Tetralithiomethane

Tetralithiomethane, also known as tetralithium carbide, is an organolithium compound with the formula CLi4. It is an extremely pyrophoric red solid and is the lithium analog of methane.

Production
Its main route of production is by the lithiation of tetrakis(chloromercurio)methane (C(HgCl)4) by tert-butyllithium. It can also be produced by the reaction of lithium metal and carbon tetrachloride at 900 °C:
 * 8 Li + CCl4 → CLi4 + 4 LiCl

However, this method also produces byproducts, such as lithium carbide.

Reactions
Tetralithiomethane hydrolyzes vigorously in contact with water producing methane gas and lithium hydroxide:
 * CLi4 + 4 H2O → CH4 + 4 LiOH

Deuterated methane CD4 can also be produced by reacting heavy water with tetralithiomethane.
 * CLi4 + 4 D2O → CD4 + 4 LiOD, where LiOD is lithium deuteroxide.

When tetralithiomethane is heated to 225 °C, it decomposes to lithium carbide and lithium metal.

Due to the known affinity of lithium ions Li+ for hydrogen molecules H2 and therefore potential applications in hydrogen storage materials, tetralithiomethane has been studied computationally for its aggregation, H2 affinity, and binding to various graphene-type surfaces.