19310-59-9

Usage

Uses

Used in Organic Synthesis:
2-cyano-3-(4-methylphenyl)prop-2-enamide is used as a versatile building block in organic synthesis for the preparation of various pharmaceuticals, agrochemicals, and other fine chemicals. Its unique structure allows for the development of a wide range of compounds with diverse applications.
Used in Pharmaceutical Development:
2-cyano-3-(4-methylphenyl)prop-2-enamide is used as a potential candidate for drug development due to its anti-inflammatory and anticancer properties. Its exact mechanisms of action and specific uses are still under investigation, but its potential in the pharmaceutical industry is promising.
Used in Agrochemicals:
2-cyano-3-(4-methylphenyl)prop-2-enamide is also used in the development of agrochemicals, where its unique properties can contribute to the creation of effective and targeted solutions for agricultural applications.

Upstream product

• 104-87-0 4-methyl-benzaldehyde 
• 107-91-5 cyanoacetic acid amide 
• 106-49-0 p-toluidine 
• 91350-14-0 2-Cyano-3-p-methylphenylpropionamid 
• 2826-25-7 2-(4-methylbenzylidene)malononitrile 
• 1352994-21-8 5-amino-3-(p-tolyl)-2,3-dihydroisoxazole-4-carbonitrile 

Downstream Products

• 1239897-77-8 C₂₄H₂₅N₃O₅ 
• 1239897-84-7 C₂₃H₂₂BrN₃O₅ 
• 1246559-26-1 6-amino-5-cyano-3-phenyl-thiine-2-thione 
• 948162-56-9 5-cyano-3-methyl-4-(4-methylphenyl)-1-phenyl-7H-pyrazolo[3,4-b]pyridin-6-one 
• 156638-76-5 4-(4-methyl-phenyl)-6-phenyl-2-(triphenylphosphoranylideneamino)-pyridine-3-carbonitrile 
• 156638-73-2 2-azido-4-(4-methyl-phenyl)-6-phenyl-pyridine-3-carbonitrile 
• 143882-76-2 2-chloro-4-(4-methylphenyl)-6-phenyl-pyridine-3-carbonitrile 
• 74873-35-1 2-amino-4-(4-methyl-phenyl)-6-phenyl-pyridine-3-carbonitrile 
• 91350-14-0 2-Cyano-3-p-methylphenylpropionamid 
• 65429-74-5 3-cyano-4-(4-methyl-phenyl)-6-phenyl-1,2-dihydro-pyridine-2-one 
• 85460-34-0 1-Amino-3-(4-methylphenyl)-3H-pyrido<2,1-b>benzothiazol-2,4-dicarbonitrile 

Relevant academic research and scientific papers

Triethylamine-catalyzed unprecedented synthesis of 2-amino-4-phenylbenzo [4, 5] imidazo [1,2-a] pyrimidine-3-carbonitrile under solvent free condition

An efficient and experimentally straightforward method for the synthesis of 2-amino-4-phenylbenzo [4,5] imidazo [1,2-a] pyrimidine-3-carbonitrile derivatives has been developed via one pot three-component reaction of 2-aminobenzimidazole, cyanoacetamide and aromatic aldehydes in the presence of triethylamine under solvent-free reaction condition. This green procedure offers several advantages such as high atom economy, short reaction time, metal-free and solvent-free reaction conditions, easy work up and column chromatography-free method with a wide range of functional group tolerance. This has made the protocol sustainable and economical.

Chitosan as a biodegradable heterogeneous catalyst for Knoevenagel condensation between benzaldehydes and cyanoacetamide

A natural biopolymer chitosan is being employed as heterogeneous solid base catalyst for the Knoevenagel condensation reaction between benzaldehydes and cyanoacetamide under mild reaction conditions. This reaction offers the direct synthesis of condensati

Tuning the Electronic Properties of 2-Cyano-3-phenylacrylamide Derivatives

We are the first to report the synthesis of a new class of 2-cyanoarylacrylamide (2-CAA) derivatives and observe that the synthesized 2-CAA shows fluorescence properties due to the formation of a dimeric interaction of hydrogen bonds between carbonyl oxygens and amide hydrogens (C=O?H-N-C=O?H-N?); i.e., dimers are linked through dimeric N-H?O hydrogen bonds. The single-crystal X-ray structure shows molecules to be hydrogen-bonded dimers, which further form a parallel stacking arrangement, mediated by significant π-π interactions. The 1H NMR and fluorescence spectral studies indicate the coexistence of amide and iminol tautomers in solution, which can be influenced by the nature of the solvent. Further, the excitation-wavelength-dependent fluorescence spectrum and the biexponential fluorescence decay profiles suggest the presence of more than one emitting species; i.e., amide and iminol tautomers coexists in solution. We have also shown that the equilibrium between the two tautomers can be tuned by the judicious choice of electron-donating or -withdrawing substituents.

