CH3CH2CH2CH2Li

CH3CH2CH2CH2Li, also known as n-butyllithium or 1-butyllithium, is an organolithium compound with the chemical formula C4H9Li. It is a colorless liquid that is highly reactive and pyrophoric, meaning it ignites spontaneously in air. It is typically supplied as a solution in hydrocarbon solvents like hexane, heptane, or cyclohexane due to its instability in pure form. n-Butyllithium is a strong base and a potent nucleophile, making it a widely used reagent in organic synthesis.

The primary application of n-butyllithium is in deprotonation reactions, where it abstracts protons from weakly acidic compounds to form carbanions. These carbanions can then undergo nucleophilic attack on electrophiles, enabling the formation of new carbon-carbon bonds. It is frequently employed in reactions such as alkylations, acylations, and the formation of Grignard reagents. Its ability to generate stabilized carbanions makes it a valuable tool for constructing complex organic molecules. Safety precautions are paramount when handling n-butyllithium due to its hazardous nature.