Sodium Amide

_NaNH2 (39.01). It is obtained by reacting metallic Na with _NH3 gas, or by reacting liquid ammonia with metallic Na in the presence of a catalyst such as _FeCl3 . It is a colorless tetragonal crystal. It consists of Na ⁺ and _NH2- ^, where Na ⁺ is surrounded ^by _NH2- in a tetrahedral shape, and N is also surrounded by Na in a distorted tetrahedral shape. Its melting point is 210 °C. It decomposes at about 500 °C. In air at room temperature, it absorbs moisture and _CO2 . When heated in moist air, it becomes NaOH, _NaNO2 , and _NH3 . It is important to store it in a tightly sealed container. If it is incompletely oxidized due to a loose stopper, it will produce an explosive brown substance. It is deliquescent and reacts violently with water to become NaOH and _NH3 . It dissolves in liquid ammonia to become an ammonobase. When molten, it dissolves metals such as Mg, Zn, Mo, and W, as well as silicates and glass. It is used in organic synthesis as a reducing agent, dehydrating agent, and condensing agent, including ammonolysis reactions, Claisen condensation, alkylation of nitriles and ketones, synthesis of indigo by cyclization of phenylglycine, and synthesis of acetylene derivatives from halides. [CAS 7782-92-5]

Source: Morikita Publishing "Chemical Dictionary (2nd Edition)" Information about the Chemical Dictionary 2nd Edition

NaNH₂(39.01)．金属NaとNH₃気体との反応や，液体アンモニアと金属NaをFeCl₃などの触媒下で反応させると得られる．無色の正方晶系結晶．Na^＋ とNH₂^－からなり，Na^＋ は四面体型にNH₂^－に囲まれ，NもNaにひずんだ四面体型に囲まれている．融点210 ℃．約500 ℃ で分解する．室温の空気中で，湿気やCO₂を吸う．湿った空気中で加熱するとNaOH，NaNO₂，NH₃になる．密栓して保存することが大切である．もし，緩い栓のため，不完全酸化されると，爆発性の褐色物質を生じる．潮解性で，水とはげしく反応して，NaOHとNH₃になる．液体アンモニアに溶けてアンモノ塩基となる．溶融したものは，Mg，Zn，Mo，Wなどの金属や，ケイ酸塩，ガラスなどを溶かす．還元剤，脱水剤，縮合剤として，有機合成などで利用され，アンモノリシス反応，クライゼン縮合，ニトリルやケトンのアルキル化，フェニルグリシンの環化によるインジゴ合成，ハロゲン化物からアセチレン誘導体の合成などに用いられる．[CAS 7782-92-5]

出典　森北出版「化学辞典（第2版）」化学辞典 第2版について　情報