88-88-0Relevant academic research and scientific papers
(Picrylamino)-1,2,4-triazole Derivatives - Thermally Stable Explosives
Chioato, Zoe L.,Klap?tke, Thomas M.,Mieskes, Frank,Stierstorfer, J?rg,Weyrauther, Michael
, p. 956 - 962 (2016)
3-(Picrylamino)-1,2,4-triazole (PATO) and 3-amino-5-(picrylamino)-1,2,4-triazole (APATO) were synthesized and analyzed. During the syntheses of the compounds, two interesting side-products were isolated. The reactions of PATO and APATO with different nitrogen-rich bases, such as ammonia, hydrazine, triethylamine, and triaminoguanidine, resulted in the deprotonation of both triazole compounds and the formation of the corresponding salts (cation/anion ratio = 1:1). The compounds were obtained at ambient temperature in H2O or EtOH as qualitatively pure products with the characteristic properties of secondary explosives. The compounds were characterized by multinuclear NMR, IR, and Raman spectroscopy as well as mass spectrometry. The low-temperature structures of two compounds were determined by single-crystal X-ray diffraction. The thermal stabilities were measured by differential scanning calorimetry (DSC). The sensitivities were determined through the BAM drophammer and friction tests. The heats of formation were calculated by the atomization method from the CBS-4M enthalpies and the densities determined by X-ray diffraction or pycnometry. Several detonation parameters including the detonation pressure, detonation velocity, detonation energy, and detonation temperature were computed with the EXPLO5 code.
Synthesis of pyridinium N-aryl/N-heteroarylcyclic ylides as potential energetic materials
Zhang, Hong,Wang, Zuoquan,Jabeen, Farukh,Gopinathan-Pillai, Girinath,Zhou, Wenfeng,Steel, Peter J.,Hall, C. Dennis,Katritzky, Alan R.
, p. 20 - 24 (2016)
The synthesis, characterization, and energetic properties of several types of nitrogen-rich pyridinium ylides are reported.
Synthesis, characterization and energetic properties of novel 1-methyl-1,2,4-triazolium N-aryl/N-pyridinyl ylids
Zhang, Hong,Wang, Zuoquan,Ghiviriga, Ion,Pillai, Girinath G.,Jabeen, Farukh,Arami, Justin A.,Zhou, Wenfeng,Steel, Peter J.,Dennis Hall,Katritzky, Alan R.
, p. 1079 - 1085 (2017)
Synthesis, characterization and energetic properties of novel, nitrogen-rich 1-methyl-1,2,4-triazolium N-aryl/N-pyridinyl ylids 3a–m are reported.
Synthesis and structural analysis of some nitroderivatives of a dopamine analog
M?d?lan, Augustin M.,Matache, Mihaela,Ionita, Petre
, p. 103 - 107 (2021/02/05)
Starting from 3,4-dimetoxyphenethylamine and 1-fluoro-2.4-dinitrobenzene, 1-chloro-2,4,6-trinitrobenzene and 4-chloro-7-nitro-1,2,3-benzoxadiazole, the corresponding secondary amines 1-3 were obtained through classical nucleophilic substitution. These were characterized by UV-Vis, fluorescence, IR, 1H- and 13C-NMR. For compound 2 the X-ray structure was also obtained.
Synthesis and biological evaluation of 2,4,6-trinitroaniline derivatives as potent antitumor agents
?nder, Ferah C?mert,Ay, Mehmet,Güng?r, Tu?ba,Hac?o?lu, Nelin,K??kar, Feray,Tokay, Esra
, p. 1629 - 1641 (2020/10/19)
Abstract: Nitro group-containing compounds are well known as effective anticancer drugs. The aim of the study is to synthesize a series of trinitroaniline derivatives to determine their potential antitumor activities on diverse cancer cell models, anti-apoptotic and anti-metastatic features on hepatoma cells. The anti-proliferative studies show that IC50 values of N-phenyl-2,4,6-trinitroaniline, N-(2,4,6-trinitrophenyl)naphthalen-1-amine, N-(2,4,6-trinitrophenyl)naphthalen-2-amine, N-(3-nitrophenyl)-2,4,6-trinitroaniline were similar to IC50 value of cisplatin in Hep3B cells. In fact, IC50 value of N-(3,5-difluorophenyl)-2,4,6-trinitroaniline is better than cisplatin. In addition, all compounds could decrease the expression of the cell cycle checkpoint protein cyclin D1. To investigate the effect of compounds on the apoptotic pathway, mRNA and protein expressions of Bcl-2 and Bax were analyzed with qRT-PCR and Western blot. Annexin V staining assay, apoptotic mRNA and protein analysis indicate that N-isopropyl-2,4,6-trinitroaniline, N-(2,4,6-trinitrophenyl)-5-methylisoxazole-3-amine, N-(3-nitrophenyl)-2,4,6-trinitroaniline, N-(4-nitrophenyl)-2,4,6-trinitroaniline induce intrinsic apoptosis by increasing the ratio of Bax/Bcl-2 expression. In addition, colony formation and wound healing assays confirmed that these compounds also inhibit the metastatic activity of Hep3B cells. 2,4,6-Trinitroaniline derivatives, especially N-(3-nitrophenyl)-2,4,6-trinitroaniline might be used as candidate for the development of new antitumor drugs. Graphic abstract: [Figure not available: see fulltext.].
