that can be easily made from commercially available and inexpensive starting materials. The application of these salts to Pd-catalyzed reactions is described. The palladium (Pd) catalyst generated in situ was highly effective under mild reaction conditions.

Method for synthesizing substituted acrylonitrile with one-pot process

The invention provides a method for synthesizing substituted acrylonitrile with a one-pot process. Beta-aryl substituted acrylonitrile is prepared from 0.01-1.0 mol of aryl substituted methanol or heterocycle substituted methanol as a raw material and a solvent adopting acetonitrile with the concentration of 0.2-2.0 mol/L under the alkaline action. In the oxygen atmosphere, a semiconductor photocatalyst is added, the mixture reacts under assistance of light illumination, and the reaction speed and the yield can be greatly increased. Raw materials for a reaction are easy to obtain, the method is simple and convenient, and the product has important application value.

Pd(0)-Arg-boehmite: As Reusable and Efficient Nanocatalyst in Suzuki and Heck Reactions

Abstract: The direct supporting of Pd-arginine complex on boehmite nanoparticles (Pd(0)-Arg-boehmite) was reported as a moisture- and air-stable, heterogeneous, excellent and novel organometallic catalyst, which applied for the Suzuki and Heck cross coupling reactions through coupling of phenylboronic acid, 3,4-difluoro phenylboronic acid, sodium tetraphenyl borate, butyl acrylate, methyl acrylate, acrylonitrile and styrene with a wide range of aryl halide including Cl, Br and I. Pd(0)-Arg-boehmite was prepared for the first time via simple, environmental and inexpensive procedure in water and ethanol without inert atmosphere or high temperature using commercially available materials, and characterized by XRD, TGA, TEM, SEM, EDS and ICP-OES techniques. The leaching of palladium and heterogeneity test of this catalyst was studied by hot filtration and ICP-OES techniques; resulting we found that this catalyst was demonstrated remarkable and excellent recyclability. Graphical Abstract: Boehmite nanoparticles were prepared by inexpensive procedure in water at room temperature and directly immobilized with a new type of Pd-arginine complex. After characterization of this catalyst, its application has been studied for the C–C coupling reactions. [Figure not available: see fulltext.]

Immobilized NNN Pd-complex on magnetic nanoparticles: Efficient and reusable catalyst for Heck and Sonogashira coupling reactions

A highly efficient and easily recyclable magnetic nanoparticle supported palladium catalyst was developed and applied in the Heck and Sonogashira reactions in order to show its catalytic applicability in Pd-catalyzed C-C coupling protocols. The catalyst was prepared using a simple chemical process. First, the prepared Fe3O4@SiO2 nanoparticles were reacted with (3-chloropropyl)-trimethoxysilane (3-CPTMS) in order to synthesis chloro-functionalized magnetic nanoparticles (CPS-MNPs). The substitution reaction of synthetic NNN ligand with CPS-MNPs yields the production of CPS-MNPs-NNN ligand. Finally, immobilization of palladium species on CPS-MNPs-NNN ligand surface afforded CPS-MNPs-NNN-Pd catalyst. The structure and morphology of the prepared nanocatalyst was characterized using various methods such as SEM, TEM, XPS, EDX, CHN, ICP, XRD, FT-IR and VSM techniques. The TEM images show that the sizes of the palladium catalyst are in the range of 8-15 nm. The Heck and Sonogashira coupling reactions were performed in the presence of a catalytic amount of this catalyst system (0.5 mol%) and good yields of products were obtained. Due to the magnetic nature of the catalyst it can be separated from the reaction mixture easily by applying an external magnetic field. Heterogeneity tests affirmed that the catalytic activity stayed indefectible during multiple reaction cycles.