- Optimization Studies on Synthesis of TKX-50
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A systematic study of TKX-50 and ABTOX synthesis using both Klap?tke and Tselinskii modified procedures is described. The influence of temperature, moisture, acid amount and nature on the most critical synthesis step – diazidoglyoxime cyclization is shown. Experimental results show that presence of moisture in reaction mixture leads to product yield decreasing. The reaction temperature is another key parameter affecting product yield. High reaction temperature shows negative influence on the product yield in Klap?tke method. In Tselinskii procedure the yield of product grows with the reaction temperature increasing. For Klap?tke one-pot method, combination of N-methyl-2-pyrrolidone with 1,4-dioxane is the best solvent, whereas Tselinskii one-pot procedure gives high yield of product when combination of toluene with 0.5 equiv. of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) is used. Using optimized conditions one-pot five-step synthesis of TKX-50 starting from glyoxime is successfully performed and scaled up to 50 g.
- Golenko, Yulia D.,Topchiy, Maxim A.,Asachenko, Andrey F.,Nechaev, Mikhail S.,Pleshakov, Dmitriy V.
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- Novel insensitive energetic-cocrystal-based BTO with good comprehensive properties
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Combining a layer construction strategy with cocrystallization techniques, we designed and prepared a structurally unusual 1H,1′H-5,5′-bistetrazole-1,1′-diolate (BTO) based energetic cocrystal, which we also confirmed by single-crystal X-ray diffraction and powder-crystal X-ray diffraction. The obtained cocrystal crystallizes in a triclinic system, P-1 space group, with a density of 1.72 g cm-3. The properties including the thermal stability, sensitivity and detonation performance of the cocrystal were analyzed in detail. In addition, the thermal decomposition behavior of the cocrystal was studied by differential calorimetry and thermogravimetry tandem infrared spectroscopy. The results indicated that the cocrystal exhibits strong resistance to thermal decomposition up to 535.6 K. The cocrystal also demonstrates a sensitivity of >50 J. Moreover, its formation enthalpy was estimated to be 2312.0 kJ mol-1, whereas its detonation velocity and detonation pressure were predicted to be 8.213 km s-1 and 29.1 GPa, respectively, by applying K-J equations. Therefore, as expected, the obtained cocrystal shows a good comprehensive performance, which proves that a high degree of layer-by-layer stacking is essential for the structural density, thermal stability and sensitivity.
- Tao, Jingjing,Jin, Bo,Chu, Shijin,Peng, Rufang,Shang, Yu,Tan, Bisheng
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- Synthesis of bis-Isoxazole-bis-Methylene Dinitrate: A Potential Nitrate Plasticizer and Melt-Castable Energetic Material
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The efficient and scalable synthesis of 3,3′-bis-isoxazole-5,5′-bis-methylene dinitrate and its energetic properties are described. The material has favorable sensitivity properties; energetic properties point toward its potential as both a melt-castable secondary explosive and as a propellant plasticizer.
- Wingard, Leah A.,Guzmán, Pablo E.,Johnson, Eric C.,Sabatini, Jesse J.,Drake, Gregory W.,Byrd, Edward F. C.
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- Synthesis and Synthetic Application of Chloro- And Bromofuroxans
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Furoxans are potentially useful heteroaromatic units in pharmaceuticals and agrichemicals. However, the applications for furoxan-based compounds have been hampered due to the underdevelopment of their synthetic methods. Herein, we report a new synthetic approach for the synthesis of chloro- and bromofuroxans. The starting materials were dichloro- and dibromofuroxans, and the substituents were directly introduced to the furoxan ring in a modular fashion. The synthesized monohalofuroxans served as substrates for the installation of a second substituent to prepare further functionalized furoxans.
