n-Butyllithium

When BuBr is the precursor, the product is a homogeneous solution, consisting of a mixed cluster containing both LiBr and BuLi, together with a small amount of octane.

A popular weak acid is biphenyl-4-methanol, which gives a deeply colored dilithio derivative at the end point.

Reactions are typically conducted in tetrahydrofuran and diethyl ether, which are good solvents for the resulting organolithium derivatives (see below).

One of the most useful chemical properties of n-BuLi is its ability to deprotonate a wide range of weak Brønsted acids.

n-BuLi can deprotonate (that is, metalate) many types of C−H bonds, especially where the conjugate base is stabilized by electron delocalization or one or more heteroatoms (non-carbon atoms).

Examples include acetylenes (H−CC−R), methyl sulfides (H−CH2SR), thioacetals (H−CH(SR)2, e.g. dithiane), methylphosphines (H−CH2PR2), furans, thiophenes and ferrocene (Fe(H−C5H4)(C5H5)).

Ligands that complex Li+ such as tetrahydrofuran (THF), tetramethylethylenediamine (TMEDA), hexamethylphosphoramide (HMPA), and 1,4-diazabicyclo[2.2.2]octane (DABCO) further polarize the Li−C bond and accelerate the metalation.

[10] An example of the use of n-butyllithium as a base is the addition of an amine to methyl carbonate to form a methyl carbamate, where n-butyllithium serves to deprotonate the amine: Butyllithium reacts with some organic bromides and iodides in an exchange reaction to form the corresponding organolithium derivative.

One such synthetic pathway is the reaction of an organolithium reagent with disubstituted amides: THF is deprotonated by butyllithium, especially in the presence of TMEDA, by loss of one of four protons adjacent to oxygen.

This process, which consumes butyllithium to generate butane, induces a ring opening to give enolate of acetaldehyde and ethylene.

[11] Therefore, reactions of BuLi in THF are typically conducted at low temperatures, such as –78 °C, as is conveniently produced by a freezing bath of dry ice and acetone.

When heated, n-BuLi, analogously to other alkyllithium reagents with "β-hydrogens", undergoes β-hydride elimination to produce 1-butene and lithium hydride (LiH): Alkyl-lithium compounds are stored under inert gas to prevent loss of activity and for reasons of safety.

NFPA 704 four-colored diamond Health 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gas Flammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propane Instability 3: Capable of detonation or explosive decomposition but requires a strong initiating source, must be heated under confinement before initiation, reacts explosively with water, or will detonate if severely shocked. E.g. hydrogen peroxide Special hazard W: Reacts with water in an unusual or dangerous manner. E.g. sodium, sulfuric acid
Glass bottles containing butyllithium