Sodium Hydrazide

[16657-57-1] H3N2Na (MW 54.04) InChI = 1S/H3N2.Na/c1-2;/h1H,2H2;/q-1;+1 InChIKey = FISGLHSNQHXMGY-UHFFFAOYSA-N (capable of nucleophilic addition to alkenes,2 alkynes,3 and nitriles4 to give hydrazines, hydrazones, or amidrazones; reacts by nucleophilic substitution with electrophilic heteroarenes5 to give hydrazines5 or amines6 and with benzene halides7 or benzene sulfonates8 to give hydrazines; reacts with 1,3-dienes in presence of hydrazine to give dehydrogenated hydrazine derivatives;9 further reaction modes include reduction of unsaturated hydrocarbons10 and reductive dehalogenation,11 cleavage of CC double bonds affording a hydrocarbon and a hydrazone,12 and selective cleavage of tertiary amide bonds13) Physical Data: IR spectrum.14 Solubility: moderately sol H2NNH2, liquid NH3. Preparative Methods: obtained as a suspension of pale yellow crystals by action of Sodium Amide on anhydrous Hydrazine under pure N2 at rt in ether or at −33 °C in liquid NH3 in a special apparatus.2a The method of preparation using Na/H2NNH2 often leads to explosion, even if O2 is strictly excluded.15 Handling, Storage, and Precautions: explodes violently and regularly in contact with O2; storage is not recommended. A protective plexiglass screen (thickness 1 cm) is absolutely necessary in front of the apparatus as NaHNNH2 is prepared and reacted. In reactions with organic compounds, moderate heating (max 60 °C) is allowed. Hydrolysis of the reaction mixture is possible by very slow addition (avoidance of local overheating) of water under ice-cooling. Use in a fume hood.