- Ando, Akihiro,Hasebe, Hayu,Hayashi, Masahiko,Kim, Hojin,Matsubara, Ryosuke,Tsuneda, Takao
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- Nitrogen-rich energetic salts of 1: H,1′ H -5,5′-bistetrazole-1,1′-diolate: Synthesis, characterization, and thermal behaviors
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A series of nitrogen-rich heterocyclic 1H,1′H-5,5′-bistetrazole-1,1′-diolate salts, namely, 1,2,4-triazolium (2), 3-amino-1,2,4-triazolium (3), 4-amino-1,2,4-triazolium (4), 3,5-diamino-1,2,4-triazolium (5), 2-methylimidazolium (6), imidazolium (7), pyrazolium (8), 3-amino-5-hydroxypyrazolium (9), dicyandiamidine (10), and 2,4-diamino-6-methyl-1,3,5-triazin (11), was synthesized with cations. These energetic salts were fully characterized through FT-IR, 1H NMR, 13C NMR, and elemental analysis. The structures of 2, 3·7H2O, 6·2H2O, 8, and 10·4H2O were further confirmed through single crystal X-ray diffraction. Their thermal stabilities were investigated through differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA). The results indicated that all of the salts possess excellent thermal stabilities with decomposition temperatures ranging from 225.7 °C to 314.0 °C. On the basis of the Kamlet-Jacobs formula, we carefully calculated their detonation velocities and detonation pressures. All of the salts, except 11, exhibit promising detonation performances with a detonation pressure of 20.23-28.69 GPa and a detonation velocity of 7050-8218 m s-1. These values are much higher than those of TNT. The impact sensitivities of the compounds were determined via a Fall hammer test. All of the compounds show excellent impact sensitivities of >50 J, and this finding is higher than that of TATB (50 J). Therefore, these ionic salts with excellent energetic properties could be applied as new energetic materials.
- Shang, Yu,Jin, Bo,Peng, Rufang,Guo, Zhicheng,Liu, Qiangqiang,Zhao, Jun,Zhang, Qingchun
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- A Chlorine Gas-Free Synthesis of Dichloroglyoxime
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A new procedure for the synthesis and isolation of dichloroglyoxime is discussed. This material has historically been synthesized from glyoxime and elemental chlorine gas. Chlorine gas is difficult to handle and control in the laboratory and has a high toxicity profile. Our method for making dichloroglyoxime in high purity uses glyoxime and N-chlorosuccinimide in DMF, with a lithium chloride-based workup. Overall yields are comparable with those obtained using the procedure involving the use of chlorine gas.
- Wingard, Leah A.,Guzmán, Pablo E.,Sabatini, Jesse J.
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- Nitrogen-rich salts of 1H,1′H-5,5′-Bitetrazole-1,1′-diol: Energetic materials with high thermal stability
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1H,1′H-5,5′-Bitetrazole-1,1′-diol was synthesized starting from glyoxal, which is converted to glyoxime after treatment with hydroxylamine. Chlorination of glyoxime with Cl2 gas in ethanol and following chloro/azido exchange yields diazidoglyoxime, which is cyclized under acidic conditions (HCl gas in diethyl ether) to give 1H,1′H-5,5′- bitetrazole-1,1′-diol dihydrate (1). A large variety of nitrogen-rich salts of 1 such as the diammonium (2), the dihydrazinium (3), the bis-guanidinium (4), the bis(aminoguanidinium) (5), the diaminoguanidinium salt monohydrate (6), the triaminoguanidinium salt monohydrate (7), the 1-amino-3-nitroguanidinium salt dihydrate (8), the diaminouronium salt monohydrate (9), the bis(oxalyldihydrazidinium) (10), the oxalyldihydrazidinium salt dihydrate (11), the 3,6-dihydrazino-1,2,4,5-tetrazinium (12), the 5-aminotetrazolium (13), the bis(5-amino-1-methyl-1H-tetrazolium) salt (14), the bis(5-amino-2-methyl-2H-tetrazole) adduct (15), and the 1,5-diaminotetrazolium salt (16) were synthesized by means of Bronsted acid-base or metathesis reactions. All compounds were fully characterized by vibrational spectroscopy (IR and Raman), multinuclear NMR spectroscopy, elemental analysis, and differential scanning calorimetry (DSC) measurements. The crystal structures of 1-16 could be determined by using single-crystal X-ray diffraction. The heats of formation of 1-16 were calculated by using the atomization method on the basis of CBS-4M enthalpies. With regard to their potential use as cyclotrimethylene trinitramine (RDX) or hexanitrostilbene (HNS) replacements, several detonation parameters such as the detonation pressure, detonation velocity, explosion energy, and explosion temperature were computed using the EXPLO5 code on the basis of the experimental (X-ray) densities and calculated heats of formation. In addition, the sensitivities towards impact, friction, and electrical discharge were tested using the BAM drop hammer, a friction tester, as well as a small-scale electrical discharge device. Copyright
- Fischer, Niko,Klapoetke, Thomas M.,Reymann, Marius,Stierstorfer, Joerg
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- Twofold cycloaddition of [60]fullerene to a bifunctional nitrile oxide
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Bi-([60]fullereno[1,2-d]isoxazole-3-yl)1 (4) was synthesised by twofold 1,3-dipolar cycloaddition of [60]fullerene to cyanogen di-N-oxide (3) and characterised by 13C NMR, IR, UV/VIS and MALDI-TOF mass spectrometry. Isomeric mixtures of higher molecular copolymerisation products 5 could be detected by MALDI-TOF MS.
