2-Aminoimidazole hemisulfate
2-Aminoimidazole hemisulfate (CAS 1450-93-7), also named 2-imidazoleamine sulfate, bis(2-aminoimidazole) sulfate or 2-aminoimidazole sulfate, is the sulfuric acid salt of 2-aminoimidazole, a nitrogen-rich five-membered heterocycle related to the imidazole alkaloids found in marine sponges. It is a white to off-white crystalline solid with a melting point near 270 degrees Celsius, a reported boiling point of about 313 degrees Celsius and good solubility in water, and it is routinely supplied at 98 percent purity. The hemisulfate form stabilises the oxidation-sensitive free base and greatly simplifies purification, weighing and storage. The guanidine-like aminoimidazole unit is strongly basic and an excellent hydrogen-bond donor and acceptor, enabling metal binding, carboxylate recognition and protein interaction.
1. Pharmaceutical intermediate: a key building block for the synthesis of imidazole-based drug candidates, including kinase inhibitors, antimicrobials, anti-inflammatory agents, antiparasitic compounds and adenosine receptor ligands.
2. Heterocyclic synthesis: used to construct fused bicyclic systems such as purines, imidazopyridines and imidazopyrimidines employed in medicinal and agrochemical chemistry, and as a masked form of the free 2-aminoimidazole heterocycle.
3. Chemical biology: 2-aminoimidazoles are studied as inhibitors of bacterial biofilm formation, as guanidine bioisosteres in enzyme ligands and as scaffolds for anion and metal recognition and sensing applications.
4. Handling and storage: light and moisture sensitive; store in a sealed, dry container at ambient or reduced temperature away from strong oxidising agents, and keep away from strong acids that would liberate the free base. Avoid dust inhalation and observe standard laboratory hygiene.
Product Name: 2-Aminoimidazole hemisulfate
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