15031-03-5

Usage

Appearance

Yellow to reddish-brown crystalline powder A solid substance with a yellow to reddish-brown color and a crystalline structure.

Solubility

Insoluble in water, soluble in organic solvents It does not dissolve in water but dissolves easily in certain organic solvents.

Usage in organic synthesis

Building block for various other chemicals It serves as an essential component in the synthesis of a wide range of chemical compounds.

Applications

Manufacturing of pharmaceuticals and agrochemicals It is used as a key ingredient in the production of medications and agricultural chemicals.

Potential applications

Organic light-emitting diodes (OLEDs), fluorescent probe for metal ion detection It has been researched for its possible use in creating OLEDs and as a tool for detecting metal ions.

Safety precautions

Harmful if ingested, inhaled, or in contact with skin Proper handling and safety measures should be taken to avoid adverse health effects.

Upstream product

• 1003-29-8 2-pyrrole aldehyde 
• 109-77-3 malononitrile 
• 109-97-7 pyrrole 
• 123-06-8 Ethoxymethylenemalononitrile 
• 405219-09-2 2-(1-diethoxymethyl-1H-pyrrole-2-yl)methylenecarbodinitrile 

Downstream Products

• 771566-23-5 2-((1-(phenylsulfonyl)-1H-pyrrol-2-yl)methylene)malononitrile 
• 845294-44-2 N-acetyl-2-pyrrolylmethylidenemalononitrile 

Relevant academic research and scientific papers

Enantioselective Michael addition to vinyl phosphonatesviahydrogen bond-enhanced halogen bond catalysis

An asymmetric Michael addition of malononitrile to vinyl phosphonates was accomplished by hydrogen bond-enhanced bifunctional halogen bond (XB) catalysis. NMR titration experiments were used to demonstrate that halogen bonding, with the support of hydrogen-bonding, played a key role in the activation of the Michael acceptors through the phosphonate group. This is the first example of the use of XBs for the activation of organophosphorus compounds in synthesis. In addition, the iodo-perfluorophenyl group proved to be a better directing unit than different iodo- and nitro-substituted phenyl groups. The developed approach afforded products with up to excellent yields and diastereoselectivities and up to good enantioselectivities.

A readily accessible porous organic polymer facilitates high-yielding Knoevenagel condensation at room temperature both in water and under solvent-free mechanochemical conditions

A novel nitrogen-rich amorphous porous organic polymer has been synthesized using a microwave-assisted process. Its high chemical stability, reusability and poor solubility enable the use of the porous polymer as a metal-free heterogeneous catalyst for C–

Ammonium chloride catalyzed Knoevenagel condensation in PEG-400 as ecofriendly solvent

A simple and selective green methodology has been successfully developed for Knoevenagel condensation in polyethylene glycol-400 using 10 mol % ammonium chloride as catalyst. The method is applicable to a wide range of aromatic, heteroaromatic and α,β-unsaturated aldehydes. The reactions have been found to be clean and free from the formation of the Michael adduct.

Highly Active Copper(I)-Chalcogenone Catalyzed Knoevenagel Condensation Reaction Using Various Aldehydes and Active Methylene Compounds

First copper(I) chalcogenones catalysed Knoevenagel Condensation reactions have been reported. No illustration of the utilization of this copper-chalcogenone complex class in Knoevenagel Condensation catalysis can be found. Thus, copper(I) bis(benzimidazole-2-chalcogenone) catalysts [Cu(L1)4]+BF4? (1) and [Cu(L2)4]+BF4? (2) (L1 = bis(1-isopropyl-benzimidazole-2-selone)-3-ethyl; L2 = bis(1-isopropyl-benzimidazole-2-thione)-3-ethyl) have been utilized as catalysts in the Knoevenagel Condensation reactions. These copper(I) chalcogenone catalysts have shown high efficiency for the catalytic Knoevenagel Condensation of aryl aldehydes and active methylene compounds. In particular, complex 2, exhibit the best catalytic activities. The scope of the catalytic reactions has been investigated with 22 different molecules. The excellent catalytic activity has been depicted for various types of substrates with either electron-rich or deficient aryl aldehydes. The present investigation features relatively mild reaction conditions with good functional group tolerance and excellent yields. Graphic Abstract: The first copper(I)-chalcogenone complexes catalysed Knoevenagel Condensation reactions?have also been investigated, and revealed the best catalytic activities. [Figure not available: see fulltext.]

