Lithium naphthalene

Lithium naphthalene
	A solution of lithium naphthalenide in tetrahydrofuran
Names
	Preferred IUPAC name Lithium naphthalenide
Identifiers
CAS Number	14474-59-0;
3D model (JSmol)	Interactive image;
ChemSpider	9172277;
PubChem CID	57466756;
	InChI InChI=1S/C10H8.Li/c1-2-6-10-8-4-3-7-9(10)5-1;/h1-8H; Key: PDZGAEAUKGKKDE-UHFFFAOYSA-N;
	SMILES [Li].C1=CC=C2C=CC=CC2=C1;
Properties
Chemical formula	Li+[C10H8]−
Molar mass	135.11 g·mol−1
Appearance	Dark green crystals
Related compounds
Other cations	sodium naphthalene
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Lithium naphthalene is an organic salt with the chemical formula Li⁺[C₁₀H₈]⁻. In the research laboratory, it is used as a reductant in the synthesis of organic, organometallic, and inorganic chemistry. It is usually generated in situ. Lithium naphthalene crystallizes with ligands bound to Li⁺. The anion is a well-known example of an organic radical.