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''n''-Butyllithium C4H9Li (abbreviated ''n''-BuLi) is an
organolithium reagent In organometallic chemistry, organolithium reagents are chemical compounds that contain carbon–lithium (C–Li) bonds. These reagents are important in organic synthesis, and are frequently used to transfer the organic group or the lithium atom ...
. It is widely used as a
polymerization In polymer chemistry, polymerization (American English), or polymerisation (British English), is a process of reacting monomer, monomer molecules together in a chemical reaction to form polymer chains or three-dimensional networks. There are ...
initiator in the production of
elastomer An elastomer is a polymer with viscoelasticity (i.e. both viscosity and elasticity) and with weak intermolecular forces, generally low Young's modulus and high failure strain compared with other materials. The term, a portmanteau of ''elastic p ...
s such as
polybutadiene Polybutadiene utadiene rubber BRis a synthetic rubber. Polybutadiene rubber is a polymer formed from the polymerization of the monomer 1,3-butadiene. Polybutadiene has a high resistance to wear and is used especially in the manufacture of tir ...
or styrene-butadiene-styrene (SBS). Also, it is broadly employed as a strong base (
superbase A superbase is a compound that has a particularly high affinity for protons. Superbases are of theoretical interest and potentially valuable in organic synthesis. Superbases have been described and used since the 1850s.''Superbases for Organic ...
) in the synthesis of organic compounds as in the pharmaceutical industry. Butyllithium is commercially available as solutions (15%, 25%, 1.5  M, 2 M, 2.5 M, 10 M, etc.) in
alkane In organic chemistry, an alkane, or paraffin (a historical trivial name that also has other meanings), is an acyclic saturated hydrocarbon. In other words, an alkane consists of hydrogen and carbon atoms arranged in a tree structure in which ...
s such as
pentane Pentane is an organic compound with the formula C5H12—that is, an alkane with five carbon atoms. The term may refer to any of three structural isomers, or to a mixture of them: in the IUPAC nomenclature, however, pentane means exclusively the ' ...
,
hexane Hexane () is an organic compound, a straight-chain alkane with six carbon atoms and has the molecular formula C6H14. It is a colorless liquid, odorless when pure, and with boiling points approximately . It is widely used as a cheap, relatively ...
s, and
heptane Heptane or ''n''-heptane is the straight-chain alkane with the chemical formula H3C(CH2)5CH3 or C7H16. When used as a test fuel component in anti-knock test engines, a 100% heptane fuel is the zero point of the octane rating scale (the 100 point ...
s. Solutions in
diethyl ether Diethyl ether, or simply ether, is an organic compound in the ether class with the formula , sometimes abbreviated as (see Pseudoelement symbols). It is a colourless, highly volatile, sweet-smelling ("ethereal odour"), extremely flammable liq ...
and
THF Tetrahydrofuran (THF), or oxolane, is an organic compound with the formula (CH2)4O. The compound is classified as heterocyclic compound, specifically a cyclic ether. It is a colorless, water- miscible organic liquid with low viscosity. It is ...
can be prepared, but are not stable enough for storage. Annual worldwide production and consumption of butyllithium and other organolithium compounds is estimated at 2000 to 3000 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 Lithium hydroxide is an inorganic compound with the formula LiOH. It can exist as anhydrous or hydrated, and both forms are white hygroscopic solids. They are soluble in water and slightly soluble in ethanol. Both are available commercially. While ...
) is deposited and the color changes to orange.


