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<title>N-Butyllithium</title>

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n-Butyllithium

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<caption>n-Butyllithium

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<td style="border-right:1px solid #aaa; width:50%;"><div style="text-align:center">n-Butyllithium tetramer</div>

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<td style="width:50%;"><div style="text-align:center">n-Butyllithium hexamer</div>

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<td colspan="2" style="text-align:center; padding:2px;"><div style="text-align:center;">Close-up of the delocalized bonds between butyl and lithium</div>

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<th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Names

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<td colspan="2" style="text-align:left;"><a href="Chemical_nomenclature" title="Chemical nomenclature">IUPAC name</a>

<div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">butyllithium, tetra-μ3-butyl-tetralithium</div>

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<td colspan="2" style="text-align:left;">Other names

<div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">NBL, BuLi, 1-lithiobutane</div>

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<th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Identifiers

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<td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div>

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</style><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=109-72-8">109-72-8</a> Y</li></ul></div>

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<td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div>

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<td><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=CCCC%5BLi%5D">Interactive image</a></li></ul></div>

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<td><a href="ChEBI" title="ChEBI">ChEBI</a>

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<td><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=51469">CHEBI:51469</a> Y</li></ul></div>

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<td><a href="ChemSpider" title="ChemSpider">ChemSpider</a>

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<td><a href="ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard">ECHA InfoCard</a>

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<td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div>

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<td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> (<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</div>

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<td><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID1026821">DTXSID1026821</a> </li></ul></div>

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<div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div>

<ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C4H9.Li/c1-3-4-2;/h1,3-4H2,2H3; Y</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: MZRVEZGGRBJDDB-UHFFFAOYSA-N Y</div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/C4H9.Li/c1-3-4-2;/h1,3-4H2,2H3;/rC4H9Li/c1-2-3-4-5/h2-4H2,1H3</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: MZRVEZGGRBJDDB-NESCHKHYAE</div></div></li></ul>

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<div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div>

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<th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Properties

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<td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="Chemical_formula" title="Chemical formula">Chemical formula</a></div>

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<td>C4H9Li

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<td><a href="Molar_mass" title="Molar mass">Molar mass</a>

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<td>64.06 g·mol−1

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<td>Appearance

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<td>colorless liquid unstable usually obtained as solution

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<td><a href="Density" title="Density">Density</a>

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<td>0.68 g/cm3, solvent defined

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<td><a href="Melting_point" title="Melting point">Melting point</a>

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<td>−76 °C (−105 °F; 197 K) (<273 K)

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<td><a href="Boiling_point" title="Boiling point">Boiling point</a>

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<td>80 C

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<td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="Aqueous_solution" title="Aqueous solution">Solubility in water</a></div>

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<td>Exothermic decomposition

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<td><a href="Solubility" title="Solubility">Solubility</a>

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<td>Ethers such as <a href="Tetrahydrofuran" title="Tetrahydrofuran">THF</a>, hydrocarbons

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<td><a href="Acid_dissociation_constant" title="Acid dissociation constant">Acidity</a> (pKa)

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<td>50 (of the conjugate acid)<a href="#cite_note-1">[1]</a>

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<th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Structure

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<td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="Molecular_geometry" title="Molecular geometry">Molecular shape</a></div>

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<td>tetrameric in solution

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<td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="Dipole#Molecular_dipoles" title="Dipole">Dipole moment</a></div>

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<th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Hazards

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<td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><a href="Occupational_safety_and_health" title="Occupational safety and health">Occupational safety and health</a> (OHS/OSH):

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<td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Main hazards</div>

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<td>Pyrophoric (spontaneously combusts in air), decomposes to corrosive <a href="Lithium_hydroxide" title="Lithium hydroxide">LiOH</a>

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<td><a href="NFPA_704" title="NFPA 704">NFPA 704</a> (fire diamond)

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<th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Related compounds

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<td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related <a href="Organolithium_reagent" title="Organolithium reagent">organolithium reagents</a></div>

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<td><a href="Sec-Butyllithium" title="Sec-Butyllithium">sec-butyllithium</a> <a href="Tert-Butyllithium" title="Tert-Butyllithium">tert-butyllithium</a> <a href="Hexyllithium" title="Hexyllithium">hexyllithium</a> <a href="Methyllithium" title="Methyllithium">methyllithium</a>

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<td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related compounds</div>

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<td><a href="Lithium_hydroxide" title="Lithium hydroxide">lithium hydroxide</a>

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<td colspan="2" style="text-align:left; background:#f8eaba; color:inherit; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div>

<div style="margin-top: 0.3em;"><div style="text-align:center;">Y <a class="external text external" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=445283361&page2=N-Butyllithium">verify</a> (what is YN ?)

