Description

2-Methyl-5-nitro-1-{2-[(trimethylsilyl)oxy]ethyl}-1H-imidazole (CAS No. 89422-95-7) is a high-purity, synthetic nitroimidazole derivative with the molecular formula C₉H₁₇N₃O₃Si. This specialized organosilicon compound features a trimethylsilyl-protected hydroxyethyl group attached to the imidazole ring, enhancing its stability and reactivity in synthetic applications. With an IUPAC name of trimethyl-[2-(2-methyl-5-nitroimidazol-1-yl)ethoxy]silane, this compound is characterized by its nitro functional group at the 5-position and a methyl group at the 2-position of the imidazole core. The trimethylsilyl (TMS) ether moiety provides excellent protection for the hydroxyl group during complex organic syntheses. Supplied as a crystalline solid or powder with >95% purity (HPLC), this chemical is ideal for pharmaceutical research, medicinal chemistry, and advanced material science applications. Store under inert conditions at 2-8°C to maintain stability.

Properties

• CAS Number: 89422-95-7
• Complexity: 251
• IUPAC Name: trimethyl-[2-(2-methyl-5-nitro-imidazol-1-yl)ethoxy]silane
• InChI: InChI=1S/C9H17N3O3Si/c1-8-10-7-9(12(13)14)11(8)5-6-15-16(2,3)4/h7H,5-6H2,1-4H3
• InChI Key: JDLYLQKETMSPJR-UHFFFAOYSA-N
• Exact Mass: 243.10391795
• Molecular Formula: C9H17N3O3Si
• Molecular Weight: 243.33
• SMILES: CC1=NC=C(N1CCO[Si](C)(C)C)[N+](=O)[O-]
• Topological: 72.9
• Monoisotopic Mass: 243.10391795
• Synonyms: 2-Methyl-5-nitro-1-{2-[(trimethylsilyl)oxy]ethyl}-1H-imidazole, 89422-95-7, DTXSID40753624, JDLYLQKETMSPJR-UHFFFAOYSA-N

Application

This nitroimidazole derivative serves as a key intermediate in the synthesis of novel antimicrobial and antiprotozoal agents, particularly in the development of metronidazole analogs. The TMS-protected hydroxyethyl group allows for selective deprotection in multi-step synthetic routes. Researchers utilize this compound in nucleoside chemistry for modifying imidazole-containing scaffolds. Its nitro group participates in redox reactions important for prodrug activation studies.

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