2-Methylimidazole Explained

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.^[1]

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.^[2]

Applications

2-Methylimidazole is a precursor to the several members of the nitroimidazole antibiotics that are used to combat anaerobic bacterial and parasitic infections.^{[3] [1]}

Safety

It has low toxicity with an (rat, oral) of 1300 mg/kg, but it is strongly irritating to the skin and eyes.^[1]

2-Methylimidazole is a REACH Regulation Candidate Substance of Very High Concern due to its endocrine disrupting properties.^[4]

References

1. Ebel, K., Koehler, H., Gamer, A. O., & Jäckh, R. "Imidazole and Derivatives." In Ullmann’s Encyclopedia of Industrial Chemistry; 2002 Wiley-VCH,
2. Banerjee . Rahul . Omar Yaghi . Phan . Anh . Wang . Bo . Knobler . Carolyn . Furukawa . Hiroyasu . O'Keeffe . Michael . Yaghi . Omar M . 2008 . High-Throughput Synthesis of Zeolitic Imidazolate Frameworks and Application to CO₂ Capture . Science . 319 . 5865 . 939–943 . 10.1126/science.1152516 . 18276887. 22210227 .
3. Edwards . David I . 1993 . Nitroimidazole drugs - action and resistance mechanisms. I. Mechanism of action . Journal of Antimicrobial Chemotherapy . 31 . 1 . 9–20 . 10.1093/jac/31.1.9. 8444678 .
4. Web site: Schilliger-Musset. Christel. 2020-06-18. D(2020)4578-DC, "Inclusion of substances of very high concern in the Candidate List for eventual inclusion in Annex XIV (Decision of the European Chemicals Agency)". live. European Chemicals Agency. https://web.archive.org/web/20200630013134/https://echa.europa.eu/documents/10162/31fcbd73-6d35-06d9-35cd-42dc09362aa1 . 2020-06-30 .