1,1'-Azobis-1,2,3-triazole

1,1'-Azobis-1,2,3-triazole is a moderately explosive but comparatively stable chemical compound^{[citation needed]} which contains a long continuous chain of nitrogen atoms, with an unbroken chain of eight nitrogen atoms cyclised into two 1,2,3-triazole rings. It is stable up to 194 °C. The compound exhibits cis–trans isomerism at the central azo group: the trans isomer is more stable and is yellow, while the cis isomer is less stable and is blue. The two rings are aromatic and form a conjugated system with the azo linkage. This chromophore allows the trans compound to be isomerised to the cis when treated with an appropriate wavelength of ultraviolet light.^[1]

1,1'-Azobis-1,2,3-triazole

trans-1,1'-Azobis-1,2,3-triazole (on top) cis-1,1'-Azobis-1,2,3-triazole (on bottom)   Carbon, C   Hydrogen, H   Nitrogen, N
Names
Preferred IUPAC name 1,1′-Diazenediyldi(1H-1,2,3-triazole)
Identifiers
CAS Number	1354420-07-7
3D model (JSmol)	Interactive image
ChemSpider	26234930 26234931
PubChem CID	71308130
UNII	M7A5U2N4ZU Y
InChI InChI=1S/C4H4N8/c1-3-11(7-5-1)9-10-12-4-2-6-8-12/h1-4H/b10-9+ Key: WUPZAQSKRMYJNB-MDZDMXLPSA-N
SMILES c2cnnn2\N=N\n1ccnn1
Properties
Chemical formula	C4H4N8
Molar mass	164.132 g·mol−1
Appearance	Blue (cis isomer) Yellow (trans isomer)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Explosive
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Related compounds

In 2011, 1,1'-azobis(1,2,3,4-tetrazole) with formula C₂H₂N₁₀ was prepared by Klapötke and Piercey which has a 10-nitrogen chain.^[2] The record was later taken by a 11-nitrogen chain compound synthesized by a group of Chinese researchers.^[3][which?] A branched chain of 11-nitrogen system has also been reported as part of an unstable but highly nitrogen rich azidotetrazole derivative with formula C₂N₁₄.^[4]

1,1′-Azobis(1,2,3,4-tetrazole) (trans isomer)

See also

• HBT (explosive)
• G2ZT
• Diazene
• TKX-50