69840-49-9

Usage

Chemical class

Imidazole

Structural features

Phenylbenzyl group attached to the imidazole ring
Two carboxylic acid groups located at the 4 and 5 positions

Potential applications

Pharmaceutical research
Drug development

Biological activities

Unknown, but may have potential due to structural features

Synthesis

Can be used as a building block for the synthesis of other chemical compounds

Further research

Required to fully understand its potential uses and properties

Safety and toxicity

Not mentioned in the material provided, but should be considered in further research and testing

Stability

Not mentioned in the material provided, but should be considered in further research and testing

Solubility

Not mentioned in the material provided, but should be considered in further research and testing

Reactivity

Not mentioned in the material provided, but should be considered in further research and testing

Upstream product

• 69840-48-8 1-(α-Phenylbenzyl)imidazole-4,5-dicarbonitrile 
• 1122-28-7 4,5-dicyano-1H-imidazole 
• 91-01-0 1,1-Diphenylmethanol 

Downstream Products

• 7189-67-5 1-benzhydryl-1H-imidazole 

Relevant academic research and scientific papers

Chiral azole derivatives. 2. Synthesis of enantiomerically pure 1-alkylimidazoles

4,5-Dicyanoimidazole has been reacted with racemic and enantiopure alcohols 7 (entries 1-7) under Mitsunobu conditions to give 1-alkyl-4,5-dicyanoimidazole derivatives 8, which in turn have been transformed by hydrolysis and decarboxylation into 1-alkylimidazoles 10 in good overall yield and high enantiomeric excess. In contrast, when applied to benzyl and benzhydryl alcohols (entries 8-15), this sequence afforded the final compounds in good overall yield, but as racemic mixtures. The 1-(1-phenylalkyl)imidazole derivative (S)-(+)-24 was, however, prepared in enantiopure form starting from the corresponding (S)-(-)-α-methylbenzylamine (21) using the Marckwald procedure, which entailed the alkylation of 21 with bromoacetaldehyde dimethyl acetal, followed by the construction of the imidazole ring through reaction with potassium thiocyanate and final Ra-Ni desulfuration. Following the same procedure, (S)-(+)-10c was also synthesized, proving the stereochemical outcome of the Mitsunobu reaction.

Imidazole carboxylic acids and derivatives thereof

Benzhydryl-imidazole derivatives having carboxyl functions in the imidazole ring have valuable properties in plant protection and growth regulation in agriculture and horticulture. They are also effective as antimycotis, fungicides and herbicides and can be used for combating plant-pathogenic bacteria.