4916-28-3

Usage

Uses

Used in Pharmaceutical Industry:
(E)-Methyl 3-(phenylaMino)acrylate is used as a chemical intermediate for the synthesis of various pharmaceuticals. Its unique structure and reactivity make it a valuable component in the development of new drugs and medications.
Used in Agrochemical Industry:
In the agrochemical sector, (E)-Methyl 3-(phenylaMino)acrylate serves as an intermediate in the production of various agrochemicals. Its properties contribute to the creation of effective solutions for agricultural applications.
Used in Fragrance and Flavoring Industry:
(E)-Methyl 3-(phenylaMino)acrylate is utilized as a building block in the synthesis of fragrances and flavorings. Its aromatic nature lends itself well to the development of scents and tastes for a variety of consumer products.
Used in Chemical Research and Development:
Due to its versatile reactivity and structural features, (E)-Methyl 3-(phenylaMino)acrylate is also used as a chemical building block for research and development purposes. It aids scientists and researchers in exploring new chemical reactions and creating innovative compounds for various applications.

InChI:InChI=1/C10H11NO2/c1-13-10(12)7-8-11-9-5-3-2-4-6-9/h2-8,11H,1H3

Upstream product

• 292638-85-8 acrylic acid methyl ester 
• 62-53-3 aniline 
• 922-67-8 propynoic acid methyl ester 

Downstream Products

• 17647-23-3 1,3-diphenyl-1H-pyrazole-4-carboxylic acid methylester 
• 1476745-54-6 methyl 1,4-diphenyl-1,4-dihydropyridine-3-carboxylate 
• 38238-86-7 dimethyl 2-phenylaminoethylene-1,1-dicarboxylate 
• 1262150-42-4 (Z)-methyl 3-[(4-bromophenyl)amino]acrylate 
• 1428345-82-7 (Z)-methyl 2-bromo-3-(phenylamino)acrylate 

Relevant academic research and scientific papers

Organocatalyzed synthesis and biological activity evaluation of hybrid compounds 4H-pyrano[2,3-b]pyridine derivatives

1,4-Dihydropyridines and 4H-pyran derivatives are common and important structures in various pharmaceutical compounds. Dihydropyridines are well-known moieties in compounds that have analgesic, fungicidal, and antibacterial activities and 4H-pyran structu

Organocatalyzed regioselective and enantioselective synthesis of 1,4- and 1,2-dihydropyridines

Herein, we introduce one of the first examples of asymmetric organocatalyzed synthesis of 1,2-dihydropyridines, affording enantioselective access to and partially solving regioselectivity challenges in the synthesis of dihydropyridines. We demonstrate that through modification of organocatalysts both 1,2- and 1,4-dihydropyridines (1,2- and 1,4-DHPs) can be obtained with high regioselectivity (ratio of 1,2-DHP/1,4-DHP from 95/5 to 0/100) and enantioselectivity (33% ee for 1,2-DHPs and up to 98% ee for 1,4-DHPs) in good yields (up to 87%).

Encapsulating Au-Fe3O4 Nanodots into AIE-active Supramolecular Assemblies: Ambient Visible-light Harvesting “Dip-Strip” Photocatalyst for C?C/C?N Bond Formation Reactions

The present study demonstrates the development of a supramolecular porous ensemble consisting of hetero-oligophenylene derivative 6 and Au-Fe3O4 nanodots. Supramolecular assemblies of AIE-active hetero-oligophenylene derivative 6 served as reactors for the generation of Au-Fe3O4 nanodots. The as prepared supramolecular ensemble functioned as an efficient recyclable photocatalytic system for C(sp2)?H bond activation of anilines for the construction of quinoline carboxylates. Interestingly, the “dip catalyst” prepared by depositing PTh-co-PANI-6: Au-Fe3O4 nanodots on a filter paper served as a recyclable strip (up to 10 cycles) for C?C/C?N bond formation reaction.

Transition-metal-free synthesis of β-trifluoromethylated enamines with trifluoromethanesulfinate

We have developed a transition-metal free trifluoromethylation protocol between enamines and CF3SO2Na. A wide range of β-trifluoromethyl substituted enamines were delivered in moderate to high yields with only E-configurations.

Conjugate Addition of 3-Buytn-2-one to Anilines in Ethanol: Alkene Geometric Insights through in Situ FTIR Monitoring

A convenient, mild and effective conjugate addition of 3-butyn-2-one to a variety of anilines in ethanol is reported. The reaction was monitored and characterized through in situ FTIR, and the dynamics of the facile E/Z alkene geometry interconversion of the resultant aniline-derived enaminones was explored through NMR, FTIR and X-ray crystallography. A straightforward purification protocol that employs direct Kugelrohr distillation was identified, and the method was further extended to other amines and ynones, allowing rapid access to these interesting compounds.

Palladium-catalyzed oxidative C-N bond coupling involving a solvent-controlled regioselective bromination process

Stereoselective palladium-catalyzed oxidative C-N bond coupling reactions between aromatic amines and alkenes involving a solvent-controlled regioselective bromination process under 1 atm of oxygen atmosphere are disclosed, providing easy access to two different brominated enamines. The addition of hydrogen peroxide (30% aq) as a co-oxidant in the system is crucial for the dehydrogenative aminohalogenation under molecular oxygen (1 atm), and in such a case, the C-N bond coupling/electrophilic bromination reaction cascade is proposed. Furthermore, the different reaction media leads to a switched regioselectivity of the process.

Palladium-catalyzed oxidative coupling of aromatic primary amines and alkenes under molecular oxygen: Stereoselective assembly of (Z)-enamines

An efficient Pd-catalyzed oxidative coupling of aromatic primary amines and alkenes under molecular oxygen is disclosed. Under mild reaction conditions, it provides a rapid access to (Z)-enamine compounds with exceptional functional group tolerance and ex

Palladium-assisted multicomponent cyclization of aromatic aldehydes, arylamines and terminal olefins under molecular oxygen: An assembly of 1,4-dihydropyridines

The palladium-assisted one-pot three-component reactions of aldehydes, amines and olefins proceeded smoothly to give 2,6-unsubstituted 1,4-dihydropyridines (1,4-DHPs) using molecular oxygen as a sole oxidant. It also provides efficient Pd-catalyzed aerobic oxidation access to the anti-Markovnikov oxidative amination products of olefins from primary aromatic amines and alkenes. The method is atom-efficient, using cheap and easily available starting materials and an environmentally benign oxidant.

Solvent-free synthesis of enamines from alkyl esters of propiolic or but-2-yne dicarboxylic acid in a ball mill

A solvent-free method for the addition of amines to dialkylacetylendicarboxylates or alkylpropiolates using a planetary ball mill was developed. Conversion of educts was quantitative within five minutes without use of any catalyst or base. Beside the E-/Z

Formation of 1,2-dihydroquinoline-3-carboxylic acid derivatives from methyl 3-(arylamino)acrylates with hydrogen iodide

The reaction of methyl 3-(arylamino)acrylates with hydrogen iodide gave 1,2-dihydroquinoline-3-carboxylic acid derivatives at room temperature. This reaction proceeds efficiently in alcoholic solvent; bulky tert-butyl alcohol is the best solvent to give t