2-Methylimidazole

2-Methylimidazole

Names
Other names 2-MeIm
Identifiers
CAS Number	693-98-1
3D model (Jmol)	Interactive image
ChemSpider	12225
ECHA InfoCard	100.010.697
PubChem	12749
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)
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. 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 similuate 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]

References

1. 1 2 3 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. 
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.