Structure and bonding

''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. In the case of ''n''-BuLi, the clusters are tetrameric (in ether) or hexameric (in
cyclohexane Cyclohexane is a cycloalkane with the molecular formula . Cyclohexane is non-polar. Cyclohexane is a colorless, flammable liquid with a distinctive detergent-like odor, reminiscent of cleaning products (in which it is sometimes used). Cyclohexan ...
). The cluster is a distorted
cubane-type cluster A cubane-type cluster is an arrangement of atoms in a molecular structure that forms a cube. In the idealized case, the eight vertices are symmetry equivalent and the species has Oh symmetry. Such a structure is illustrated by the hydrocarbon cub ...
with Li and ''C''H2R groups at alternating vertices. An equivalent description describes the tetramer as a Li4
tetrahedron In geometry, a tetrahedron (plural: tetrahedra or tetrahedrons), also known as a triangular pyramid, is a polyhedron composed of four triangular faces, six straight edges, and four vertex corners. The tetrahedron is the simplest of all the o ...
interpenetrated with a tetrahedron 'C''H2Rsub>4. Bonding within the cluster is related to that used to describe diborane, but more complex since eight atoms are involved. Reflecting its electron-rich character, ''n''-butyllithium is highly reactive toward
Lewis acid A Lewis acid (named for the American physical chemist Gilbert N. Lewis) is a chemical species that contains an empty orbital which is capable of accepting an electron pair from a Lewis base to form a Lewis adduct. A Lewis base, then, is any sp ...
s. Due to the large difference between the
electronegativities Electronegativity, symbolized as , is the tendency for an atom of a given chemical element to attract shared electrons (or electron density) when forming a chemical bond. An atom's electronegativity is affected by both its atomic number and the d ...
of
carbon Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent In chemistry, the valence (US spelling) or valency (British spelling) of an element is the measure of its combining capacity with o ...
(2.55) and
lithium Lithium (from el, λίθος, lithos, lit=stone) is a chemical element with the symbol Li and atomic number 3. It is a soft, silvery-white alkali metal. Under standard conditions, it is the least dense metal and the least dense solid el ...
(0.98), the C−Li bond is highly polarized. The charge separation has been estimated to be 55–95%. For practical purposes, ''n''-BuLi can often be considered to react as the butyl
anion An ion () is an atom or molecule with a net electrical charge. The charge of an electron is considered to be negative by convention and this charge is equal and opposite to the charge of a proton, which is considered to be positive by convent ...
, ''n''-Bu, and a lithium
cation An ion () is an atom or molecule with a net electrical charge. The charge of an electron is considered to be negative by convention and this charge is equal and opposite to the charge of a proton, which is considered to be positive by convent ...
, Li+.


Preparation

The standard preparation for ''n''-BuLi is reaction of 1-bromobutane or 1-chlorobutane with Li metal: : 2 Li + C4H9X → C4H9Li + LiX (X = Cl, Br) If the lithium used for this reaction contains 1–3%
sodium Sodium is a chemical element with the symbol Na (from Latin ''natrium'') and atomic number 11. It is a soft, silvery-white, highly reactive metal. Sodium is an alkali metal, being in group 1 of the periodic table. Its only stable iso ...
, the reaction proceeds more quickly than if pure lithium is used. Solvents used for this preparation include
benzene Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, ...
, 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 Octane is a hydrocarbon and an alkane with the chemical formula , and the condensed structural formula . Octane has many structural isomers that differ by the amount and location of branching in the carbon chain. One of these isomers, 2,2,4-Tri ...
. BuLi forms a weaker complex with LiCl, so that the reaction of BuCl with Li produces a precipitate of LiCl. Solutions of butyllithium, which are susceptible to degradation by air, are standardized by
titration Titration (also known as titrimetry and volumetric analysis) is a common laboratory method of quantitative chemical analysis to determine the concentration of an identified analyte (a substance to be analyzed). A reagent, termed the ''titrant'' ...
. A popular weak acid is
biphenyl Biphenyl (also known as diphenyl, phenylbenzene, 1,1′-biphenyl, lemonene or BP) is an organic compound that forms colorless crystals. Particularly in older literature, compounds containing the functional group consisting of biphenyl less one ...
-4-methanol, which gives a deeply colored dilithio derivative at the end point.


