5940-53-4

Basic information

• Product Name: 1,2,4,5-Tetrazine-3,6-dione, 1,2-dihydro-, dihydrazone
• Synonyms: 1,2,4,5-Tetrazine-3,6-dione, 1,2-dihydro-, dihydrazone
• CAS NO: 5940-53-4
• Molecular Formula: C₂H₆N₈
• Molecular Weight: 142.12264
• Mol File: 5940-53-4.mol
• Article Data: 13

Chemical Properties

• Melting Point: 137-138 °C
• Boiling Point: 288.5±23.0 °C(Predicted)
• Appearance: /
• Density: 2.45±0.1 g/cm3(Predicted)
• PKA: 1.77±0.20(Predicted)
• CAS DataBase Reference: 1,2,4,5-Tetrazine-3,6-dione, 1,2-dihydro-, dihydrazone(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,4,5-Tetrazine-3,6-dione, 1,2-dihydro-, dihydrazone(5940-53-4)
• EPA Substance Registry System: 1,2,4,5-Tetrazine-3,6-dione, 1,2-dihydro-, dihydrazone(5940-53-4)

Safety Data

• Hazardous Substances Data: 5940-53-4(Hazardous Substances Data)

Usage

Chemical structure

A dihydrazone derivative of tetrazine-3,6-dione, which is a heterocyclic compound with a central six-membered ring containing four nitrogen atoms and two oxygen atoms.

Synthesis

Can be synthesized through chemical reactions, involving the formation of a dihydrazone group from the tetrazine-3,6-dione core.

Industrial and medical applications

Used in various industrial and medical applications due to its unique chemical properties.

Reactive intermediate

Studied for its potential use as a reactive intermediate in the synthesis of heterocyclic compounds and pharmaceuticals.

Cancer therapy

Explored for its potential use in cancer therapy, possibly due to its reactivity and ability to form complexes with other molecules.

Fluorescent probe

Studied for its potential use as a fluorescent probe in biological imaging, which could be useful for detecting and monitoring various biological processes.

Research interest

The properties and potential applications of 1,2,4,5-Tetrazine-3,6-dione, 1,2-dihydro-, dihydrazone continue to be explored in various fields of research, including chemistry, materials science, and biology.

Upstream product

• 19617-90-4 3,6-diamino-1,2,4,5-tetrazine 
• 30169-25-6 3,6-bis-(3,5-dimethyl-pyrazol-1-yl)-1,2,4,5-tetrazine 

Downstream Products

• 1071030-18-6 3,6-dibromo-1,2,4,5-tetrazine 
• 1242176-28-8 6-(2-cyclohexylidenehydrazino)-spiro[3,7-dihydro-1,2,4-triazolo[4,3-b]-1,2,4,5-tetrazine-3,1'-cyclohexane] 
• 106131-61-7 3,6-dichloro-1,2,4,5-tetrazine 

Relevant articles and documents

Synthesis, characterization, and energetic properties of diazido heteroaromatic high-nitrogen C-N compound

The synthesis, characterization, and energetic properties of diazido heteroaromatic high-nitrogen C-N compound, 3,6-diazido-1,2,4,5-tetrazine (DiAT), are reported. Its normalized heat of formation (NδHf), experimentally determined using an additive method, is shown to be the highest positive NδHf compared to all other organic molecules. The unexpected azido-tetrazolo tautomerizations and irreversible tetrazolo transformation of DiAT are remarkable compared to all other polyazido heteroaromatic high-nitrogen C-N compounds, for example, 2,4,6-triazido-1,3,5- triazine; 4,4′,6,6′-tetra(azido)hydrazo-1,3,5-triazine; 4,4′,6,6′-tetra(azido)azo-1,3,5-triazine; and 2,5,8-tri(azido)-1,3, 4,6,7,9,9b-heptaazaphenalene (heptazine).

Synthesis of the bi-heterocyclic parent ring system 1,2,4-triazolo[4,3- b][1,2,4,5]tetrazine and some 3,6-disubstituted derivatives

The synthesis of the previously unknown parent ring system was developed. Treatment of 3-hydrazino-1,2,4,5-tetrazine (4) with diethoxymethyl acetate gave the parent ring system. Similar treatment of 3-(3,5- dimethylpyrazol-1-yl)-6-hydrazino-1,2,4,5-tetrazine (2) with one carbon cyclizing reagents gave 3,6-di-substituted derivatives of the 1,2,4-tetrazine ring system.

Improved Synthesis and Thermochemical Properties of Amino- and Hydrazino-1,2,4,5-Tetrazines

[Figure not available: see fulltext.] Improved protocols for the synthesis of 3,6-diamino- and 3,6-dihydrazino-1,2,4,5-tetrazines as well as 6-amino[1,2,4]triazolo[4,3-b]-[1,2,4,5]tetrazine were developed. Combustion energies were determined by the bomb calorimetry and the enthalpies of formation in the standard state were calculated for the compounds of this study. Based on the obtained data, the contribution of the 1,2,4,5-tetrazine moiety to the enthalpy of combustion of its derivatives was estimated.

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.