111157-54-1

Basic information

• Product Name: 1H-Isoindole-1,3(2H)-dione, 2-[3-[1-(triphenylmethyl)-1H-imidazol-4-yl]-2-propenyl]-, (Z)-
• CAS NO: 111157-54-1
• Molecular Formula: C33H25N3O2
• Molecular Weight: 495.58
• Mol File: 111157-54-1.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 1H-Isoindole-1,3(2H)-dione, 2-[3-[1-(triphenylmethyl)-1H-imidazol-4-yl]-2-propenyl]-, (Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Isoindole-1,3(2H)-dione, 2-[3-[1-(triphenylmethyl)-1H-imidazol-4-yl]-2-propenyl]-, (Z)-(111157-54-1)
• EPA Substance Registry System: 1H-Isoindole-1,3(2H)-dione, 2-[3-[1-(triphenylmethyl)-1H-imidazol-4-yl]-2-propenyl]-, (Z)-(111157-54-1)

Safety Data

• Hazardous Substances Data: 111157-54-1(Hazardous Substances Data)

Upstream product

• 65273-64-5 2-(1,3-dioxoisoindolin-2-yl)ethyltriphenylphosphonium bromide 
• 33016-47-6 (1-tritylimidazol-4-yl)carboxaldehyde 

Downstream Products

• 138408-51-2 3-(1-trityl-1H-imidazol-4-yl)prop-2-enamine 

Relevant articles and documents

Synthesis of (Z)- and (E)-3-(1H-imidazol-4-yl)-2-propenamine and some 3-(1H-imidazol-4-yl)propanamines

3-(1H-Imidazol-4-yl)propanamine (6, homohistamine), an essential intermediate for the synthesis of potent impromidine-type histamine H2 receptor agonists, is efficiently prepared from trans-urocanic acid (1) by reduction of the methyl ester 2 and conversion to the saturated amide 4.Dehydration with thionyl chloride yields the nitrile 5 which is subsequently reduced to 6.Side-chain methylated 3-(1H-imidazol-4-yl)propanamines 12 are available from 1H-imidazole-4-carbaldehyde (7) and 1-(1H-imidazol-4-yl)ethanone (8), respectively, via unsaturated nitriles 10 and stepwise reduction.Cyclization of the appropiate 4-bromo-5-oxohexanenitriles 14α with formamidine in liquid ammonia and reduction of the obtained nitriles 15 furnishes ring-methylated amines 16. (E)-3-(1H-Imidazol-4-yl)-2-propenamine is obtained in six steps from the trans-ester 2 while (Z)-23 is accessible by treating 7 with triphenyl(2-phthalimidoethyl)phosphonium bromide (17) and final deprotection.These primary amines are valuable intermediates for the synthesis of impromidine analogues. Key Words: Homohistamine / Imidazole derivatives / 2-Propenamine derivatives / Impromidine