nBuLi

n-Butyllithium, often abbreviated as nBuLi, is an organolithium compound with the chemical formula CH3CH2CH2CH2Li. It is a highly reactive and pyrophoric liquid, meaning it can spontaneously ignite in air. n-BuLi is primarily used as a strong base and a nucleophile in organic synthesis.

Its strong basicity makes it capable of deprotonating a wide range of organic molecules, including alcohols, amines, and even weakly acidic C-H bonds. This deprotonation often generates carbanions, which are important intermediates in carbon-carbon bond formation reactions. As a nucleophile, n-BuLi can attack electrophilic centers, such as carbonyl groups, leading to the formation of new bonds.

n-BuLi is commercially available in various concentrations, typically dissolved in hydrocarbon solvents like hexane, heptane, or cyclohexane. Due to its reactivity and pyrophoric nature, it must be handled under an inert atmosphere, such as nitrogen or argon, using specialized techniques like Schlenk lines or glove boxes. Its reactivity also necessitates careful storage at low temperatures to prevent decomposition. Common applications include lithiation reactions, such as the formation of organometallic reagents, and as an initiator in anionic polymerization.