30169-25-6

Basic information

• Product Name: 3,6-Bis(3,5-dimethyl-1H-pyrazol-1-yl)-1,2,4,5-tetrazine
• Synonyms: 3,6-Bis(3,5-dimethyl-1H-pyrazol-1-yl)-1,2,4,5-tetrazine;3,6-Bis(2,4-DiMethyl-1H-pyrrol-1-yl)-1,2,4,5-tetrazine;3,6-BIS(3,5-DIMETHYL-1H-PYRAZOL-1-YL)-1,2,4,5-TETRAAZIN;bis(3,5-diMethyl-1H-pyrazol-1-yl)-1,2,4,5-tetrazine;3,6-bis(2,4-dimethylpyrrol-1-yl)-1,2,4,5-tetrazine
• CAS NO: 30169-25-6
• Molecular Formula: C₁₂H₁₄N₈
• Molecular Weight: 270.29316
• Mol File: 30169-25-6.mol
• Article Data: 21

Chemical Properties

• Melting Point: 216-218℃
• Boiling Point: 533.695 °C at 760 mmHg
• Flash Point: 276.569 °C
• Appearance: /
• Density: 1.44
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: -4.09±0.31(Predicted)
• CAS DataBase Reference: 3,6-Bis(3,5-dimethyl-1H-pyrazol-1-yl)-1,2,4,5-tetrazine(CAS DataBase Reference)
• NIST Chemistry Reference: 3,6-Bis(3,5-dimethyl-1H-pyrazol-1-yl)-1,2,4,5-tetrazine(30169-25-6)
• EPA Substance Registry System: 3,6-Bis(3,5-dimethyl-1H-pyrazol-1-yl)-1,2,4,5-tetrazine(30169-25-6)

Safety Data

• Hazardous Substances Data: 30169-25-6(Hazardous Substances Data)

Usage

Description

3,6-Bis(3,5-dimethyl-1H-pyrazol-1-yl)-1,2,4,5-tetrazine is a chemical compound characterized by its unique molecular structure, featuring two 3,5-dimethyl-1H-pyrazol-1-yl groups attached to a 1,2,4,5-tetrazine core. 3,6-Bis(3,5-dimethyl-1H-pyrazol-1-yl)-1,2,4,5-tetrazine is known for its potential applications in various fields due to its distinct chemical properties.

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

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 
• 270588-65-3 3-(3,5-dimethyl-pyrazol-1-yl)-6-thiomorpholin-4-yl-[1,2,4,5]tetrazine 
• 270588-63-1 3-(3,5-dimethyl-1H-pyrazol-1-yl)-6-(4-methyl-1-piperazinyl)-1,2,4,5-tetrazine 
• 270588-75-5 3-(3,5-dimethyl-1H-pyrazol-1-yl)-6-methoxy-1,2,4,5-tetrazine 
• 193335-14-7 6-(3,5-dimethylpyrazol-1-yl)-N-(3-methyl-2-pyridyl)-1,2,4,5-tetrazin-3-amine 
• 270588-84-6 3,6-bis(4-chloro-3,5-dimethylpyrazol-1-yl)-1,2,4,5-tetrazine 
• 270588-67-5 [6-(3,5-dimethyl-pyrazol-1-yl)-[1,2,4,5]tetrazin-3-yl]-p-tolyl-amine 
• 270588-70-0 N-(4-chlorophenyl)-6-(3,5-dimethyl-1H-pyrazol-1-yl)-1,2,4,5-tetrazin-3-amine 
• 270588-74-4 [6-(3,5-dimethyl-pyrazol-1-yl)-[1,2,4,5]tetrazin-3-yl]-(4-methoxy-phenyl)-amine 
• 270588-53-9 3-(3,5-dimethylpyrazol-1-yl)-6-(2-hydroxyethylamino)-1,2,4,5-tetrazine 

Relevant articles and documents

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.

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.

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.