Triaminoguanidine

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Triaminoguanidine
Names
IUPAC names
N,N,N''-Triaminoguanidine
N,N,N''-Triaminoiminomethanediamine
Other names
Hydrazinecarbohydrazonhydrazide
Properties
CH8N6
Molar mass 104.115 g/mol
Appearance Colorless solid
Melting point 112–120 °C (234–248 °F; 385–393 K) [1]
Hazards
Safety data sheet None
Related compounds
Related compounds
Guanidine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Triaminoguanidine or N,N',N''-triaminoguanidine in an organic chemical compound with the formula CH8N6. It is a guanidine derivative, where each of the three amines has one NH2 substitute.

Properties

Chemical

Triaminoguanidine will react with acids to form salts.

Triaminoguanidine will react with acetylacetone to form dihydro-3,6-bis(3,5-dimethylpyrazol-1-yl)-1,2,4,5-tetrazine.[2][3]

Physical

Triaminoguanidine is a colorless solid, poorly soluble in water.

Availability

Triaminoguanidine is sold by chemical suppliers, albeit it's more available in in salt form rather than freebase.

Preparation

Addition of an aq. solution of hydrazine (aka hydrazine hydrate) to guanidinium chloride will yield triaminoguanidine. The reaction taked place in dry dioxane, under inert atmosphere, under reflux for 2 hours.[4]

To prepare the freebase from one of its salts, a strong base, like sodium hydroxide, followed by recrystallization from solution. If an anhydrous product is desired, a different base, like sodium methoxide (prepared by adding sodium metal to anhydrous methanol) can be used instead.

C(NHNH2)3Cl + CH3ONa → (NNH2)C(NHNH2)2 + CH3OH + NaCl

The sodium salt will precipitate out of the solution, while the freebase guanidine will remain in solution. The solution is further concentrated by evaporating most of the methanol, then the compound is recrystallized from the solution.

Projects

  • Make triaminoguanidine salts

Handling

Safety

There is little data about this compound's toxicity, but given that it's a base, it should be handled with care.

Storage

In closed airtight bottles, away from acids.

Disposal

Should be neutralized with a strong oxidizing solution.

References

  1. Carignan; Satriana; Journal of Organic Chemistry; vol. 32; (1967); p. 285, 289
  2. Glidewell, Christopher; Lightfoot, Philip; Royles, Brodyck J. L.; Smith, David M.; Journal of the Chemical Society. Perkin Transactions 2 (2001); nb. 6; (1997); p. 1167 - 1174
  3. https://onlinelibrary.wiley.com/doi/10.1002/jhet.5570280844
  4. Zhu, Jun; Hiltz, Jonathan; Lennox, R. Bruce; Schirrmacher, Ralf; Chemical Communications; vol. 49; nb. 87; (2013); p. 10275 - 10277

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