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Chemical compound From Wikipedia, the free encyclopedia
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.
Names | |
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Preferred IUPAC name
2-Methyl-1H-imidazole | |
Other names
2-MeIm | |
Identifiers | |
3D model (JSmol) |
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ChemSpider | |
ECHA InfoCard | 100.010.697 |
PubChem CID |
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UNII | |
CompTox Dashboard (EPA) |
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Properties | |
C4H6N2 | |
Molar mass | 82.10 g/mol |
Appearance | white or colorless solid |
Melting point | 145 °C (293 °F; 418 K) |
Boiling point | 270 °C (518 °F; 543 K) |
0.29 g/ml | |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards |
causes skin rashes and eye irritation |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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]
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]
It has low toxicity with an LD50 (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]
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