The Many Faces of FOX‐7: A Precursor to High‐Performance Energetic Materials

Gao, Haixiang; Shreeve, Jean’ne M.

doi:10.1002/ange.201501973

Cited by 17 publications

(18 citation statements)

References 32 publications

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“…Considering the good stability of the triazine and the powerful performance of the gem ‐dinitromethyl group, the combination of gem ‐dinitromethyl and triazine may be a good strategy to prepared energetic materials with good energetic performance and high mechanical stability. Although potassium 3‐dinitromethyl‐[1,2,4]triazine has been reported, no detailed procedure was listed, no other salts with nitrogen‐rich cations based on 3‐dinitromethyl‐[1,2,4]triazine were prepared before, and the properties of potassium salt is unsatisfactory. In view of the fact that the introduction of nitrogen‐rich cations is a good method to improve properties, we presented the syntheses, characterizations, and performance of a series of energetic compounds featuring the triazine and gem ‐dinitromethyl group, which use FOX‐7 as the starting material (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

Nitrogen‐rich Salts based on 3‐Dinitromethyl‐[1,2,4]triazine: Synthesis, Characterization, and Performance

Dong

Yang

et al. 2019

Zeitschrift anorg allge chemie

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1,1-Diamino-2,2-dinitroethylene (FOX-7), one of the most well-known energetic materials, has attracted broad attention around the world. To extend the chemistry of FOX-7, we present here a series of energetic salts based on 3-dinitromethyl-[1,2,4]triazine, which is prepared from FOX-7. All these salts were fully characterized using 1 H NMR, 13 C NMR, IR, and elemental analysis. In addition, the potassium salt (2), ammonium salt (5), and guanidinium salt (7) were further confirmed by single-crystal X-ray diffraction. Extensive hydrogen * Dr. Z. Ye E-Mail: yezw@njust.edu.cn [a] School of Chemical Engineering

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Section: Introductionmentioning

confidence: 99%

Nitrogen‐rich Salts based on 3‐Dinitromethyl‐[1,2,4]triazine: Synthesis, Characterization, and Performance

Dong

Yang

et al. 2019

Zeitschrift anorg allge chemie

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“…A more effective oxidative coupling of FOX-7 was achieved with sodium hypochlorite, resulting in formation of 4-4 and its isomer 4-5 in higher yields. 57 Additionally, reactions of 1-bromo-1,1-dinitro-2-(N-bromoamidino)ethane with TCICA give two analogous azo-bridged FOX-7 compounds (4-7 and 4-8). Given their high density, good detonation performance, and hypergolic properties, these FOX-7 derivatives with N−halogen functionalities demonstrate a wide range of potential applications for both high-performance explosives and propellants.…”

Section: ■ Introductionmentioning

confidence: 99%

Dancing with Energetic Nitrogen Atoms: Versatile N-Functionalization Strategies for N-Heterocyclic Frameworks in High Energy Density Materials

2015

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Nitrogen-rich heterocycles represent a unique class of energetic frameworks featuring high heats of formation and high nitrogen content, which have generated considerable research interest in the field of high energy density materials (HEDMs). Although traditional C-functionalization methodology of aromatic hydrocarbons has been fully established, studies on N-functionalization strategies of nitrogen-containing heterocycles still have great potential to be exploited by virtue of forming diverse N-X bonds (X = C, N, O, B, halogen, etc.), which are capable of regulating energy performance and the stability of the resulting energetic compounds. In this sense, versatile N-functionalization of N-heterocyclic frameworks offers a flexible strategy to meet the requirements of developing new-generation HEDMs. In this Account, the role of strategic N-functionalization in designing new energetic frameworks, including the formation of N-C, N-N, N-O, N-B and N-halogen bonds, is emphasized. In the family of N-functionalized HEDMs, energetic derivatives, by virtue of forming N-C bonds, are the most widely used type due to the good nucleophilic capacity of most heterocyclic backbones. Although introduction of carbon tends to decrease energetic performance, significant improvement in material sensitivity makes this strategy attractive for safety concerns. More importantly, most "explosophores" can be readily introduced into the N-C linkage, thus providing a promising route to various HEDMs. Formation of additional N-N bonds typically gives rise to higher heats of formation, implying the potential enhancement in detonation performance. In many cases, the increased hydrogen bonding interactions within N-N functionalized heterocycles also improve thermal stability accordingly. Introduction of a single N,N'-azo bridge into several azole moieties leads to an extended nitrogen chain, demonstrating a new strategy for designing high-nitrogen compounds. The strategy of N-O functionalization has become an increasingly efficient tool for exploring new HEDMs with both high energy and low sensitivity. As a highly dense building block, introduction of oxygen not only improves density significantly but also gives rise to a better oxygen balance. Furthermore, the N-O functionalized strategy is highly suitable for a broad variety of N-heterocycles including five-membered azoles and six-membered azines. Newly explored N-halogen and N-B functionalization strategies have endowed the resulting HEDMs with some new energetic characteristics. Typical examples include the N-halogenated fused triazole and FOX-7 as potential hypergolic oxidizers with very short ignition delay times. In addition, some exploratory studies of N-B functionalized heterocycles have expanded energetic applications as hypergolic ionic liquids, green pyrotechnic colorants, and high-oxygen carriers. Overall, flexible N-functionalization methodologies involving different N-X bond formation have not only provided an efficient approach to diverse energetic ingredients but also expanded...

