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The restaurant, seen from above. Also, it is broadly employed as a strong base superbase in the synthesis of organic compounds as in the pharmaceutical industry.
Solutions in diethyl ether and THF can be prepared, but are not stable enough for storage. Annual worldwide production and consumption of butyllithium and other organolithium compounds is estimated at tonnes.
Although butyllithium is colorless, n- butyllithium is usually encountered as a pale yellow solution in alkanes. Such solutions are stable indefinitely if properly stored,  but in practice, they degrade upon aging.
Fine white precipitate lithium hydroxide is deposited and the color changes to orange. The tendency to aggregate is common for organolithium compounds.
The aggregates are held together by delocalized covalent bonds between lithium and the terminal carbon of the butyl chain. The cluster is a distorted cubane-type cluster with Li and C H 2 R groups at alternating vertices.
An equivalent description describes the tetramer as a Li 4 tetrahedron interpenetrated with a tetrahedron [ C H 2 R] 4. Bonding within the cluster is related to that used to describe diborane, but more complex since eight atoms are involved.
Reflecting its "electron-deficient character," n -butyllithium is highly reactive toward Lewis bases. Due to the large difference between the electronegativities of carbon 2.
The standard preparation for n -BuLi is reaction of 1-bromobutane or 1-chlorobutane with Li metal: Solvents used for this preparation include benzene , cyclohexane, and diethyl ether.
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.
Solutions of butyllithium, which are susceptible to degradation by air, are standardized by titration. A popular weak acid is biphenyl methanol, which gives a deeply colored dilithio derivative at the end point.
Butyllithium is principally valued as an initiator for the anionic polymerization of dienes , such as butadiene. Isoprene can be polymerized stereospecifically in this way.
Also of commercial importance is the use of butyllithium for the production of styrene-butadiene polymers. Even ethylene will insert into BuLi.
Furthermore, in addition to being a strong nucleophile, n-BuLi binds to aprotic Lewis bases, such as ethers and tertiary amines , which partially disaggregate the clusters by binding to the lithium centers.
Its use as a strong base is referred to as metalation. Reactions are typically conducted in tetrahydrofuran and diethyl ether , which are good solvents for the resulting organolithium derivatives see below.
The stability and volatility of the butane resulting from such deprotonation reactions is convenient, but can also be a problem for large-scale reactions because of the volume of a flammable gas produced.
The kinetic basicity of n -BuLi is affected by the solvent or cosolvent. Such additives can also aid in the isolation of the lithiated product, a famous example of which is dilithioferrocene.
It is kinetically more reactive than butyllithium and is often used to accomplish difficult metalations. The butoxide anion complexes the lithium and effectively produces butylpotassium, which is more reactive than the corresponding lithium reagent.