3785-90-8

Usage

Chemical Properties

yellow amorphous powder

Uses

Inhibitor of transducin GTPase activity

InChI:InChI=1/C10H6N2O/c11-6-9(7-12)5-8-1-3-10(13)4-2-8/h1-5,13H

Upstream product

• 123-08-0 4-hydroxy-benzaldehyde 
• 109-77-3 malononitrile 
• 62309-99-3 phenoxymethylene-malononitrile 
• 90-15-3 α-naphthol 
• 100-67-4 potassium phenolate 
• 114569-19-6 N-(p-hydroxybenzylidene)-p-aminoacetophenone 
• 623-05-2 (4-hydroxyphenyl)methanol 
• 59276-27-6 4-(dimethoxymethyl)phenol 

Downstream Products

• 19310-87-3 4-(2,2-dicyanovinyl)phenyl acetate 
• 132524-83-5 3-Amino-1-(4-hydroxy-phenyl)-1H-4-oxa-5-aza-phenanthrene-2-carbonitrile 
• 132524-80-2 2-amino-5,6-dihydro-4-(4-hydroxyphenyl)-6-methyl-5-oxo-4H-pyrano[3,2-c]quinoline-3-carbonitrile 
• 130944-11-5 2-amino-4-(4-hydroxyphenyl)-4H-benzo[h]chromene-3-carbonitrile 
• 78016-49-6 4-Hexyl-benzoic acid 4-(2,2-dicyano-vinyl)-phenyl ester 
• 78016-52-1 4-Hexyloxy-benzoic acid 4-(2,2-dicyano-vinyl)-phenyl ester 
• 78016-53-2 4-n-Nonyloxybenzoesaeure-4'-(2,2-dicyanethenyl)phenylester 
• 78106-03-3 4-Pentanoyloxy-benzoic acid 4-(2,2-dicyano-vinyl)-phenyl ester 
• 78016-54-3 4-(2'2'-dicyanoethenyl)phenyl 4-n-heptanoyloxybenzoate 
• 78016-55-4 4-Hexyloxycarbonyloxy-benzoic acid 4-(2,2-dicyano-vinyl)-phenyl ester 
• 78016-51-0 4-Pentyloxy-benzoic acid 4-(2,2-dicyano-vinyl)-phenyl ester 
• 128937-88-2 4-(octadeca-10,12-diynoyloxy)benzylidenemalononitrile 
• 85302-99-4 7-Butyl-9,10-dihydro-phenanthrene-2-carboxylic acid 4-(2,2-dicyano-vinyl)-phenyl ester 
• 5553-97-9 Tyrphostin A₆₃ 

Relevant academic research and scientific papers

Photoacid as ICT probe for ground state proton transfer process from solute to solvents

In present work, 2-(4-Hydroxybenzylidene)malononitrile (HyDC) acts as a photoacid and intramolecular charge transfer (ICT) probe for monitoring solvent specific ground state proton transfer (GSPT) process from solute to solvents. Presence of electron accepting group in HyDC, photoacidic nature and GSPT process are enhanced and observed by UV–Vis spectroscopy. HyDC shows microsolvation behavior with protic solvents at ground state. Microsolvated clusters of HyDC with solvents are formed and supported by experimental and theoretical results.

Elementary and efficient catalyst process for the Knoevenagel condensation of araldehydes with arylmethylidene malononitrile

A comparative study of the Knoevenagel condensation of an aromatic aldehyde with an active methylene compound (e.g., malononitrile or ethyl cyanoacetate), using solvent free grindstone conditions and microwave irradiation is reported. Our solvent free app

Knoevenagel condensation in aqueous media promoted by 2,2′-bipyridinium dihydrogen phosphate as a green efficient catalyst

A 2,2′-Bipyridine-based ionic compound named 2,2′-bipyridinium dihydrogen phosphate was synthesized by addition of phosphoric acid to a solution of 2,2′-Bipyridine in dichloromethane. After the characterization using FT-IR, mass, 1H, 13C and 31P NMR techniques, it was used as a Bronsted dicationic acidic catalyst for the promotion of the synthesis of 2-arylidene malononitrile and 5-arylidene barbituric acid derivatives via Knoevenagel condensation reaction in water. Some of the advantages of this method are the utilization of an easy preparable, cost-effective and eco-friendly organic salt as a catalyst within high rates and yields of the reactions, simple and quick work-up and acceptable reusability of the catalyst.

