17557-81-2Relevant academic research and scientific papers
Safer and Convenient Synthesis of 3,4-Dicyanofuroxan
Johnson, Eric C.,Bukowski, Eric J.,Sausa, Rosario C.,Sabatini, Jesse J.
, p. 1275 - 1279 (2019)
A safer, convenient, cost-effective, and scalable synthesis for 3,4-dicyanofuroxan (C4N4O2) is described. Dropwise treatment of a well-stirred suspension of cyanoacetic acid in dichloromethane with concentrated mixed acid (HNO3/H2SO4) affords dicyanofuroxan in 72% yield and in 84% purity after liquid chromatography analysis. Single crystal X-ray diffraction studies further confirm the product and yield its molecular conformation and crystal packing. During the dropwise addition of mixed acid, self-heating occurs, and this event is necessary for the reaction to adequately proceed. However, such self-heating is limited to the refluxing temperature of dichloromethane. This new method supersedes the previous methods used to synthesize dicyanofuroxan, which were low-yielding and of significantly lower purity, irreproducible, relied on expensive reagents, and suffered from dangerous exothermic profiles.
High Energy Density Materials Incorporating 4,5-Bis(dinitromethyl)-Furoxanate and 4,5-Bis(dinitromethyl)-3-Oxy-Furoxanate
Zhai, Lianjie,Qu, Xiaoni,Wang, Bozhou,Bi, Fuqiang,Chen, Sanping,Fan, Xuezhong,Xie, Gang,Wei, Qing,Gao, Shengli
, p. 1156 - 1159 (2016)
3-Oxy-furoxanate is immobilized in a heterometallic energetic metal–organic framework (MOFs). Two furoxan-based MOFs ([Ag2K4(BDOFO)(BDFO)2(H2O)6]n, [K2(BDFO)]n) and a salt ([(BDFO2?)(NH2NH3 +)2(H2O)]n (BDOFO2?=4,5-bis(dinitromethyl)-3-oxy-furoxanate, BDFO2?=4,5-bis(dinitromethyl)-furoxanate) are synthesized and their energetic performance evaluated. This study outlines the systematic investigation of detonation performance of 3-oxy-furoxan and its derivatives.
Potassium 4,5-Bis(dinitromethyl)furoxanate: A Green Primary Explosive with a Positive Oxygen Balance
He, Chunlin,Shreeve, Jean'ne M.
, p. 772 - 775 (2016)
Potassium 4,5-bis(dinitromethyl)furoxanate was synthesized readily from cyanoacetic acid. It was characterized by IR spectroscopy, elemental analysis, NMR spectroscopy, and differential scanning calorimetry (DSC), and the structure was confirmed by X-ray single-crystal diffraction. Its positive oxygen balance, high density (2.130 g cm-3), sensitivity (IS=2 J, FS=5 N), and calculated heat of formation (-421.0 kJ mol-1), combined with its calculated superior detonation performance (D=7759.0 m s-1, P=27.3 GPa), make it a competitive replacement as a green primary explosive.
Energetic 1,2,5-Oxadiazolo-Pyridazine and its N-Oxide
Tang, Yongxing,He, Chunlin,Imler, Gregory H.,Parrish, Damon A.,Shreeve, Jean'ne M.
, p. 15022 - 15025 (2017)
Achieving an energetic compound, which exhibits high performance and insensitivity, is important in the field of energetic materials and remains a major challenge. Herein, we found that oxidation of 4,7-diaminopyridazino[4,5-c]furoxan (5) with a mixture of 50 % hydrogen peroxide and trifluoroacetic anhydride gave 6-amino-7-nitro-[1,2,5]oxadiazolo[3,4-c]pyridazine (7) and its N-oxide derivative (8). The oxidation of 5 with hypofluorous acid (HOF) was also studied. Compound 8 displayed an energetic performance compared to triaminotrinitrobenzene (TATB) and insensitive properties (impact sensitivity (IS) 36 J and friction sensitivity (FS)>360 N). Such excellent properties make 8 attractive for high-performance applications, in which insensitivity is important.
Bis(Nitroxymethylisoxazolyl) Furoxan: A Promising Standalone Melt-Castable Explosive
Johnson, Eric C.,Sabatini, Jesse J.,Chavez, David E.,Wells, Lucille A.,Banning, Joseph E.,Sausa, Rosario C.,Byrd, Edward F. C.,Orlicki, Joshua A.
