Sodium hydrazide

Sodium hydrazide is an inorganic compound with the formula NaN₂H₃. It is a pale yellow solid that detonates when in contact with air, water, or alcohol.^[1]

Sodium hydrazide

Names
Systematic IUPAC name Sodium aminoazanide
Other names Sodium diazanide
Identifiers
CAS Number	13598-47-5
3D model (JSmol)	Interactive image
ChemSpider	9963794
PubChem CID	11789120
InChI InChI=1S/H3N2.Na/c1-2;/h1H,2H2;/q-1;+1
SMILES N[NH-].[Na+]
Properties
Chemical formula	NaN2H3
Molar mass	54.03 g/mol
Appearance	Pale-yellow solid[1]
Melting point	100 °C (212 °F; 373 K)[2] (decomposes)
Solubility in water	Detonates on contact[3]
Solubility	Detonates on contact with alcohols, insoluble in benzene, diethyl ether, soluble in anhydrous hydrazine and ammonia[3][4]
Hazards
GHS labelling:
Pictograms
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

History and preparation

Sodium hydrazide was first observed as a mixture with sodium hydroxide in 1895 when excess sodium metal was added to hydrazine hydrate under nitrogen.^[5] Subsequently, sodium hydrazide was isolated in pure form by Wilhelm Schlenk in 1915 by the reaction of sodium metal and anhydrous hydrazine, followed by removal of the excess hydrazine by heating to 60 °C:^[1][3]

2Na + 2N₂H₄ → 2NaN₂H₃ + H₂

It can also be produced by the reaction of sodium amide or sodium hydride and hydrazine.^[6]

Properties

Sodium hydrazide is a pale-yellow solid that detonates when heated above 100 °C.^[2] It also detonates when in contact with air, water, or alcohol, such as ethanol.^[3][7] Due to this, it is used as a suspension in benzene or diethyl ether in organic reactions. It is capable of doing nucleophilic additions to various compounds, such as nitriles, which is converted to amidrazones.^[2][4]