2013
DOI: 10.5560/znb.2013-3237
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Thermally Stable 3,6-Disubstituted 1,2,4,5-Tetrazines

Abstract: Several 3,6-disubstituted 1,2,4,5-tetrazines were synthesized by nucleophilic substitution using 3,6-bis-(3,5-dimethyl-pyrazol-1-yl)-1,2,4,5-tetrazine and 3,6-dichloro-1,2,4,5-tetrazine as electrophiles. All new compounds were characterized by 1 H NMR, 13 C NMR and vibrational spectroscopy, mass spectrometry and elemental analysis (C,H,N). For analysis of the thermostability, differential scanning calorimetry (DSC) was used. Especially, the symmetrically bis-3,5-diamino-1,2,4-triazolyl-substituted derivative s… Show more

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Cited by 26 publications
(17 citation statements)
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“…Therefore, they are considered as green energetic materials used in solid propellants, explosives, and civil combustible gas generators [6]. The derivatives of tetrazine have been widely investigated due to their perfect performances in the field of propellants, explosives, pyrotechnics [14][15][16][17][18][19] and biological activity [20,21]. However, most of literatures focus on the synthesis, crystal structure and properties of the symmetrical structures instead of the unsymmetrical ones ( Figure 1).…”
Section: Introductionmentioning
confidence: 99%
“…Therefore, they are considered as green energetic materials used in solid propellants, explosives, and civil combustible gas generators [6]. The derivatives of tetrazine have been widely investigated due to their perfect performances in the field of propellants, explosives, pyrotechnics [14][15][16][17][18][19] and biological activity [20,21]. However, most of literatures focus on the synthesis, crystal structure and properties of the symmetrical structures instead of the unsymmetrical ones ( Figure 1).…”
Section: Introductionmentioning
confidence: 99%
“…Synthesis. IEF-12 was synthesized using a slightly modified protocol previously reported by Kläpotke et al 8 Briefly, 3,5-diamino-1,2,4-triazole (DATR; 1 g, 10.08 mmol) was dissolved in 25 mL of N,N'-dimethylformamide (DMF) at a room temperature (RT) using extensive alternate sonication and stirring until bulky crystals of DATR completely disappeared, yielding paleyellow solution. Then, a solution of dichlorotetrazine (0.377 g, 2.50 mmol) in 5 mL of acetonitrile was added dropwisely for 0.5 h. The product started to precipitate immediately.…”
Section: Methodsmentioning
confidence: 99%
“…For instance, Chavez & Hiskey reported the synthesis and propellant properties of the bis(tetrazolylaminotetrazine), with a low impact sensitivity, non-explosive, non-pyrotechnic and nonflammable character. 7 Kläpotke et al 8 explored the nucleophilic substitution in s-tetrazine using high electrophilic properties of 3,6dichloro-1,2,4,5-tetrazine to obtain a series of five new HEDMs. Amongst them, bis-3,5diamino-1,2,4-triazolyl-1,2,4,5-tetrazine (BDTT) was distinguished by its outstanding thermal stability (> 370 °C).…”
Section: Introductionmentioning
confidence: 99%
“…General procedure for the synthesis of compounds 9 a, 10 a, and 12 a : Ammonia was bubbled through a solution of the 1,2,4,5‐tetrazine compound ( 9 b ,21b 10 b ,21a or 12 b 21a) (5 mmol) in toluene (50 mL) with stirring for 30 min. The resulting solid was collected by filtration, washed with toluene, and dried to give compounds 9 a , 10 a , or 12 a.…”
Section: Methodsmentioning
confidence: 99%
“…3‐Amino‐6‐(3‐amino‐5‐nitro‐1H‐1,2,4‐triazol‐1‐yl)‐1,2,4,5‐tetrazine‐2,4‐di‐N‐oxide monohydrate ( 11 ) : Compound 11 was prepared using the general procedure and purified on silica gel (1:1 hexane‐EtOAc). The starting material was 3‐amino‐6‐(3,5‐diamino‐1 H ‐1,2,4‐triazol‐1‐yl)‐1,2,4,5‐tetrazine ( 11 a ) 21b. Yellow solid; yield: 25 %; IR (KBr): $\tilde \nu $ =3442, 3314, 1638, 1572, 1527, 1474, 1341, 1311, 1105, 844 cm −1 ; 1 H NMR: δ =8.62 (s, 2 H), 7.82 ppm (s, 2 H); 13 C NMR: δ =144.0, 148.6, 151.0, 162.7 ppm; elemental analysis calcd (%) for C 4 H 4 N 10 O 4 ⋅H 2 O (274.05): C 17.52, H 2.21, N 51.09; found: C 17.87, H 2.53, N 51.87.…”
Section: Methodsmentioning
confidence: 99%