5466-79-5

Basic information

• Product Name: (2E)-3-(4-methoxyphenyl)-N,N-dimethylprop-2-enamide
• Synonyms: (2E)-3-(4-Methoxyphenyl)-N,N-dimethylacrylamide; 2-propenamide, 3-(4-methoxyphenyl)-N,N-dimethyl-, (2E)-
• CAS NO: 5466-79-5
• Molecular Formula: C₁₂H₁₅NO₂
• Molecular Weight: 205.253
• Mol File: 5466-79-5.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 388.5°C at 760 mmHg
• Flash Point: 188.7°C
• Density: 1.07g/cm³
• Vapor Pressure: 3.06E-06mmHg at 25°C
• Refractive Index: 1.558
• CAS DataBase Reference: (2E)-3-(4-methoxyphenyl)-N,N-dimethylprop-2-enamide(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-3-(4-methoxyphenyl)-N,N-dimethylprop-2-enamide(5466-79-5)
• EPA Substance Registry System: (2E)-3-(4-methoxyphenyl)-N,N-dimethylprop-2-enamide(5466-79-5)

Safety Data

• Hazardous Substances Data: 5466-79-5(Hazardous Substances Data)

Usage

General Description

(2E)-3-(4-methoxyphenyl)-N,N-dimethylprop-2-enamide is a chemical compound with the molecular formula C13H17NO2. It is a yellow crystalline solid that is commonly used in research and as a building block for the synthesis of other organic compounds. (2E)-3-(4-methoxyphenyl)-N,N-dimethylprop-2-enamide is an N,N-dimethylamino derivative of cinnamamide, a class of chemicals known for their potential pharmacological activities. The (2E)-3-(4-methoxyphenyl)-N,N-dimethylprop-2-enamide may have various applications in organic synthesis and medicinal chemistry, and further research is ongoing to investigate its potential uses and characteristics.

Upstream product

• 830-09-1 3-(4'-methoxyphenyl)propenoic acid 
• 124-40-3 dimethyl amine 
• 2680-03-7 N,N-Dimethylacrylamide 
• 696-62-8 para-iodoanisole 
• 68-12-2 N,N-dimethyl-formamide 
• 768-60-5 4-methoxyphenylacetylen 
• 127-19-5 N,N-dimethyl acetamide 
• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 830-09-1 3-(4'-methoxyphenyl)propenoic acid 

Relevant articles and documents

Copper(I)-Catalyzed Asymmetric 1,4-Conjugate Hydrophosphination of α,β-Unsaturated Amides

A catalytic asymmetric conjugate hydrophosphination of α,β-unsaturated amides is accomplished by virtue of the strong nucleophilicity of copper(I)-PPh2 species, which provides an array of chiral phosphines bearing an amide moiety in high to excellent yields with excellent enantioselectivity. Furthermore, the dynamic kinetic resolution of unsymmetrical diarylphosphines (HPAr1Ar2) is successfully carried out through the copper(I)-catalyzed conjugate addition to α,β-unsaturated amides, which affords P-chiral phosphines with good-to-high diastereoselectivity and high enantioselectivity. 1H NMR studies show that the precoordination of HPPh2 to copper(I)-bisphosphine complex is critical for the efficient deprotonation by Barton's Base. Moreover, the relative stability of the copper(I)-(R,RP)-TANIAPHOS complex in the presence of excessive HPPh2, confirmed by 31P NMR studies, is pivotal for the high asymmetric induction, as the ligand exchange between bisphosphine and HPPh2 would significantly reduce the enantioselectivity. At last, a double catalytic asymmetric conjugate hydrophosphination furnishes the corresponding product in high yield with high diastereoselectivity and excellent enantioselectivity, which is transformed to a chiral pincer palladium complex in moderate yield. This chiral palladium complex is demonstrated as an excellent catalyst in the asymmetric conjugate hydrophosphination of chalcone.

Palladium-catalyzed intermolecular addition of formamides to alkynes

A novel palladium system for an intermolecular addition of formamides to alkynes has been developed. The reaction of formamides with internal alkynes in the presence of a palladium catalyst with acid chloride as an additive afforded (E)-α,β-unsaturated amides regio- and stereoselectively. The same catalyst system realized the first example of the addition of formamides to terminal alkynes giving the corresponding α,β-unsaturated amides bearing a terminal methylene moiety as major products. The present reaction was widely applicable to substrates with various functionalities. This method also could be applied to the reaction of N,N-disubstituted formamides with norbornene. A hydridopalladium species would be formed as a key intermediate with in situ generated HCl under the reaction conditions.