30169-25-6

Usage

Uses

Used in Pharmaceutical Industry:
3,6-Bis(3,5-dimethyl-1H-pyrazol-1-yl)-1,2,4,5-tetrazine is used as a reagent for the preparation of 3-arylamino-6-benzylamino-1,2,4,5-tetrazines, which possess antimalarial activities. These tetrazine derivatives are of significant interest in the development of new drugs to combat malaria, a disease that affects millions of people worldwide.
3,6-Bis(3,5-dimethyl-1H-pyrazol-1-yl)-1,2,4,5-tetrazine plays a crucial role in the synthesis of these potential antimalarial agents, contributing to the ongoing efforts to find more effective treatments for this life-threatening disease. By facilitating the creation of new chemical entities with proven biological activity, 3,6-Bis(3,5-dimethyl-1H-pyrazol-1-yl)-1,2,4,5-tetrazine supports the advancement of pharmaceutical research and development in the fight against malaria.

Upstream product

• 30169-21-2 3,6-bis(3,5-dimethylpyrazol-1-yl)-1,4-dihydro-1,2,4,5-tetrazine 
• 5329-29-3 triaminoguanidine hydrochloride 
• 123-54-6 acetylacetone 
• 30169-21-2 3,6-bis(3,5-dimethyl-1H-pyrazol-1-yl)-1,4-dihydro-1,2,4,5-tetrazine 

Downstream Products

• 19617-90-4 3,6-diamino-1,2,4,5-tetrazine 
• 5940-53-4 3,6-dihydrazinyl-1,2,4,5-tetrazine 
• 67-51-6 3,5-dimethyl-1H-pyrazole 
• 270588-64-2 4-(6-(3,5-dimethyl-1H-pyrazol-1-yl)-1,2,4,5-tetrazin-3-yl)morpholine 
• 270588-75-5 3-(3,5-dimethyl-1H-pyrazol-1-yl)-6-methoxy-1,2,4,5-tetrazine 
• 270588-70-0 N-(4-chlorophenyl)-6-(3,5-dimethyl-1H-pyrazol-1-yl)-1,2,4,5-tetrazin-3-amine 
• 270588-69-7 (3,4-dimethyl-phenyl)-[6-(3,5-dimethyl-pyrazol-1-yl)-[1,2,4,5]tetrazin-3-yl]-amine 
• 30169-21-2 3,6-bis(3,5-dimethyl-1H-pyrazol-1-yl)-1,4-dihydro-1,2,4,5-tetrazine 
• 270588-66-4 6-(3,5-dimethyl-1H-pyrazol-1-yl)-N-phenyl-1,2,4,5-tetrazin-3-amine 
• 270588-68-6 [6-(3,5-dimethyl-pyrazol-1-yl)-[1,2,4,5]tetrazin-3-yl]-m-tolyl-amine 
• 30169-21-2 3,6-bis(3,5-dimethylpyrazol-1-yl)-1,4-dihydro-1,2,4,5-tetrazine 
• 680975-05-7 1-butyl-3,6-bis(3',5'-dimethylpyrazol-1'-yl)-1,4-dihydro-1,2,4,5-tetrazine 

Relevant academic research and scientific papers

An Unusual Layered Crystal Packing Gives Rise to a Superior Thermal Stability of Energetic Salt of 3,6-Bishydrazino-1,2,4,5-tetrazine

Five energetic salts of 3,6-bishydrazino-1,2,4,5-tetrazine (BHT), namely (BHT)2(NTO)3 (3), (BHT)(BTT)·2H2O (4), (BHT)(DNP)2 (5), (BHT)(NATr)2 (6), and (BHT)(FOX-7)2 (7), were synthesized and fully characterized by elemental analysis, FT-IR, and mass spectra. The crystal structures of salts 3 and 4 were obtained and determined. Sensitivities towards outside stimuli and thermal behaviors of all the compounds were investigated, besides, thermodynamics of both 3 and 4 were calculated as well. The compounds 3–7 exhibit splendid thermal stabilities and satisfactory sensitivities simultaneously. Notably, unlike the previously known layered packing, compound 4 was found to adopt an unusual layered crystal packing with arch layers alternately arranged upward or downward. It may play an important role in contributing to its superior thermal stability (350 °C), providing an enlightening thinking to design new highly thermal stable energetic materials.

