2-Methylimidazole

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)
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).

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]

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

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 (5865): 939–943. doi:10.1126/science.1152516. PMID 18276887. S2CID 22210227.
  3. ^ Edwards, David I (1993). "Nitroimidazole drugs - action and resistance mechanisms. I. Mechanism of action". Journal of Antimicrobial Chemotherapy. 31 (1): 9–20. doi:10.1093/jac/31.1.9. PMID 8444678.
  4. ^ 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)"". European Chemicals Agency. Archived from the original on 2020-06-30.