methyl ketones, cyclohexanone, phenylacetic acid and its derivatives and diphenylmethane. Acetylacetone loses two protons to form a dianion. Sodium amide will also deprotonate indole and piperidine. Related non-nucleophilic bases It is however poorly soluble in solvents other than ammonia. Its use has been superseded by the related reagents sodium hydride, sodium bis(trimethylsilyl)amide (NaHMDS), and lithium diisopropylamide (LDA). Other reactions Rearrangement with orthodeprotonation Oxirane synthesis Indole synthesis Chichibabin reaction Safety Sodium amide decomposes violently on contact with water, producing ammonia and sodium hydroxide: When burned in oxygen, it will give oxides of sodium (which react with the produced water, giving sodium hydroxide) along with nitrogen oxides: In the presence of limited quantities of air and moisture, such as in a poorly closed container, explosive mixtures of peroxides may form. This is accompanied by a yellowing or browning of the solid. As such, sodium amide is to be stored in a tightly closed container, under an atmosphere of an inert gas. Sodium amide samples which are yellow or brown in color represent explosion risks. References Metal amides Reagents for organic chemistry Sodium compounds