Alkaline earth metal salts of 3,6-bis-nitroguanyl-1,2,4,5-tetrazine: Promising perchlorate-free environmentally friendly pyrotechnic components

Alkaline earth metal salts (magnesium, 2; calcium, 3; strontium, 4; barium, 5) with nitrogen-rich 3,6-bis-nitroguanyl-1,2,4,5-tetrazine anion (DNGTz2?) were prepared and characterized by elemental analysis, infrared, and multinuclear NMR spectroscopy. All new compounds were further characterized by single-crystal X-ray diffraction measurements. Full analysis of the crystal structures and graph sets of hydrogen bonds were conducted out. The results revealed a large-scale conjugation effect of DNGTz anion in all four salts and a middle to high densities ranging from 1.751 (2) to 2.296 (5)?g·cm?3. Both 3 and 4 were one-dimensional coordination polymers and show zig-zag chain, whereas 5 crystalized in a two-dimensional sql topological network. Differential scanning calorimetry (DSC) and thermogravimetric (TG) analysis revealed the good thermal stability of all the new salts. Meanwhile, their specific heat capacities are in inverse proportion to atomic number of the metal cations. The constant-volume combustion energy of 2–5 was determined experimentally, and the standard molar enthalpy of formation was backcalculated to evaluate their energetic performance. Impact sensitivity test disclosed that all the four metal salts were insensitive towards impact with a value higher than 40 J. Flame burning test supports their potential application as the environmentally friendly perchlorate-free pyrotechnic components.

Nucleophilic Attack on Nitrogen in Tetrazines by Silyl-Enol Ethers

The nucleophilic addition of silyl-enol ethers to nitrogen in 3-monosubstituted s-tetrazines mediated by BF3 is reported. The preference for this azaphilic addition over the usually observed inverse electron demand Diels-Alder reactions was evaluated theoretically and corroborated by experiments. The substrate dependency of this unusual reaction was rationalized by determination of the activation barriers and on the basis of the activation strain model by employing density functional theory.

TETRAZINE AND AZOLES BASED IONIC MATERIALS FOR PROPELLANTS AND ITS MANUFACTURING METHOD THEREOF

The present invention relates to an azole-based ionic material for tetrazine-based propellant and a manufacturing method thereof. An azole-based ionic material for a tetrazine-based propellant comprising tetrazine-based azole-based cations in which 1 or 2 azole-based cations are connected to each other based on tetrazine is provided.

Tetrazine-furazan ring high-nitrogen energetic compound and synthesis method thereof

The invention relates to a tetrazine-furazan ring high-nitrogen energetic compound and a synthesis method thereof. The compound is named as 4-amino-N-(3-amino-[1,2,4]triazolo[4,3-b][1,2,4,5-]tetrazine)-1,2,5-oxadiazole-3-amine. The preparation method comprises the following steps: dissolving a compound 2 in DMF, adding sodium hydride under the protection of nitrogen, stirring for 23-26 minutes atthe room temperature, adding a compound 1, reacting for 38-42 minutes, and after the reaction is finished, separating and purifying by column chromatography to obtain a target compound. Furazan ring is used as a latent nitro group and introduced into a tetrazine ring, the energy density and detonation velocity of the compound can be improved, the oxygen balance can be improved, and the synthesis method is simple and safe to operate, short in reaction time, green and environment-friendly.

