Neopentyllithium

Neopentyllithium is an organolithium compound with the chemical formula C5H11Li. Commercially available, it is a strong, non-nucleophilic base sometimes encountered in organometallic chemistry.

Neopentyllithium
Names
IUPAC name
Neopentyllithium
Preferred IUPAC name
2,2-Dimethylpropyllithium
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.212.899
UNII
  • InChI=1S/C5H11.Li/c1-5(2,3)4;/h1H2,2-4H3; ☒N
    Key: UWLFCNHEPBTLHT-UHFFFAOYSA-N ☒N
  • InChI=1/C5H11.Li/c1-5(2,3)4;/h1H2,2-4H3;/rC5H11Li/c1-5(2,3)4-6/h4H2,1-3H3
    Key: UWLFCNHEPBTLHT-OBZUOXEOAE
  • CC(C)(C)C[Li]
Properties
C5H11Li
Molar mass 78.08 g·mol−1
Melting point 145.71 °C (294.28 °F; 418.86 K)
Boiling point 389.39 °C (732.90 °F; 662.54 K)
Decomposes
Solubility Hydrocarbons, THF, ether
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Further reading
  • Fraenkel, Gideon; Chow, Albert; Winchester, William R. (1990). "Structure and dynamic behavior of solvated neopentyllithium monomers, dimers, and tetramers: proton, carbon-13 and lithium-6 NMR". Journal of the American Chemical Society. 112 (17): 6190–6198. doi:10.1021/ja00173a005.
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