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n-butyllithium
Sign in to saveAlso known as butyllithium
thumb|Glass bottles containing butyllithium '''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.
Chemical data
- Formula
- C4H9Li
- Molecular weight
- 64.1 g/mol
- IUPAC name
- lithium butane
- SMILES
- [Li+].CCC[CH2-]
- InChIKey
- DLEDOFVPSDKWEF-UHFFFAOYSA-N
- Polar surface area
- 0 Ų
- H-bond donors
- 0
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
~10 min read
Encyclopedic overview
14 sectionsContents
- Structure and bonding
- Preparation
- Applications
- Reactions
- Metalation
- Halogen–lithium exchange
- Transmetalations
- Carbonyl additions
- Degradation of THF
- Thermal decomposition
- Safety
- See also
- References
- Further reading
thumb|Glass bottles containing butyllithium '''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.
Excerpted from Wikipedia’s “n-butyllithium” article, available under the CC BY-SA 4.0 licence.