1,5-diamino-1 H tetrazole

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Structural formula
Structural formula of 1,5-diamino-1H-tetrazole
General
Surname 1,5-diamino-1 H tetrazole
other names
  • 1 H -Tetrazole-1,5-diamine ( IUPAC )
  • 1,5-diaminotetrazole
  • 1,5-diamino-1 H -1,2,3,4-tetrazole
  • DAT
Molecular formula CH 4 N 6
Brief description

colorless crystals

External identifiers / databases
CAS number 2165-21-1
PubChem 307904
ChemSpider 272173
Wikidata Q15810510
properties
Molar mass 100.083 g mol −1
Physical state

firmly

density

1.571 g cm −3 (19.85 ° C)

Melting point

187-190  ° C

safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

1,5-Diamino-1 H -tetrazole is a heterocyclic , highly explosive compound that belongs to the group of organic tetrazoles . With a nitrogen content of 83.97%, the compound is a tetrazole derivative rich in nitrogen .

history

The preparation of the substance by reacting thiocarbazide with sodium azide and lead (II) oxide was first described in 1931 by R. Stolle.

Presentation and extraction

The synthesis of 1,5-diamino-1 H -tetrazole can be prepared by the reaction of Aminoguanidiniumchlorid with nitrous acid, carried out, wherein a Azidoguanylchlorid occurs as an intermediate. The compound can also be obtained by reacting cyanazide with hydrazine . An intermediate azidohydrazone is formed here, which then forms the target compound with ring closure.

Preparation of 1,5-diamino-1H-tetrazole

Another synthesis is based on thiosemicarbazide , which can be easily obtained from potassium thiocyanate and hydrazine in an acidic medium. In the first step, the intermediate compound 1-hydrazinylenemethanimine is obtained by reaction with lead oxide . This yields by reaction with hydrazoic acid under the ring-closing 1,5-diamino-1 H -tetrazole.

Preparation of 1,5-diamino-1H-tetrazole

properties

1,5-Diamino-1 H -tetrazole is a crystalline solid that melts at 187-190 ° C. A strongly exothermic decomposition with a heat of decomposition of −850 kJ mol −1 is observed above the melting point . The compound crystallizes in a monoclinic crystal lattice with the space group P 2 1 / c (space group no. 14) . The compound can occur in two tautomeric structures. Template: room group / 14

Tautomers

As a basic compound, salts are formed with acids. The 1,5-diamino-1 H -tetrazolium chloride (CH 4 N 6 · HCl, CAS No. 23685-20-3) is formed with hydrochloric acid .

use

The compound is used to produce other high-energy salts. Examples are:

  • 1,5-diamino-1 H -tetrazolium nitrate (CH 4 N 6 · HNO 3 , CAS No. 95335-56-1)
  • 1,5-diamino-1 H -tetrazolium picrate (CH 4 N 6 · C 6 H 3 N 3 O 7 , CAS No. 95335-57-2)
  • 1,5-diamino-1 H -tetrazolium perchlorate (CH 4 N 6 · HClO 4 )

The dinitramide salt can be obtained via the perchlorate with potassium dinitramide.

Individual evidence

  1. ↑ a b c Tao, G.-H .; Guo, Y .; Parrish, DA; Shreeve, JM: Energetic 1,5-diamino-4H-tetrazolium nitro-substituted azolates in J. Mat. Chem. 20 (2010) 2999-3005, doi : 10.1039 / B925267C .
  2. ↑ a b c Lyakhov, AS; Gaponics, PN; Voitekhovich, SV: 1,5-Diamino-1H-1,2,3,4-tetrazole in Acta Cryst. C, Cryst. Struct. Comm. 57 (2001) 185-186, doi : 10.1107 / S010827010001622X .
  3. ↑ a b Raap, R .: Amination of tetrazoles with hydroxylamine-O-sulfonic acid: 1- and 2-aminotetrazoles . In: Canadian Journal of Chemistry . 47, 1969, pp. 3677-3681, doi : 10.1139 / v69-606 .
  4. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  5. ↑ a b Joo, Y.-H .; Twamley, B .; Garg, S .; Shreeve, JM: Energetic Nitrogen-Rich Derivatives of 1,5-Diaminotetrazole in Angew. Chem. 120 (2008) 6332-6335, doi : 10.1002 / anie.200801886 .
  6. ↑ Stolle, R .; Gaertner, E .: About amino-1-amino-5-tetrazole and amino-1-hydrazino-5-tetrazole in J. Prakt. Chem. 132 (1931) 209-226, doi : 10.1002 / prac.19311320115 .
  7. ↑ Galvez-Ruiz, JC; Holl, G .; Karaghiosoff, K .; Klapötke, TM ; Loehnwitz, K .; Mayer, P .; Noeth, H .; Polborn, K .; Rohbogner, CJ; Suter, M .; Weigand, JJ: Derivatives of 1,5-Diamino-1 H -tetrazole: A New Family of Energetic Heterocyclic-Based Salts in Inorg. Chem. 44 (2005) 4237-4253, doi : 10.1021 / ic050104g .
  8. ↑ a b Klapötke, TM: Chemistry of High-Energy Materials , 2nd Edition, 2012 Walter de Gruyter GmbH & Co. KG, Berlin / Boston, ISBN 978-3-11-027358-8 , pp. 161-163, (accessed via De Gruyter Online).
  9. ↑ Lesnikovich, AI; Ivashkevich, OA; Levchik, SV; Balabanovich, AI; Gaponics, PN; Kulak, AA: Thermal decomposition of aminotetrazoles in Thermochim. Acta 388 (2002) 233-251, doi : 10.1016 / S0040-6031 (02) 00027-8 .
  10. ↑ Levchik, SV; Balabanovich, AI; Ivashkevich, OA; Lesnikovich, AI; Gaponics, PN; Costa, L .: The thermal decomposition of aminotetrazoles. Part 2. 1-methyl-5-aminotetrazole and 1,5-diaminotetrazole in Thermochim. Acta 225 (1993) 53-65, doi : 10.1016 / 0040-6031 (93) 85082-K .