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Sodium hydrazide

From Wikipedia, the free encyclopedia
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 mass54.03 g/mol
AppearancePale-yellow solid[1]
Melting point100 °C (212 °F; 373 K)[4] (decomposes)
Detonates on contact[2]
SolubilityDetonates on contact withalcohols, insoluble inbenzene,diethyl ether, soluble in anhydroushydrazine andammonia[2][3]
Hazards
GHS labelling:
GHS01: Explosive
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

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

History and preparation

[edit]

Sodium hydrazide was first observed as a mixture withsodium hydroxide in 1895 when excesssodium metal was added to hydrazine hydrate under nitrogen.[5] Subsequently, sodium hydrazide was isolated in pure form byWilhelm Schlenk in 1915 by the reaction of sodium metal and anhydroushydrazine, 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 ofsodium amide orsodium hydride and hydrazine.[6]

Properties

[edit]

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 asethanol.[2][7] Due to this, it is used as a suspension inbenzene ordiethyl ether in organic reactions. It is capable of doing nucleophilic additions to various compounds, such asnitriles, which are converted toamidrazones.[4][3]

References

[edit]
  1. ^abcGoubeau, 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. ^abcdSchlenk, 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. ^abKauffmann, 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. ^abcKauffmann, 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. Retrieved6 July 2025.
Inorganic
Halides
Chalcogenides
Pnictogenides
Oxyhalides
Oxychalcogenides
Oxypnictogenides
Metalates
Others
Organic
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