Azidoazide azide

August 17, 2020
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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.

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Azidoazide azide fast 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
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