Hydroquinone and benzoquinone-catalyzed aqueous Knoevenagel condensation

A Knoevenagel condensation of various aldehydes with malononitrile effectively proceeded in the presence of hydroquinone/benzoquinone mixed catalysts at room temperature in H2O. Furthermore, γ-deuterium-labeled α,β-unsaturated nitrile derivatives were als

Structure and electronics in 1H-pyrrol-2-ylmethylene compounds

In this report, we present the synthesis and characterization of 1H-pyrrol-2-ylmethylenes, prepared from Knoevenagel condensations between pyrrole aldehydes and several organic CH acids. New compounds were characterized by a variety of spectroscopic metho

Ammonium chloride: An efficient and environmentally benign catalyst for knoevenagel condensation of carbonyl and active methylene compounds

In the present study, a rapid, simple and an efficient procedure for the Knoevenagel condensation of various carbonyl and active methylene compounds in ethanol at a moderate temperature in the presence of a catalytic amount of an efficient, environmentall

An Efficient and Reusable Multifunctional Composite Magnetic Nanocatalyst for Knoevenagel Condensation

A range of multifunctional magnetic metal-organic framework nanomaterials consisting of various mass ratios of the metal-organic framework MIL-53(Fe) and magnetic SiO 2 @NiFe 2 O 4 nanoparticles were designed, prepared, ch

An Efficient One-pot Three-component Method for the Synthesis of 5-Amino-3-(2-oxo-2H-chromen-3-yl)-7-aryl-7H-thiazolo[3,2-a]pyridine-6,8-dicarbonitriles

A facile, convenient, and adequate method has been developed for the synthesis of novel 5-amino-3-(2-oxo-2H-chromen-3-yl)-7-aryl-7H-thiazolo[3,2-a]pyridine-6,8-dicarbonitriles (6) by employing 2-(4-(2-oxo-2H-chromen-3-yl)thiazol-2-yl)acetonitrile (3) as an important precursor. Initially, we have synthesized the target compounds in a stepwise manner and then approached a tandem method to examine the feasibility of one-pot method. Subsequently, one-pot three-component protocol has been established for the synthesis of title compounds by the reaction of 3 with benzaldehyde and malononitrile in refluxing ethanol engender a new six-membered thiazolo[3,2-a]?pyridine as a hybrid scaffold. Reaction conditions were optimized for this reaction and a broad substrate scope with various aryl and heteroaryl aldehydes make this protocol very practical, attractive, and worthy. Mechanistic aspects for the formation of these compounds were outlined comprehensively. Characterization of these newly synthesized compounds was achieved by means of IR, 1H NMR, 13C NMR, and HRMS.

An efficient one-pot four-component Gewald reaction: Synthesis of substituted 2-aminothiophenes with coumarin–thiazole scaffolds under environmentally benign conditions

An elegant and efficient method has been outlined for the synthesis of novel 5-amino-4-[4-(2-oxo-2H-chromen-3-yl)thiazol-2-yl]-3-arylthiophene-2-carbonitriles employing a one-pot four-component reaction of various aldehydes, 2-[4-(2-oxo-2H-chromen-3-yl)thiazol-2-yl]acetonitrile, malononitrile and molecular sulfur independently in the presence of L-proline as a catalyst, under green reaction conditions. In an alternative approach, initially, the Knoevenagel condensation of these various aldehydes has been carried out with active methylene compounds malononitrile or 2-[4-(2-oxo-2H-chromen-3-yl)thiazol-2-yl]acetonitrile to obtain the corresponding condensed compounds. These compounds then further subjected to a one-pot three-component Gewald reaction with molecular sulfur using sodium bicarbonate as a simple and inexpensive catalyst to obtain the target compounds. The effect of solvent and catalyst on these reactions has been screened to obtain the optimal conditions. The advantages of this protocol are the use of mild reaction conditions at ambient temperature, environmental friendliness, good yields in faster reaction times, convenient operation procedures, and broad substrate scope.