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“…The resulting orange precipitate was filtered off, washed with methanol, and dried to obtain the potassium salt 2 (82%). Raman (1064 nm, 500 mW): ν = 3280 (3), 1595 (5), 1503 (12), 1397 (32), 1352 (44), 1238 (31), 1172 (36), 1132 (39), 1123 (34), 1083 (4), 926 (10), 852 (100), 750 (9), 653 (9), 525 (12). Anal.…”

Section: ■ Introductionmentioning

confidence: 99%

“…The water-free product was obtained by dehydration at 70 °C for 24 h under high vacuum. Raman (1064 nm, 800 mW): ν = 3380 (5), 3290 (7), 1709 (7), 1589 (10), 1555 (25), 1535 (52), 1423 (21), 1379 (30), 1353 (76), 1300 (100), 1270 (46), 1206 (30), 1147 (27), 1103 (50), 1048 (26), 959 (7), 873 (91), 802 (9), 789 (8), 751 (13). Mass spectometry (MS) (DEI+) m/e: 206.…”

Section: ■ Introductionmentioning

confidence: 99%

“…1 H NMR ([D 6 ]DMSO): δ = 12.17 (s, 1H, CNH), 7.69 (s, 2H, CNH), 6.93 (s, 4H, CONH 2 ), 13 C NMR ([D 6 ]DMSO): δ = 154.0 (CO), 149.5 (CO), 140.5 (CNN), 123.5 (br, CNO 2 ) ppm. 15 (12), 3007 (22), 1776 (14), 1603 (31), 1577 (81), 1398 (13), 1372 (25), 1323 (24), 1243 (18), 1186 (22), 1153 ((26), 1104 (28), 939 (100), 914 (32), 870 (8), 795 (8), 619 (10), 573 (9), 538 (16) Potassium (1-Carbamoyl-5-oxo-1,2,4-triazol-3-yl) dinitromethanide (6_K). 5 (0.49 g, 2.0 mmol) was stirred in water (10 mL), and a saturated solution of potassium bicarbonate was added to the reaction mixture until the pH value was stable at ∼7.5.…”

Section: ■ Introductionmentioning

confidence: 99%

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The Exciting Chemistry of 1,1-Diamino-2,2-dinitroethene and 1-Amino-1-hydrazino-2,2-dinitroethene

2017

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1,1-Diamino-2,2-dinitroethene (FOX-7) is a relatively new highly energetic material, with good explosive performance and low sensitivity against mechanical stimuli and thermal stress. Therefore, on the one hand, FOX-7 is very stable and a starting material with fairly low reactivity. On the other hand, chlorosulfonyl isocyanate ClSONCO is a very reactive reagent and represents a highly activated form of isocyanic acid HNCO. New derivatives of FOX-7 and its hydrazine analogue 1-amino-1-hydrazino-2,2-dinitroethene, as well as unusual potassium salts, are described. Besides the usual spectroscopic characterization, the structures of all compounds were investigated and discussed by single-crystal X-ray diffraction. The compounds demonstrate good thermal stabilities, very high densities, and excellent sensitivity values. The heats of formation were calculated, and together with the room-temperature densities, the energetic parameters were estimated. The compounds are potential candidates as insensitive high-energy-density materials and starting materials for further chemistry.

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The Many Faces of FOX‐7: A Precursor to High‐Performance Energetic Materials

Abstract: New derivatives of 1,1-diamino-2, 2-dinitroethene (FOX-7) are reported. These highly oxygen-and nitrogen-rich compounds were fully characterized using IR and multinuclear NMR spectroscopy,

Cited by 17 publications

References 32 publications

Nitrogen‐rich Salts based on 3‐Dinitromethyl‐[1,2,4]triazine: Synthesis, Characterization, and Performance

Nitrogen‐rich Salts based on 3‐Dinitromethyl‐[1,2,4]triazine: Synthesis, Characterization, and Performance

Dancing with Energetic Nitrogen Atoms: Versatile N-Functionalization Strategies for N-Heterocyclic Frameworks in High Energy Density Materials

The Exciting Chemistry of 1,1-Diamino-2,2-dinitroethene and 1-Amino-1-hydrazino-2,2-dinitroethene

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