Applications

Butyllithium is principally valued as an initiator for the anionic
polymerization In polymer chemistry, polymerization (American English), or polymerisation (British English), is a process of reacting monomer, monomer molecules together in a chemical reaction to form polymer chains or three-dimensional networks. There are ...
of
diene In organic chemistry a diene ( ) (diolefin ( ) or alkadiene) is a covalent compound that contains two double bonds, usually among carbon atoms. They thus contain two alk''ene'' units, with the standard prefix ''di'' of systematic nomenclature. ...
s, such as
butadiene 1,3-Butadiene () is the organic compound with the formula (CH2=CH)2. It is a colorless gas that is easily condensed to a liquid. It is important industrially as a precursor to synthetic rubber. The molecule can be viewed as the union of two viny ...
. The reaction is called "carbolithiation": : C4H9Li + CH2=CH−CH=CH2 → C4H9−CH2−CH=CH−CH2Li
Isoprene Isoprene, or 2-methyl-1,3-butadiene, is a common volatile organic compound with the formula CH2=C(CH3)−CH=CH2. In its pure form it is a colorless volatile liquid. Isoprene is an unsaturated hydrocarbon. It is produced by many plants and animals ...
can be polymerized stereospecifically in this way. Also of commercial importance is the use of butyllithium for the production of
styrene-butadiene Styrene-butadiene or styrene-butadiene rubber (SBR) describe families of synthetic rubbers derived from styrene and butadiene (the version developed by Goodyear is called Neolite). These materials have good abrasion resistance and good aging st ...
polymers. Even
ethylene Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula or . It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon-carbon double bonds). Ethylene i ...
will insert into BuLi.


Reactions

Butyllithium is a strong base (p''K''a ≈ 50), but it is also a powerful
nucleophile In chemistry, a nucleophile is a chemical species that forms bonds by donating an electron pair. All molecules and ions with a free pair of electrons or at least one pi bond can act as nucleophiles. Because nucleophiles donate electrons, they are ...
and
reductant In chemistry, a reducing agent (also known as a reductant, reducer, or electron donor) is a chemical species that "donates" an electron to an (called the , , , or ). Examples of substances that are commonly reducing agents include the Earth meta ...
, depending on the other reactants. Furthermore, in addition to being a strong nucleophile, ''n''-BuLi binds to aprotic Lewis bases, such as ethers and tertiary
amine In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituen ...
s, which partially disaggregate the clusters by binding to the lithium centers. Its use as a strong base is referred to as
metalation Metalation (Alt. spelling: Metallation) is a chemical reaction that forms a bond to a metal. This reaction usually refers to the replacement of a halogen atom in an organic molecule with a metal atom, resulting in an organometallic compound. In the ...
. Reactions are typically conducted in
tetrahydrofuran Tetrahydrofuran (THF), or oxolane, is an organic compound with the formula (CH2)4O. The compound is classified as heterocyclic compound, specifically a cyclic ether. It is a colorless, water-miscible organic liquid with low viscosity. It is ma ...
and
diethyl ether Diethyl ether, or simply ether, is an organic compound in the ether class with the formula , sometimes abbreviated as (see Pseudoelement symbols). It is a colourless, highly volatile, sweet-smelling ("ethereal odour"), extremely flammable liq ...
, which are good solvents for the resulting organolithium derivatives (see below).


