Article · Wikipedia archive · Last revised Jun 19, 2026

Triazane

Triazane is an inorganic compound with the chemical formula NH2NHNH2 or N3H5. Triazane is the third simplest acyclic azane after ammonia and hydrazine. It can be synthesized from hydrazine but is unstable and cannot be isolated in the free base form, only as salt forms such as triazanium sulfate. Attempts to convert triazanium salts to the free base release only diazene and ammonia. Triazane has been stabilized as a complex ion with zeolitic silver structures. Triazane has also been synthesized in electron-irradiated ammonia ices and detected as a stable gas-phase product after sublimation.

Last revised
Jun 19, 2026
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Triazane
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Names
Systematic IUPAC name
Triazane1
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/H5N3/c1-3-2/h3H,1-2H2
    Key: PYHOFAHZHOBVGV-UHFFFAOYSA-N
  • NNN
Properties
N3H5
Molar mass 47.061 g·mol−1
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Triazane is an inorganic compound with the chemical formula NH2NHNH2 or N3H5.2 Triazane is the third simplest acyclic azane after ammonia and hydrazine. It can be synthesized from hydrazine but is unstable and cannot be isolated in the free base form, only as salt forms such as triazanium sulfate.3 Attempts to convert triazanium salts to the free base release only diazene and ammonia.4 Triazane has been stabilized as a complex ion with zeolitic silver structures.5 Triazane has also been synthesized in electron-irradiated ammonia ices and detected as a stable gas-phase product after sublimation.6

Compounds containing the triazane skeleton

Several compounds containing the triazane skeleton are known, including 1-methyl-1-nitrosohydrazine (NH2−N(CH3)−N=O), produced from the solventless reaction of methylhydrazine (CH3NHNH2) and an alkyl nitrite (R−O−N=O):7

CH3NHNH2 + RONO → NH2N(CH3)NO + ROH

1-Methyl-1-nitrosohydrazine is a colorless solid, sensitive to impact, but not to friction. It melts at 45 °C and decomposes at 121 °C.7

References

References

  1. "triazane - PubChem Public Chemical Database". The PubChem Project. USA: National Center for Biotechnology Information.
  2. IUPAC Goldbook
  3. H. Al Rasheed, Hessa; M. Malebari, Azizah; A. Dahlous, Kholood; El-Faham, Ayman (2020-06-11). "Synthesis and Characterization of New Series of 1,3-5-Triazine Hydrazone Derivatives with Promising Antiproliferative Activity". Molecules. 25 (11): 2708. doi:10.3390/molecules25112708. ISSN 1420-3049. PMC 7321239. PMID 32545272.
  4. Wiberg, Holleman & Wiberg. Inorganic Chemistry. p 627. ISBN 9780123526519
  5. Heo, Nam Ho; Kim, Yang; Kim, Jong Jin; Seff, Karl (2016-03-17). "Surprising Intrazeolitic Chemistry of Silver". The Journal of Physical Chemistry C. 120 (10): 5277–5287. doi:10.1021/acs.jpcc.5b11490. ISSN 1932-7447.
  6. Förstel, Maksyutenko, Jones, Sun, Chen, Chang, & Kaiser. "Detection of the Elusive Triazane Molecule ([N
    3    H
    5    ]    ) in the Gas Phase", ChemPhysChem, 2015, 16, 3139.
  7. Miró Sabaté, Carles; Delalu, Henri (2012). "Synthesis, Characterization, and Energetic Properties of Nitroso Compounds". Zeitschrift für anorganische und allgemeine Chemie. 638 (2): 336–344. doi:10.1002/zaac.201100446. ISSN 1521-3749.
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