5688-82-4

Usage

Uses

Used in Fluorescent Dye Applications:
[(3,4,5-trimethoxyphenyl)methylene]malononitrile is used as a fluorescent dye for biological imaging, allowing researchers to visualize and study cellular structures and processes with high specificity and sensitivity.
Used in Organic Synthesis:
As a precursor for the synthesis of other organic compounds, [(3,4,5-trimethoxyphenyl)methylene]malononitrile is utilized in the production of various chemicals that have applications in different industries, such as pharmaceuticals, agrochemicals, and materials science.
Used in Polymer Synthesis:
[(3,4,5-trimethoxyphenyl)methylene]malononitrile is used as a reagent in the creation of polymers, which are essential in the development of new materials with specific properties for various applications, including packaging, automotive, and electronics.
Used in Research and Development:
In the field of organic chemistry, [(3,4,5-trimethoxyphenyl)methylene]malononitrile is employed in research and development processes to explore new reactions, mechanisms, and potential applications of this versatile compound.
Used in Industrial Processes:
[(3,4,5-trimethoxyphenyl)methylene]malononitrile is also important in various industrial processes, where it is used to synthesize intermediates and final products that are utilized in a wide range of applications, from pharmaceuticals to specialty chemicals.

InChI:InChI=1/C13H12N2O3/c1-16-11-5-9(4-10(7-14)8-15)6-12(17-2)13(11)18-3/h4-6H,1-3H3

Upstream product

• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 109-77-3 malononitrile 
• 324022-77-7 C₁₈H₁₉NO₄ 
• 66-25-1 hexanal 
• 112-54-9 Dodecanal 
• 59276-37-8 3,4,5-trimethoxybenzaldehyde dimethyl acetal 

Downstream Products

• 343221-00-1 2-cyano-(3,4,5-trimethoxy)hydrocinnamonirile 
• 122424-05-9 2-[2-Cyclohepta-2,4,6-trienylidene-1-(3,4,5-trimethoxy-phenyl)-ethylidene]-malononitrile 
• 170030-57-6 6-amino-4-(3,4,5-trimethoxyphenyl)-3-methyl-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile 
• 242480-92-8 2-amino-5,6,7,8-tetrahydro-4-(3,4,5-trimethoxyphenyl)-7,7-dimethyl-5-oxo-4H-chromene-3-carbonitrile 
• 49581-12-6 5-<(3,4,5-trimethoxyphenyl) methylene>-2,4,6 (1H,3H,5H)pyrimidinetrione 

Relevant academic research and scientific papers

Facile synthesis of 3,4-fused tricyclic indoles with a seven-membered ring through a three-component reaction of 4-hydroxyindole, aldehyde, and malonodinitrile or ethyl cyanoacetate

Three-component reactions of 4-hydroxyindole, aldehydes, and malonodinitrile or ethyl cyanoacetate were developed for the first time by using either potassium fluoride or diethylamine as a catalyst, which provided an easy access to 3,4-fused tricyclic indoles in good to excellent yield. The merits of this synthesis route are attributed to its simplicity, practicality, efficiency, and eco-friendliness, as well as the easy availability of the catalyst.

New insights into the exploitation of oxidized carbon nitrides as heterogeneous base catalysts

In this work, the development of a novel efficient heterogeneous catalytic system capable of driving Knoevenagel condensation reactions between benzaldehydes and malononitrile was reported. Specifically, we explored a post-synthetic modification of graphitic carbon nitride (g-CN) through a strong oxidation treatment by acid mixture (HNO3/H2SO4). The as-prepared oxidized CN material (CNO) shows a large number of surface acidic moieties, that can be easily deprotonated through an aqueous alkaline wash with different bases (NaOH, K2CO3, t-BuOK), to introduce a high density of reactive basic sites. The best catalyst is obtained with NaOH as the base (CNO-NaOH), and displays high reactivity and good tolerance towards functional group variations of the reagents, thus emerging as a potential new recyclable carbon nitride-based structure for organic base catalysis.

Nanochannel-based {BaZn}-organic framework for catalytic activity on the cycloaddition reaction of epoxides with CO2and deacetalization-Knoevenagel condensation

Herein, the rare combination of BaII (5s) and ZnII (3d) in the presence of the structure-oriented TDP6- ligand generated the nanochannel-based hybrid material {[(CH3)2NH2]2[BaZn(TDP)(H2O)]·DMF·5H2O}n (NUC-51, H6TDP = 2,4,6-tri(2,4-dicarboxyphenyl)pyridine), which possesses excellent physicochemical characteristics such as nanoscopic channels, high porosity, large specific surface area, and high heat/water-resistance. To the best of our knowledge, this is the first 3D [BaIIZnII(CO2)6(H2O)]-based nano-porous host framework, whose activated state possesses the coexistence of Lewis acid-base sites including 4-coordinated Zn2+ ions, 7-coordinated Ba2+ ions, uncoordinated carboxyl oxygen atoms, and Npyridine atoms. Catalytic experiments exhibited that activated NUC-51a possesses a high catalytic activity on the cycloaddition reactions of epoxides with CO2 at 55 °C, which can be ascribed to its structural advantages of nanoscale channels and rich bifunctional active sites. Moreover, NUC-51a could significantly accelerate the deacetalization-Knoevenagel condensation reaction in DMSO solvent at 70 °C.