- Irngartinger, Hermann,Weber, Anton
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- Preparation and characterization of nitrogen-rich bis-1-methylimidazole1H,1′H-5,5′-bistetrazole-1,1′-diolate energetic salt
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A new nitrogen-rich energetic salt of bis-1-methylimidazole 1H,1′H-5,5′-bistetrazole-1,1′-diolate salt, (1-M)2BTO, was synthesized and characterized (FT-IR, 1H NMR, 13C NMR, elemental analysis, and X-ray single-crystal diffraction). Results indicated that (1-M)2BTO crystallizes in the triclinic space group P-1. The thermal decomposition behavior of (1-M)2BTO was determined by differential scanning calorimetry (DSC) and thermogravimetric tandem infrared spectroscopy. The decomposition peak temperature of (1-M)2BTO was 530 K, which suggested that the salt is strong heat resistance. The apparent activation energies were 130.56 kJ mol?1 (Kissinger’s method) and 132.50 kJ mol?1 (Ozawa’s method), respectively. The enthalpy of formation for the salt was calculated as 917.3 kJ mol?1. The detonation velocity and detonation pressure of (1-M)2BTO were 7448 m s?1 and 20.7 GPa, respectively, using the Kamlet-Jacobs equation. Furthermore, the sensitivity test results showed that its impact sensitivity is greater than 50 J and friction sensitivity is 180 N, indicating that it has a lower sensitivity.
- Luo, Liqiong,Jin, Bo,Peng, Rufang,Shang, Yu,Xiao, Lipengcheng,Chu, Shijin
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- Merging Halogen-Atom Transfer (XAT) and Cobalt Catalysis to Override E2-Selectivity in the Elimination of Alkyl Halides: A Mild Route towardcontra-Thermodynamic Olefins
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We report here a mechanistically distinct tactic to carry E2-type eliminations on alkyl halides. This strategy exploits the interplay of α-aminoalkyl radical-mediated halogen-atom transfer (XAT) with desaturative cobalt catalysis. The methodology is high-yielding, tolerates many functionalities, and was used to access industrially relevant materials. In contrast to thermal E2 eliminations where unsymmetrical substrates give regioisomeric mixtures, this approach enables, by fine-tuning of the electronic and steric properties of the cobalt catalyst, to obtain high olefin positional selectivity. This unprecedented mechanistic feature has allowed access tocontra-thermodynamic olefins, elusive by E2 eliminations.
- Zhao, Huaibo,McMillan, Alastair J.,Constantin, Timothée,Mykura, Rory C.,Juliá, Fabio,Leonori, Daniele
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supporting information
p. 14806 - 14813
(2021/09/18)
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- METHOD FOR SYNTHESIS OF TKX-50 USING INSENSITIVE INTERMEDIATE
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The present invention relates to a method for synthesis of TKX-50 using an insensitive intermediate and, more specifically, to a method for producing TKX-50, the method comprising the steps of: preparing DCG as a starting material; forming a THP-DAG intermediate from the DCG; and synthesizing TKX-50 through the THP-DAG intermediate.