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<div style="margin-top: 0.3em; text-align: center;">Infobox references</div>

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n-Butyllithium C4H9Li (abbreviated n-BuLi) is an <a href="Organolithium_reagent" title="Organolithium reagent">organolithium reagent</a>. It is widely used as a <a href="Polymerization" title="Polymerization">polymerization</a> initiator in the production of <a href="Elastomer" title="Elastomer">elastomers</a> such as <a href="Polybutadiene" title="Polybutadiene">polybutadiene</a> or <a href="Styrene-butadiene" title="Styrene-butadiene">styrene-butadiene-styrene (SBS)</a>. Also, it is broadly employed as a strong <a href="Base_(chemistry)" title="Base (chemistry)">base</a> (<a href="Superbase" title="Superbase">superbase</a>) in the <a href="Organic_synthesis" title="Organic synthesis">synthesis of organic compounds</a> as in the pharmaceutical industry.

Butyllithium is commercially available as solutions (15%, 25%, 1.5 <a href="Molarity" class="mw-redirect" title="Molarity">M</a>, 2 M, 2.5 M, 10 M, etc.) in <a href="Alkane" title="Alkane">alkanes</a> such as <a href="Pentane" title="Pentane">pentane</a>, <a href="Hexane" title="Hexane">hexanes</a>, and <a href="Heptane" title="Heptane">heptanes</a>. Solutions in <a href="Diethyl_ether" title="Diethyl ether">diethyl ether</a> and <a href="THF" class="mw-redirect" title="THF">THF</a> 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.<a href="#cite_note-2">[2]</a>

Although butyllithium is colorless, n-butyllithium is usually encountered as a pale yellow solution in alkanes. Such solutions are stable indefinitely if properly stored,<a href="#cite_note-Brandsma-3">[3]</a> but in practice, they degrade upon aging, where a fine white precipitate (<a href="Lithium_hydride" title="Lithium hydride">lithium hydride</a>) is deposited and the color changes to orange.<a href="#cite_note-Brandsma-3">[3]</a><a href="#cite_note-4">[4]</a>

<div class="mw-heading mw-heading2"><h2 id="Structure_and_bonding">Structure and bonding</h2></div>

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</style><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="Organolithium_reagent" title="Organolithium reagent">Organolithium reagent</a></div>

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.<a href="#cite_note-5">[5]</a> In the case of n-BuLi, the clusters are tetrameric (in ether) or hexameric (in <a href="Cyclohexane" title="Cyclohexane">cyclohexane</a>). The cluster is a distorted <a href="Cubane-type_cluster" title="Cubane-type cluster">cubane-type cluster</a> with Li and CH2R groups at alternating vertices. An equivalent description describes the tetramer as a Li4 <a href="Tetrahedron" title="Tetrahedron">tetrahedron</a> interpenetrated with a tetrahedron [CH2R]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 <a href="Lewis_acid" class="mw-redirect" title="Lewis acid">Lewis acids</a>.

Due to the large difference between the <a href="Electronegativity" title="Electronegativity">electronegativities</a> of <a href="Carbon" title="Carbon">carbon</a> (2.55) and <a href="Lithium" title="Lithium">lithium</a> (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 <a href="Anion" class="mw-redirect" title="Anion">anion</a>, n-Bu−, and a lithium <a href="Cation" class="mw-redirect" title="Cation">cation</a>, Li+.

<div class="mw-heading mw-heading2"><h2 id="Preparation">Preparation</h2></div>

The standard preparation for n-BuLi is reaction of <a href="1-bromobutane" class="mw-redirect" title="1-bromobutane">1-bromobutane</a> or <a href="1-chlorobutane" class="mw-redirect" title="1-chlorobutane">1-chlorobutane</a> with Li metal:<a href="#cite_note-Brandsma-3">[3]</a>

If the lithium used for this reaction contains 1–3% <a href="Sodium" title="Sodium">sodium</a>, the reaction proceeds more quickly than if pure lithium is used. Solvents used for this preparation include <a href="Benzene" title="Benzene">benzene</a>, 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 <a href="Octane" title="Octane">octane</a>. BuLi forms a weaker complex with LiCl, so that the reaction of BuCl with Li produces a precipitate of <a href="Lithium_chloride" title="Lithium chloride">LiCl</a>.