Attempts to access a series of pyrazoles lead to new hydrazones with antifungal potential against candida species including azole‐resistant strains

The treatment of benzylidenemalononitriles with phenylhydrazines in refluxing ethanol did not provide pyrazole derivatives, but instead furnished hydrazones. The structure of hydra-zones was secured by X‐ray analysis. The chemical proof was also obtained by direct reaction of 3,4,5‐trimethoxybenzaldehyde with 2,4‐dichlorophenylhydrazine. Newly synthesized hydrazones were tested against eight Candida spp. strains in a dose response assay to determine the minimum inhibitory concentration (MIC99). Five compounds were identified as promising antifungal agents against Candida spp. (C. albicans SC5314, C. glabrata, C. tropicalis, C. parapsilosis and C. glabrata (R azoles)), with MIC99 values ranging from 16 to 32 μg/mL and selective antifungal activity over cy-totoxicity.

Synthesis of 5H-indeno[1,2-b]pyridine derivatives: Antiproliferative and antimetastatic activities against two human prostate cancer cell lines

This study describes the direct synthesis of 2-amino-4-(phenylsubstituted)-5H-indeno[1,2-b]pyridine-3-carbonitrile derivatives 5–21, through sequential multicomponent reaction of aromatic aldehydes, malononitrile, and 1-indanone in the presence of ammonium acetate and acetic acid (catalytic). The biological study showed that compound 10 significantly impeded proliferation of the cell lines PC-3, LNCaP, and MatLyLu. The antimetastatic effects of compound 10 could be related with inhibition of MMP9 in the PC-3 and LNCaP human cell lines. On the basis of a study of the structure–activity relationship of these compounds, we propose that the presence of two methoxy groups at positions 6 and 7 of the indeno nucleus and a 4-hydroxy-3-methoxy phenyl substitution pattern at position 4 of the pyridine ring is decisive for these types of molecules to exert?very good antiproliferative and antimetastatic activities.

Effect of Substituents on the Crystal Structures, Optical Properties, and Catalytic Activity of Homoleptic Zn(II) and Cd(II) β-oxodithioester Complexes

Five novel zinc(II) and cadmium(II) β-oxodithioester complexes, [Zn(L1)2] (1), [Zn(L2)2]n (2), [Zn(L3)2]n (3) [Cd(L1)2]n (4), [Cd(L2)2]n (5), with β-oxodithioester ligands, where L1 = 3-(methylthio)-1-(thiophen-2-yl)-3-thioxoprop-1-en-1-olate, L2 = 3-(methylthio)-1-(pyridin-3-yl)-3-thioxoprop-1-en-1-olate, and L3 = 3-(methylthio)-1-(pyridin-4-yl)-3-thioxoprop-1-en-1-olate, were synthesized and characterized by elemental analysis, IR, UV-vis, and NMR spectroscopy (1H and 13C{1H}). The solid-state structures of all complexes were ascertained by single-crystal X-ray crystallography. The β-oxodithioester ligands are bonded to Zn(II)/Cd(II) metal ions in an Oa§S and N chelating/chelating-bridging fashion leading to the formation of 1D (in 2-4) and 2D (in 5) coordination polymeric structures, but complex 1 was obtained as a discrete tetrahedral molecule. Complex 4 crystallizes in the C2 chiral space group and has been studied using circular dichroism (CD) spectroscopy. The multidimensional assemblies in these complexes are stabilized by many important noncovalent C-H···π(ZnOSC3, chelate), ?···?, C-H···?, and H···H interactions. The catalytic activities of 1-5 in reactions involving C-C and C-O bond formation have been studied, and the results indicated that complex 3 can be efficiently utilized as a heterogeneous bifunctional catalyst for the Knoevenagel condensation and multicomponent reactions to develop biologically important organic molecules. The luminescent properties of complexes were also studied. Interestingly, zinc complexes 1-3 showed strong lumniscent emission in the solid state, whereas cadmium complexes 4 and 5 exhibited bright luminescent emission in the solution phase. The semiconducting behavior of the complexes was studied by solid-state diffuse reflectance spectra (DRS), which showed optical band gaps in the range of 2.49-2.62 eV.

