Butyl Lithium

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  • Butyllithium may refer to one of three isomeric organolithium reagents used in chemical synthesis: n-Butyllithium, sec-Butyllithium, tert-Butyllithium.

  • n-Butyllithium (abbreviated n-BuLi) is an organolithium reagent. It is widely used as a polymerization initiator in the production of elastomers such as polybutadiene or styrene-butadiene-styrene (SBS).

  • Butyllithium is commercially available as solutions (15%, 25%, 2 M, 2.5 M, 10 M, etc.) in alkanes such as pentane, hexanes, and heptanes. Solutions in diethyl ether and THF can be prepared, but are not stable enough for storage.

  • Although it is a colourless liquid, n-butyllithium is usually encountered as a pale yellow solution in alkanes.

  • n-BuLi exists as a cluster both in the solid state and in a solution. 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 standard preparation for n-BuLi is reaction of 1-bromobutane or 1-chlorobutane with Li metal.If the lithium used for this reaction contains 1-3% sodium, the reaction proceeds more quickly than if pure lithium is used. Solvents used for this preparation include benzene, cyclohexane, and diethyl ether.

  • One of the most useful chemical properties of n-BuLi is its ability to deprotonate a wide range of weak Brønsted acids. t-Butyllithium and s-butyllithium are more basic.

  • Butyllithium reacts with some organic bromides and iodides in an exchange reaction to form the corresponding organolithium derivative.

  • sec-Butyllithium is an organometallic compound with the formula CH3CHLiCH2CH3, abbreviated sec-BuLi or s-BuLi. This chiral organolithium reagent is used as a source of sec-butyl carbanion in organic synthesis.

  • sec-BuLi react with carbonyl compounds and esters to form alcohols. With copper(I) iodide sec-BuLi forms lithium di-sec-butylcuprates.

  • tert-Butyllithium is a chemical compound with the formula (CH3)3CLi. As an organometallic compound, it has applications in organic synthesis (see also Grignard reaction) since it is a sufficiently strong base to deprotonate many carbon acids, including benzene.

  • A common use of simple commercially available organolithium compounds (like n-BuLi, sec-BuLi, t-BuLi) is as very strong bases.

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