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.
Contents
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
- ↑ Carignan; Satriana; Journal of Organic Chemistry; vol. 32; (1967); p. 285, 289
- ↑ 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
- ↑ https://onlinelibrary.wiley.com/doi/10.1002/jhet.5570280844
- ↑ Zhu, Jun; Hiltz, Jonathan; Lennox, R. Bruce; Schirrmacher, Ralf; Chemical Communications; vol. 49; nb. 87; (2013); p. 10275 - 10277