Solutions of butyllithium, which are susceptible to degradation by air, are standardized by <a href="Titration" title="Titration">titration</a>. A popular weak acid is <a href="Biphenyl" title="Biphenyl">biphenyl</a>-4-methanol, which gives a deeply colored dilithio derivative at the end point.<a href="#cite_note-6">[6]</a>

<div class="mw-heading mw-heading2"><h2 id="Applications">Applications</h2></div>

Butyllithium is principally valued as an initiator for the anionic <a href="Polymerization" title="Polymerization">polymerization</a> of <a href="Diene" title="Diene">dienes</a>, such as <a href="Butadiene" title="Butadiene">butadiene</a>.<a href="#cite_note-7">[7]</a> The reaction is called "carbolithiation":

<a href="Isoprene" title="Isoprene">Isoprene</a> can be polymerized stereospecifically in this way. Also of commercial importance is the use of butyllithium for the production of <a href="Styrene-butadiene" title="Styrene-butadiene">styrene-butadiene</a> polymers. Even <a href="Ethylene" title="Ethylene">ethylene</a> will insert into BuLi.<a href="#cite_note-8">[8]</a>

<div class="mw-heading mw-heading2"><h2 id="Reactions">Reactions</h2></div>

Butyllithium is a strong base (pKb ≈ −36), but it is also a powerful <a href="Nucleophile" title="Nucleophile">nucleophile</a> and <a href="Reductant" class="mw-redirect" title="Reductant">reductant</a>, 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 <a href="Amine" title="Amine">amines</a>, which partially disaggregate the clusters by binding to the lithium centers. Its use as a strong <a href="Base_(chemistry)" title="Base (chemistry)">base</a> is referred to as <a href="Metalation" title="Metalation">metalation</a>. Reactions are typically conducted in <a href="Tetrahydrofuran" title="Tetrahydrofuran">tetrahydrofuran</a> and <a href="Diethyl_ether" title="Diethyl ether">diethyl ether</a>, which are good solvents for the resulting organolithium derivatives (see below).

<div class="mw-heading mw-heading3"><h3 id="Metalation">Metalation</h3></div>

<div role="note" class="hatnote navigation-not-searchable">Main article: <a href="Organolithium_reagent" title="Organolithium reagent">Organolithium reagent</a></div>

One of the most useful chemical properties of n-BuLi is its ability to deprotonate a wide range of weak <a href="Br%C3%B8nsted_acid" class="mw-redirect" title="Brønsted acid">Brønsted acids</a>. t-Butyllithium and s-butyllithium are more basic. n-BuLi can deprotonate (that is, metalate) many types of C−H bonds, especially where the <a href="Conjugate_base" class="mw-redirect" title="Conjugate base">conjugate base</a> is stabilized by electron <a href="Delocalization" class="mw-redirect" title="Delocalization">delocalization</a> 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. <a href="Dithiane" title="Dithiane">dithiane</a>), methylphosphines (H−CH2PR2), <a href="Furan" title="Furan">furans</a>, <a href="Thiophene" title="Thiophene">thiophenes</a> and <a href="Ferrocene" title="Ferrocene">ferrocene</a> (Fe(H−C5H4)(C5H5)).<a href="#cite_note-9">[9]</a> In addition to these, it will also deprotonate all more acidic compounds such as alcohols, amines, <a href="Enol" title="Enol">enolizable</a> carbonyl compounds, and any overtly acidic compounds, to produce alkoxides, amides, enolates and other salts of lithium, respectively. The stability and <a href="Volatility_(chemistry)" title="Volatility (chemistry)">volatility</a> of the <a href="Butane" title="Butane">butane</a> resulting from such <a href="Deprotonation" title="Deprotonation">deprotonation</a> 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. Ligands that complex Li+ such as <a href="Tetrahydrofuran" title="Tetrahydrofuran">tetrahydrofuran</a> (THF), <a href="Tetramethylethylenediamine" title="Tetramethylethylenediamine">tetramethylethylenediamine</a> (TMEDA), <a href="Hexamethylphosphoramide" title="Hexamethylphosphoramide">hexamethylphosphoramide</a> (HMPA), and 1,4-diazabicyclo[2.2.2]octane (<a href="DABCO" title="DABCO">DABCO</a>) 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.

