388564-75-8

Basic information

• Product Name: 1H-Imidazole-5-carboxaldehyde, 1-(phenylmethoxy)-
• CAS NO: 388564-75-8
• Molecular Formula: C11H10N2O2
• Molecular Weight: 202.213
• Mol File: 388564-75-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1H-Imidazole-5-carboxaldehyde, 1-(phenylmethoxy)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Imidazole-5-carboxaldehyde, 1-(phenylmethoxy)-(388564-75-8)
• EPA Substance Registry System: 1H-Imidazole-5-carboxaldehyde, 1-(phenylmethoxy)-(388564-75-8)

Safety Data

• Hazardous Substances Data: 388564-75-8(Hazardous Substances Data)

Upstream product

• 121779-19-9 1-(benzyloxy)imidazole 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 395685-74-2 (3-benzyloxy-3H-imidazol-4-yl)-methanol 

Relevant articles and documents

Synthesis of 4- and 5-substituted 1-hydroxyimidazoles through directed lithiation and metal-halogen exchange

Electrophiles were introduced regioselectively at the 5-position of 1-(benzyloxy)imidazole by lithiation at C-5 after protection of C-2 with a chloro or a trimethylsilyl group. Subsequent treatment with an electrophile afforded 5-substituted 1-(benzyloxy)-2-chloroimidazoles 8-13 and 5-substituted 1-(benzyloxy)imidazoles 3-5, the 2-(trimethylsilyl) group being lost during workup. Electrophiles were introduced regioselectively at the 4-position of 1-(benzyloxy)imidazole by bromine-lithium exchange of 4-bromo-2-chloro-1-(benzyloxy)imidazoles, protected at C-5 with chloro or trimethylsilyl groups, followed by reaction with an electrophile. The 5-(trimethylsilyl) group was removed via base-catalyzed desilylation. Chlorine at C-2 and O-benzyl groups were removed by palladium-catalyzed hydrogenolysis.