2972-84-1

Usage

Uses

Used in Organic Synthesis:
(naphthalen-2-ylmethylidene)propanedinitrile is utilized as a building block in the preparation of various organic compounds, contributing to the diversity and complexity of synthesized molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (naphthalen-2-ylmethylidene)propanedinitrile is used as an intermediate in the production of bioactive molecules, playing a crucial role in the development of new drugs and therapeutic agents.
Used in Agrochemical Industry:
(naphthalen-2-ylmethylidene)propanedinitrile also finds application in the agrochemical industry, where it serves as an intermediate for the synthesis of various agrochemical products, potentially enhancing crop protection and yield.
Used for Antimicrobial and Antifungal Applications:
(naphthalen-2-ylmethylidene)propanedinitrile is known for its potent antimicrobial and antifungal properties, making it a valuable component in the development of products aimed at controlling microbial and fungal infections.

Upstream product

• 13577-85-0 N,N-dimethyl-2-naphthylcarboxamide 
• 109-77-3 malononitrile 
• 1592-38-7 2-Naphthalenemethanol 
• 66-99-9 β-naphthaldehyde 

Downstream Products

• 5553-90-2 2-(naphthalen-2-ylmethyl)malononitrile 
• 1153740-44-3 2-amino-3,5-dicarbonitrile -4-(naphthalen-2-yl)-6-(phenylthio)pyridine 
• 21461-46-1 (E)-2-(2-nitrovinyl)naphthalene 

Relevant academic research and scientific papers

A Dynamic Three-Dimensional Covalent Organic Framework

A guest-induced reversible crystal-structure transformation is identified in a new 3D covalent organic framework (COF) by comprehensive analyses using powder X-ray diffraction, organic vapor sorption isotherm, and 129Xe NMR spectroscopy. The revolving imine bond in interpenetrating 3D networks is uncovered as the key to the dynamic behavior, the potential applications of which are illustrated by gas separation and heterogeneous catalysis, thus paving the way to the design of stimuli-responsive and multifunctional COF materials.

Two Cu(II) coordination polymers: Heterogeneous catalytic Knoevenagel condensation reaction and treatment activity on atherosclerosis via regulating the expression of the COX-2 in vascular endothelial cells

By altering auxiliary nitrogen-donor ligands, two novel coordination polymers (CPs) containing Cu(II) formulated as [Cu2.5(L)(trz)2(H2O)2]·2H2O (1) (Htrz = 1,2,4-triazole and H3L = 5-(4-car

A Stable Y(III)-Based Amide-Functionalized Metal-Organic Framework for Propane/Methane Separation and Knoevenagel Condensation

Here, a Y(III)-based metal-organic framework, JLU-MOF112 {[Y3(μ3-O)2(μ3-OH)(H2O)2(BTCTBA)2]·2[(CH3)2NH2]·5DMF·C6H5Cl·4H2O}, has been successfully synthesized under solvothermal conditions. JLU-MOF112 was constructed with amide-functionalized tricarboxylate ligands and Y(III)-based infinite chains, where the Y3 repeating units are arranged in a trans order. The overall framework could be viewed as a novel (3,5)-connected net with two types of channels along the [100] and [010] directions. JLU-MOF112 possesses a large BET surface area (1553 m2 g-1), a permanent pore volume (0.67 cm3 g-1), and outstanding thermal and chemical stability, which give JLU-MOF112 potential for the purification of natural gas, especially the equimolar separation of C3H8/CH4 with a high selectivity of 176. In addition, benefiting from the amide functional groups as Br?nsted basic sites and the exposure of open metal sites as Lewis acid sites after activation, JLU-MOF112 can serve as a high-efficiency heterogeneous catalyst for Knoevenagel condensation by the reactions of malononitrile with benzaldehyde (yield of 98%, turnover number of 392, and turnover frequency of 3.27 min-1) and diverse aldehyde compounds. A rational mechanism was put forward that the Knoevenagel condensation was catalyzed by the synergistic effect of the Lewis acid sites and Br?nsted basic sites, engendering the polarization of the carbonyl groups and the deprotonation of the methylene groups for nucleophilic attack.

Flexible thiourea linked covalent organic frameworks

Exploring covalent organic frameworks with new linkages is regarded as an efficient method to modulate the corresponding properties, and a new linkage is essential to the progress of this field. Herein, condensation of 1,3,5-triformylphloroglucinol with 1,1′-(1,4-phenylene)bis(thiourea), 1,1′-(2,5-dimethyl-1,4-phenylene)bis(thiourea) or 1,1′-(3,3′-dimethyl-[1,1′-biphenyl]-4,4′-diyl)bis(thiourea) were applied to construct COFs with thiourea linkages for the first time.