<dl><dd>Fe(C5H5)2 + 2 LiC4H9 + 2 TMEDA → 2 C4H10 + Fe(C5H4Li)2(TMEDA)2</dd></dl>

<a href="Schlosser's_base" title="Schlosser's base">Schlosser's base</a> is a <a href="Superbase" title="Superbase">superbase</a> produced by treating butyllithium with <a href="Potassium_tert-butoxide" title="Potassium tert-butoxide">potassium t-butoxide</a>. It is kinetically more reactive than butyllithium and is often used to accomplish difficult <a href="Metalation" title="Metalation">metalations</a>. 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.<a href="#cite_note-10">[10]</a>

An example of the use of n-butyllithium as a base is the addition of an amine to methyl carbonate to form a methyl <a href="Carbamate" title="Carbamate">carbamate</a>, where n-butyllithium serves to deprotonate the amine:

<dl><dd>n-BuLi + R2NH + (MeO)2CO → R2NCO2Me + LiOMe + BuH</dd></dl>

<div class="mw-heading mw-heading3"><h3 id="Halogen–lithium_exchange">Halogen–lithium exchange</h3></div>

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:

This <a href="Lithium%E2%80%93halogen_exchange" class="mw-redirect" title="Lithium–halogen exchange">lithium–halogen exchange</a> reaction is useful for preparation of several types of RLi compounds, particularly <a href="Aryl" class="mw-redirect" title="Aryl">aryl</a>lithium and some <a href="Vinyl_group" title="Vinyl group">vinyl</a>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 <a href="Dehydrohalogenation" title="Dehydrohalogenation">dehydrohalogenation</a> reactions, in which n-BuLi serves as a base:

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 <a href="Tert-Butyllithium" title="Tert-Butyllithium">t-BuLi</a> 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).<a href="#cite_note-Brandsma-3">[3]</a>

<div class="mw-heading mw-heading3"><h3 id="Transmetalations">Transmetalations</h3></div>

A related family of reactions are the <a href="Transmetalation" title="Transmetalation">transmetalations</a>, wherein two organometallic compounds exchange their metals. Many examples of such reactions involve lithium exchange with <a href="Tin" title="Tin">tin</a>:

<dl><dd>C4H9Li + Me3SnAr → C4H9SnMe3 + LiAr   (where Ar is aryl and Me is methyl)</dd></dl>

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 <a href="Metal" title="Metal">metals</a> and <a href="Metalloid" title="Metalloid">metalloids</a> which undergo such exchange reactions are organic compounds of <a href="Organomercury" class="mw-redirect" title="Organomercury">mercury</a>, <a href="Organoselenium_chemistry" title="Organoselenium chemistry">selenium</a>, and <a href="Tellurium" title="Tellurium">tellurium</a>.

<div class="mw-heading mw-heading3"><h3 id="Carbonyl_additions">Carbonyl additions</h3></div>

Organolithium reagents, including n-BuLi are used in synthesis of specific <a href="Aldehyde" title="Aldehyde">aldehydes</a> and <a href="Ketone" title="Ketone">ketones</a>. One such synthetic pathway is the reaction of an organolithium reagent with disubstituted <a href="Amide" title="Amide">amides</a>:

<dl><dd>R1Li + R2CONMe2 → LiNMe2 + R2C(O)R1</dd></dl>

<div class="mw-heading mw-heading3"><h3 id="Degradation_of_THF">Degradation of THF</h3></div>

THF is deprotonated by butyllithium, especially in the presence of <a href="TMEDA" class="mw-redirect" title="TMEDA">TMEDA</a>, 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 <a href="Ethanal" class="mw-redirect" title="Ethanal">acetaldehyde</a> and <a href="Ethene" class="mw-redirect" title="Ethene">ethylene</a>.<a href="#cite_note-11">[11]</a> Therefore, reactions of BuLi in THF are typically conducted at low temperatures, such as −78 °C, as is conveniently produced by a <a href="Freezing_bath" class="mw-redirect" title="Freezing bath">freezing bath</a> of <a href="Dry_ice" title="Dry ice">dry ice</a> and acetone. Higher temperatures (−25 °C or even −15 °C) are also used.