Metalation

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. ''n''-BuLi can deprotonate (that is, metalate) many types of C−H bonds, especially where the
conjugate base A conjugate acid, within the Brønsted–Lowry acid–base theory, is a chemical compound formed when an acid donates a proton () to a base—in other words, it is a base with a hydrogen ion added to it, as in the reverse reaction it loses a ...
is stabilized by electron
delocalization In chemistry, delocalized electrons are electrons in a molecule, ion or solid metal that are not associated with a single atom or a covalent bond.IUPAC Gold Boo''delocalization''/ref> The term delocalization is general and can have slightly diff ...
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 A dithiane is a heterocyclic compound composed of a cyclohexane core structure wherein two methylene bridges (-- units) are replaced by sulfur centres. The three isomeric parent heterocycles are 1,2-dithiane, 1,3-dithiane and 1,4-dithiane. 1,3 ...
), methylphosphines (''H''−CH2PR2),
furan Furan is a heterocyclic organic compound, consisting of a five-membered aromatic ring with four carbon atoms and one oxygen atom. Chemical compounds containing such rings are also referred to as furans. Furan is a colorless, flammable, highly ...
s,
thiophene Thiophene is a heterocyclic compound with the formula C4H4S. Consisting of a planar five-membered ring, it is aromatic as indicated by its extensive substitution reactions. It is a colorless liquid with a benzene-like odor. In most of its reacti ...
s and
ferrocene Ferrocene is an organometallic compound with the formula . The molecule is a complex consisting of two cyclopentadienyl rings bound to a central iron atom. It is an orange solid with a camphor-like odor, that sublimes above room temperature, a ...
(Fe(''H''−C5H4)(C5H5)). In addition to these, it will also deprotonate all more acidic compounds such as alcohols, amines,
enol In organic chemistry, alkenols (shortened to enols) are a type of reactive structure or intermediate in organic chemistry that is represented as an alkene ( olefin) with a hydroxyl group attached to one end of the alkene double bond (). The te ...
izable carbonyl compounds, and any overtly acidic compounds, to produce alkoxides, amides, enolates and other salts of lithium, respectively. The stability and volatility of the
butane Butane () or ''n''-butane is an alkane with the formula C4H10. Butane is a gas at room temperature and atmospheric pressure. Butane is a highly flammable, colorless, easily liquefied gas that quickly vaporizes at room temperature. The name but ...
resulting from such
deprotonation Deprotonation (or dehydronation) is the removal (transfer) of a proton (or hydron, or hydrogen cation), (H+) from a Brønsted–Lowry acid in an acid–base reaction.Henry Jakubowski, Biochemistry Online Chapter 2A3, https://employees.csbsju.ed ...
reactions is convenient, but can also be a problem for large-scale reactions because of the volume of a flammable gas produced. : LiC4H9 + RH → C4H10 + RLi The kinetic basicity of ''n''-BuLi is affected by the solvent or cosolvent. Ligands that complex Li+ such as
tetrahydrofuran Tetrahydrofuran (THF), or oxolane, is an organic compound with the formula (CH2)4O. The compound is classified as heterocyclic compound, specifically a cyclic ether. It is a colorless, water-miscible organic liquid with low viscosity. It is ma ...
(THF),
tetramethylethylenediamine Tetramethylethylenediamine (TMEDA or TEMED) is a chemical compound with the formula (CH3)2NCH2CH2N(CH3)2. This species is derived from ethylenediamine by replacement of the four amine hydrogens with four methyl groups. It is a colorless liquid, ...
(TMEDA),
hexamethylphosphoramide Hexamethylphosphoramide, often abbreviated HMPA, is a phosphoramide (an amide of phosphoric acid) with the formula This colorless liquid is a useful reagent in organic synthesis. Structure and reactivity HMPA is the oxide of the highly basic ter ...
(HMPA), and 1,4-diazabicyclo .2.2ctane (
DABCO DABCO (1,4-diazabicyclo .2.2ctane), also known as triethylenediamine or TEDA, is a bicyclic organic compound with the formula N2(C2H4)3. This colorless solid is a highly nucleophilic tertiary amine base, which is used as a catalyst and reagent i ...
) further polarize the Li−C bond and accelerate the metalation. Such additives can also aid in the isolation of the lithiated product, a famous example of which is dilithioferrocene. :Fe(C5H5)2 + 2 LiC4H9 + 2 TMEDA → 2 C4H10 + Fe(C5H4Li)2(TMEDA)2
Schlosser's base Schlosser's base (or Lochmann-Schlosser base) describes various superbasic mixtures of an alkyllithium compound and a potassium alkoxide. The reagent is named after Manfred Schlosser, although he uses the term ''LICKOR superbase'' (LIC denoting the ...
is a
superbase A superbase is a compound that has a particularly high affinity for protons. Superbases are of theoretical interest and potentially valuable in organic synthesis. Superbases have been described and used since the 1850s.''Superbases for Organic ...
produced by treating butyllithium with potassium ''t''-butoxide. It is kinetically more reactive than butyllithium and is often used to accomplish difficult
metalation Metalation (Alt. spelling: Metallation) is a chemical reaction that forms a bond to a metal. This reaction usually refers to the replacement of a halogen atom in an organic molecule with a metal atom, resulting in an organometallic compound. In the ...
s. While some ''n''-butylpotassium is present and is a stronger base than ''n''-BuLi, the reactivity of the mixture is not exactly the same as isolated ''n''-butylpotassium. 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 In organic chemistry, a carbamate is a category of organic compounds with the general formula and structure , which are formally derived from carbamic acid (). The term includes organic compounds (e.g., the ester ethyl carbamate), formally o ...
, where ''n''-butyllithium serves to deprotonate the amine: : ''n''-BuLi + R2NH + (MeO)2CO → R2NCO2Me + LiOMe + BuH


