Description

1-((2-(Trimethylsilyl)ethoxy)methyl)-2-bromo-1H-imidazole-4-carbonitrile (CAS No. 854044-51-2) is a high-purity, organosilicon-protected imidazole derivative designed for advanced synthetic applications in pharmaceutical and materials research. With the molecular formula C₁₀H₁₆BrN₃OSi and IUPAC name 2-bromo-1-(2-trimethylsilylethoxymethyl)imidazole-4-carbonitrile, this compound features a reactive bromo-substituted imidazole core, a cyano group for further functionalization, and a SEM (2-(trimethylsilyl)ethoxymethyl) protecting group for enhanced stability during multi-step syntheses. Ideal for nucleophilic substitution, cross-coupling reactions, and heterocyclic chemistry, this reagent is rigorously tested via HPLC, GC, and NMR to ensure ≥95% purity. Packaged under inert gas to prevent degradation, it is available in gram to kilogram quantities with optional custom synthesis and analytical documentation.

Properties

• CAS Number: 854044-51-2
• Complexity: 273
• IUPAC Name: 2-bromo-1-(2-trimethylsilylethoxymethyl)imidazole-4-carbonitrile
• InChI: InChI=1S/C10H16BrN3OSi/c1-16(2,3)5-4-15-8-14-7-9(6-12)13-10(14)11/h7H,4-5,8H2,1-3H3
• InChI Key: XDLFZSWZSHTGJY-UHFFFAOYSA-N
• Exact Mass: 301.02460
• Molecular Formula: C10H16BrN3OSi
• Molecular Weight: 302.24
• SMILES: C[Si](C)(C)CCOCN1C=C(N=C1Br)C#N
• Topological: 50.8
• Monoisotopic Mass: 301.02460
• Synonyms: 854044-51-2, 1-((2-(Trimethylsilyl)ethoxy)methyl)-2-bromo-1H-imidazole-4-carbonitrile, 2-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carbonitrile, 2-Bromo-1-(2-trimethylsilylethoxymethyl)imidazole-4-carbonitrile, 2-Bromo-1-((2-(trimethylsilyl)ethoxy)-methyl)-1H-imidazole-4-carbonitrile, 1H-Imidazole-4-carbonitrile, 2-bromo-1-[[2-(trimethylsilyl)ethoxy]methyl]-, MFCD12964153, C10H16BrN3OSi, SCHEMBL1858224, XDLFZSWZSHTGJY-UHFFFAOYSA-N, AKOS027255540, AS-54844, DB-202833, CS-0036908, W10478, 2-bromo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-4-carbonitrile, 2-Bromo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-4carbonitrile

Application

This SEM-protected bromoimidazole derivative serves as a versatile intermediate in the synthesis of pharmaceutical agents, particularly for kinase inhibitors and antiviral compounds. Its reactive bromo and cyano groups enable palladium-catalyzed cross-coupling (e.g., Suzuki, Heck) to construct complex heterocycles. The SEM group facilitates selective deprotection under mild acidic conditions, making it valuable for parallel synthesis and combinatorial chemistry workflows in drug discovery.

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