Constructing a 3D-layered energetic metal-organic framework with the strong stacking interactions of hydrogen-bridged rings: The way to an insensitive high energy complex

Energetic metal-organic frameworks (EMOFs) have drawn considerable attention due to their good energetic performances and acceptable sensitivity. Among these, 3D EMOFs show good thermal stability and mechanical insensitivity. Nevertheless, most of the 3D EMOFs have porous structures and relatively low crystal density, which is closely related to the energetic performances. This structural feature makes the preparation of 3D EMOFs with high density important and challenging. Herein, we present an efficient approach to construct 3D-layered EMOFs with strong stacking interactions, particularly the stacking of hydrogen-bridged rings, to solve the aforementioned contradiction. In this strategy, two EMOFs possessing layered structures with the same ligand and the metal center, named 1 and 2, were rationally designed and synthesized. EMOF 1 exhibits a 1D chain structure with a "head-to-tail"stacking mode, while EMOF 2 has a 3D architecture with a "head-to-head"stacking mode. The crystal structure and the molecular interaction analyses disclosed that the stacking of hydrogen-bridged rings in 2 are stronger than that in 1 and they play a more important role than π-stacking in the higher packing efficiency of 2. TG-DSC-MS-FTIR simultaneous tests showed that 2 has better thermal stability due to the improved structural reinforcement. As expected, 2 exhibits higher density, better energetic performance, and safety than 1 and possesses detonation velocity comparable to that of cyclo-1,3,5-trimethylene-2,4,6-trinitramine (RDX). Our approach highlights the importance of the crystal packing architecture and the stacking interactions on the energetic properties of EMOFs and offers a new approach for the design and synthesis of high-performance insensitive energetic complexes.

ADDITIVE FOR IMPARTING LOW HEAT BUILD-UP TO RUBBER COMPONENT

Provided is an additive for imparting low heat build-up to a rubber component, wherein the additive includes a tetrazine compound represented by general formula (1): (wherein X1 and X2 are the same or different and represent a hydrogen atom or an alkyl, alkylthio, aralkyl, aryl, arylthio, heterocyclic, or amino group; and each of these groups may have one or more substituents), or a salt thereof.

s-Tetrazines as a New Electrode-Active Material for Secondary Batteries

Because of the limitations of conventional metal-oxide-based electrodes, studies on organic redox-active materials as alternative electrodes for secondary batteries are emerging. However, reported organic electrode materials are still limited to a few kinds of organic redox groups. Therefore, the development of new redox-active groups for high-performance electrode materials is indispensable. Here, we evaluate s-tetrazine derivatives as a new electrode material in Li-ion batteries and study their charge/discharge mechanisms by ex situ XPS measurements. The porous carbon CMK-3 was introduced to encapsulate the s-tetrazines, which allowed 100 % utilization of the theoretical capacity and stable cycle performance of the s-tetrazines by preventing dissolution of the molecules into the electrolytes. This new class of redox-active group can pave the way for the next-generation of energy storage systems.

Single-molecule magnet behaviour in a tetranuclear DyIII complex formed from a novel tetrazine-centered hydrazone Schiff base ligand

Two analogous tetranuclear lanthanide complexes have been synthesized with the general formula [Ln4(vht)4(MeOH)8](NO3)4·aMeOH·bH2O, where H2vht = (3,6-bis(vanillidenehydrazinyl)-1,2,4,5-tetrazine) and Ln = DyIII (1), GdIII (2). These complexes are characterized by several techniques; including single-crystal X-ray diffraction, SQUID magnetometry and single-crystal micro-SQUID hysteresis loop measurements. Elucidation of the crystal structure of the complexes shows that the lanthanide ions are bridged by a tetrazine ring, a rare bridging moiety for lanthanide ions. Magnetic studies reveal that both 1 and 2 exhibit weak ferromagnetic exchange interactions between Ln ions, and 1 displaying Single-Molecule Magnet (SMM) behaviour with a magnetisation reversal barrier of Ueff = 158 K (τ0 = 1.06 × 10?7 s).

Hydrogen sulfide fluorescent probe as well as preparation method and application thereof

The invention provides a series of hydrogen sulfide fluorescent probe compounds and a preparation method thereof. A fluorescent probe can be used for detecting hydrogen sulfide and has very good selectivity for the hydrogen sulfide; when being mixed in a water solution or a buffer solution, the fluorescent probe can be used for detecting in vitro hydrogen sulfide. The fluorescent probe compounds can autonomously penetrate cell membranes into cells, and can be used for intracellular hydrogen sulfide imaging.