n-Butyllithium

n-Butyllithium is an organolithium compound, C₄H₉Li, widely used as a strong base and nucleophile in organic synthesis. It is typically supplied as a solution and reacts readily with air and water.

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Organolithium reagent: An organometallic compound containing a carbon–lithium bond, used chiefly as a base or carbon nucleophile. n-Butyllithium is a widely used member of this reagent family.
Directed ortho metalation: A regioselective metalation of an aromatic ring next to a directing substituent, commonly using a strong base. n-Butyllithium can remove an ortho proton to create a site for subsequent functionalization.
sec-Butyllithium: An organolithium compound with formula C₄H₉Li in which lithium is bonded to a secondary butyl carbon. Its greater steric hindrance and different structure can change selectivity relative to n-butyllithium.
Butane: A four-carbon alkane with molecular formula C₄H₁₀. Protonation of n-butyllithium produces butane, a useful way to view its basic reaction.
Pyrophoric reagent handling: Laboratory procedures for safely transferring and storing substances that can ignite spontaneously in air. n-Butyllithium requires controlled inert-atmosphere handling to limit fires and exposure.
Lithium–carbon bond: A highly polar covalent bond between lithium and carbon in organolithium compounds. Its polarity gives the butyl carbon strong basic and nucleophilic character.
Enolate: A resonance-stabilized anion formed by deprotonating the alpha carbon of a carbonyl compound. n-Butyllithium can form enolates that serve as nucleophiles in carbon–carbon bond formation.
tert-Butyllithium: An organolithium compound with formula C₄H₉Li in which lithium is bonded to a tertiary butyl carbon. It is generally more reactive and more pyrophoric than n-butyllithium.
Hexane: A six-carbon alkane commonly used as a nonpolar solvent. Commercial n-butyllithium is often supplied in hydrocarbon solvents such as hexane.
Schlenk line: A glass apparatus that uses vacuum and inert gas to handle air- and moisture-sensitive substances. Schlenk techniques help exclude air and water during n-butyllithium reactions.