1671-87-0

Usage

Uses

Used in Chemical Synthesis:
3,6-Di-2-pyridyl-1,2,4,5-tetrazine is used as a key component in the preparation of mononuclear, cyclic tetranuclear, and 1-D helical-chain Cu(II) complexes. This is achieved through metal-assisted hydrolysis, which allows for the creation of these complexes with specific properties and potential applications.
Used in Coordination Chemistry:
In the field of coordination chemistry, 3,6-Di-2-pyridyl-1,2,4,5-tetrazine is used in the synthesis of novel cyclic tetranuclear ZnII complexes. These complexes exhibit unique structural and electronic properties, making them valuable for further research and potential applications in various areas.
Used in Organic Chemistry:
3,6-Di-2-pyridyl-1,2,4,5-tetrazine is also utilized in the synthesis of substituted 3,6-di(2-pyridyl)pyridazines through inverse electron demand Diels Alder reaction with alkenes or alkynes. This reaction provides a route to access a variety of novel and potentially useful compounds with diverse applications in organic chemistry and related fields.
Used in Materials Science:
The solid-state reaction of 3,6-Di-2-pyridyl-1,2,4,5-tetrazine with fullerene C60, facilitated by high-speed vibration milling, opens up possibilities for the development of new materials with unique electronic, optical, and structural properties. These materials could have potential applications in various industries, such as electronics, energy storage, and nanotechnology.

InChI:InChI=1/C12H8N6/c1-3-7-13-9(5-1)11-15-17-12(18-16-11)10-6-2-4-8-14-10/h1-8H

Upstream product

• 74222-83-6 benzamidine hydrochloride dihydrate 
• 65520-11-8 2-cyano-pyridine hydrochloride 
• 100-70-9 2-Cyanopyridine 
• 75-05-8 acetonitrile 
• 1671-86-9 3,6-bis(2-pyridyl)-1,2-dihydro-1,2,4,5-tetrazine 
• 1671-86-9 3,6-di(pyridin-2-yl)-1,4-dihydro-1,2,4,5-tetrazine 
• 19081-87-9 N,N'-bis(picolinamide)azine 

Downstream Products

• 289-80-5 1,2-diazine 
• 86453-53-4 13-Phenyl-4,7-di-2-pyridyl-5,6,11,13,15-pentaazapentacyclo<8.5.2.0^2,9.0^3,8.0^11,15>heptadeca-3,5,7,16-tetraen-12,14-dion 
• 126976-84-9 (3,6-bis(2-pyridyl)-1,2,4,5-tetrazine)(Au(PPh₃))2⁽¹⁺⁾ radical 
• 442848-17-1 [RuH(CO)(PPh₃)2(3,6-bis(2-pyridyl)-1,2,4,5-tetrazine)]PF₆ 
• 1055982-99-4 1,4-dipyridin-2-yl-2,4a,5,6,7,8,9,10-octahydro-cycloocta[d]pyridazine 
• 1031820-30-0 C₂₀H₁₃BrN₄ 
• 1031820-25-3 4-(4-nitrophenyl)-3,6-di(2-pyridyl)pyridazine 
• 1031820-29-7 C₂₆H₁₈N₄ 
• 1031820-51-5 1,3,5-tris{3,6-bis(2-pyridyl)pyridazin-4-yl}benzene 
• 1031820-41-3 C₂₀H₁₃BrN₄ 
• 1031820-33-3 C₂₄H₂₂N₄ 

Relevant academic research and scientific papers

A novel route to fully substituted 1H-pyrazoles

A novel one-step synthesis route to fully substituted pyrazol-4-ols is reported. This simple yet nonobvious method for the construction of pyrazol-4-ols by the condensation-fragmentation-cyclization-extrusion reactions of thietanones with 1,2,4,5-tetrazin

