1-Diazidocarbamoyl-5-azidotetrazole

{{Chembox

| Name =

| ImageFile = 1-Diazidocarbamoyl-5-azidotetrazole.png

| PIN = N-(5-Azido-1H-tetrazol-1-yl)carbonimidoyl diazide

| OtherNames = {{ubl|1-Diazidocarbamoyl-5-azidotetrazole|5-Azido-1-diazidocarbamoyltetrazole|N-(5-Azido-1H-tetrazol-1-yl)carbonimidic diazide}}

| Section1 = {{Chembox Identifiers

| CASNo = 1306278-47-6

| CASNo_Ref = {{cite web |title=Azidoazide azide |url=https://www.acs.org/content/acs/en/molecule-of-the-week/archive/a/azidoazide-azide.html |website=American Chemical Society |language=en |date=17 August 2020 |access-date=13 September 2021 |archive-date=28 October 2020 |archive-url=https://web.archive.org/web/20201028181732/https://www.acs.org/content/acs/en/molecule-of-the-week/archive/a/azidoazide-azide.html |url-status=live }}{{Cascite|changed|}}

| PubChem = 101796054

| SMILES = N(=[N+]=[N-])C1=NN=NN1N=C(N=[N+]=[N-])N=[N+]=[N-]

| Abbreviations = AA

| ChemSpiderID = 30649737

| StdInChI = 1S/C2N14/c3-11-6-1(7-12-4)10-16-2(8-13-5)9-14-15-16

| StdInChIKey = ROKXTJDNIZBVDB-UHFFFAOYSA-N

}}

| Section2 = {{Chembox Properties

| C=2 | N=14

| Density = 1.723 g·cm⁻³{{cite web|last1=Martin|first1=Franz Albert|title=Novel Energetic Materials based on 1,5-Diaminotetrazole and 3,5-Diamino-1H-1,2,4-triazole|url=https://edoc.ub.uni-muenchen.de/14061/1/Martin_Franz_Albert.pdf|access-date=24 February 2018|pages=80–87|archive-date=16 April 2021|archive-url=https://web.archive.org/web/20210416094502/https://edoc.ub.uni-muenchen.de/14061/1/Martin_Franz_Albert.pdf|url-status=live}}

| MeltingPtC = 78

| BoilingPt = Violent explosion at 110 °C

| SolubleOther = Soluble in diethyl ether, acetone, hydrocarbons, chlorinated hydrocarbons{{Cite patent|title=Isocyanogen tetraazide and its preparation|pubdate=1961-06-27|country=US|number=2990412|assign=Olin Mathieson Chemical Corp.|inventor1-last=Grundmann|inventor1-first=Christoph J.|inventor2-last=Schnabel|inventor2-first=Wilhelm Joseph}}

}}

| Section3 = {{Chembox Structure

| Structure_ref = {{cite journal |last1=Klapötke |first1=Thomas M. |last2=Martin |first2=Franz A. |last3=Stierstorfer |first3=Jörg |title=C₂N₁₄: An Energetic and Highly Sensitive Binary Azidotetrazole |journal=Angewandte Chemie International Edition |date=26 April 2011 |volume=50 |issue=18 |pages=4227–4229 |doi=10.1002/anie.201100300|pmid=21472944 |doi-access=free }}

| CrystalStruct = orthorhombic

| SpaceGroup = Pbcn

| LattConst_a = 18.1289

| LattConst_b = 8.2128

| LattConst_c = 11.4021

| UnitCellVolume = 1697.6

| UnitCellFormulas = 8

}}

| Section4 = {{Chembox Thermochemistry

| DeltaHf = 357 kcal·mol⁻¹{{cite web|last1=Lowe|first1=Derek|title=Things I Won't Work With: Azidoazide Azides, More Or Less|url=https://www.science.org/content/blog-post/things-i-won-t-work-azidoazide-azides-more-or-less|work=Science Magazine|publisher=American Association for the Advancement of Science|access-date=24 February 2018|date=9 January 2013|archive-date=7 May 2021|archive-url=https://web.archive.org/web/20210507110923/https://blogs.sciencemag.org/pipeline/archives/2013/01/09/things_i_wont_work_with_azidoazide_azides_more_or_less|url-status=live}} (1495 kJ·mol⁻¹)

}}

| Section5 = {{Chembox Explosive

| ShockSens = <0.25 J

| FrictionSens = <1 N

| DetonationV = 8960 m·s⁻¹

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| Section6 =

| Section7 = {{Chembox Hazards

| MainHazards = will unpredictably and violently detonate – part of the nitrogen highly energetic compounds family.

| NFPA-H =

| NFPA-F =

| NFPA-R =

| NFPA-S =

| ExploLimits =

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1-Diazidocarbamoyl-5-azidotetrazole, often jokingly referred to as azidoazide azide, is a heterocyclic inorganic compound with the formula C₂N₁₄.{{cite journal|last1=Klapötke|first1=Thomas M.|last2=Martin|first2=Franz A.|last3=Stierstorfer|first3=Jörg|title=C₂N₁₄: An Energetic and Highly Sensitive Binary Azidotetrazole|journal=Angewandte Chemie International Edition|date=26 April 2011|volume=50|issue=18|pages=4227–4229|doi=10.1002/anie.201100300|pmid=21472944|doi-access=free}} It is a highly reactive and extremely sensitive explosive.