n-Butyllithium

n-Butyllithium
n-Butyllithium tetramer
n-Butyllithium hexamer

Close-up of the delocalized bonds between butyl and lithium
Names
IUPAC name
butyllithium, tetra-μ3-butyl-tetralithium
Other names
NBL, BuLi,
1-lithiobutane
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.003.363
UNII
  • InChI=1S/C4H9.Li/c1-3-4-2;/h1,3-4H2,2H3; Y
    Key: MZRVEZGGRBJDDB-UHFFFAOYSA-N Y
  • 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
C4H9Li
Molar mass 64.06 g·mol−1
Appearance colorless liquid
unstable
usually obtained
as solution
Density 0.68 g/cm3, solvent defined
Melting point −76 °C (−105 °F; 197 K) (<273 K)
Boiling point 80 C
Exothermic decomposition
Solubility Ethers such as THF, hydrocarbons
Acidity (pKa) 50 (of the conjugate acid)
Structure
tetrameric in solution
0 D
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Pyrophoric (spontaneously combusts in air),
decomposes to corrosive LiOH
NFPA 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).
Y verify (what is YN ?)
Infobox references

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 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. Fine white precipitate (lithium hydride) is deposited and the color changes to orange.

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