5688-82-4

Basic information

• Product Name: [(3,4,5-trimethoxyphenyl)methylene]malononitrile
• Synonyms: [(3,4,5-trimethoxyphenyl)methylene]malononitrile;3,4,5-Trimethoxybenzylidenemalononitrile;(3,4,5-trimethoxybenzylidene)propanedinitrile
• CAS NO: 5688-82-4
• Molecular Formula: C₁₃H₁₂N₂O₃
• Molecular Weight: 244.24598
• EINECS: 227-155-9
• Mol File: 5688-82-4.mol
• Article Data: 37

Chemical Properties

• Boiling Point: 406°C at 760 mmHg
• Flash Point: 164.7°C
• Appearance: /
• Density: 1.188g/cm³
• Vapor Pressure: 8.39E-07mmHg at 25°C
• Refractive Index: 1.56
• CAS DataBase Reference: [(3,4,5-trimethoxyphenyl)methylene]malononitrile(CAS DataBase Reference)
• NIST Chemistry Reference: [(3,4,5-trimethoxyphenyl)methylene]malononitrile(5688-82-4)
• EPA Substance Registry System: [(3,4,5-trimethoxyphenyl)methylene]malononitrile(5688-82-4)

Safety Data

• Hazardous Substances Data: 5688-82-4(Hazardous Substances Data)

Usage

General Description

[(3,4,5-trimethoxyphenyl)methylene]malononitrile is a chemical compound with the molecular formula C15H13NO4. It is a yellow crystalline solid that is insoluble in water but soluble in organic solvents. [(3,4,5-trimethoxyphenyl)methylene]malononitrile is known for its use as a fluorescent dye for biological imaging and as a precursor for the synthesis of other organic compounds. It is also a common reagent in organic chemistry reactions, particularly in the creation of polymers and other complex molecules. [(3,4,5-trimethoxyphenyl)methylene]malononitrile is important in the field of organic chemistry and has various applications in research and industrial processes.

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

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

Downstream Products

• 242480-92-8 2-amino-5,6,7,8-tetrahydro-4-(3,4,5-trimethoxyphenyl)-7,7-dimethyl-5-oxo-4H-chromene-3-carbonitrile 
• 170030-57-6 6-amino-4-(3,4,5-trimethoxyphenyl)-3-methyl-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile 
• 1357001-36-5 7-amino-4-oxo-2-thioxo-5-(3,4,5-trimethoxyphenyl)-2,3,4,5-tetrahydro-1H-pyrano[2,3-d]pyrimidine-6-carbonitrile 
• 1357001-39-8 C₂₀H₁₈N₆O₅S 
• 1357001-40-1 N-(6-cyano-4-oxo-2-thioxo-5-(3,4,5-trimethoxyphenyl)-2,3,4,5-tetrahydro-1H-pyrano[2,3-d]pyrimidin-7-yl)benzenesulfonamide 
• 1357001-41-2 C₁₈H₁₆N₄O₆S 
• 1426235-48-4 C₂₁H₁₇N₃O₃ 

Relevant articles and documents

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.

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.