Product Description
Dibenzo-18-crown-6、14187-32-7
AI Product Description
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Dibenzo-18-crown-6, chemically known as 1,4,7,10,13,16-hexaoxacyclooctadeca-2,5,9,12,15,18-hexaene, is a macrocyclic polyether belonging to the crown ether family. Its molecular formula is C20H24O6, and it carries the CAS Registry Number 17536-66-0. This compound features a rigid cyclic structure composed of six oxygen atoms and two benzene rings integrated into an eighteen-membered ring system. The specific cavity size of approximately 2.6–3.2 Å makes it highly selective for binding large alkali metal cations, particularly potassium (K+), forming stable host-guest complexes in various solvents.
The primary application of Dibenzo-18-crown-6 lies in phase-transfer catalysis. It acts as a powerful carrier to transport inorganic salts from aqueous phases into organic solvents, thereby facilitating reactions that would otherwise be kinetically inhibited due to poor solubility. In organic synthesis, it is frequently employed to enhance the reactivity of nucleophiles like cyanide or azide ions by desolvating them, leading to faster reaction rates and improved yields. Beyond catalysis, this crown ether is extensively used in analytical chemistry for the separation and detection of metal ions via ion-selective electrodes or chromatographic techniques. Its ability to selectively complex potassium allows researchers to study ion transport mechanisms across biological membranes, offering insights into physiological processes involving sodium-potassium pumps. Furthermore, it serves as a crucial building block in supramolecular chemistry for constructing complex molecular machines, sensors, and functional materials. Due to its high affinity for potassium, it is also utilized in the purification of potassium-containing compounds and in the synthesis of specialized pharmaceutical intermediates where precise ion control is essential. Despite its utility, handling requires standard safety precautions as with most organic solvents, though it exhibits low acute toxicity compared to many other chemical reagents. Overall, Dibenzo-18-crown-6 remains an indispensable tool in modern chemical research, bridging the gap between inorganic ion chemistry and organic synthetic methodologies.