, p. 237 - 239 (2020)
The synthesis and crystal structure of the heterocyclic explosive bis(nitroxymethylisoxazolyl) furoxan, C10H6N6O10, are described. In addition, we report its physical properties and theoretical performance. This material was found to exhibit standalone melt-castable explosive properties, with a melting point of 89.8 °C and an onset decomposition temperature of 193.8 °C. Bis(nitroxymethylisoxazolyl) furoxan features an insensitive behavior to impact, friction, and electrostatic discharge, with a calculated detonation pressure about 25 % higher than the state-of-the-art melt-castable explosive TNT.
Bis(1,2,4-oxadiazolyl) Furoxan: A Promising Melt-Castable Eutectic Material of Low Sensitivity
Johnson, Eric C.,Bukowski, Eric J.,Sabatini, Jesse J.,Sausa, Rosario C.,Byrd, Edward F. C.,Garner, Melissa A.,Chavez, David E.
, p. 319 - 322 (2019)
A scalable synthesis of bis(1,2,4-oxadiazoyl) furoxan, C6H2N6O4, its physical properties, and its theoretical performance values are described. Previous attempts to synthesize this compound required expensive reagents, and/or time-consuming synthesis processes and low overall yields. In addition to disclosing a streamlined synthesis of bis(1,2,4-oxadiazolyl) furoxan, we report its molecular configuration and crystal structure, as well as its correct melting point. Bis(1,2,4-oxadiazolyl) furoxan exhibits a very insensitive behavior to impact, friction, and electrostatic discharge, with a calculated detonation pressure 20 % higher than that of TNT. Given its physical properties and theoretical performance values, this material can be classified as a promising ingredient in the development of melt-castable eutectic technology.
Preparation method of 3,4-dicyanofuroxan
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Paragraph 0027 0031; 0035; 0040, (2017/09/18)
The invention discloses a preparation method of 3,4-dicyanofuroxan (DCFO). The preparation method comprises the following specific steps: adding nitric-sulfuric acid into a dichloromethane dispersion liquid of cyanoacetic acid, and continuously stirring the mixture to finish reaction; then cooling the mixture; continuously adding cold water into a reaction system; then separating a solvent phase and a water phase from an extraction liquid; washing the solvent phase with saturated table salt water to neutral; performing drying, filtration and solvent recovery on the solvent phase to separate a 3,4-dicyanofuroxan solid product. By replacing a trifluoroacetic acid reaction medium by dichloromethane, the yield of a target product is remarkably increased, the method is simple and feasible to operate, and the raw materials are easily available and are relatively low in cost. By dropwise adding a mixed acid nitrifying agent into a non-reactive medium, influence of water in the raw material on reaction can be removed, the probability of side reactions is reduced, heat released in acid adding and reaction processes is more immediately and uniformly diffused, and the process safety is improved and the yield of the target product is increased.
An efficient access to (1H-tetrazol-5-yl)furoxan ammonium salts via a two-step dehydration/[3+2]-cycloaddition strategy
Fershtat, Leonid L.,Epishina, Margarita A.,Kulikov, Alexander S.,Ovchinnikov, Igor V.,Ananyev, Ivan V.,Makhova, Nina N.
, p. 6764 - 6775 (2015/08/24)
A general, highly effective two-step approach for direct synthesis of (1H-tetrazol-5-yl)furoxan ammonium salts with various functional substituents based on initial effective synthesis of cyanofuroxans by dehydration of furoxancarboxylic acid amides by th
Novel reaction of [bis(acyloxy)iodo]arenes
Sheremetev, Aleksei B.,Konkina, Svetlana M.
, p. 277 - 278 (2007/10/03)
The reaction of [(diacetoxy)iodo]benzene with furazan dicarboxylic acid was accompanied by a novel decarboxylative ring-cleavage reaction; the cyanogen N-oxide, reactive intermediate generated in the process, was dimerised or trapped by a dipolarophile.
Novel synthesis of 3,4-dicyanofuroxan
Mel'nikova,Novikova,Khmel'nitskii,Sheremetev
, p. 30 - 31 (2007/10/03)
3,4-Dicyanofuroxan was synthesised by diazotization of aminofurazans bearing the second substituent that can be eliminated as a cationic species.