<div class="mw-heading mw-heading3"><h3 id="Thermal_decomposition">Thermal decomposition</h3></div>

When heated, n-BuLi, analogously to other alkyllithium reagents with "β-hydrogens", undergoes <a href="Beta-hydride_elimination" class="mw-redirect" title="Beta-hydride elimination">β-hydride elimination</a> to produce <a href="1-butene" class="mw-redirect" title="1-butene">1-butene</a> and <a href="Lithium_hydride" title="Lithium hydride">lithium hydride</a> (LiH):

<div class="mw-heading mw-heading2"><h2 id="Safety">Safety</h2></div>

Alkyl-lithium compounds are stored under inert gas to prevent loss of activity and for reasons of safety. n-BuLi reacts violently with water:

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:

<ul><li><a href="Propynyllithium" title="Propynyllithium">Propynyllithium</a>, an organometallic compound.</li></ul>

<div class="mw-heading mw-heading2"><h2 id="References">References</h2></div>

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</style><cite id="CITEREFBernier" class="citation web cs1">Bernier, David. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170509123404/http://www.d-bernier.fr/pKa.php">"Some useful pKa values"</a>. Org@Work. Archived from <a rel="nofollow" class="external text" href="http://www.d-bernier.fr/pKa.php">the original</a> on 9 May 2017. Retrieved 26 May 2017.</cite>

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<li id="cite_note-2"><a href="#cite_ref-2">^</a> <cite id="CITEREFSchwindeman2014" class="citation journal cs1">Schwindeman, James A. (1 August 2014). "Preparation, Properties, and Safe Handling of Commercial Organolithiums: Alkyllithiums, Lithium sec-Organoamides, and Lithium Alkoxides". Organic Process Research & Development. 18 (10): 1192–1210. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fop500161b">10.1021/op500161b</a>.</cite>

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<li id="cite_note-Brandsma-3">^ <a href="#cite_ref-Brandsma_3-0">a</a> <a href="#cite_ref-Brandsma_3-1">b</a> <a href="#cite_ref-Brandsma_3-2">c</a> <a href="#cite_ref-Brandsma_3-3">d</a> <cite id="CITEREFBrandsma,_L.Verkruijsse,_H._D.1987" class="citation book cs1">Brandsma, L.; Verkruijsse, H. D. (1987). Preparative Polar Organometallic Chemistry I. Berlin: <a href="Springer-Verlag" class="mw-redirect" title="Springer-Verlag">Springer-Verlag</a>. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>3-540-16916-4</bdi>.</cite>.

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<li id="cite_note-4"><a href="#cite_ref-4">^</a> <cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/GB/en/product/sial/20160">"n-Butyllithium solution"</a>. sigmaaldrich.com. Retrieved 17 August 2023.</cite>

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<li id="cite_note-5"><a href="#cite_ref-5">^</a> Elschenbroich, C. ”Organometallics” (2006) Wiley-VCH: Weinheim. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>3-527-29390-6</bdi>.

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<li id="cite_note-6"><a href="#cite_ref-6">^</a> <cite id="CITEREFJuaristi,_E.Martínez-Richa,_A.García-Rivera,_A.Cruz-Sánchez,_J._S.1983" class="citation journal cs1">Juaristi, E.; Martínez-Richa, A.; García-Rivera, A.; Cruz-Sánchez, J. S. (1983). "Use of 4-Biphenylmethanol, 4-Biphenylacetic Acid and 4-Biphenylcarboxylic Acid/Triphenylmethane as Indicators in the Titration of Lithium Alkyls. Study of the Dianion of 4-Biphenylmethanol". The Journal of Organic Chemistry. 48 (15): 2603–2606. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fjo00163a038">10.1021/jo00163a038</a>.</cite>

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<li id="cite_note-7"><a href="#cite_ref-7">^</a> Ulrich Wietelmann and Richard J. Bauer "Lithium and Lithium Compounds" in Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F14356007.a15_393">10.1002/14356007.a15_393</a>.

