85102-92-7

Basic information

• Product Name: 1H-Imidazole-5-methanol, 1-[(4-nitrophenyl)methyl]-
• CAS NO: 85102-92-7
• Molecular Formula: C11H11N3O3
• Molecular Weight: 233.227
• Mol File: 85102-92-7.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1H-Imidazole-5-methanol, 1-[(4-nitrophenyl)methyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Imidazole-5-methanol, 1-[(4-nitrophenyl)methyl]-(85102-92-7)
• EPA Substance Registry System: 1H-Imidazole-5-methanol, 1-[(4-nitrophenyl)methyl]-(85102-92-7)

Safety Data

• Hazardous Substances Data: 85102-92-7(Hazardous Substances Data)

Upstream product

• 18600-42-5 4-nitrobenzylamine hydrochloride 
• 114772-19-9 1-(4-Nitrobenzyl)-2-Mercapto-5-Hydroxymethylimidazole 
• 822-55-9 (1H-imidazol-4-yl)methanol 
• 100-11-8 1-bromomethyl-4-nitro-benzene 

Downstream Products

• 1101905-90-1 1-(4-Nitrobenzyl)-5-Chloromethyl Imidazole HCl salt 
• 125665-53-4 N-[4-(5-Hydroxymethyl-imidazol-1-ylmethyl)-phenyl]-phthalamic acid 
• 85103-02-2 1-(4-nitrobenzyl)-1H-imidazole-5-carbaldehyde 

Relevant articles and documents

Preparation of a clinically investigated ras farnesyl transferase inhibitor

The synthesis of ras farnesyl-protein transferase inhibitor 1 is described on a multi-kilogram scale. Retrosynthetic analysis reveals chloromethylimidazole 2 and a piperazinone 3 as viable precursors. The 1,5-disubstituted imidazole system was regioselectively assembled via an improved Marckwald imidazole synthesis. A new imidazole dethionation procedure has been developed to convert the Marckwald mercaptoimidazole product to the desired imidazole. This methodology was found to be tolerant of a variety of functional groups providing good to excellent yields of 1,5-disubstituted imidazoles. A new Mitsunobu cyclization strategy was developed to prepare the arylpiperazinone fragment 3.

Process for making 1,5-disubstituted imidazoles

The present invention is directed to a process for synthesizing 1,5-disubstituted imidazoles, which are useful in the preparation of farnesyl-protein transferase inhibitors.

Synthesis of N1-Aryl- and N1-Benzyl Substituted Imidazole-4- and Imidazole-5-carbaldehydes

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