2-Methylimidazole

2-Methylimidazole.svg 115 2-methylimidazole.jpg 2-Methyl-1H-imidazole 2-MeIm 2-mImH 693-98-1 correct CAS correct FDA T0049Z45LZ 12749 12225 39837 Cc1[nH]ccn1 1/C4H6N2/c1-4-5-2-3-6-4/h2-3H,1H3,(H,5,6) LXBGSDVWAMZHDD-UHFFFAOYAM 1S/C4H6N2/c1-4-5-2-3-6-4/h2-3H,1H3,(H,5,6) LXBGSDVWAMZHDD-UHFFFAOYSA-N C4H6N2 82.10 g/mol white or colorless solid 145 270 0.29 g/ml causes skin rashes and eye irritation 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.Ebel, K., Koehler, H., Gamer, A. O., & Jäckh, R. "Imidazole and Derivatives." In Ullmann’s Encyclopedia of Industrial Chemistry; 2002 Wiley-VCH, 10.1002/14356007.a13_661 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. 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 2008Sci...319..939B 22210227 Applications 2-Methylimidazole is a precursor to the several members of the nitroimidazole antibiotics that are used to combat anaerobic bacterial and parasitic infections. 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 Safety It has low toxicity with an (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.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)" https://echa.europa.eu/documents/10162/31fcbd73-6d35-06d9-35cd-42dc09362aa1 live European Chemicals Agency https://web.archive.org/web/20200630013134/https://echa.europa.eu/documents/10162/31fcbd73-6d35-06d9-35cd-42dc09362aa1 2020-06-30 References Category:Imidazoles