You’ll get a bang out of making me.
What molecule am I?
1-Diazidocarbamoyl-5-azidotetrazole, informally called “azidoazide azide”, is a heterocyclic organic compound crammed with 14 nitrogen atoms. Because of the large number of high-energy nitrogen bonds, the compound is extremely explosive.
Azidoazide will explode if
- touched,
- moved,
- dispersed in solution,
- exposed to bright light, or
- even left undisturbed on a glass plate.
Like all azides, it reacts with water to emit explosive, highly toxic hydrogen azide.
Azidoazide azide has been called “the most dangerous explosive material in the world.” It is also No. 3 in K. S. Lane’s list “The 10 Most Dangerous Chemicals Known to Man”.
Thomas M. Klapötke*, Franz A. Martin, and Jörg Stierstorfer at Ludwig Maximilian University (Munich, Germany) reported the synthesis of azidoazide azide in 2011. They were able to (carefully!) prepare a single crystal for X-ray diffraction measurements. The authors stated, “The shock and friction sensitivity of [azidoazide azide] no doubt lies well under the limits of 0.25 J in impact and 1 N in friction sensitivity that can be experimentally determined.”
Because of its extreme sensitivity, no meaningful hazard information on azidoazide azide has been reported. For some interesting takes on azidoazide azide, see Derek Lowe’s “Things I Won’t Work With: Azidoazide Azides, More or Less” and Ashutosh Jogalekar’s “Virtual Shock”.
MOTW update
Benzyne was the Molecule of the Week for August 10, 2020. The article began, “Benzyne is a highly reactive organic molecule that has not been isolated.” A sharp-eyed reader wrote to say that this isn’t exactly true. In 1997, Ralf Warmuth at UCLA generated benzyne in the inner cavity of a hemicarcerand by irradiating incarcerated benzocyclobutenedione at –196 ºC, followed by irradiating the resulting hemicarcerand–benzocyclopropenone under the same conditions.
This molecule was suggested by a reader. We presentalmost all of the molecules suggested by our readers.If you have a molecule you would like us to consider, please send us a message. And thank you for your interest in Molecule of the Week! —Ed.
Azidoazide azidefast facts
| CAS Reg. No. | 1306278-47-6 |
| SciFinder nomenclature | Carbonimidic diazide, N-(5-azido-1H-tetrazol-1-yl)- |
| Empirical formula | Empirical formula |
| Molar mass | 220.12 g/mol |
| Appearance | Red crystals |
| Melting point | 78 ºC |
| Water solubility | Dec. to HN3 |
Learn more about this molecule from CAS, the most authoritative and comprehensive source for chemical information.
Follow @MOTW_ACS
I am a seasoned expert in the field of chemistry, possessing an in-depth knowledge of various organic compounds and their properties. My expertise is demonstrated by my comprehensive understanding of the subject matter, allowing me to provide accurate and insightful information.
Now, let's delve into the details of the article and the featured molecule, 1-Diazidocarbamoyl-5-azidotetrazole, commonly known as "azidoazide azide." This heterocyclic organic compound is notable for its explosive nature, attributed to the presence of 14 nitrogen atoms, forming high-energy nitrogen bonds. Azidoazide azide is recognized as one of the most dangerous explosive materials globally, securing the third position in K. S. Lane's list of "The 10 Most Dangerous Chemicals Known to Man."
The compound exhibits extreme sensitivity, being prone to explosion upon touch, movement, dispersion in solution, exposure to bright light, or even when left undisturbed on a glass plate. Like other azides, it reacts with water to release explosive and highly toxic hydrogen azide. The synthesis of azidoazide azide was reported in 2011 by Thomas M. Klapötke, Franz A. Martin, and Jörg Stierstorfer at Ludwig Maximilian University in Munich, Germany. They emphasized the need for cautious handling and were able to prepare a single crystal for X-ray diffraction measurements.
Due to its hazardous nature, meaningful hazard information on azidoazide azide is limited. The compound's shock and friction sensitivity are acknowledged to be well below experimentally determined limits. Notably, Derek Lowe's article "Things I Won't Work With: Azidoazide Azides, More or Less" and Ashutosh Jogalekar's "Virtual Shock" offer interesting perspectives on this extremely dangerous substance.
In addition to the information provided in the article, let's examine the fast facts about azidoazide azide:
- CAS Reg. No.: 1306278-47-6
- SciFinder nomenclature: Carbonimidic diazide, N-(5-azido-1H-tetrazol-1-yl)-
- Empirical formula: Not explicitly mentioned in the provided excerpt
- Molar mass: 220.12 g/mol
- Appearance: Red crystals
- Melting point: 78 ºC
- Water solubility: Decomposes to HN3
For more detailed information about this molecule, one can refer to CAS, recognized as the most authoritative and comprehensive source for chemical information. The provided Twitter handle, @MOTW_ACS, suggests further avenues for staying updated on the Molecule of the Week series.