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Paragraph 0066
(2021/06/04)
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- Bis(Substituted Phenylamino)Glyoxime derivatives: Synthesis, characterization, and antimicrobial evaluation
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In present work, a set of bis(substituted phenylamino) glyoxime derivatives are presented by the dropwise addition of corresponding primary aryl amines to the dichloroglyoxime (1). Reactions of corresponding primary aryl amines containing various substituents in different positions with dichloroglyoxime (1) gave thirteen compounds. The structural characterization of a set of bis(substituted phenylamino) glyoxime derivatives have been performed on the basis of FTIR, mass, proton, and carbon NMR methods. The crystal structure of compound 3a has been determined by X-ray diffraction on a single crystal. The NMR spectrum and X-ray data of 3a show that two hydroxyl groups of dioxime situated at anti position. Furthermore, all of the synthesized compounds (3a-m) were tested for in vitro both antimicrobial activity. The minimal inhibitory concentrations (MICs) against 7 bacteria and 3 yeasts were also determined. Among them, compound 3f was the most potent compound against S. aureus with the value of MIC = 9.76 μg/mL for the antibacterial activity, in addition to this, compound 3i has a good potency against S. aureus and C. tropicalis (MIC = 78.12 μg/mL) for both antibacterial and antifungal activities, respectively.
- Bayrak, Nilüfer,Matarac?-Kara, Emel,Ozbek-Celik, Berna,Tuyun, Ama? Fatih,Y?ld?r?m, Hatice,Y?ld?z, Mahmut
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- Method for preparation of insensitive high explosive
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The present invention provides a method for the preparation of an insensitive high enthalpy explosive Dihydroxylammonium 5,5′-bistetrazole-1,1′-diolate (TKX-50) in the presence of N,N-dimethylformamide, N,N-dimethylacetamide, or N-Methyl-2-pyrrolidone as a solvent via a four-step, one-pot reaction route to obtain a final product after four reaction steps. The more dangerous intermediate diazidoglyoxime may be solved by the one-pot method without the need of isolation. Further, the cyclization reaction is carried out in the presence of dropwisely added concentrated sulfuric acid to replace hydrochloric gas so no hydrochloric gas generator is needed to greatly reduce the amount of waste acid so as to effectively reduce the cost by avoiding using hydrochloric gas steel cylinders which require much safety equipment.
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Page/Page column 7-10
(2021/11/03)
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- SYNTHESIS OF TKX-50 USING INSENSITIVE INTERMEDIATE
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The present invention relates to a method for synthesizing TKX-50 using an insensitive intermediate. More specifically, the present invention relates to a method for manufacturing TKX-50 comprising the following steps: preparing DCG as a starting material; forming a THP-DAG intermediate from the DCG; and synthesizing TKX-50 through the THP-DAG intermediate. The present invention allows an operator to synthesize TKX-50 more safely.(AA) Glyoxal(BB) GlyoximeCOPYRIGHT KIPO 2020
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Paragraph 0061; 0062
(2020/05/01)
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- SYNTHESIS OF TKX-50 USING INSENSITIVE INTERMEDIATE
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TKX-50 Is a method for synthesizing, using an obtuse intermediate, in which DCG is prepared from the starting material; and DCG is formed from THP-DAG, and; is synthesized through the THP-DAG intermediate. TKX-50. The method of; comprising the steps, TKX-50 and. (by machine translation)
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Paragraph 0024; 0061-0062
(2020/06/06)
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- FUNCTIONALITY PROTECTED DIAZIDOGLYOXIME AND SYNTHESIS METHOD OF THE SAME
