Synthesis and properties of 1,5-diaminotetrazole

Гапоник, П. Н.; Karavai, V. P.

doi:10.1007/bf00505966

Cited by 29 publications

(35 citation statements)

References 4 publications

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“…1-Methyl-and 5-amino-2-methyl-1H-tetrazole, [53] 5-amino-1,4-dimethyl-1H-tetrazolium iodide, [54] 5-amino-1,3-dimethyl-1H-tetrazolium iodide, [55] 1,5-diamino-1H-tetrazole, [56] 1,5-diamino-4-methyl-1H-tetrazolium iodide, [18d] guanazine [57] and methylguanazinium iodide [58] were prepared by previously published procedures. In addition, 5-amino-1H-tetrazolium picrate, [19] 1,5-diamino-1H-tetrazolium picrate [20a] and guanazinium picrate [59a] were synthesized by modified literature procedures as indicated below.…”

Section: Methodsmentioning

confidence: 99%

1,2,4‐Triazolium and Tetrazolium Picrate Salts: “On the Way” from Nitroaromatic to Azole‐Based Energetic Materials

Klapötke¹,

Sabaté²

2008

Eur J Inorg Chem

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A family of energetic salts based on the picrate anion and several azolium cations were synthesized either by new methods or by known literature procedures. The cations of choice were the following: 5-amino-1H-tetrazolium (1), 5-amino-1-methyl-1H-tetrazolium (2), 5-amino-2-methyl-1H-tetrazolium (3), 5-amino-1,4-dimethyl-1H-tetrazolium (4), 5-amino-1,3-dimethyl-1H-tetrazolium (5), 1,5-diamino-1H-tetrazolium (6), 1,5-diamino-4-methyl-1H-tetrazolium (7), 3,4,5-triamino-1,2,4-triazolium or guanazinium (8) and 3,4,5-triamino-1-methyl-1,2,4-triazolium or methylguanazinium (9). A summary of the 15 N NMR shifts for all compounds is given, and the proton-/methyl-induced shifts (PISs/MISs) are discussed with relation to the crystal structures. Because hydrogen bonding plays an important role in determining the density and thus the performance of energetic materials, the crystal structures are discussed in detail. In addition, tests to

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Section: Methodsmentioning

confidence: 99%

1,2,4‐Triazolium and Tetrazolium Picrate Salts: “On the Way” from Nitroaromatic to Azole‐Based Energetic Materials

Klapötke¹,

Sabaté²

2008

Eur J Inorg Chem

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“…From the reactions of 1 with 2 a and 2 b, the corresponding isopropylidene-[5-(4-trifluoromethyl-1,2,3-triazol-1-yl)tetrazol-1-yl]am-A C H T U N G T R E N N U N G ine, 3 a, and isopropylidene-[5-(4-pentafluorosulfanyl-1,2,3-triazol-1-yl)tetrazol-1-yl]amine, 3 b, were formed in 47 % and 66 % yield, respectively (Entries 1 and 3). Whereas, in the reactions with 2 c-f, starting material 1 was recovered (10-48 %) together with [9] which was formed as a byproduct (5-32 %). In a separate experiment, which was carried out in the absence of alkyne under the same reaction conditions, the azido group of 1 was found to decompose into an amino group to yield 4 (yield 20 %).…”

Section: Resultsmentioning

confidence: 93%

5‐(1,2,3‐Triazol‐1‐yl)tetrazole Derivatives of an Azidotetrazole via Click Chemistry

