52287-59-9

Basic information

• Product Name: (E)-2-cyano-3-(4-methylphenyl)acrylamide
• Synonyms: (E)-2-cyano-3-(4-methylphenyl)acrylamide
• CAS NO: 52287-59-9
• Molecular Weight: 186.213
• Mol File: 52287-59-9.mol

Chemical Properties

• CAS DataBase Reference: (E)-2-cyano-3-(4-methylphenyl)acrylamide(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-2-cyano-3-(4-methylphenyl)acrylamide(52287-59-9)
• EPA Substance Registry System: (E)-2-cyano-3-(4-methylphenyl)acrylamide(52287-59-9)

Safety Data

• Hazardous Substances Data: 52287-59-9(Hazardous Substances Data)

Upstream product

• 22141-39-5 2-(hydroxy(p-tolyl)methyl)acrylonitrile 
• 104-87-0 4-methyl-benzaldehyde 
• 109-77-3 malononitrile 
• 107-91-5 cyanoacetic acid amide 
• 104-84-7 para-methylbenzylamine 
• 2826-25-7 2-(4-methylbenzylidene)malononitrile 

Downstream Products

• 120284-59-5 3-Cyano-6-[(E)-cyanoimino]-4-phenyl-2-p-tolyl-piperidine-3-carboxylic acid amide 
• 98011-29-1 6-Amino-2-thioxo-4-p-tolyl-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid amide 
• 65429-79-0 3-cyano-4-(4-methylphenyl)-5,6-dimethyl-2(1H)-pyridone 
• 65429-74-5 3-cyano-4-(4-methyl-phenyl)-6-phenyl-1,2-dihydro-pyridine-2-one 

Relevant articles and documents

Oxidative Olefination of Benzylamine with an Active Methylene Compound Mediated by Hypervalent Iodine (III)

Hypervalent iodine-mediated oxidative olefination of amines with an active methylene compound provides a rapid gateway towards the formation of electrophilic alkenes under mild reaction conditions in good to excellent yields. This is an efficient protocol for the preparation of substituted electrophilic alkenes.

Synthesis of 2-cyanoacrylamides through Pd-catalyzed monohydration of methylenemalononitriles

A straightforward and efficient method has been developed for the synthesis of 2-cyanoacrylamide from 2-methylenemalononitriles through monohydration. A series of methylenemalononitriles underwent the reaction under mild and simple reaction conditions wit

Triflic acid-catalyzed metal-free synthesis of (: E)-2-cyanoacrylamides and 3-substituted azetidine-2,4-diones

A TfOH-catalyzed highly efficient synthesis of biologically active (E)-2-cyanoacrylamides and 3-substituted azetidine-2,4-diones has been reported with 64-94% yields under metal-free conditions. The reaction proceeds through sequential Knoevenagel condens

An efficient catalyst-free one-pot synthesis of primary amides from the aldehydes of the Baylis-Hillman reaction

Herein, a facile and efficient method for the preparation of allyl amides from the aldehyde of Baylis-Hillman adducts has been developed using a hydroxylamine/methanol system under a catalyst-free condition. The effects of solvents and temperature on the reaction and substituents on the phenyl ring have been examined. This method is best demonstrated by its advantages such as operational simplicity, moderate to excellent yields, short reaction time, and simple reaction procedure. Most importantly, the reaction proceeds smoothly in the absence of a catalyst and an external oxidant.

Cascade synthesis of 2-pyridones using acrylamides and ketones

Microwave assisted non-catalytic condensation of 2-cyanoacetamide with aromatic aldehydes, and enolate mediated Michael-type addition to acrylamide followed by oxidative cyclization, produce 2-pyridones in good to excellent yield. Unsymmetrical ketones produce two regioisomeric enolates, therefore thermodynamic and kinetic products of butan-2-one and pentan-2-one have been isolated and fully characterized. This journal is

Homogeneous and stereoselective copper(II)-catalyzed monohydration of methylenemalononitriles to 2-cyanoacrylamides

A facile and efficient route for the homogeneous and highly stereoselective monohydration of substituted methylenemalononitriles to (E)-2-cyanoacrylamides catalyzed by copper(II) acetate monohydrate in acetic acid containing 2% water is described, and a mechanism is proposed. The protocol has proved to be suitable for the monohydration of dicyanobenzenes and 2-substituted malononitriles.

Tandem Knoevenagel-[3+2] cycloaddition-elimination reactions: One-pot synthesis of 4,5-disubstituted 1,2,3-(NH)-triazoles

Sodium azide has been found to catalyse Knoevenagel condensation between aromatic aldehyde and cyano compound with active methylene hydrogens and this has led to a successful route for the one pot synthesis of 4,5-disubstituted 1,2,3-(NH)-triazoles from a

Arylcyanoacrylamides as inhibitors of the Dengue and West Nile virus proteases

The 3-aryl-2-cyanoacrylamide scaffold was designed as core pharmacophore for inhibitors of the Dengue and West Nile virus serine proteases (NS2B-NS3). A total of 86 analogs was prepared to study the structure-activity relationships in detail. Thereby, it turned out that the electron density of the aryl moiety and the central double bond have a crucial influence on the activity of the compounds, whereas the influence of substituents of the amide residue is less relevant. The para-hydroxy substituted analog was found to be the most potent inhibitor in this series with a Ki-value of 35.7 μM at the Dengue and 44.6 μM at the West Nile virus protease. The aprotinin competition assay demonstrates a direct interaction of the inhibitor molecule with active centre of the Dengue virus protease. The target selectivity was studied in a counterscreen with thrombin and found to be 2.8:1 in favor of DEN protease and 2.3:1 in favor of WNV protease, respectively.

Microwave assisted Knovenagel condensation using NaCL and NH4OAc-AcOH system as catalysts under solvent-free conditions

Microwave assisted Knoevenagel condensation of aromatic aldehydes I with active methylene compounds 2 under solvent-free conditions to prepare arylidene compounds 3 in excellent yields using cheap and readily available NaCl and ammonium acetate acetic acid mixture as catalysts has been reported.