|Preferred IUPAC name
3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||142.070 g·mol−1|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Reacting sodium oxamate (the sodium salt of oxamic acid) with hydrochloric acid yields some tetraketopiperazine. A higher yield result from reacting ethyl oxalate with sodium ethoxide. Yet another way to make tetraketopiperazine is a condensation of oxamide with ethyl oxalate with sodium ethoxide present.
The nitrogen atoms in tetraketopiperazine are slightly acidic losing their hydrogen atoms as ions. Salts of tetraketopiperazine exist. Tetraketopiperazine reacts with sodium bicarbonate to yield a monosodium salt. A disodium salt results from reaction with sodium hydroxide or sodium alkoxide. These are likely to be tautomeric with a hydrogen moving to an oxygen atom. Potassium salts also exist. A monosilver salt can be made from a silver compound and a dissolved tetraketopiperazine potassium salt. Ammonia and mercury salts of tetraketopiperazine also exist. Tetraketopiperazine also can form a monohydrazone.
When heated tetraketopiperazine does not melt, but turns black at 250°C.
pKa is 4.8 and the second pKa2 is 8.2.
- de Mouilpied, Alfred Theophilus; Rule, Alexander (1907). "XVI.—Tetraketopiperazine". J. Chem. Soc., Trans. 91: 176–183. doi:10.1039/CT9079100176.
- Bellamy, A. J.; Golding, P. (2007). "The Study of Some Potential New Synthetic Routes to LLM-105 (2,6-Diamino-3,5-dinitropyrazine 1-oxide)". Central European Journal of Energetic Materials. 4 (7): 33–57.
- Owens, J.L.; Dryhurst, G. (November 1976). "Electrochemical reduction of tetraketopiperazine". Analytica Chimica Acta. 87 (1): 37–50. doi:10.1016/S0003-2670(01)83118-4.