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<li id="cite_note-8"><a href="#cite_ref-8">^</a> <cite id="CITEREFDelaney1991" class="citation journal cs1">Delaney, M. S. (20 January 1991). "The rate of ethylene polymerization initiated by various chelating tertiary diamine : n-butyllithium complexes". Journal of Applied Polymer Science. 42 (2): 533–541. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fapp.1991.070420226">10.1002/app.1991.070420226</a>.</cite>

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<li id="cite_note-9"><a href="#cite_ref-9">^</a> <cite id="CITEREFSanders,_R.Mueller-Westerhoff,_U._T.1996" class="citation journal cs1">Sanders, R.; Mueller-Westerhoff, U. T. (1996). "The Lithiation of Ferrocene and Ruthenocene — A Retraction and an Improvement". <a href="Journal_of_Organometallic_Chemistry" title="Journal of Organometallic Chemistry">Journal of Organometallic Chemistry</a>. 512 (1–2): 219–224. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0022-328X%2895%2905914-B">10.1016/0022-328X(95)05914-B</a>.</cite>

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<li id="cite_note-10"><a href="#cite_ref-10">^</a> <cite id="CITEREFSchlosserStrunk1984" class="citation journal cs1">Schlosser, Manfred; Strunk, Sven (January 1984). <a rel="nofollow" class="external text" href="https://linkinghub.elsevier.com/retrieve/pii/S0040403901800149">"The "super-basic" butyllithium/potassium tert-butoxide mixture and other lickor-reagents"</a>. Tetrahedron Letters. 25 (7): 741–744. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0040-4039%2801%2980014-9">10.1016/S0040-4039(01)80014-9</a>.</cite>

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<li id="cite_note-11"><a href="#cite_ref-11">^</a> <cite id="CITEREFClaydenYasin2002" class="citation journal cs1">Clayden, Jonathan; Yasin, Samreen A. (11 February 2002). <a rel="nofollow" class="external text" href="https://pubs.rsc.org/en/content/articlelanding/2002/nj/b109604d">"Pathways for decomposition of THF by organolithiums: the role of HMPA"</a>. New Journal of Chemistry. 26 (2): 191–192. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2FB109604D">10.1039/B109604D</a>. <a href="ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/1369-9261">1369-9261</a>.</cite>

</li>

</ol></div></div>

<div class="mw-heading mw-heading2"><h2 id="Further_reading">Further reading</h2></div>

<ul><li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20050923163434/http://fmclithium.com/products/products_p.asp">FMC Lithium manufacturer's product sheets</a></li>

<li><a rel="nofollow" class="external text" href="http://environmentalchemistry.com/yogi/chemicals/cn/Butyllithium.html">Environmental Chemistry directory</a></li>

<li>Weissenbacher, Anderson, Ishikawa, Organometallics, July 1998, p681.7002, Chemicals Economics Handbook SRI International</li>

<li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20041116061121/http://www.epa.gov/chemrtk/butylith/c13633.pdf">HPV test plan, submitted by FMC Lithium to EPA</a></li>

<li>Ovaska, T. V. e-EROS <a href="Encyclopedia_of_Reagents_for_Organic_Synthesis" title="Encyclopedia of Reagents for Organic Synthesis">Encyclopedia of Reagents for Organic Synthesis</a> "n-Butyllithium." Wiley and sons. 2006. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F047084289X.rb395">10.1002/047084289X.rb395</a></li>

<li>Greenwood, N. N.; Earnshaw, A. Chemistry of the Elements, 2nd ed. 1997: Butterworth-Heinemann, Boston.</li></ul>

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</style><div id="Lithium_compounds_(list)359" style="font-size:114%;margin:0 4em"><a href="Lithium" title="Lithium">Lithium</a> <a href="Lithium_compounds" class="mw-redirect" title="Lithium compounds">compounds</a> (list)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Inorganic_compound" title="Inorganic compound">Inorganic</a> <a href="List_of_inorganic_compounds#Li" title="List of inorganic compounds">(list)</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em">

<li><a href="Lithium_tetrachloroaluminate" title="Lithium tetrachloroaluminate">LiAlCl4</a></li>

<li><a href="Lithium_aluminium_germanium_phosphate" title="Lithium aluminium germanium phosphate">Li1+xAlxGe2−x(PO4)3</a></li>

