| Title |
1,3,6,8-Tetranitrocarbazole (TNC): efficient one-pot synthesis, X-ray crystallographic analysis, and property evaluation |
| Authors |
Šarlauskas, Jonas ; Jonušis, Mantas ; Jonušienė, Simona ; Čėnas, Narimantas ; Krikštopaitis, Kastis ; Stankevičiūtė, Jonita ; Anusevičius, Žilvinas |
| DOI |
10.22211/cejem/215879 |
| Full Text |
|
| Is Part of |
Central European journal of energetic materials.. Warsaw : Łukasiewicz Research Network – Institute of Industrial Organic Chemistry. 2025, vol. 22, Nr. 4, p. 470-495.. ISSN 1733-7178. eISSN 2353-1843 |
| Keywords [eng] |
energetic materials ; 1,3,6,8-tetranitrocarbazole ; synthesis ; HPLC-MS analysis ; X-ray diffraction |
| Abstract [eng] |
Nitro-substituted derivatives of carbazole represent an important class of compounds with numerous industrial applications, including their role as components of energetic materials. A systematic review of the literature revealed that an effective, practical synthesis method for producing tetranitrocarbazole (TNC) remains elusive. In the present work, we report the development of a new and efficient one-pot nitration procedure utilizing potassium nitrate in fuming sulphuric acid (oleum). This nitration system, comprising potassium nitrate in oleum (20% SO₃), was found to be significantly more effective for the synthesis of 1,3,6,8-tetranitro-9H-carbazole (1,3,6,8-TNC) (C12H5N5O8) than the conventional nitration utilizing fuming nitric acid. A monocrystal of pure 1,3,6,8-TNC was used for the detailed X-ray structure determination. It was found that TNC crystallizes in the monoclinic crystal system, space group P21/c, specific crystal density: 1.765 (calc. from X-ray analysis, at –100 °C) or 1.73 g/cm3 (at 20 °C, by pycnometry). The main properties of TNC are: formula weight: 347.21; melting point: 296 °C; flash point: 350 °C. 1,3,6,8-TNC can be used in various applications in millitary practice, including pyrotechnic compositions and formulations of some specific secondary explosives. The electron-accepting ability and quantum mechanical properties of TNC closely resemble those of tetryl. Its overall explosive properties are expected to be close to those of TNT and picramide. |
| Published |
Warsaw : Łukasiewicz Research Network – Institute of Industrial Organic Chemistry |
| Type |
Journal article |
| Language |
English |
| Publication date |
2025 |
| CC license |
|
