2826-25-7

Usage

Uses

Used in Forensic Science:
2-(4-METHYLBENZYLIDENE)-MALONONITRILE is used as a component of fingerprint powder for its fluorescent properties, which aid in the detection of latent fingerprints, particularly on non-porous surfaces.
Used in the Textile Industry:
2-(4-METHYLBENZYLIDENE)-MALONONITRILE is used as a fluorescent dye, contributing to the vibrancy and visibility of textiles in various applications.
Used in Organic Synthesis:
2-(4-METHYLBENZYLIDENE)-MALONONITRILE is used as a precursor for the synthesis of various organic compounds, highlighting its importance in the creation of new chemical entities.
While 2-(4-METHYLBENZYLIDENE)-MALONONITRILE is considered to be a low toxicity compound, it is still essential to exercise caution during handling to prevent skin and eye irritation.

InChI:InChI=1/C11H8N2/c1-9-2-4-10(5-3-9)6-11(7-12)8-13/h2-6H,1H3

Upstream product

• 104-87-0 4-methyl-benzaldehyde 
• 109-77-3 malononitrile 
• 97651-32-6 p-tolylmethylenecyanothioacetamide 
• 18440-58-9 1-(N-phenylhydrazono)-1-chloropropanone 
• 75482-50-7 2-(2-phenylhydrazono)-2-chloro-1-phenylethanone 
• 2700-22-3 Benzylidenemalononitrile 
• 1867-38-5 4-chlorobenzylidenemalonodinitrile 
• 35779-32-9 1,3,5-tris(4-methylphenyl)-2,4-diazapenta-1,4-diene 
• 124397-40-6 (E)-N-(4-bromophenyl)-1-(p-tolyl)methanimine 
• 670-54-2 ethenetetracarbonitrile 
• 99-91-2 para-chloroacetophenone 
• 98-86-2 acetophenone 
• 5553-86-6 (4-methylbenzyl)malononitrile 
• 589-18-4 4-Methylbenzyl alcohol 

Downstream Products

• 77008-32-3 2,4,6-tri-p-tolyl-piperidine-3,3,5,5-tetracarbonitrile 
• 21448-20-4 1-(p-Tolyl)-2,2-dicyanhexen-⁽⁴⁾ 
• 21448-30-6 3-(p-Tolyl)-1.1.1-triphenyl-2.2-dicyan-propan 
• 21447-88-1 1-Phenyl-3-(p-tolyl)-2.2-dicyan-propanon-⁽¹⁾ 
• 21448-14-6 1-(p-Tolyl)-2,2-dicyan-penten-⁽⁴⁾ 
• 114772-53-1 2-Cyano-4'-methylbiphenyl 
• 134079-94-0 2-amino-5,7-dihydro-5-oxo-4-p-tolyl-4H-furo[3,4-b]pyran-3-carbonitrile 
• 130028-56-7 2,2-dicyano-3-(4-methylphenyl)cyclopropane-1,1-dicarboxylate de diethyle 
• 85460-34-0 1-Amino-3-(4-methylphenyl)-3H-pyrido<2,1-b>benzothiazol-2,4-dicarbonitrile 
• 120-03-6 2-(p-tolyl)-1H-benzimidazole 
• 150651-39-1 iFSP₁ 
• 343362-46-9 (E)-2-(1H-Benzoimidazol-2-yl)-3-p-tolyl-acrylonitrile 
• 134305-33-2 3-amino-4-cyano-5-(p-tolyl)benzocoumarin 
• 5553-86-6 (4-methylbenzyl)malononitrile 

Relevant academic research and scientific papers

Synthesis, characterization of polystyrene-phosphate films and their application as heterogeneous catalyst for Knoevenagel condensation in solvent-free conditions

Abstract: Novel film catalysts of the polystyrene (Ps) and trimethyl phosphate (P) nanoparticles were synthesized on glass substrates by soft chemistry using doctor blade method. Subsequently, the prepared Ps–P film catalysts were characterized by various

Pseudo six-component stereoselective synthesis of 2,4,6-triaryl-3,3,5,5-tetracyanopiperidines

The Kn?venagel–Michael–Mannich cascade reaction of aromatic aldehyde (3 equiv.), malononitrile (2 equiv.) and ammonium acetate or aqueous ammonia provides convenient stereoselective access to cis,cis-2,4,6-triaryl-3,3,5,5-tetracyanopiperidines in 62–94% y

Nanochannel {InZn}-Organic Framework with a High Catalytic Performance on CO2Chemical Fixation and Deacetalization-Knoevenagel Condensation

The rare combination of InIII 5p and ZnII 3d in the presence of a structure-oriented TDP6- ligand led to a robust hybrid material of {(Me2NH2)[InZn(TDP)(OH2)]·4DMF·4H2O}n (NUC-42) with the interlaced hierarchical nanochannels (hexagonal and cylindrical) shaped by six rows of undocumented [InZn(CO2)6(OH2)] clusters, which represented the first 5p-3d nanochannel-based heterometallic metal-organic framework. With respect to the multifarious symbiotic Lewis acid-base and Br?nsted acid sites in the high porous framework, the catalytic performance of activated NUC-42a upon CO2 cycloaddition with styrene oxide was evaluated under solvent-free conditions with 1 atm of CO2 pressure, which exhibited that the reaction could be well completed at ambient temperature within 48 h or at 60 °C within 4 h with high yield and selectivity. Moreover, because of the acidic function of metal sites and a central free pyridine in the TDP6- ligand, deacetalization-Knoevenagel condensation of acetals and malononitrile could be efficiently facilitated by an activated sample of NUC-42a under lukewarm conditions.