<li><a href="Lithium_aluminium_hydride" title="Lithium aluminium hydride">LiAlH4</a></li>

<li><a href="Lithium_aluminate" title="Lithium aluminate">LiAlO2</a></li>

<li>LiAsF6</li>

<li><a href="Lithium_hexafluoroarsenate" title="Lithium hexafluoroarsenate">LiAsF6</a></li>

<li>LiBSi2</li>

<li>LiBrO</li>

<li>LiBrO2</li>

<li>LiBrO3</li>

<li>LiBrO4</li>

<li><a href="Lithium_lactate" title="Lithium lactate">CH3CH(OH)COOLi</a></li>

<li>LiCHO2</li>

<li>LiCNO</li>

<li><a href="Lithium_hypochlorite" title="Lithium hypochlorite">LiClO</a></li>

<li>LiClO2</li>

<li><a href="Lithium_chlorate" title="Lithium chlorate">LiClO3</a></li>

<li><a href="Lithium_perchlorate" title="Lithium perchlorate">LiClO4</a></li>

<li><a href="Lithium_cobalt_oxide" title="Lithium cobalt oxide">LiCoO2</a></li>

<li><a href="Caesium_lithium_borate" title="Caesium lithium borate">CsLiB6O10</a></li>

<li><a href="FLiBe" title="FLiBe">FLiBe</a></li>

<li><a href="Lithium_iron_phosphate" title="Lithium iron phosphate">LiFePO4</a></li>

<li><a href="FLiNaK" title="FLiNaK">FLiNaK</a></li>

<li><a href="Lithium_tetrahydridogallate" title="Lithium tetrahydridogallate">LiGaH4</a></li>

<li><a href="Lithium_bicarbonate" title="Lithium bicarbonate">LiHCO3</a></li>

<li>LiHSO3</li>

<li>LiHSO4</li>

<li><a href="Lithium_sodium_nitroxylate" class="mw-redirect" title="Lithium sodium nitroxylate">LiNaNO2</a></li>

<li><a href="Lithium_niobate" title="Lithium niobate">LiNbO3</a></li>

<li><a href="Lithium_thiocyanate" title="Lithium thiocyanate">LiSCN</a></li>

<li><a href="Lithium_tantalate" title="Lithium tantalate">LiTaO3</a></li>

<ul><li><a href="Neodymium-doped_yttrium_lithium_fluoride" title="Neodymium-doped yttrium lithium fluoride">Neodymium-doped</a></li></ul></li>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Organic (<a href="Lithium_soap" title="Lithium soap">soaps</a>)</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Hemolithin" title="Hemolithin">Hemolithin (extraterrestrial protein)</a></li>

<li><a href="Organolithium_reagent" title="Organolithium reagent">Organolithium reagents</a>

<ul><li><a href="Gilman_reagent" title="Gilman reagent">Gilman reagent</a></li></ul></li>

<li><a href="Lithium_acetate" title="Lithium acetate">CH3COOLi</a></li>

<li><a href="Sec-Butyllithium" title="Sec-Butyllithium">CH3CHLiCH2CH3</a></li>

<li><a href="Vinyllithium" title="Vinyllithium">LiC2H3 Vinyllithium</a></li>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Minerals</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Amblygonite" title="Amblygonite">Amblygonite</a></li>

<li>Berezanskite</li>

<li>Brannockite</li>

<li>Cryolithionite</li>

<li>Darapiosite</li>

<li>Darrellhenryite</li>

<li><a href="Elbaite" title="Elbaite">Elbaite</a>

<ul><li>Fluorine Elbaite</li>

<li><a href="Fluor-liddicoatite" title="Fluor-liddicoatite">Fluor-liddicoatite</a></li></ul></li>

<li>Emeleusite</li>

<li><a href="Eucryptite" title="Eucryptite">Eucryptite LiAlSiO4</a></li>

<li><a href="Faizievite" title="Faizievite">Faizievite</a></li>

<li><a href="Hectorite" title="Hectorite">Hectorite</a></li>

<li><a href="Hsianghualite" title="Hsianghualite">Hsianghualite</a></li>

<li><a href="Jadarite" title="Jadarite">Jadarite LiNaSiB3O7OH</a></li>

<li><a href="Keatite" title="Keatite">Keatite Li(AlSi2O6)</a></li>

<li><a href="Kunzite" class="mw-redirect" title="Kunzite">Kunzite</a></li>

<li>Lavinskyite</li>

<li><a href="Lepidolite" title="Lepidolite">Lepidolite</a></li>

<li><a href="Lithiophilite" title="Lithiophilite">Lithiophilite LiMnPO4</a></li>

<li><a href="Lithiophosphate" title="Lithiophosphate">Lithiophosphate Li3PO4</a></li>

