Triazido-2,4,6-trinitrobenzene

5-Triazido-2,4,6-trinitrobenzene (TATNB, TNTAB) was first prepared by Oldfich Turek in 1924 by the action of sodium azide on l,3,5-trichloro-2,4,6-trinitrobenzene [153, 154]. 

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Benzenetrifuroxan (66) is a powerful explosive which was first synthesised by Turek in 1931 by heating 1,3,5-triazido-2,4,6-trinitrobenzene (65) to its melting point (131 °C) the latter prepared from the reaction of 1,3,5-trichloro-2,4,6-trinitrobenzene with sodium azide in aqueous ethanol. 

Kursunskii and Apina [214] examined the kinetics of the transformation of 1,3,5-triazido-2,4,6-trinitrobenzene into benzotrisfuroxane at 70-115 0. The reaction is of the first order with activation energy 26 kcal/mol. 

For example, l-azido-2,4,6-tiinitrobenzene with one azido group in the molecule has the character of a secondary explosive (its sensitivity is too low for primary explosive) whereas 1,3,5-triazido-2,4,6-trinitrobenzene is a typical primary explosive. 

Triazido-2,4,6-trinitrobenzene can be easy synthesized by the action of alkaline azide on 1,3,5-trichloro-2,4,6-trinitrobenzene. The product is slightly soluble in the reaction mixture from which it precipitates. The sodium azide can be used in the form of an aqueous ethanol solution while l,3,5-trichloro-2,4,6-trinitrobenzene in the form of an acetone solution or alone [153, 154,159, 160]. Purification of TATNB may be done by crystallization from solvents such as chloroform [153,154,159,160], acetic acid, or mixture of acetic acid and acetone 1/1 (the last mixture is recommended for preparation of single crystals for stractural studies) [155]. 

It is explosive [1], and the limited thermal stability is reduced by traces of triazido-trinitrobenzene as impurity [2]. It is shock sensitive [3],... 

Lead is present in most of the primary explosives and thus use of such primary explosives results in corresponding adverse environmental impact. Therefore, development of lead-free primary explosives is an important area of research. Several new explosives such as l,3,5-triazido-2,4,6-trinitrobenzene (TATNB) and... 

Most organic azides do not possess the properties required for primary explosives and generally can be characterized by low physical and chemical stability (lower alkyl azides, sulfuryl azide explode even spontaneously [8, 11]), high sensitivity to mechanical stimuli (lower aUcyl azides, acyl azides e.g., carbonyl diazide explode on contact with a glass rod [30]), low thermal stability (e.g., cyanogen azide, l,3,5-triazido-2,4,6-trinitrobenzene, dicyanamid azide, esters of azidoacetic acid [8]), or sensitivity to light [127]. 

Turek, O. l,3,5-Triazido-2,4,6-trinitrobenzen, nova inicialna vybusina. Chtanicky obzor 7, 76-79 97-104 (1932)... 

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