2-Methylimidazole

2-Methylimidazole
Names
	Preferred IUPAC name 2-Methyl-1H-imidazole
	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;
UNII	T0049Z45LZ ;
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)
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]

References

^ ^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
^ 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.
^ 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.

[Ebel-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: 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.

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