Temperature dependent NIR emitting lanthanide-PMO/silica hybrid materials

Two materials-A mesoporous silica (MS) and a periodic mesoporous organosilica (PMO) functionalized with dipyridyl-pyridazine (dppz) units were grafted with near-infrared (NIR) emitting lanthanide (Nd3+, Er3+, Yb3+) complexes in an attempt to obtain hybrid NIR emitting materials. The parent materials: dppz-vSilica and dppz-ePMO were prepared by a hetero Diels-Alder reaction between 3,6-di(2-pyridyl)-1,2,4,5-Tetrazine (dptz) and the double bonds of either ethenylene-bridged PMO (ePMO) or vinyl-silica (vSilica) and subsequent oxidation. The dppz-vSilica is reported here for the first time. The prepared lanthanide-PMO/silica hybrid materials were studied in depth for their luminescence properties at room temperature and chosen Nd3+ and Yb3+ samples also at low temperature (as low as 10 K). We show that both the dppz-vSilica and dppz-ePMO materials can be used as "platforms" for obtaining porous materials showing NIR luminescence. To obtain NIR emission these materials can be excited either in the UV or Vis region (into the π → π? transitions of the ligands or directly into the f-f transitions of the Ln3+ ions). More interestingly, when functionalized with Nd3+ or Yb3+ β-diketonate complexes these materials showed interesting luminescence properties over a wide temperature range (10-360 K). The Yb3+ materials were investigated for their potential use as ratiometric temperature sensors.

Functionalized 2,5-dipyridinylpyrroles by electrochemical reduction of 3,6-dipyridinylpyridazine precursors

The ring contraction of pyridinylpyridazine derivatives into the corresponding pyrroles by electrochemical reduction was studied, and the influence of the substituents of the pyridazine precursors on the process is discussed. Cyclic voltammetry studies underlines the electron-withdrawing or -donating effect of the substituent on the pyridazine ring, which determines the reaction pathway of their preparative electrolysis. The ring-contraction process, with extrusion of nitrogen, proceeds by two subsequent two-electron, two-proton processes via a 1,2-dihydropyridazine intermediate. The latter can either rearrange into an isolable 1,4-dihydropyridazine or undergo formation of pyrroles by disproportionation or by a second electrochemical reduction involving two-electrons and two protons. X-ray structure, fluorescence spectra, and conformational analysis of pyridinylpyrrole sequences supported this study. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

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 Assists Reduction of Water by Phosphines: Application in the Mitsunobu Reaction

Reaction of 3,6-disubstituted-1,2,4,5-tetrazines with water and PEt3forms the corresponding 1,4-dihydrotetrazine and OPEt3. Thus PEt3, as a stoichiometric reductant, reduces water, and the resulting two reducing equivalent

BIO-ORTHOGONAL DRUG ACTIVATION

The invention relates to a Prodrug activation method, for therapeutics, wherein use is made of abiotic reactive chemical groups that exhibit bio-orthogonal reactivity towards each other. The invention also relates to a Prodrug kit comprising at least one Prodrug and at least one Activator, wherein the Prodrug comprises a Drug and a first Bio-orthogonal Reactive Group (the Trigger), and wherein the Activator comprises a second Bio-orthogonal Reactive Group. The invention also relates to targeted therapeutics used in the above-mentioned method and kit. The invention particularly pertains to antibody-drug conjugates and to bi- and trispecific antibody derivatives.

3,6-Substituted-1,2,4,5-tetrazines: Tuning reaction rates for staged labeling applications

Cycloaddition reactions involving tetrazines have proven to be powerful bioorthogonal tools for various applications. Conceivably, sequential and selective labeling using tetrazine-based reactions can be achieved by tuning the reaction rate. By varying th

Click to release: Instantaneous doxorubicin elimination upon tetrazine ligation

Eliminated without a trace: The fastest click reaction, the highly selective inverse-electron-demand Diels-Alder reaction, has been modified to enable selective bioorthogonal release. Thus, the click reaction of a tetrazine with a drug-bound trans-cyclooctene caused the instantaneous release of the drug and CO2 (see scheme). One possible application is the chemically triggered release, and thereby activation, of a drug from a tumor-bound antibody-drug conjugate. Copyright

Clicking 1,2,4,5-tetrazine and cyclooctynes with tunable reaction rates

Substituted tetrazines have been found to undergo facile inverse electron demand Diels-Alder reactions with "tunable" reaction rates.

PHARMACEUTICAL COMPOSITION FOR TREATING OF CANCER COMPRISING PYRIDYLPYRIDAZINE COMPOUNDS OR THEIR TRANSITION METAL COMPLEXES

The present invention relates to a pharmaceutical composition for the treatment of cancer, which contains, as an active ingredient, a pyridylpyridazine compound or a transition metal complex thereof. As described above, the pyridylpyridazine compounds according to the present invention and the transition metal complexes thereof have anticancer activity and can be easily prepared at low cost. Thus, these compounds are useful as anticancer agents against various cancers, including lung cancer, adenocarcinoma, skin cancer, colon cancer, uterine cancer and brain cancer, which are expressed due to immune system abnormality.