QUINUCLIDINE

Quinuclidine is white to light yellow crystalline powder at room temperature and pressure, soluble in most organic solvents, relatively poor solubility in water. The quinuclidine ring molecule contains a lone pair of electrons that can form hydrogen bonds. This gives the quinuclidine ring molecule some hydrogen bond acceptor and donor properties, allowing it to form hydrogen bonding interactions with other molecules. In addition, the compound molecule contains a lone pair of electrons that can accept protons to produce the corresponding ionic form. Under weakly acidic conditions, the quinuclidine ring can be protonated to form positively charged ions.

Quinuclidine acts as a catalyst, a chemical building block and is used in organic synthesis. It is employed to prepare quinine and alkaloids. It finds application as a ligand, which is useful in the studies of OsO4-catalyzed dihydroxylation of olefins. It plays an important role in the formation of onium salts used testing of PAC-antagonist activity.

ChEBI: Quinuclidine is a saturated organic heterobicyclic parent and a member of quinuclidines.

A poison by ingestion and skin contact. Low toxicity by inhalation. A moderate skin and severe eye irritant.

Crystallise it from diethyl ether. The hydrochloride has m 364-365o(dec) (from EtOH or n-BuOH), and the picrate has m 225o (from aqueous EtOH). [Beilstein 20 H 144, 20 II 71, 20 III/IV 1966, 20/4 V 335.]