675123-17-8

Basic information

• Product Name: 2-Propenoic acid, 3-[1-(phenylmethyl)-1H-imidazol-4-yl]-, methyl ester, (2E)-
• CAS NO: 675123-17-8
• Molecular Formula: C14H14N2O2
• Molecular Weight: 242.277
• Mol File: 675123-17-8.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 2-Propenoic acid, 3-[1-(phenylmethyl)-1H-imidazol-4-yl]-, methyl ester, (2E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propenoic acid, 3-[1-(phenylmethyl)-1H-imidazol-4-yl]-, methyl ester, (2E)-(675123-17-8)
• EPA Substance Registry System: 2-Propenoic acid, 3-[1-(phenylmethyl)-1H-imidazol-4-yl]-, methyl ester, (2E)-(675123-17-8)

Safety Data

• Hazardous Substances Data: 675123-17-8(Hazardous Substances Data)

Upstream product

• 100-44-7 benzyl chloride 
• 70346-51-9 (E)-methyl 3-(1H-imidazol-4-yl)acrylate 
• 100-39-0 benzyl bromide 

Downstream Products

• 954426-12-1 (2E)-3-(1-benzyl-1H-imidazol-4-yl)propenoic acid 
• 916050-44-7 ethyl (4E)-2-(benzhydrylideneamino)-5-(1-benzyl-1H-imidazol-4-yl)pent-4-enoate 
• 916050-52-7 ethyl 5-[(4E)-3-(1-benzyl-1H-imidazol-4-yl)]-2-nitro-2-(2-propynyl)pent-4-enoate 
• 916050-40-3 dimethyl 2-[(2E)-3-(1-benzyl-1H-imidazol-4-yl)-2-propenyl]-2-(2-propynyl)malonate 
• 916050-49-2 2-[(2E)-3-(1-benzyl-1H-imidazol-4-yl)-prop-2-enyl]pyrrolo[1,2-c]imidazole-1,3-dione 
• 916050-45-8 ethyl (4E)-5-(1-benzyl-1H-imidazol-4-yl)-2-nitropent-4-enoate 
• 916050-27-6 (2E)-3-(1-benzyl-1H-imidazol-4-yl)-2-propenyl ethyl carbonate 
• 916050-24-3 (2E)-3-(1-benzyl-1H-imidazol-4-yl)-2-propenyl acetate 
• 675123-19-0 (E)-1-benzyl-4-(3-(tert-butyldimethylsilyloxy)prop-1-enyl)-1H-imidazole 
• 941287-31-6 1-(1-benzyl-1H-imidazol-4-yl)-3-[N-benzyl-N-(tert-butoxycarbonyl)amino]propene 
• 941287-30-5 CNH₂C₇H₇HC₂H₂C₃N₂H₂C₇H₇ 

Relevant articles and documents

Preparation and diels-alder chemistry of 4-vinylimidazoles

(Chemical Equation Presented) Various 4-vinylimidazole derivatives have been prepared from the corresponding 4-iodoimidazoles or from urocanic acid. Several methods for the elaboration of these vinylimidazoles and their Diels-Alder reactions are reported. All of the vinylimidazoles prepared in the course of this study react with N-phenylmaleimide quite readily with mild thermal activation providing a single cycloadduct, in most cases the initial, nonaromatic adduct. With more electron rich substrates, there is a tendency for these initial cycloadducts to undergo aromatization, ene reaction, and oxidation although this can be circumvented to a large extent by the choice of reaction conditions. Limited reactions were observed with other dienophiles, providing the expected cycloadducts in most cases, although an abnormal adduct was obtained in one case with dimethyl acetylene dicarboxylate. These substrates also participate in regioselective Diels-Alder reactions with monoactivated dienophiles, but require fairly forcing conditions, thus only providing the aromatized cycloadducts in modest yields. An investigation of substituent effects at the 2-position of the imidazole moiety was undertaken, in which electron-donating and weakly electron-withdrawing substituents are tolerated. In addition, several substrates with terminally substituted vinyl moieties have been investigated.

A convenient synthesis of 1,4-disubstituted imidazoles

An efficient method for the regioselective protection of 4-alkyl-, 4-iodo, 4-vinylimidazoles has been developed via an alkylation-isomerization sequence with various imidazole-protecting groups. The initially formed mixture of 4/5-alkyl-, 4/5-iodo, and 4/5-vinylimidazoles are isomerized to the corresponding 4-isomers on treatment of a DMF solution with a small amount of RX and heating at 75°C.