Nitro derivatives of 2,1,3-benzothiadiazole 1-oxides: synthesis, structural study, and NO release
Konstantinova,Knyazeva,Gatilov, Yu. V.,Zlotin,Rakitin
, p. 95 - 101 (2018/04/27)
A convenient one-pot synthesis of nitro derivatives of 2,1,3-benzothiadiazole 1-oxides by the reaction of o-nitroanilines with sulfur monochloride was developed. The structural features of 4-nitrobenzothiadiazole and its N-oxide were considered. High in vitro release of nitric oxide (69%) was found for a 6-nitro-2,1,3-benzothiadiazole sample by the Griess assay, which indicated good prospects for this class of compounds.
Thermal characterization and theoretical and experimental comparison of picryl chloride derivatives of heterocyclic energetic compounds
Yigiter, Aynur Ozler,Atakol, Melike Kundurac?,Levent Aksu,Atakol, Orhan
, p. 2199 - 2213 (2017/02/26)
There were 10 nitrogen-rich energetic compounds prepared by the reaction of 2,4,6-trinitrochlorobenzen (picryl chloride) with pyrazole, 1,2,4-triazole, imidazole, 3-aminopyrazole, 3-nitropyrazole, 3-amino-1,2,4-triazole, 3-nitro-1,2,4-triazole, 3,5-diamino-1,2,4-triazole and guanidine. These compounds were characterized with IR spectra, elemental analysis and 1H NMR and 13C NMR methods. They were also examined with thermogravimetry and differential thermal analyses. The heat generated after the explosion was measured by the use of differential scanning calorimetry. The formation enthalpies of some of the products synthesized were determined by the use of Gaussian 09 software, and probable products were estimated from the data reported in the literature. Finally, theoretical explosion energies of these compounds were calculated using the theoretical formation enthalpies and compared with experimental data.
Synthesis and Investigation of 2,6-Bis(picrylamino)-3,5-dinitro-pyridine (PYX) and Its Salts
Klap?tke, Thomas M.,Stierstorfer, J?rg,Weyrauther, Michael,Witkowski, Tomasz G.
, p. 8619 - 8626 (2016/07/07)
2,6-Bis(picrylamino)pyridine (1; pre-PYX) and 2,6-bis(picrylamino)-3,5-dinitropyridine (2; PYX) were synthesized using an improved literature method. Compounds 1 and 2 were reinvestigated in detail and the X-ray structures (1: ρ=1.698 g cm?3at 173 K; 2: ρ=1.757 g cm?3at 298 K) are given. The reactions of 2 with different bases, such as alkali metal hydroxides (sodium, potassium, rubidium, cesium), and N-bases (ammonia, hydrazine, hydroxylamine, guanidinium carbonate, aminoguanidine bicarbonate) are reported, as well as metathesis reactions producing energetic salts. Several energetic compounds were synthesized and characterized for the first time using vibrational (IR, Raman) and multinuclear NMR spectroscopy, mass spectrometry, elemental analysis, and DSC. The crystal structures of four energetic salts were determined using low temperature single-crystal X-ray diffraction. Heats of formation for the metal-free species were calculated using the Gaussian 09 software. Detonation parameters were estimated using the EXPLO5 program. The sensitivities towards impact, friction, and electrostatic discharge were also determined.
Formation constants in C-H hydrogen bonding. 4. Effects of cyano, nitro, and trifluoromethyl substituents in aromatic compounds
Lorand, John P.
, p. 186 - 205 (2015/02/19)
Formation constants ( Keq) have been measured using 1H NMR for H-bond complexes with HMPA in CCl 4of 35 aromatic compounds variously substituted with cyano, nitro, and trifluoromethyl groups; several compounds contained F and Cl. The three strongly polar groups enhance H-bonding significantly, usually in the order NO2 > CN > CF3; all are superior to Cl and F. 1,3,5-Trinitrobenzene fails to H-bond at all; however, TNT, its tert-butyl analog, and trinitro-m-xylene show significant Keq values. Coplanarity of nitro groups with the ring blocks approach of HMPA, probably via intramolecular H-bonds. The buttressing effect is evident in some crowded compounds.
Synthesis, single crystal structure and performance of N-substituted derivatives of dinitroimidazole
Hou, Kehui,Ma, Congming,Liu, Zuliang
, p. 2837 - 2844 (2013/09/12)
The N-substituted derivatives of dinitroimidazoles have been synthesized for application as energetic materials. The synthesized compounds were fully characterized by 1H 13C NMR spectroscopy and elemental analysis. Most of them were determined by single crystal X-ray diffraction. The calculated densities of the compounds range between 1.89 and 1.91 g cm -3 and the experimental densities between 1.75 and 1.84 g cm -3, as obtained by X-ray crystallographic analysis. Notably, densities of the N-substituted derivatives of dinitroimidazoles are increased when two amino groups are introduced but decreased when one amino group is introduced.
