19748-13-1

Basic information

• Product Name: 3-methyl-1-(2-oxo-2-phenylethyl)-1H-imidazol-3-ium
• Synonyms: 1H-imidazolium, 1-methyl-3-(2-oxo-2-phenylethyl)-; 1-Methyl-3-(2-oxo-2-phenyl-ethyl)-3H-imidazol-1-ium
• CAS NO: 19748-13-1
• Molecular Formula: Br*C₁₂H₁₃N₂O
• Molecular Weight: 201.2439
• Mol File: 19748-13-1.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: 3-methyl-1-(2-oxo-2-phenylethyl)-1H-imidazol-3-ium(CAS DataBase Reference)
• NIST Chemistry Reference: 3-methyl-1-(2-oxo-2-phenylethyl)-1H-imidazol-3-ium(19748-13-1)
• EPA Substance Registry System: 3-methyl-1-(2-oxo-2-phenylethyl)-1H-imidazol-3-ium(19748-13-1)

Safety Data

• Hazardous Substances Data: 19748-13-1(Hazardous Substances Data)

Usage

Structure

Imidazolium salt with methyl substituent at 3-position and phenylethyl ketone group at 1-position

Uses

Precursor for synthesis of heterocyclic compounds, potential applications in organic and medicinal chemistry

Research

Studied for potential applications in pharmaceutical and bioactive molecule preparation, unique reactivity and biological activity studied in research

Upstream product

• 98-86-2 acetophenone 
• 616-47-7 1-methyl-1H-imidazole 
• 769-42-6 1,3-dimethylbarbituric acid 
• 100-52-7 benzaldehyde 
• 70-11-1 α-bromoacetophenone 

Downstream Products

• 4114-28-7 diethyl hydrazodicarboxylate 
• 130090-72-1 triethyl 2-[(1E)-N-(ethoxycarbonyl)-2-oxo-2-phenylethanehydrazonoyl]hydrazine-1,1,2-tricarboxylate 

Relevant articles and documents

Cascade [4 + 1] annulation via more environmentally friendly nitrogen ylides in water: Synthesis of bicyclic and tricyclic fused dihydrofurans

A novel imidazolium ylide activated [4 + 1] annulation approach is described for the diastereoselective synthesis of bicyclic and tricyclic fused dihydrofurans in water. This cascade annulation presumably proceeds via a Michael reaction triggered zwitteri

Synthesis and antimicrobial action of aminoketones

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DABCO-catalyzed multi-component domino reactions for the one-pot efficient synthesis of diverse and densely functionalized benzofurans in water

An efficient, three-component strategy for the improved synthesis of a pharmaceutically interesting diverse kind of multi-functionalized benzofurans via one-pot two-step domino protocol with high diastereoselectivity in excellent yields has been established. The synthesis was achieved by reacting phenacyl bromides, N-heterocycles, aromatic aldehydes, and cyclic 1,3-dicarbonyl compounds in the presence of a catalytic amount of DABCO (1,4-diazabicyclo[2.2.2]octane) as an inexpensive, impressive, and readily available catalyst in water under reflux. In this process in total three new bonds (two C–C and one C–O) form in one pot. Short reaction time, excellent yields, no chromatographic purification, and evasion of environmentally hazardous or toxic catalysts and organic solvents in the entire reaction process may make this protocol very useful for academia and industry.

Triplet phenacylimidazoliums-catalyzed photocycloaddition of 1,4-dihydropyridines: An experimental and theoretical study

The photocycloadditions of 1,4-dihydropyridines (DHPs) were achieved by using phenacylimidazoliums (PIms) as photosensitizers. Irradiation of DHPs 3a-g in the presence of PIms 1a-e and 2 performed an efficient formation of 3,9-diazatetraasteranes in shorter times under a lower power lamp. The mechanism of photocycloaddition catalyzed by PIm was studied by laser flash photolysis and theoretical DFT computation. These time-resolved results showed that the triplet excited states of PIms were generated with high efficiency and detected by their characteristic ultraviolet absorptions, which were quenched by DHP at almost diffusion controlled rate. Theoretical studies suggest that PIm is involved in the photocycloaddition process through the 3(DHP? PIm)* triplet complexes and assists the stabilization of intermediates. All subsequent steps are predicted to be favorable and exothermic, leading to the cage dimers.