Enhanced catalytic activity of bio-fabricated ZnO NPs prepared by ultrasound-assisted route for the synthesis of tetraketone and benzylidenemalonitrile in hydrotropic aqueous medium

Abstract: Mushroom-like mesoporous and hexagonal ZnO nanoparticles were synthesized from plant extract and chemical method respectively, by co-precipitation method in aqueous medium. Different morphological forms of ZnO NPs were characterized by XRD, TGA, FESEM, EDX, FTIR, UV–Vis and BET. Neem (Azadirachta indica) leaf extract and ultrasound irradiation have a crucial role in the formation of different morphologies of ZnO NPs. ZnO NPs synthesized from plant extract and hydrotrope show a synergistic effect that leads to efficient synthesis of benzylidenemalonitrile and tetraketone derivatives at room temperature in water. Simple preparation of the catalyst, excellent yields, reusability of catalyst with consistent activity and ease of product isolation are the most significant advantages of this green protocol. Graphic abstract: [Figure not available: see fulltext.]

Magnetic core-shell dendritic mesoporous silica nanospheres anchored with diamine as an efficient and recyclable base catalyst

In the present study, diamine-functionalized magnetic core-shell dendritic mesoporous silica nanospheres have been successfully synthesized by an oil-water biphasic stratification-coating strategy. The shape, size and morphology of the synthesized magnetic nanocatalyst could be characterized by various physicochemical techniques such as, field emission scanning electron microscopy (FE-SEM) and transmission electron microscopy (TEM). The characteristic information about the successful immobilization of various functionalities on the nanospheres could be obtained with the help of X-ray powder diffraction (XRD) patterns, Fourier transform-infrared spectroscopy (FT-IR), energy dispersive X-ray spectroscopy (EDX) and thermo-gravimetric analysis (TGA). The details about the magnetic behaviour and surface area of the nanocatalyst could be acquired by vibrating sample magnetometry (VSM) and BET surface analysis, respectively. The synthesized diamine-functionalized magnetic nanoparticles were then explored as a highly efficient catalyst for the Knoevenagel condensation and one-pot synthesis of polyhydroquinolines using aromatic/heteroaromatic aldehydes and aliphatic aldehydes with active methylene compounds under very mild conditions. The synthesized magnetic core-shell dendritic mesoporous silica nanospheres had large surface areas. This large surface area and pore volume could facilitate a proper interaction and penetration of the reactant molecules with the basic amine groups present on the dendritic mesoporous silica nanospheres. The supported nanocatalyst revealed no sign of leaching of the amine groups present inside the dendrimers and therefore, could be reused up to nine times without any noteworthy loss in catalytic activity.

Photo-bleachable visible light initiator as well as preparation method and application thereof

The invention discloses a photo-bleachable visible light initiator as well as a preparation method and application thereof, and belongs to the field of visible light photocuring. In the prior art, inthe visible light photocuring process, a curing system can absorb visible light, so that the penetrability of visible light is reduced, and the curing depth of the curing system is reduced. The photo-bleachable visible light initiator provided by the invention can successfully initiate visible light free radical photopolymerization, and a polymerized material can be changed from colored to colorless and transparent, so that the material application range is widened, and the curing depth is increased. The invention also provides a preparation method of the photo-bleachable visible light initiator. According to the preparation method, an aromatic aldehyde and a compound containing active methylene are subjected to condensation reaction to prepare the photo-bleachable visible light initiator.The synthesis method of the photo-bleachable visible light initiator is simple, the absorption wavelength of the photo-bleachable visible light initiator can be adjusted and changed through molecularstructure adjustment to adapt to light sources with different wavelengths, and the application range is wide.

Synthesis, in vitro and in silico screening of 2-amino-4-aryl-6-(phenylthio) pyridine-3,5-dicarbonitriles as novel α-glucosidase inhibitors

Inhibition of α-glucosidase enzyme is of prime importance for the treatment of diabetes mellitus (DM). Apart of many organic scaffolds, pyridine based compounds have previously been reported for wide range of bioactivities. The current study reports a series of pyridine based synthetic analogues for their α-glucosidase inhibitory potential assessed by in vitro, kinetics and in silico studies. For this purpose, 2-amino-4-aryl-6-(phenylthio)pyridine-3,5-dicarbonitriles 1–28 were synthesized and subjected to in vitro screening. Several analogs, including 1–3, 7, 9, 11–14, and 16 showed many folds increased inhibitory potential in comparison to the standard acarbose (IC50 = 750 ± 10 μM). Interestingly, compound 7 (IC50 = 55.6 ± 0.3 μM) exhibited thirteen-folds greater inhibition strength than the standard acarbose. Kinetic studies on most potent molecule 7 revealed a competitive type inhibitory mechanism. In silico studies have been performed to examine the binding mode of ligand (compound 7) with the active site residues of α-glucosidase enzyme.