85127-45-3

Basic information

• Product Name: methyl 3-(2H-imidazol-1-yl)-3-phenylacrylate
• Synonyms: methyl 3-(2H-imidazol-1-yl)-3-phenylacrylate
• CAS NO: 85127-45-3
• Molecular Weight: 228.25
• Mol File: 85127-45-3.mol

Chemical Properties

• CAS DataBase Reference: methyl 3-(2H-imidazol-1-yl)-3-phenylacrylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 3-(2H-imidazol-1-yl)-3-phenylacrylate(85127-45-3)
• EPA Substance Registry System: methyl 3-(2H-imidazol-1-yl)-3-phenylacrylate(85127-45-3)

Safety Data

• Hazardous Substances Data: 85127-45-3(Hazardous Substances Data)

Upstream product

• 288-32-4 1H-imidazole 
• 21770-48-9 methyl 2,3-dibromo-3-phenylpropanoate 
• 103-26-4 Methyl cinnamate 
• 98-88-4 benzoyl chloride 
• 18156-74-6 1-(Trimethylsilyl)imidazole 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 

Downstream Products

• 3461-50-5 methyl trans-3-methylcinnamate 
• 50487-01-9 (2E)-3-methoxy-1-phenylbut-2-en-1-one 
• 7713-79-3 3-phenyl-5-isoxazolone 
• 939-05-9 3-hydroxy-5-phenylisoxazole 
• 85127-46-4 5-phenyl-5-(1-imidazolyl)-3-isoxazolidinone 
• 91164-88-4 3-((Z)-2-Methoxycarbonyl-1-phenyl-vinyl)-1-methyl-3H-imidazol-1-ium; iodide 
• 38750-49-1 3-methoxy-3-phenypropenoate 
• 34875-03-1 methyl 3-phenyl-3-phenylsulfanylpropenoate 
• 83256-92-2 (Z)-3-Phenyl-3-pyrrolidin-1-yl-acrylic acid methyl ester 

Relevant articles and documents

A thermal cascade route to pyrroloisoindolone and pyrroloimidazolones

(Chemical Equation Presented) Flash vacuum pyrolysis (FVP) of indol-1-ylacrylate derivatives 11 and 15 or the isomeric indol-3-ylacrylates 21, 22, and 24 at 925°C (0.05 Torr) provides pyrrolo[1,2-a]indol-3-ones 2, 18, 28, and 29 in 53-90% yield by a cascade mechanism that involves a sigmatropic migration, elimination, electrocyclization sequence. Pyrrolo[1,2-a]imidazol-5- ones 3 and pyrrolo[1,2-c]imidazol-5-ones 4 were similarly obtained by FVP of corresponding 2,5-unsubstituted imidazol-1-ylacrylates (e.g., 33), with the former isomer predominating in ca. 80:20 ratio. Migration to the 2-position is therefore favored in the initial sigmatropic shift. FVP of 2-substituted imidazol-1-ylacrylates 35, 37, and 51 (825-875°C) instead give pyrrolo[1,2-c]imidazol-5-ones 56-58 only (88-91%), and that of 4,5-disubstituted imidazol-1-ylacrylates 39 and 41 (825-850°C) provide pyrrolo[1,2-a] imidazol-5-ones 59 and 60 exclusively (93-95%), and thus the selectivity of the initial shift can be controlled by the presence of substituents on the imidazole 2- and 5-positions. FVP of the benzimidazole analogues 61 and 62 at 950°C gave the pyrrolo[1,2-a]benzimidazol-1-ones 6 (71%) and 63 (36%), respectively.

Synthesis of functionalized 1-vinylazoles by a novel Wittig reaction of 1-acylazoles

Wittig reaction of aromatic and heteroaromatic 1-acylimidazoles, 1-acyl-1,2,4-triazoles, and 1-acylbenzimidazoles with acceptor-stabilized phosphoranes was found to be a convenient method for the preparation of the E isomers of 1-vinylazoles.

The Compounds Related to 3-(1-Imidazolyl)-2-alken-1-ones. Preparation and Reactions

Compounds related to 3-(1-imidazolyl)-2-alken-1-ones, 3-(1-imidazolyl)-2-alkenoic acid derivatives and 2-alken-1-ones having heterocycles on the C-3 carbon were prepared.The reaction of nucleophiles with these compounds was also discussed.