Sodium tert-butoxide



Sodium tert-butoxide is the chemical compound with the formula 3CONa. It is a strong base and a non-nucleophilic base. It is flammable and moisture sensitive. It is sometimes written in chemical literature as sodium t-butoxide. It is similar in reactivity to the more common potassium tert-butoxide.
The compound can be produced by treating tert-butyl alcohol with sodium hydride.

Uses

The main application for sodium tert-butoxide is as a non-nucleophilic base. It has been widely used in the Buchwald–Hartwig amination, as in this typical example:

Structure

Sodium tert-butoxide forms clusters in the solid state, both hexamers and nonamers.
hexamer
nonamer

Toxicity

Sodium t-butoxide is extremely destructive to tissue of the mucous membranes and upper respiratory tract, eyes, and skin.