Halogen–lithium exchange

Butyllithium reacts with some organic bromides and iodides in an exchange reaction to form the corresponding organolithium derivative. The reaction usually fails with organic chlorides and fluorides: : C4H9Li + RX → C4H9X + RLi (X = Br, I) This lithium–halogen exchange reaction is useful for preparation of several types of RLi compounds, particularly
aryl In organic chemistry, an aryl is any functional group or substituent derived from an aromatic ring, usually an aromatic hydrocarbon, such as phenyl and naphthyl. "Aryl" is used for the sake of abbreviation or generalization, and "Ar" is used as ...
lithium and some
vinyl Vinyl may refer to: Chemistry * Polyvinyl chloride (PVC), a particular vinyl polymer * Vinyl cation, a type of carbocation * Vinyl group, a broad class of organic molecules in chemistry * Vinyl polymer, a group of polymers derived from vinyl m ...
lithium reagents. The utility of this method is significantly limited, however, by the presence in the reaction mixture of ''n''-BuBr or ''n''-BuI, which can react with the RLi reagent formed, and by competing
dehydrohalogenation In chemistry, dehydrohalogenation is an elimination reaction which removes a hydrogen halide from a substrate. The reaction is usually associated with the synthesis of alkenes, but it has wider applications. Dehydrohalogenation from alkyl halid ...
reactions, in which ''n''-BuLi serves as a base: : 2 C4H9Br + RLi → 2 C4H9R + LiBr : 2 C4H9Li + R′CH=CHBr → 2 C4H10 + R′C≡CLi + LiBr These side reaction are significantly less important for RI than for RBr, since the iodine–lithium exchange is several orders of magnitude faster than the bromine–lithium exchange. For these reasons, aryl, vinyl and primary alkyl iodides are the preferred substrates, and ''t''-BuLi rather than ''n''-BuLi is usually used, since the formed ''t''-BuI is immediately destroyed by the ''t''-BuLi in a dehydrohalogenation reaction (thus requiring two equivalents of ''t''-BuLi). Alternatively, vinyl lithium reagents can be generated by direct reaction of the vinyl halide (e.g. cyclohexenyl chloride) with lithium or by tin–lithium exchange (see next section).


Transmetalations

A related family of reactions are the
transmetalation Transmetalation (alt. spelling: transmetallation) is a type of organometallic reaction that involves the transfer of ligands from one metal to another. It has the general form: :M1–R + M2–R′ → M1–R′ + M2–R where R and R′ can be, but ...
s, wherein two organometallic compounds exchange their metals. Many examples of such reactions involve lithium exchange with
tin Tin is a chemical element with the symbol Sn (from la, stannum) and atomic number 50. Tin is a silvery-coloured metal. Tin is soft enough to be cut with little force and a bar of tin can be bent by hand with little effort. When bent, t ...
: : C4H9Li + Me3SnAr → C4H9SnMe3 + LiAr (where Ar is aryl and Me is methyl) The tin–lithium exchange reactions have one major advantage over the halogen–lithium exchanges for the preparation of organolithium reagents, in that the product tin compounds (C4H9SnMe3 in the example above) are much less reactive towards lithium reagents than are the halide products of the corresponding halogen–lithium exchanges (C4H9Br or C4H9Cl). Other
metal A metal (from Greek μέταλλον ''métallon'', "mine, quarry, metal") is a material that, when freshly prepared, polished, or fractured, shows a lustrous appearance, and conducts electricity and heat relatively well. Metals are typicall ...
s and
metalloid A metalloid is a type of chemical element which has a preponderance of material property, properties in between, or that are a mixture of, those of metals and nonmetals. There is no standard definition of a metalloid and no complete agreement on ...
s which undergo such exchange reactions are organic compounds of
mercury Mercury commonly refers to: * Mercury (planet), the nearest planet to the Sun * Mercury (element), a metallic chemical element with the symbol Hg * Mercury (mythology), a Roman god Mercury or The Mercury may also refer to: Companies * Merc ...
,
selenium Selenium is a chemical element with the symbol Se and atomic number 34. It is a nonmetal (more rarely considered a metalloid) with properties that are intermediate between the elements above and below in the periodic table, sulfur and tellurium, ...
, and
tellurium Tellurium is a chemical element with the symbol Te and atomic number 52. It is a brittle, mildly toxic, rare, silver-white metalloid. Tellurium is chemically related to selenium and sulfur, all three of which are chalcogens. It is occasionally fou ...
.