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Is a,sectional view of a diazidoglycol protected with a functional group according to an embodiment of the present invention 1, which is represented by the following Formula : [Formula 1] (Wherein, R denotes tetrahydropyranyl (Tetrahydropyranyl; THP), methyl (Methyl; Me), methoxymethyl (Methoxymethyl; MOM),methoxymethyl (Methoxythiomethyl; MTM),methoxymethyl (Benzyloxymethyl; BOM), 2- methoxymethyl-(2-Methoxymethyl; MEM), 2-(-methoxymethyl)-methoxybenzyl ((2-(Trimethylsilyl)ethoxymethyl); SEM), trimethylsilyl-(Tetrahydrofuranyl; THF), t-methoxyethyl-(t-Butyl),methoxyethyl-(Allyl),trimethoxyacetate (Benzyl), p- dimethoxymethyl (p-Methoxybenzyl), 3,4-methylsilyl (3,4-Dimethoxybenzyl), o-trimethoxyethyl] (o-Nitrobenzyl), p-trimethoxyethyl -t- triethylsilyl (p-Nitrobenzyl),trimethoxyethyl] (Chloroacetate),butyl (Triphenylmethyl), (Triphenylmethoxyacetate),methylsilyl-(Benzoate) hexyl p- (Di-t-butylmethylsilyl; DTBMS), (Trimethylsilyl; TMS),(Acetate; Ac), methoxybenzyl (Triethylsilyl; TES),(Methoxyacetate), trimethoxyethyl] (Pivaloate), (Triisopropylsilyl; TIPS), t-trimethoxyethyl (p-Toluenesulfonate; Ts). (t-Butyldimethylsilyl; TBDMS), t-trimethoxyethyl]-butyl-(t-Butyldiphenylsilyl; TBDPS),).methylsilyl-triethylsilyl-trimethoxyethyl]-benzenesulfonate (Diphenylmethylsilyl; DPMS). (by machine translation)
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Paragraph 0087; 0091-0093
(2020/06/09)
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- METHOD FOR PREPARING DIHYDROXYLAMMONIUM 5,5'-BISTETRAZOLE-1,1'-DIOLATE
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The present invention relates to a method for manufacturing dihydroxylammonium 5,5andprime;-bistetrazole-1,1andprime;-diolate. More specifically, the present invention relates to the method for manufacturing dihydroxylammonium 5,5andprime;-bistetrazole-1,1andprime;-diolate using a diaminoglyoxime intermediate. The present invention can provide a safe and convenient method for manufacturing TKX-50.(AA) ^(13)C-NMR spectrum of TKX-50COPYRIGHT KIPO 2019
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Paragraph 0061; 0065-0067
(2019/05/15)
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- Preparation method of dichloroglyoxime solid
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The invention relates to a preparation method of dichloroglyoxime solid. According to the method, glyoxime, hydrochloric acid and oxydol are used as raw materials for preparing the dichloroglyoxime through oxidization reaction and chlorination reaction. Compared with the existing synthesis method, the method belongs to a novel simple and reliable synthesis method of the dichloroglyoxime, and has the advantages that the reaction conditions are mild; the operation is simple; the product yield is high, and the like. The use and generation of toxic and harmful Cl2 can be avoided; the method is particularly suitable for amplified production and can easily realize the amplified production.
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Paragraph 0032-0055
(2019/02/04)
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- INSENSITIVE PLASTICIZER AND MELT-CASTABLE ENERGETIC MATERIAL
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A method and compound includes mixing dichloroglyoxime with an alcohol containing an alkyne functional group in methanol to create a mixture; adding a salt compound and water to the mixture to create bis-isoxazole diol; and nitrating the bis-isoxazole diol to create 3,3′-bis-isoxazole-5,5′-bis-methylene dinitrate, which has the structural formula: The alcohol containing an alkyne functional group may include propargyl alcohol. The salt compound may include sodium bicarbonate. The method may include nitrating the bis-isoxazole diol with nitric acid. The nitric acid may include at least a concentration of 90% nitric acid in water. Alternatively, the method may include nitrating the bis-isoxazole diol with 100% nitric acid and acetic anhydride. The salt compound and the water may be added to the mixture over at least a six-hour period. The method may include mixing the mixture after adding the salt compound and the water for at least ten hours.
