2-Methylimidazole
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 Debus-Radziszewski [imidazole synthesis|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 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.