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2-Methylimidazole

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2-Methylimidazole
Names
Preferred IUPAC name
2-Methyl-1H-imidazole
Other names
2-MeIm
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.010.697 Edit this at Wikidata
UNII
  • InChI=1S/C4H6N2/c1-4-5-2-3-6-4/h2-3H,1H3,(H,5,6)
    Key: LXBGSDVWAMZHDD-UHFFFAOYSA-N
  • InChI=1/C4H6N2/c1-4-5-2-3-6-4/h2-3H,1H3,(H,5,6)
    Key: LXBGSDVWAMZHDD-UHFFFAOYAM
  • Cc1[nH]ccn1
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)
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).

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 LD50 (rat, oral) of 1300 mg/kg, but it is strongly irritating to the skin and eyes.[1]

References

  1. ^ a b c Ebel, K., Koehler, H., Gamer, A. O., & Jäckh, R. "Imidazole and Derivatives." In Ullmann’s Encyclopedia of Industrial Chemistry; 2002 Wiley-VCH, doi:10.1002/14356007.a13_661
  2. ^ Banerjee, Rahul; 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: 939–943. doi:10.1126/science.1152516. PMID 18276887.
  3. ^ Edwards, David I (1993). "Nitroimidazole drugs - action and resistance mechanisms. I. Mechanism of action". Journal of Antimicrobial Chemotherapy. 31: 9–20. doi:10.1093/jac/31.1.9.