2-Methylimidazole

2-Methylimidazole

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

It is prepared by condensation of glyoxal, ammonia, and acetaldehyde, a Radziszewski reaction. Nitration gives 5-nitro derivative.

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-Methylimidazole is a precursor to the several members of the nitroimidazole antibiotics that are used to combat anaerobic bacterial and parasitic infections.

Dimetridazole

Metronidazole

Secnidazole

Ornidazole

Tinidazole

Carnidazole

It has low toxicity with an LD₅₀ (rat, oral) of 1300 mg/kg, but it is strongly irritating to the skin and eyes.