biostudies-literatureUnknown5(7)Chen CThe N-N single bond is inherently intriguing due to its high energy storage capacity, whether in polynitrogen systems or nitramine-based molecules. However, the synthesis of compounds featuring exceptionally weak N-N single bonds is often hindered by their intrinsic high reactivity and instability. Here, we report the design and synthesis of a monocyclic dual <i>N</i>-nitramine with an ultralow N-N bond dissociation energy: 2,4-dinitroamino-5-nitro-2,4-dihydro-3<i>H</i>-1,2,4-triazol-3-one (<b>2</b>). This compound was obtained via the nitration of the diaminonation intermediate of NTO and exhibits a remarkably high crystal density (1.969 g cm^-3 at 298 K and 2.025 g cm^-3 at 100 K), along with outstanding detonation performances (<i>D</i>v = 9072 m s^- 1, <i>JACS Au3603-3611https://www.ebi.ac.uk/biostudies/studies/S-EPMC12308370biostudies-literatureMonocyclic Bis(&lt;i&gt;N&lt;/i&gt;‑nitramine) Triazole: A High-Density Energetic Material with Exceptionally Weak N-N Bond.PMC12308370Liu YTang MZhang YHuang WZeng ZNiu MChen CCheng GXiao CTang YfalseMonocyclic Bis(&lt;i&gt;N&lt;/i&gt;‑nitramine) Triazole: A High-Density Energetic Material with Exceptionally Weak N-N Bond.The N-N single bond is inherently intriguing due to its high energy storage capacity, whether in polynitrogen systems or nitramine-based molecules. However, the synthesis of compounds featuring exceptionally weak N-N single bonds is often hindered by their intrinsic high reactivity and instability. Here, we report the design and synthesis of a monocyclic dual <i>N</i>-nitramine with an ultralow N-N bond dissociation energy: 2,4-dinitroamino-5-nitro-2,4-dihydro-3<i>H</i>-1,2,4-triazol-3-one (<b>2</b>). This compound was obtained via the nitration of the diaminonation intermediate of NTO and exhibits a remarkably high crystal density (1.969 g cm^-3 at 298 K and 2.025 g cm^-3 at 100 K), along with outstanding detonation performances (<i>D</i>v = 9072 m s^- 1, <i>2025-01-01T00:00:00Z2025 Jul2026-03-31T10:44:14.217Z2025-08-27T03:06:50.412ZS-EPMC123083704074701310.1021/jacsau.5c00609