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Paragraph 0013; 0039
(2019/03/08)
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- PREPARATION METHOD FOR HIGH PURITY AND HIGH YIELD DICHLOROGLYOXIME
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The present invention relates to a method for synthesizing dichloroglyoxime (DCG). The present invention provides a method for preparing DCG by performing chlorination reaction with glyoxime, concentrated hydrochloric acid (HCl conc.), and potassium mono peroxy sulfate (Oxone^andreg;) in a dimethylformamide (DMF) solvent at room temperature. An objective of the present invention is to develop a production method which can obtain high purity DCG in a solid state by mass-synthesizing at a high yield.COPYRIGHT KIPO 2018
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Paragraph 0027-0028; 0032
(2018/05/09)
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- Bis-isoxazole tetranitrate (BITN): a high-energy propellant plasticizer and melt-castable eutectic explosive ingredient
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A method and compound includes mixing a salt compound to 2-butyne-1,4-diol in an alcohol to create a mixture; adding a solution of dichloroglyoxime in an alcohol to the mixture to create 3,3′-bis-isoxazole-4,4′,5,5′-tetryltetramethanol; and nitrating the 3,3′-bis-isoxazole-4,4′,5,5′-tetryltetramethanol to create 3,3′-bis-isoxazole-4,4′,5,5′-tetrylbis(methylene) tetranitrate, which has the structural formula: The alcohol may include ethanol, wherein the adding may occur at 60° C., or alternatively the adding may occur at 80° C. The alcohol may include n-butanol, wherein the adding may occur at 100° C., or alternatively the adding may occur at 120° C. The mixing may occur at 120° C. The method may further include cooling the nitrated 3,3′-bis-isoxazole-4,4′,5,5′-tetryltetramethanol to 0° C.; stirring the cooled nitrated 3,3′-bis-isoxazole-4,4′,5,5′-tetryltetramethanol for at least four hours creating a precipitate; warming the precipitate; pouring the precipitate onto ice while stirring creating a solid material; collecting the solid material; and drying the solid material to yield the 3,3′-bis-isoxazole-4,4′,5,5′-tetrylbis(methylene) tetranitrate.
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- Production of dichloroglyoxime
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The present invention addresses the problem of providing a dichloroglyoxime production method by which dichloroglyoxime, which can be used as an industrial anti-bacterial agent, a preservative, a slime control agent or the like, can be obtained with greater safety and efficiency. In order to solve this problem, the present invention provides a method for producing dichloroglyoxime by reacting glyoxal with hydroxylamine and then chlorinating, the method additionally including: a step of incorporating a water-immiscible low boiling point organic solvent; a step of incorporating 20-90% of water following completion of the chlorination so as to cause separation into two layers, and then separating the organic layer; and a step of removing a water-miscible low boiling point organic solvent from the organic layer.
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Paragraph 0034-0041
(2017/12/27)
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- Synthesis, thermal behavior, and energetic properties of diuronium 1H,1′H-5,5′-bistetrazole-1,1′-diolate salt
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A new nitrogen-rich energetic salt called diuronium 1H,1′H-5,5′-bistetrazole-1,1′-diolate (DUBTO) was first synthesized by reacting urea with 1H,1′H-5,5′-bistetrazole-1,1′-diolate dihydrate (H2BTO 2H2O). The structure of this new energetic salt was fully characterized through single-crystal X-ray diffraction, FT-IR, 1H NMR, 13C NMR, and elemental analysis. DUBTO was crystallized in the monoclinic space group P21/n. The thermal stability was investigated through differential scanning calorimetry (DSC) and thermogravimetric tandem infrared spectrometry. Results showed that DUBTO contained one endothermic process and two exothermic processes. The second exothermic process is mainly intense exothermic decomposition with a mass loss of approximately 69.3% in the temperature range of 523.8–594.6?K. The non-isothermal kinetic parameters of the main exothermic process were calculated based on methods proposed by Kissinger and Ozawa-Doyle. Based on the Kamlet-Jacobs formula, the detonation velocity and detonation pressure of DUBTO were calculated as 8267?m?s?1 and 29.15?GPa, respectively.
