2-Methylimidazole

2-Methylimidazole

Names
Preferred IUPAC name 2-Methyl-1H-imidazole
Other names 2-MeIm 2-mImH
Identifiers
CAS Number	693-98-1  Y
3D model (JSmol)	Interactive image
ChemSpider	12225
ECHA InfoCard	100.010.697
PubChem CID	12749
UNII	T0049Z45LZ  Y
CompTox Dashboard (EPA)	DTXSID4022107
InChI 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
SMILES Cc1[nH]ccn1
Properties
Chemical formula	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)
Solubility in water	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). Infobox references

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]}

• Nitroimidazole antibiotics and antiprotozoals containing 2-methylimidazole cores:
• 
  Dimetridazole
• 
  Metronidazole
• 
  Secnidazole
• 
  Ornidazole
• 
  Tinidazole
• 
  Carnidazole

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. 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. Bibcode:2008Sci...319..939B. 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.