Abe¹,

Tao²,

Joo³

et al. 2009

Chemistry A European J

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N-C bonded (non-bridged) 5-(1,2,3-triazol-1-yl)tetrazoles were synthesized by the Cu(I)-catalyzed 1,3-dipolar azide-alkyne cycloaddition click reaction using 5-azido-N-(propan-2-ylidene)-1H-tetrazole (1). For example, the click reaction of 1 in the presence of CuSO(4)5 H(2)O and Na ascorbate at 65-70 degrees C for 48 h in CH(3)CN/H(2)O co-solvent was found to be limited to only terminal alkynes that have electron-withdrawing groups, CF(3)C[triple chemical bond]CH (2 a) and SF(5)C[triple chemical bond]CH (2 b), giving rise to isopropylidene-[5-(4-trifluoromethyl-1,2,3-triazol-1-yl)tetrazol-1-yl]amine (3 a) and isopropylidene-[5-(4-pentafluorosulfanyl-1,2,3-triazol-1-yl)tetrazol-1-yl]amine (3 b) in 47 % and 66 % yields, respectively. When carried out under conditions using CuI and 2,6-lutidine as catalysts at 0 degrees C for 13 h in CHCl(3), the click reaction was versatile toward alkynes even those having electron-donating groups. Properties of new products were determined and compared with those of 1. Heats of formation, detonation pressures, detonation velocities and impact sensitivities are reported for these new 5-(1,2,3-triazol-1-yl)tetrazoles.

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“…Initially, the direct formation of 1-amino-5-azidotetrazole (1) from 1,5-diaminotetrazole (DAT), first synthesized by Gaponik et al, [14] was favored. A direct diazotation of the amino group in the 5-position with sodium nitrite and hydrochloric acid was not possible because the attack took place at the amino group on the 1-position, thereby resulting in a ring opening and destruction of the heterocyclic ring system.…”

Section: Results and Discussion Synthesismentioning

confidence: 99%

“…Between 1000 and 500 cm À1 , many strongly coupled stretching and deformation modes of the entire molecule and especially deformation (in-plane and out-of-plane) and torsion modes of the tetrazole rings are observed. N NMR spectroscopic studies could not be performed due to the amount of material required of these highly energetic compounds, 14 N NMR spectroscopic studies in [D 6 ]DMSO and CDCl 3 revealed clearly assignable resonances for the nitrogen atoms of the azide groups. Compound 1 revealed only two signals in the NMR spectra.…”

Section: Spectroscopic Datamentioning

confidence: 97%

New Azidotetrazoles: Structurally Interesting and Extremely Sensitive

Klapötke¹,

Krumm²,

Martin³

et al. 2011

Chemistry An Asian Journal

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The treatment of triaminoguanidinium chloride with two equivalents of sodium nitrite under acidic conditions, followed by the cyclization with stoichiometric amounts of either sodium hydroxide solution or solid sodium carbonate yielded 1-amino-5-azidotetrazole (1), 5-azido-1-diazidocarbamoyltetrazole (2), and 1-(aminoazidocarbamoyl)-5-azidotetrazole (3). The three novel compounds could be isolated by short-column liquid chromatography by using chloroform in reasonable yields. The mechanism of the formation as well as the decomposition pathway of the materials was investigated and a full characterization of all three compounds is presented. Compounds 1-3 have been characterized by means of Raman and IR as well as multinuclear NMR spectroscopy, mass spectrometry, and X-ray diffraction studies. Thermal stabilities have been evaluated by differential scanning calorimetry. Theoretical calculations have been performed to ensure the assignment of the vibrational modes obtained from Raman and IR measurements. The sensitivity values obtained from our measurements reflect the behavior of the compounds, which show an extremely high sensitivity toward mechanical as well as thermal stimuli.

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Synthesis and properties of 1,5-diaminotetrazole

Cited by 29 publications

References 4 publications

1,2,4‐Triazolium and Tetrazolium Picrate Salts: “On the Way” from Nitroaromatic to Azole‐Based Energetic Materials

1,2,4‐Triazolium and Tetrazolium Picrate Salts: “On the Way” from Nitroaromatic to Azole‐Based Energetic Materials

5‐(1,2,3‐Triazol‐1‐yl)tetrazole Derivatives of an Azidotetrazole via Click Chemistry

New Azidotetrazoles: Structurally Interesting and Extremely Sensitive

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