Azeoazide azide: Synthesis, structure, and safety of a nitrogen-rich explosive candidate

Introduction

In this episode, the Chemistry World podcast delves into azeoazide azide, a nitrogen-rich molecule that has captivated chemists for its instability and potential applications. The host recounts a compound built from two carbon atoms and 14 nitrogen atoms, with a nitrogen content of roughly 89.1% by weight, earning it infamous status among energetic materials. The opening frames the central tension: is this the most explosive compound ever synthesized, and what does that imply for science and safety?

"The most explosive chemical compound ever created" - Francis Addison.

Naming, Structure, and Historical Context

The episode explains that although the Munich team identified the correct structure in 2011, they were not the first to synthesize the open form of C2N14; a 1961 patent described an open-chain azide variant in place of a tetrazole ring. Further work in 2013 showed that at room temperature the supposed open form cyclizes to a tetrazole, meaning the open structure described in the patent does not exist under those conditions. With conflicting structural descriptions, naming has been contentious, alternating between systematic designations like 1,2-diazodicarbamyl tetrazole and more accessible labels such as isocyanogen-tetrazide-azide. The host notes a poetic but imperfect popular name that stuck in broader circles: Azeoazide azide.

"the whole thing is trembling on the verge of not existing at all" - Deryck Lowe.

Safety Challenges and Experiments

The core of the podcast centers on the safety risks. The Munich group reported detonation thresholds that were far below their measured readings, windswept by the compound’s extreme energy content. Tests using as little as 0.25 joules in impact and 1 Newton in friction could trigger explosive decomposition. There were instances where simply touching a sample with a spatula caused an explosion. When crystals were subjected to a 150 milliwatt laser in a Raman spectrometer, the energy again caused an explosion, underscoring the material’s volatility. At least one paper notes that compound 2 detonated several times during the Rahman measurement, a reminder of the persistent danger in handling energetic nitrogen-rich species.

"even their smallest possible loadings, 0.25 joules in impact and 1 Newton in friction, were enough to trigger explosive decomposition" - Francis Addison.

Potential Uses and Practicality

Beyond hazard, the discussion considers whether azeoazide azide could offer practical value. The 1961 patent hinted at a primary detonator role, capable of triggering larger secondary explosives, and later work supported that concept in theory. The Munich team calculated detonation velocities around 750 meters per second faster than a currently explored green alternative to lead azide, 246-triazidotriazine. However, the compound’s extreme instability makes it impractical for real-world use. The narrative concludes that while its energetic potential is theoretically intriguing, safety concerns severely limit any practical application outside controlled laboratory environments. The host closes with a note of cautious realism: the compound’s volatility means it is unlikely to find legitimate industrial use, and those tempted to make it should recognize they are “on the verge of not existing at all.”

"the compound has a detonation velocity around 750 m per second faster than that of 246 triazidotriazine" - Munich research team.

Conclusion

The episode leaves listeners with a clear takeaway: azeoazide azide represents a remarkable case study in how structure, naming, and safety concerns shape the boundaries of chemical possibility. While it may illuminate fundamental aspects of energetic materials and reaction dynamics, its practical utility remains out of reach, constrained by the very properties that make it scientifically fascinating.