<li>Manandonite</li>

<li><a href="Manganoneptunite" class="mw-redirect" title="Manganoneptunite">Manganoneptunite</a></li>

<li><a href="Nambulite" title="Nambulite">Nambulite</a></li>

<li><a href="Neptunite" title="Neptunite">Neptunite</a></li>

<li>Olympite</li>

<li><a href="Petalite" title="Petalite">Petalite LiAlSi4O10</a></li>

<li><a href="Pezzottaite" title="Pezzottaite">Pezzottaite Cs(Be2Li)Al2Si6O18</a></li>

<li><a href="Rossmanite" class="mw-redirect" title="Rossmanite">Rossmanite</a></li>

<li><a href="Saliotite" title="Saliotite">Saliotite</a></li>

<li>Sogdianite</li>

<li><a href="Spodumene" title="Spodumene">Spodumene LiAl(SiO3)2</a></li>

<li><a href="Sugilite" title="Sugilite">Sugilite</a></li>

<li>Tiptopite</li>

<li><a href="Tourmaline" title="Tourmaline">Tourmaline</a></li>

<li><a href="Triphylite" title="Triphylite">Triphylite LiFePO4</a></li>

<li><a href="Zabuyelite" title="Zabuyelite">Zabuyelite Li2CO3</a></li>

<li><a href="Zektzerite" title="Zektzerite">Zektzerite</a></li>

<li><a href="Zinnwaldite" title="Zinnwaldite">Zinnwaldite</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Hypothetical_chemical_compound" title="Hypothetical chemical compound">Hypothetical</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Lithium_beryllide" title="Lithium beryllide">LixBey</a></li>

<li>HLiHe+</li>

<li>LiFHeO</li>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other Li-related</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Aluminium%E2%80%93lithium_alloy" class="mw-redirect" title="Aluminium–lithium alloy">Aluminium–lithium alloys</a></li>

<li><a href="Heteroatom-promoted_lateral_lithiation" title="Heteroatom-promoted lateral lithiation">Heteroatom-promoted lateral lithiation</a></li>

<li><a href="LB_buffer" title="LB buffer">LB buffer</a></li>

<li><a href="Lithium_atom" title="Lithium atom">Lithium atom</a></li>

<li><a href="Lithium_(medication)" title="Lithium (medication)">Lithium medication</a></li>

<li><a href="Lithium_nickel_cobalt_aluminium_oxides" title="Lithium nickel cobalt aluminium oxides">LiNixCoyAlzO2</a></li>

<li><a href="Lithium_nickel_manganese_cobalt_oxides" title="Lithium nickel manganese cobalt oxides">LiNixMnyCozO2</a></li>

<li><a href="Lithium_soap" title="Lithium soap">Lithium soap</a></li>

<li><a href="Lithium_Triangle" title="Lithium Triangle">Lithium Triangle</a></li>

<li><a href="Lucifer_yellow" title="Lucifer yellow">Lucifer yellow</a></li>

<li><a href="Magnesium_alloy#Magnesium–lithium_alloys" title="Magnesium alloy">Magnesium–lithium alloys</a></li>

<li><a href="NASICON" title="NASICON">NASICON</a></li>

<li><a href="Environmentally_friendly_red_light_flare" title="Environmentally friendly red light flare">Environmentally friendly red light flare</a></li></ul>

</div></td></tr></tbody></table></div></div><div><div class="zim-footer">

This article is issued from <a class="external text" title="Last edited on 2025-05-24" href="https://en.wikipedia.org/wiki/?title=N-Butyllithium&oldid=1292005199">Wikipedia</a>. The text is available under <a class="external text" href="https://creativecommons.org/licenses/by-sa/4.0/deed.en">Creative Commons Attribution-Share Alike 4.0</a> unless otherwise noted. Additional terms may apply for the media files.

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