Introduction of succinimide as a green and sustainable organo-catalyst for the synthesis of arylidene malononitrile and tetrahydrobenzo[b] pyran derivatives

Aim and Objective: In this work, we tried to introduce a non-toxic and stable organic compound named succinimide as a green and efficient organo-catalyst for the promotion of the synthesis of arylidene malononitrile and tetrahydrobenzo[b]pyran derivatives

Effect of supramolecular polymeric aggregation in room temperature ionic liquids (RTILs) on catalytic activity in the synthesis of 4H-chromene derivatives and Knoevenagel condensation

RTILs exhibit supramolecular self-assembled polymeric aggregation due to noncovalent interactions. The influence of the aggregation behaviour of RTILs on catalytic activity is evident but still poorly understood. The present work focuses on establishing a

Design and Development of Amine Functionalized Mesoporous Cubic Silica Particles: A Recyclable Catalyst for Knoevenagel Condensation

Abstract: The amine functionalized cubic mesoporous silica nanoparticles (cSiO2-NH2) were successfully synthesized through biphasic stratification approach. The synthesized material was characterised by various spectroscopic and phys

Supported copper on a diamide-diacid-bridged PMO: an efficient hybrid catalyst for the cascade oxidation of benzyl alcohols/Knoevenagel condensation

In this study, a novel periodic mesoporous organosilica (PMO) containing diamide-diacid bridges was conveniently prepared using ethylenediaminetetraacetic dianhydride to support Cu(ii) species and affording supramolecular Cu@EDTAD-PMO nanoparticles efficiently. Fourier transform infrared (FT-IR) and energy dispersive X-ray (EDX) spectroscopy, thermogravimetric analysis (TGA), X-ray diffraction (XRD), field emission scanning electron microscopy (FESEM), Brunauer-Emmett-Teller (BET) analysis, and high-resolution transmission electron microscopy (HRTEM) results confirmed the successful synthesis of Cu@EDTAD-PMO. The stabilized Cu(ii) nanoparticles inside the mesochannels of the new PMO provided appropriate sites for selective oxidation of different benzyl alcohol derivatives to their corresponding benzaldehydes and subsequent Knoevenagel condensation with malononitrile. Therefore, Cu@EDTAD-PMO can be considered as a multifunctional heterogeneous catalyst, which is prepared easily through a green procedure and demonstrates appropriate stability with almost no leaching of the Cu(ii) nanoparticles into the reaction medium, and easy recovery through simple filtration. The recycled Cu@EDTAD-PMO was reused up to five times without significant loss of its catalytic activity. The stability, recoverability, and reusability of the designed heterogeneous catalyst were also studied under various reaction conditions.

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.

Supramolecular polymeric aggregation behavior and its impact on catalytic properties of imidazolium based hydrophilic ionic liquids

Ionic Liquids (ILs) self-assemble to form supramolecular polymeric clusters/aggregates. The aggregation behavior of ILs influences its activity in the organic synthesis. However, the precise role of ILs in organic reactions is still unknown. It is, therefore, important to comprehend the supramolecular polymeric aggregation behavior of ILs. We are exploring the supramolecular polymeric aggregation behavior of ILs using Electrospray Ionization Mass Spectrometry (ESI-MS). We have synthesized four hydrophilic ILs (1–4) and investigated their aggregation behavior and its impact on catalytic activity in Carbon-Carbon bond formation (Knoevenagel and Claisen-Schmidt condensation). Here, we show that the aggregation behavior of ILs depends on the type and nature of cation and anion. ESI-MS (?ve) spectra reveals two different type of aggregation i.e. [CnAn+1]? & [A2 + H+]?. We have found that catalytic activity increases with increased [CnAn+1]? supramolecular aggregation. Consequently, highest yield of products obtained in ILs which show decreased anion-anion aggregation [A2 + H+]? abundance in ESI-MS. We anticipate our results to be a starting point for the establishment of desired ILs for organic synthesis.

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.