Development of an efficient, one-pot, multicomponent protocol for synthesis of 8-hydroxy-4-phenyl-1,2-dihydroquinoline derivatives

A one-pot quick and efficient multicomponent reaction has been developed for the synthesis of a new series of functionalized 8-hydroxy-4-phenyl-1,2-dihydroquinoline derivatives using 30 mol% ammonium acetate in ethanol as solvent. This economical protocol

Three Resorcin[4]arene-Based Two-Dimensional Zn(II) Supramolecular Isomers Synthesized via a Structure-Directing Strategy for Knoevenagel Condensation

Herein, in the presence of three structure-directing agents (SDAs), a family of imidazole-functionalized resorcin[4]arene-based coordination polymers (CPs), [Zn(TIC4R)(HCOO)]·HCOO·0.5DMF·1.5H2O (1), [Zn(TIC4R)(CN)]·HCOO·DMF·2.5H2O (2), and [Zn(TIC4R)(H2O)

Two new calix[4]resorcinarene-based coordination cages adjusted by metal ions for the Knoevenagel condensation reaction

Two new calix[4]resorcinarene-based coordination cages, namely, [Zn4(TPC4R)(PDC)4]·2DMF·6H2O (1-Zn) and [In11(TPC4R)2(PDC)16(μ2-OH)2(H2O)2]·[(CH

Phosphine-Catalyzed (4 + 2) Annulation of δ-Sulfonamido-Substituted Enones with 1,1-Dicyanoalkenes: Synthesis of Piperidine Derivatives

The δ-sulfonamido-substituted enones were employed as phosphine acceptor in phosphine-catalyzed (4 + 2) annulation of 1,1-dicyanoalkenes. They served as a four-membered synthon to react with 1,1-dicyanoalkenes under mild reaction conditions, producing pip

Photoelectrochemical and thermal characterization of aromatic hydrocarbons substituted with a dicyanovinyl unit

Seven aromatic hydrocarbons bearing a dicyanovinyl unit were prepared to determine the relationship between both the number of aromatic rings and location of acceptor substituent on their thermal and optoelectronic properties. Additionally, the density functional theory calculations were performed. The obtained compounds showed temperatures of the beginning of thermal decomposition in the range of 137–289 °C, being above their respective melting points found between 88 and 248 °C. They were electrochemically active and showed quasi-reversible reduction process (except for 2-(phen-1-yl)methylene)malononitrile). Electrochemically estimated energy band gaps were below 3.0 eV, in the range of 2.10–2.50 eV. The absorption and emission spectra were recorded in CHCl3 and NMP and in solid state. All compounds strongly absorbed radiation with absorption maximum ranging from 307 to 454 nm ascribed to the intramolecular charge transfer between the donor and acceptor units. The aromatic hydrocarbons were luminescent in all investigated media and exhibited higher photoluminescence quantum yields in the solid state due to the aggregation induced emission phenomena. Electroluminescence ability of selected compounds was tested in a diode with guest-host configuration. Additionally, the selected compound together with a commercial N719 was applied in the dye-sensitized solar cell.

Synthesis, biological evaluation, and molecular modeling of nitrile-containing compounds: Exploring multiple activities as anti-Alzheimer agents

Based on the monoamine oxidase (MAO) inhibition properties of aminoheterocycles with a carbonitrile group we have carried out a systematic exploration to discover new classes of carbonitriles endowed with dual MAO and AChE inhibitory activities, and Aβ anti-aggregating properties. Eighty-three nitrile-containing compounds, 13 of which are new, were synthesized and evaluated. in vitro screening revealed that 31, a new compound, presented the best lead for trifunctional inhibition against MAO A (0.34 μM), MAO B (0.26 μM), and AChE (52 μM), while 32 exhibited a lead for selective MAO A (0.12 μM) inhibition coupled to AChE (48 μM) inhibition. Computational analysis revealed that the malononitrile group can find an advantageous position with the aromatic cleft and FAD of MAO A or MAO B. However, the total binding energy can be handicapped by an internal penalty caused by twisting of the ligand molecule and subsequent disruption of the conjugation (32 in MAO B compared to the conjugated 31). Conjugation is also important for AChE as well as the hydrophilic character of malononitrile that allows this group to be in close contact with the aqueous environment as seen for 83. Although the effect of 31 and 32 against Aβ1–42, was very weak, the effect of 63 and 65, and of the new compound 75, indicated that these compounds were able to disaggregate Aβ1–42 fibrils. The most effective was 63, a (phenylhydrazinylidene)propanedinitrile derivative that also inhibited MAO A (1.65 μM), making it a potential lead for Alzheimer's disease application.