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Issue 43, 2008
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Bistetrazolylamines—synthesis and characterization

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The acid-catalyzed cyclization reaction of sodium dicyanamide and sodium azide in the ratio of 1 : 2 afforded 5,5′-bis(1H-tetrazolyl)amine (H2bta, 2) in high yield (88%) as the monohydrate. Dehydration of 2·H2O at elevated temperature and reduced pressure gave anhydrous 2, while recrystallization from DMSO yielded 2·H2O·DMSO. 2 was converted into 5,5′-bis(2-methyltetrazolyl)methylamine (Me3bta, 6) in two steps. In the first step, 2 was twice deprotonated with sodium hydroxide and alkylated with MeI producing 5,5′-bis(2-methyltetrazolyl)amine (Me2bta, 5) in moderate yield (55%). The second step involved the alkylation of 5 with dimethyl sulfate in alkaline solution (72%). In all cases, the obtained colorless, crystalline compounds were fully characterized by vibrational (IR, Raman) spectroscopy, multinuclear NMR spectroscopy, mass spectrometry, elemental analysis, X-ray structure determination, and initial safety testing (impact, friction and electrical spark sensitivity). According to the UN Recommendations for the “Transport of Dangerous Goods”, compounds 2·H2O, 5, and 6 are classified as “insensitive” while 2 is described as “sensitive”. The thermal behaviors were investigated using differential scanning calorimetry (DSC). The heats of formation (ΔfHm° (2*H2O) = 203 kJ mol−1, ΔfHm° (2) = 633 kJ mol−1, ΔfHm° (5) = 350 kJ mol−1, ΔfHm° (6) = 583kJ mol−1) were calculated using heats of combustioncomb.H (2·H2O) = −1714 kJ mol−1, Δcomb.H (2) = −1858 kJ mol−1, Δcomb.H (5) = −2932 kJ mol−1, Δcomb.H (6) = −3843 kJ mol−1) obtained from oxygen bomb calorimetry. In addition, explosion parameters such as the detonation velocity (D(2·H2O) = 7792 m s−1, D(2) = 9120 m s−1, D(5) = 7291 m s−1, D(6) = 7851 m s−1) and detonation pressure (P(2·H2O) = 220 kbar, P(2) = 343 kbar, P(5) = 172 kbar, P(6) = 205 kbar) were calculated using the program EXPLO5. “Koenen tests” were successfully performed for compound 2 using critical diameters of 8 mm and 10 mm.

Graphical abstract: Bistetrazolylamines—synthesis and characterization

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Supplementary files

Article information

02 Jul 2008
16 Aug 2008
First published
01 Oct 2008

J. Mater. Chem., 2008,18, 5248-5258
Article type

Bistetrazolylamines—synthesis and characterization

T. M. Klapötke, P. Mayer, J. Stierstorfer and J. J. Weigand, J. Mater. Chem., 2008, 18, 5248
DOI: 10.1039/B811273H

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