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Topic summary

N-Butyllithium

Close-up of the delocalized bonds between butyl and lithium
Names IUPAC name
butyllithium, tetra-μ3-butyl-tetralithium
Other names
1-lithiobutane
Identifiers
3D model (JSmol)
Abbreviations BL
NBL
BuLi
n-BuLi
nBuLi
BuLi ChEBI
ChemSpider
ECHA InfoCard100.003.363
UNII
  • InChI=1S/C4H9.Li/c1-3-4-2;/h1,3-4H2,2H3;
    Key: MZRVEZGGRBJDDB-UHFFFAOYSA-N
  • InChI=1/C4H9.Li/c1-3-4-2;/h1,3-4H2,2H3;/rC4H9Li/c1-2-3-4-5/h2-4H2,1H3
    Key: MZRVEZGGRBJDDB-NESCHKHYAE
  • CCCC[Li]
Properties C4H9LiMolar mass64.06 g·mol Appearance colorless liquid
unstable
usually obtained
as solution Density0.68 g/cm, solvent defined Melting point−76 °C (−105 °F; 197 K) (<273 K) Boiling point80 C Exothermic decomposition SolubilityEthers such as THF, hydrocarbons Acidity (pKa) 50 (of the conjugate acid) Structure tetrameric in solution 0 DHazards Occupational safety and health (OHS/OSH):
Main hazards
Pyrophoric (spontaneously combusts in air),
decomposes to corrosive LiOHNFPA 704 (fire diamond)
3
4
3
W
Related compounds sec-butyllithium
tert-butyllithium
hexyllithium
methyllithium
Related compounds
lithium hydroxide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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n-Butyllithium C4H9Li (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). Also, it is broadly employed as a strong base (superbase) in the synthesis of organic compounds, such 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 alkanes such as pentane, hexanes, and heptanes. 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 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, where a fine white precipitate (lithium hydride) is deposited and the color changes to orange.

Wikipedia source