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

changed changed 477185426 1,3,5-Triazido-2,4,6-trinitrobenzene structure.svg 180 Skeletal formula of TATNB TATNB-3D-spacefill.png 180 Space-filling model of the TATNB molecule 1,3,5-Triazido-2,4,6-trinitrobenzene TATNB correct chemspider 56578 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 LIPDUIOSIFXENT-UHFFFAOYAO c1(c(c(c(c(c1[N+](=O)[O-])N=[N+]=[N-])[N+](=O)[O-])N=[N+]=[N-])[N+](=O)[O-])N=[N+]=[N-] correct chemspider 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 correct chemspider LIPDUIOSIFXENT-UHFFFAOYSA-N correct CAS 29306-57-8 correct FDA 25NHL6Y97G 62844 O=[N+](c1c(N=[N+]=[N-])c([N+]([O-])=O)c(N=[N+]=[N-])c([N+]([O-])=O)c1N=[N+]=[N-])[O-] C043826 6 12 6 yellow crystals 131 °CYu. M. Burov G. M. Nazin G. B. Manelis Retardation of Monomolecular Reactions in the Solid Phase Russian Chemical Bulletin 48 7 1250–1254 1999 10.1007/BF02495284 95970971 monoclinic P21/c, No. 14 765.8 kJ/mol 3200 kJ/mol 7350 m/s 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.Matyáš Robert Primary Explosives Pachman Jiří Springer Science & Business Media 2013 9783642284366 118–121 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. 600px|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.David Adam Konstantin Karaghiosoff Thomas M. Klapötke Thomas M. Klapötke Gerhard Holl Manfred Kaiser Triazidotrinitro Benzene: 1,3,5-(N3)3-2,4,6-(NO2)3C6 Propellants Explos. Pyrotech. 2002 27 1 7–11 10.1002/1521-4087(200203)27:1<7::AID-PREP7>3.0.CO;2-J 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.B. L. Korsunskii T. A. Apina Kinetics of the Thermal Decomposition of 1,3,5-Triazido-2,4,6-trinitrobenzene in Solution Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science 20 9 1971–1973 1971 10.1007/BF00854439 420px|Decomposition of 1,3,5-triazido-2,4,6-trinitrobenzene The compound explodes if rapidly heated above 168 °C. References Category:Explosive chemicals Category:Organoazides Category:Nitrobenzene derivatives