- Shang, Yu,Jin, Bo,Liu, Qiangqiang,Peng, Rufang,Guo, Zhicheng,Zhang, Qingchun
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p. 519 - 525
(2016/12/30)
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- One-pot process for preparation of ammonium and hydroxyl ammonium derivatives of bis 5,5′-tetrazole-1,1′-dihydroxide
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A one-pot process for preparing ammonium and hydroxylammonium salts of bis 5,5′-tetrazole-1,1′-dihydroxide, specifically, diammonium bis 5,5′-tetrazole-1,1′-diolate (ABTOX) and dihydroxylammonium 5,5′-bistetrazole-1,1′-diolate (TKX-50). The process requires the reaction of sodium azide, dichloroglyoxime, HCl in dioxane solution to form bis 5,5′-tetrazole-1,1′-dihydroxide and treating this product with either ammonium chloride to produce ABTOX or hydroxylamine hydrochloride to produce TKX-50.
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(2017/05/31)
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- N -Oxides light up energetic performances: Synthesis and characterization of dinitraminobisfuroxans and their salts
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4,4′-Diamino-[3,3′-bi(1,2,5-oxadiazole)]-5,5′-dioxide and 4,4′-diamino-[3,3′-bi(1,2,5-oxadiazole)]-2,2′-dioxide were nitrated in 100% HNO3 at -10 °C to give 4,4′-dinitramino-[3,3′-bi(1,2,5-oxadiazole)]-5,5′-dioxide (3) and 4,4′-diamino-[3,3′-bi(1,2,5-oxadiazole)]-2,2′-dioxide (4). Nine nitrogen-rich salts were prepared and were characterized by infrared and multinuclear NMR spectroscopy, elemental analysis, differential scanning calorimetry (DSC) and X-ray single crystal diffraction in some cases. Their detonation properties were evaluated by EXPLO 5 code using the measured density and calculated heat of formation. The sensitivities were determined by standard BAM methods. Several of the new molecules exhibit detonation and other properties which compete with or exceed those of HMX.
- He, Chunlin,Tang, Yongxing,Mitchell, Lauren A.,Parrish, Damon A.,Shreeve, Jean'Ne M.
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supporting information
p. 8969 - 8973
(2016/07/06)
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- A click chemistry approach to 5,5′-disubstituted-3,3′- bisisoxazoles from dichloroglyoxime and alkynes: Luminescent organometallic iridium and rhenium bisisoxazole complexes
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5,5′-Disubstituted-3,3′-bisisoxazoles are prepared in one step by the dropwise addition of aqueous potassium hydrogen carbonate to a mixture of dichloroglyoxime and terminal alkynes. The reaction exhibits a striking preference for the 5,5′-disubstituted 3,3′-bisisoxazole over the 4,5′-regioisomer. Organometallic iridium and rhenium bisisoxazole complexes are luminescent with emission wavelengths varying depending upon the identity of the 5,5′-substituent (phenyl, butyl).
- Van Der Peet, Phillip L.,Connell, Timothy U.,Gunawan, Christian,White, Jonathan M.,Donnelly, Paul S.,Williams, Spencer J.
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p. 7298 - 7304
(2013/08/23)
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- Pushing the limits of energetic materials - The synthesis and characterization of dihydroxylammonium 5,5′-bistetrazole-1,1′- diolate
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The safe preparation and characterization (XRD, NMR and vibrational spectroscopy, DSC, mass spectrometry, sensitivities) of a new explosive dihydroxylammonium 5,5′-bistetrazole-1,1′-diolate (TKX-50) that outperforms all other commonly used explosive materials is detailed. While much publicized high-performing explosives, such as octanitrocubane and CL-20, have been at the forefront of public awareness, this compound differs in that it is simple and cheap to prepare from commonly available chemicals. TKX-50 expands upon the newly exploited field of tetrazole oxide chemistry to produce a material that not only is easily prepared and exceedingly powerful, but also possesses the required thermal insensitivity, low toxicity, and safety of handling to replace the most commonly used military explosive, RDX (1,3,5-trinitro-1,3,5-triazacyclohexane). In addition, the crystal structures of the intermediates 5,5′-bistetrazole-1,1′-diol dihydrate, 5,5′-bistetrazole-1,1′-diol dimethanolate and dimethylammonium 5,5′-bistetrazole-1,1′-diolate were determined and presented.
- Fischer, Niko,Fischer, Dennis,Klapoetke, Thomas M.,Piercey, Davin G.,Stierstorfer, Joerg
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supporting information
p. 20418 - 20422
(2013/02/25)
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