1,3,5-Triazido-2,4,6-trinitrobenzene

1,3,5-Triazido-2,4,6-trinitrobenzene

Skeletal formula of TATNB
Space-filling model of the TATNB molecule
Names
Preferred IUPAC name 1,3,5-Triazido-2,4,6-trinitrobenzene
Identifiers
CAS Number	29306-57-8 checkY
3D model (JSmol)	Interactive image Interactive image
Abbreviations	TATNB
ChemSpider	56578 checkY
ECHA InfoCard
E number
MeSH	C043826
PubChem CID	62844
UNII	25NHL6Y97G checkY
CompTox Dashboard (EPA)	{{#property:P3117}}
InChI InChI=1S/C6N12O6/c7-13-10-1-4(16(19)20)2(11-14-8)6(18(23)24)3(12-15-9)5(1)17(21)22 checkY Key: LIPDUIOSIFXENT-UHFFFAOYSA-N checkY InChI=1/C6N12O6/c7-13-10-1-4(16(19)20)2(11-14-8)6(18(23)24)3(12-15-9)5(1)17(21)22 Key: LIPDUIOSIFXENT-UHFFFAOYAO
SMILES O=[N+](c1c(N=[N+]=[N-])c([N+]([O-])=O)c(N=[N+]=[N-])c([N+]([O-])=O)c1N=[N+]=[N-])[O-] c1(c(c(c(c(c1[N+](=O)[O-])N=[N+]=[N-])[N+](=O)[O-])N=[N+]=[N-])[N+](=O)[O-])N=[N+]=[N-]
Properties
Chemical formula	C6N12O6
Molar mass	336.144 g·mol−1
Appearance	yellow crystals
Melting point	131 °C
Structure
Crystal structure	monoclinic
Space group	P21/c, No. 14
Thermochemistry
Std enthalpy of formation (ΔfH⦵298)	765.8 kJ/mol
Std enthalpy of combustion (ΔcH⦵298)	3200 kJ/mol
Explosive data
Detonation velocity	7350 m/s
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). ☒N verify (what is checkY☒N ?) Infobox references

1,3,5-Triazido-2,4,6-trinitrobenzene, also known as TATNB (triazidotrinitrobenzene) and TNTAZB (trinitrotriazidobenzene), is an aromatic high explosive composed of a benzene ring with three azido groups (-N₃) and three nitro groups (-NO₂) alternating around the ring, giving the chemical formula C₆(N₃)₃(NO₂)₃. Its detonation velocity is 7,350 meters per second, which is comparable to TATB (triaminotrinitrobenzene).

Preparation

The compound was first synthesized in 1924 by Oldřich Turek. It can be prepared by the reaction of 1,3,5-trichloro-2,4,6-trinitrobenzene with sodium azide. 1,3,5-trichloro-2,4,6-trinitrobenzene is obtained from the nitration of 1,3,5-trichlorobenzene with nitric acid and sulfuric acid.

Synthesis of 1,3,5-triazido-2,4,6-trinitrobenzene from 1,3,5-trichlorobenzene

Another route uses the nitration of 1,3,5-triazido-2,4-dinitrobenzene.

Properties

Chemical Properties

Even at low temperatures, the compound slowly decomposes by giving off nitrogen gas, converting into benzotrifuroxan. This reaction proceeds quantitatively within 14 hours at 100 °C. As a solution in m-xylene, first order kinetics were observed for the decomposition, with a half-life of 340 minutes at 70 °C, 89 minutes at 80 °C, and 900 seconds at 100 °C.

Decomposition of 1,3,5-triazido-2,4,6-trinitrobenzene

The compound explodes if rapidly heated above 168 °C.