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
CAS Number	7412-67-1 Y
3D model (JSmol)	Interactive image
ChemSpider	10660196 N
ECHA InfoCard	100.212.899
PubChem CID	10898631
UNII	Y3X266EZG5 Y
CompTox Dashboard (EPA)	DTXSID80447510
InChI 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
SMILES CC(C)(C)C[Li]
Properties
Chemical formula	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)
Solubility in water	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). N verify (what is YN ?) 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.