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Sodium hydrazide

Sodium hydrazide
Names
Systematic IUPAC name
Sodium aminoazanide
Other names
  • Sodium diazanide
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/H3N2.Na/c1-2;/h1H,2H2;/q-1;+1
  • N[NH-].[Na+]
Properties
NaN2H3
Molar mass 54.03 g/mol
Appearance Pale-yellow solid[1]
Melting point 100 °C (212 °F; 373 K)[4] (decomposes)
Detonates on contact[2]
Solubility Detonates on contact with alcohols, insoluble in benzene, diethyl ether, soluble in anhydrous hydrazine and ammonia[2][3]
Hazards
GHS labelling:
GHS01: Explosive
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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]

History and preparation

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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][2]

2Na + 2N2H4 → 2NaN2H3 + H2

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

Properties

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Sodium hydrazide is a pale-yellow solid that detonates when heated above 100 °C.[4] It also detonates when in contact with air, water, or alcohol, such as ethanol.[2][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.[4][3]

References

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  1. ^ a b c Goubeau, J.; Kull, U. (1962). "Die Schwingungsspektren von Natrium- und Zinkhydrazid". Zeitschrift für anorganische und allgemeine Chemie. 316 (3–4): 182–189. doi:10.1002/zaac.19623160310. ISSN 0044-2313.
  2. ^ a b c d Schlenk, W.; Weichselfelder, Th. (1915). "Zur Kenntnis des Hydrazins". Berichte der Deutschen Chemischen Gesellschaft. 48 (1): 669–676. doi:10.1002/cber.19150480190. ISSN 0365-9496.
  3. ^ a b Kauffmann, Thomas (2001). "Sodium Hydrazide". Encyclopedia of Reagents for Organic Synthesis. Chichester, UK: John Wiley & Sons, Ltd. doi:10.1002/047084289x.rs072. ISBN 978-0-471-93623-7.
  4. ^ a b c Kauffmann, Th.; Hacker, H.; Hage, S. M.; Hansen, J.; Henkler, H.; Kosel, Ch.; Lötzsch, K.; Müller, Horst; Rauch, E.; Schoeneck, W.; Schulz, J.; Sobel, J.; Spaude, S.; Weber, R.; Wolf, D.; Zengel, H. (1964). "Reactions of Sodium Hydrazide with Organic Compounds". Angewandte Chemie International Edition in English. 3 (5): 342–353. doi:10.1002/anie.196403421. ISSN 0570-0833.
  5. ^ de Bruyn, C. A. Lobry (1895). "Sur l'hydrate d'hydrazine". Recueil des Travaux Chimiques des Pays-Bas. 14 (3): 85–88. doi:10.1002/recl.18950140302. ISSN 0165-0513.
  6. ^ Welsh, T. W. B. (1915). "ANHYDROUS HYDRAZINE. II. ELECTROLYSIS OF a SOLUTION OF SODIUM HYDRAZIDE IN ANHYDROUS HYDRAZINE.1". Journal of the American Chemical Society. 37 (3): 497–508. Bibcode:1915JAChS..37..497W. doi:10.1021/ja02168a006. ISSN 0002-7863.
  7. ^ "sodium hydrazide". Chemister. Retrieved 6 July 2025.