474623-05-7

Basic information

• Product Name: 1H-Imidazole-2-carboxaldehyde,1-(2-propenyl)-(9CI)
• Synonyms: 1H-Imidazole-2-carboxaldehyde,1-(2-propenyl)-(9CI)
• CAS NO: 474623-05-7
• Molecular Formula: C₇H₈N₂O
• Molecular Weight: 136.15122
• Product Categories: AMINETERTIARY
• Mol File: 474623-05-7.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1H-Imidazole-2-carboxaldehyde,1-(2-propenyl)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Imidazole-2-carboxaldehyde,1-(2-propenyl)-(9CI)(474623-05-7)
• EPA Substance Registry System: 1H-Imidazole-2-carboxaldehyde,1-(2-propenyl)-(9CI)(474623-05-7)

Safety Data

• Hazardous Substances Data: 474623-05-7(Hazardous Substances Data)

Upstream product

• 106-95-6 allyl bromide 
• 10111-08-7 2-imidazolecarbaldehyde 
• 18994-75-7 1-allyl-2-hydroxymethylimidazole 
• 31410-01-2 1-allylimidazole 

Downstream Products

• 474623-18-2 (+)-7-amino-6,7-dihydro-6-hydroxymethyl-5H-pyrrolo[1,2-a]imidazole 
• 474623-14-8 (6R*,8S*)-8-amino-6-hydroxy-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine 
• 474623-14-8 (6R,8S)-8-amino-6-hydroxy-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine 
• 474623-14-8 (6S,8R)-8-amino-6-hydroxy-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine 
• 474623-18-2 (6R*,7S*)-7-amino-6,7-dihydro-6-hydroxymethyl-5H-pyrrolo[1,2-a]imidazole 

Relevant articles and documents

N-Heterocyclic carbene-catalysed intramolecular hydroacylation to form basic nitrogen-containing heterocycles

We report catalytic, intramolecular hydroacylations of N-allylimidazole-2-carboxaldehydes and N-allylbenzimidazole-2-carboxaldehydes. These exo-selective hydroacylations occur in the presence of a N-heterocyclic carbene catalyst to generate 5,6-dihydro-7H-pyrrolo[1,2-α]imidazol-7-ones and 1,2-dihydro-3H-benzo[d]pyrrolo[1,2-α]imidazol-2-ones in high yields (66-99%). In addition, hydroacylations of N-allylimidazole-2-carboxaldehydes in the presence of a chiral, non-racemic NHC catalyst occur, forming 5,6-dihydro-7H-pyrrolo[1,2-α]imidazol-7-ones in moderate-to-high yields (39-98%) with modest enantioselectivities (56-79% ee).

Synthetic approach to imidazo[1,2-a]pyridine derivatives by the intramolecular nitrone cycloaddition methodology

N-Benzyl and (R)-N-(α-phenylethyl) nitrones derived from 1-allyl-2-imidazolecarbaldehyde underwent intramolecular cycloaddition to give predominantly bridged-ring products, namely 5,6,8,9-tetrahydro-6,9-methanoimidazo[2,1-d][1,2,5]oxadiazepine derivatives. Catalytic hydrogenation of the latter furnished both racemic and enantiopure 6,8-functionalised 5,6,7,8-tetrahydro-imidazo[1,2-a]pyridines.