| Customization: | Available |
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| CAS No.: | 288-32-4 |
| Formula: | C3h4n2 |
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| Product names | Imidazole |
| CAS No | 288-32-4 |
Chemical Properties
Imidazole is a heterocyclic organic compound with a five-membered ring containing two nitrogen atoms at positions 1 and 3. It is a moderately strong base (pKb = 7.0) and a weak acid (pKa = 14.9). The presence of electron-withdrawing groups can make imidazole derivatives even stronger acids. Imidazole is stable up to 400°C and exhibits significant aromatic character, undergoing typical electrophilic aromatic substitution reactions.
Synthesis
Imidazole can be synthesized through several methods:
Debus Method: Glyoxal, formaldehyde, and ammonia react to form imidazole.
Radiszewski Synthesis: Glyoxal reacts with an aldehyde (e.g., benzaldehyde) in the presence of ammonia.
Wallach Synthesis: Phosphorus oxychloride reacts with N,N'-disubstituted oxamide, followed by reduction with hydroiodic acid.
Marckwald Synthesis: 3-Mercaptoimidazoles are formed from reactions involving cyanates or thiocyanates.
Reactions
Electrophilic Substitution: Imidazole is more reactive than other five-membered heterocycles, with electrophilic attack preferred at the 4(5) position.
Halogenation: Bromination yields 2,4,5-tribromoderivatives, while iodination under alkaline conditions produces 2,4,5-triiodoimidazole.
Nucleophilic Substitution: Nucleophilic attack is possible at the C2 position if electron-withdrawing groups are present.
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