Carbonyl additions

Organolithium reagents, including ''n''-BuLi are used in synthesis of specific
aldehyde In organic chemistry, an aldehyde () is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl grou ...
s and
ketone In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double bo ...
s. One such synthetic pathway is the reaction of an organolithium reagent with disubstituted
amide In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a compound with the general formula , where R, R', and R″ represent organic groups or hydrogen atoms. The amide group is called a peptide bond when it is ...
s: : R1Li + R2CONMe2 → LiNMe2 + R2C(O)R1


Degradation of THF

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 Acetaldehyde (IUPAC systematic name ethanal) is an organic chemical compound with the formula CH3 CHO, sometimes abbreviated by chemists as MeCHO (Me = methyl). It is a colorless liquid or gas, boiling near room temperature. It is one of the mos ...
and
ethylene Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula or . It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon-carbon double bonds). Ethylene i ...
. 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 Dry ice is the solid form of carbon dioxide. It is commonly used for temporary refrigeration as CO2 does not have a liquid state at normal atmospheric pressure and sublimates directly from the solid state to the gas state. It is used primarily a ...
and acetone. Higher temperatures (−25 °C or even −15 °C) are also used.


Thermal decomposition

When heated, ''n''-BuLi, analogously to other alkyllithium reagents with "β-hydrogens", undergoes β-hydride elimination to produce
1-butene 1-Butene (or 1-Butylene) is the organic compound with the formula CH3CH2CH=CH2. It is a colorless gas that is easily condensed to give a colorless liquid. It is classified as a linear alpha-olefin. It is one of the isomers of butene (butylene). I ...
and
lithium hydride Lithium hydride is an inorganic compound with the formula Li H. This alkali metal hydride is a colorless solid, although commercial samples are grey. Characteristic of a salt-like (ionic) hydride, it has a high melting point, and it is not solub ...
(LiH): : C4H9Li → LiH + CH3CH2CH=CH2


Safety

Alkyl-lithium compounds are stored under inert gas to prevent loss of activity and for reasons of safety. ''n''-BuLi reacts violently with water: : C4H9Li + H2O → C4H10 +
LiOH Lithium hydroxide is an inorganic compound with the formula LiOH. It can exist as anhydrous or hydrated, and both forms are white hygroscopic solids. They are soluble in water and slightly soluble in ethanol. Both are available commercially. While ...
This is an exergonic and highly exothermic reaction. If oxygen is present the butane produced may ignite. BuLi also reacts with CO2 to give lithium pentanoate: : C4H9Li + CO2 → C4H9CO2Li


See also

* Propynyllithium, an organometallic compound.


References


Further reading


FMC Lithium manufacturer's product sheets


* Weissenbacher, Anderson, Ishikawa, ''Organometallics'', July 1998, p681.7002, Chemicals Economics Handbook SRI International
HPV test plan, submitted by FMC Lithium to EPA
* Ovaska, T. V. ''e-EROS
Encyclopedia of Reagents for Organic Synthesis The ''Encyclopedia of Reagents for Organic Synthesis'' is published in print and online by John Wiley & Sons Ltd. The online version is also known as e-EROS. The encyclopedia contains a description of the use of reagents used in organic chemistry. ...
'' "''n''-Butyllithium." Wiley and sons. 2006. * Greenwood, N. N.; Earnshaw, A. ''Chemistry of the Elements'', 2nd ed. 1997: Butterworth-Heinemann, Boston. {{DEFAULTSORT:Butyllithium, N- Lithium compounds Organolithium compounds Reagents for organic chemistry Superbases