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Chemical compound
2-Methylimidazole is an organic compound that is structurally related to imidazole with the chemical formula CH3C3H2N2H. It is a white or colorless solid that is highly soluble in polar organic solvents and water. It is a precursor to a range of drugs and is a ligand in coordination chemistry.
Synthesis and reactions.
It is prepared by condensation of glyoxal, ammonia and acetaldehyde, a Radziszewski reaction. Nitration gives 5-nitro derivative.
2-Methylimidazole is a sterically hindered imidazole that is used to simulate the coordination of histidine to heme complexes. It can be deprotonated to make imidazolate-based coordination polymers.
Applications.
2-Methylimidazole is a precursor to the several members of the nitroimidazole antibiotics that are used to combat anaerobic bacterial and parasitic infections.
Safety.
It has low toxicity with an LD50 (rat, oral) of 1300 mg/kg, but it is strongly irritating to the skin and eyes.
2-Methylimidazole is a REACH Regulation Candidate Substance of Very High Concern due to its endocrine disrupting properties.