Determination of thermodynamic affinities of various polar olefins as hydride, hydrogen atom, and electron acceptors in acetonitrile

A series of 69 polar olefins with various typical structures (X) were synthesized and the thermodynamic affinities (defined in terms of the molar enthalpy changes or the standard redox potentials in this work) of the polar olefins obtaining hydride anions, hydrogen atoms, and electrons, the thermodynamic affinities of the radical anions of the polar olefins (X ?-) obtaining protons and hydrogen atoms, and the thermodynamic affinities of the hydrogen adducts of the polar olefins (XH?) obtaining electrons in acetonitrile were determined using titration calorimetry and electrochemical methods. The pure Ci - 'C π-bond heterolytic and homolytic dissociation energies of the polar olefins (X) in acetonitrile and the pure Ci - 'C π-bond homolytic dissociation energies of the radical anions of the polar olefins (X?-) in acetonitrile were estimated. The remote substituent effects on the six thermodynamic affinities of the polar olefins and their related reaction intermediates were examined using the Hammett linear free-energy relationships; the results show that the Hammett linear free-energy relationships all hold in the six chemical and electrochemical processes. The information disclosed in this work could not only supply a gap of the chemical thermodynamics of olefins as one class of very important organic unsaturated compounds but also strongly promote the fast development of the chemistry and applications of olefins.

Ammonium fluoride as an inexpensive catalyst for Knoevenagel condensation in solvent-free conditions under microwave irradiation

Ammonium fluoride (NH4F) has been found to be an inexpensive catalyst for Knoevenagel condensation between aromatic aldehydes 1 and active methylene compounds 2 to afford arylidene derivatives 3 in excellent yields.

Synthesis of functionalized 2,3-dihydroisoxazoles by domino reactions in water and unexpected ring-opening reactions of 2,3-dihydroisoxazoles

α,α-Dicyanoolefins react with hydroxylamine to afford 2,3-dihydroisoxazoles (2,3-dihydroisoxazoles can be easily isolated by filtration) in excellent yields under mild and environmentally benign conditions. A one-pot reaction in tandem with an unexpected ring-opening of 2,3-dihydroisoxazoles has been developed as well.

Condensation reactions of aromatic aldehydes with active methylene compounds catalyzed by alkaline ionic liquid

The Knoevenagel condensation reactions of aromatic aldehydes with active methylene compounds catalyzed by the functionalized ionic liquid, 1-n-butyl-3-methylimmidazolium hydroxide ([bmim]OH), were carried out under grinding, heating, and microwave irradia

Synthesis of polysubstituted dihydropyridines by four-component reactions of aromatic aldehydes, malononitrile, arylamines, and acetylenedicarboxylate

A practical and efficient procedure for the preparation of the polysubstituted dihydropyridines was developed through a unique four-component reaction of aromatic aldehydes, malononitrile, arylamines, and acetylenedicarboxylate in ethanol in the presence of triethylamine as a base promoter. This four-component reaction is atom-efficient, high-yielding, and applicable to a wide variety of four-component reactions.

Microwave-enhanced Knoevenagel condensation catalysed by NH 2so3NH4

Ammonium sulphamate catalyses the efficient Knoevenagel condensation of aromatic aldehydes 1 with active methylene compounds in solvent-free conditions under microwave irradiation to give arylidene derivatives 3. The yields are excellent and purity is hig

A facile experimental method to determine the hydride affinity of polarized olefins in acetonitrile

(Chemical Equation Presented) Choosing a suitable hydride reducing agent and thermodynamic analysis of reduction mechanisms is facilitated by experimental hydride affinities ΔHH-A, which are reported herein for 28 polarized olefins 1 in acetonitrile (see scheme). The method should also be applicable to ketones, aldehydes, and imines.