MOFs assembled from C 3symmetric ligands: Structure, iodine capture and role as bifunctional catalysts towards the oxidation-Knoevenagel cascade reaction

Three new NiII/CoII-metal organic frameworks were self-assembled by the reaction of C3 symmetric 1,3,5-tribenzoic acid (H3BTC) and 2,4,6-tris(4-pyridyl)-1,3,5-triazine (4-TPT) ligands and NiII/CoII salts under solvothermal conditions. Isomorphous MOF1 and MOF2 exhibit a 3D pillar-layer framework based on binuclear M2(OH)(COO)2 units connected by tritopic BTC3- and 4-TPT ligands with a novel (3,5)-connected topology net. MOF3 displays a 3-fold interpenetrated 3D network exhibiting a (3,4)-connected topology net. The porous MOF3 can reversibly take up I2. The activated MOFs contain both Lewis acid (NiII center) and basic (uncoordinated pyridyl or carboxylic groups) sites, and act as bifunctional acid-base catalysts. The catalytic measurements demonstrate that the activated MOF3 exhibits good activities for benzyl alcohol oxidation and the Knoevenagel reaction and can be recycled and reused for at least four cycles without losing its structural integrity and high catalytic activity. Thus, the catalytic properties for the oxidation-Knoevenagel cascade reaction have also been studied.

A ru-complex tethered to a N-rich covalent triazine framework for tandem aerobic oxidation-knoevenagel condensation reactions

Herein, a highly N-rich covalent triazine framework (CTF) is applied as support for a RuIII complex. The bipyridine sites within the CTF provide excellent anchoring points for the [Ru(acac)2(CH3CN)2]PF6 complex. The obtained robust RuIII@bipy-CTF material was applied for the selective tandem aerobic oxidation-Knoevenagel condensation reaction. The presented system shows a high catalytic performance (>80% conversion of alcohols to α, β-unsaturated nitriles) without the use of expensive noble metals. The bipy-CTF not only acts as the catalyst support but also provides the active sites for both aerobic oxidation and Knoevenagel condensation reactions. This work highlights a new perspective for the development of highly efficient and robust heterogeneous catalysts applying CTFs for cascade catalysis.

Triazole-directed fabrication of polyoxovanadate-based metal-organic frameworks as efficient multifunctional heterogeneous catalysts for the Knoevenagel condensation and oxidation of alcohols

By introducing 4-amino-1,2,4-triazole (4-NH2-trz), three new polyoxovanadate-based metal-organic frameworks (PMOFs) [Ni3(4-NH2-trz)6][V6O18]·3H2O (1), [Co3(4-NH2-trz)6][V6O18]·3H2O (2) and [Cu3OH(4-NH2-trz)3H2O][VO3]5·H2O (3) have been synthesized and thoroughly characterized by single-crystal X-ray diffraction (SXRD), powder X-ray diffraction (PXRD), infrared spectroscopy (FT-IR), thermogravimetric (TG) analysis and elemental analysis (EA). Among them, PMOFs1and2had similar structures containing [V6O18]6?clusters; however, PMOF3was isolated as a structure containing a [VO3]55?cluster when the amount of the 4-NH2-trz ligand was reduced to half with the other synthesis conditions being the same as those of PMOFs1and2except for the transition-metal chlorides. Furthermore, the negative charges of polyoxovanadate [V6O18]6?and [VO3]55?anions were balanced by trinuclear complex cations [Ni3(4-NH2-trz)6]6?for1, [Co3(4-NH2-trz)6]6?for2and [Cu3OH(4-NH2-trz)3H2O]5?for3, respectively. PMOFs1-3were further used as heterogeneous catalysts in the Knoevenagel condensation under solvent-free conditions and showed high catalytic activity. PMOF1showed moderate catalytic activities in the oxidation of various aromatic alcohols using H2O2as an oxidant. Moreover, PMOF1could be reused at least three times without losing its activity.

Biguanide-functionalized hierarchical porous covalent organic frameworks for efficient catalysis of condensation reactions

Covalent organic frameworks (COFs) can be rationally designed with desired physicochemical properties for a far-ranging application in catalytic systems. Herein, a biguanide-functionalized covalent organic framework was designed and prepared via N-alkylat

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

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.

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.