2-Methylbenzimidazole

Chemical properties

light beige to brown crystalline powder. Soluble in alcohol, ether, hot water and sodium hydroxide solution, insoluble in benzene.

The Uses of 2-Methylbenzimidazole

• 2-Methylbenzimidazole is an important pharmacophore widely used in medicinal chemistry for the synthesis of various antibacterial and antifungal agents.
• It can be used as a key precursor to synthesize substituted benzimidazo[1,2-a]quinolones.
• It can be used in the synthesis of reversible solid-to-liquid phase transition coordination polymer crystals.
• 2-Methylbenzimidazole also exhibits corrosion inhibition.

Definition

ChEBI: 2-Methyl-1H-benzo[d]imidazole is a member of benzimidazoles.

Preparation

2-Methylbenzimidazole is synthesized by the condensation of o-phenylenediamine with acetic acid. The mixture of o-phenylenediamine and acetic acid is heated at 100°C for 2 hours and then cooled slowly. 10% sodium hydroxide solution is added slowly to the mixture until it is slightly alkaline. The mixture is filtered and washed with cold water. The crude product is then recrystallized with water and decolorized with activated charcoal to obtain the final product. The yield is 68%.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 26, p. 1163, 1989 DOI: 10.1002/jhet.5570260447
Chemical and Pharmaceutical Bulletin, 17, p. 1153, 1969 DOI: 10.1248/cpb.17.1153

Safety Profile

Poison by intravenous route. Moderately toxic by ingestion. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.