6830-78-0

Usage

Uses

Used in Chemical Synthesis:
3,6-Diphenyl-1,2,4,5-tetrazine is used as a key intermediate in the preparation of dihydropyridazine derivatives through its reaction with cis,cis-cycloocta-1,5-diene. This application takes advantage of its ability to participate in inverse electron demand Diels-Alder reactions, allowing for the creation of complex molecular structures.
Used in Research and Development:
The electron transport characteristics of 3,6-diphenyl-1,2,4,5-tetrazine (DPT) have been studied using the density functional theory (DFT) method, which aids in understanding its potential applications in various fields, such as materials science and electronics.
Used in Fullerene Chemistry:
3,6-Diphenyl-1,2,4,5-tetrazine undergoes thermal Diels-Alder reactions with C60, resulting in monoadducts with a diaryldihydropyridazine function nested atop the fullerene. This application highlights its utility in the synthesis of novel fullerene-based materials with potential applications in areas such as energy storage and conversion, as well as in the development of new materials with unique electronic properties.

InChI:InChI=1/C14H10N4/c1-3-7-11(8-4-1)13-15-17-14(18-16-13)12-9-5-2-6-10-12/h1-10H

Upstream product

• 14478-73-0 3,6-diphenyl-1,2-dihydro-1,2,4,5-tetrazine 
• 532-28-5 (RS)-mandelonitrile 
• 32252-82-7 1-chloro-1,4-diphenyl-2,3-diazabutadiene 
• 100-47-0 benzonitrile 
• 4903-36-0 N-phenyl-benzimidoyl chloride 
• 74222-83-6 benzamidine hydrochloride dihydrate 
• 65520-11-8 2-cyano-pyridine hydrochloride 
• 106-49-0 p-toluidine 
• 106-47-8 4-chloro-aniline 
• 613-94-5 benzoic acid hydrazide 
• 100-01-6 4-nitro-aniline 
• 62008-66-6 1-(5α-cholestan-3β-yl)-1-phenylmethylenedimethylammonium chloride 
• 95309-27-6 1,4-dihydro-1-(4-methylphenyl)-3,6-diphenyl-s-tetrazine 
• 79834-70-1 N-(2-Chlor-ethyl)benzamidchlorid 

Downstream Products

• 107413-56-9 3,6-diphenyl-2,5-dihydropyridazine-4-carbonitrile 
• 2272-58-4 3,4,6-triphenyl-pyridazine 
• 34950-38-4 3,4,5,6-tetraphenylpyridazine 
• 891-22-5 3,6-diphenylpyridazine 
• 2272-60-8 4a-morpholin-4-yl-1,4-diphenyl-5,6,7,7a-tetrahydro-4aH-cyclopenta[d]pyridazine 
• 57015-09-5 (5Z,8Z,10Z)-1,4-diphenyl-3,11a-dihydro-oxonino[4,5-d]pyridazine 
• 56118-40-2 1,4-diphenyl-9b-pyrrolidin-1-yl-4a,9b-dihydro-benzo[4,5]furo[2,3-d]pyridazine 
• 69956-67-8 4,7-diphenyl-(3ar,3bc,3cr',7ac',7bc,7cc,7dc,7ec)-3a,3b,3c,7a,7b,7c,7d,7e-octahydro-cyclopropa[3,4][1,3]dioxolo[4',5':5,6]pentaleno[1,2-d]pyridazine 
• 63456-15-5 2,2-dimethyl-4,7-diphenyl-(3ar,3bc,3cr',7ac',7bc,7cc,7dc,7ec)-3a,3b,3c,7a,7b,7c,7d,7e-octahydro-cyclopropa[3,4][1,3]dioxolo[4',5':5,6]pentaleno[1,2-d]pyridazine 
• 82488-82-2 3,6-Diphenyl-4-(2,2-dimethyl-3-amino)-propyl-pyridazin 
• 82488-98-0 1,4-Diphenyl-7,7-dimethyl-7,8-dihydro-pyrrolo<2,3-d>pyridazin 
• 82488-97-9 3,6-Diphenyl-4-(3-amino-3-methyl)-propyl-pyridazin 
• 104739-25-5 2,3-Dihydro-1-methyl-4,7-diphenyl-1H-pyrrolo<2,3-d>pyridazin 
• 87439-77-8 3,5,6-triphenyl-1,4-dihydropyridazine 

Relevant academic research and scientific papers

Bridge-Clamp Bis(tetrazine)s with [N]8 π-Stacking Interactions and Azido-s-Aryl Tetrazines: Two Classes of Doubly Clickable Tetrazines

Click chemistry at a tetrazine core is useful for bioorthogonal labeling and crosslinking. Introduced here are two new classes of doubly clickable s-aryl tetrazines synthesized by Cu-catalyzed cross-coupling. Homocoupling of o-brominated s-aryl tetrazines leads to bis(tetrazine)s structurally characterized by tetrazine cores arranged face-to-face. [N]8 π-stacking interactions are essential to the conformation. Upon inverse electron demand Diels–Alder (iEDDA) cycloaddition, the bis(tetrazine)s produce a unique staple structure. The o-azidation of s-aryl tetrazines introduces a second proximal intermolecular clickable function that leads to double click chemistry opportunities. The stepwise introduction of fluorophores and then iEDDA cycloaddition, including bioconjugation to antibodies, was achieved on this class of tetrazines. This method extends to (thio)etherification, phosphination, trifluoromethylation and the introduction of various bioactive nitrogen-based heterocycles.

SYNTHETIC SPHINGOLIPID INSPIRED MOLECULES WITH HETEROAROMATIC APPENDAGES, METHODS OF THEIR SYNTHESIS AND METHODS OF TREATMENT

Small molecules compounds and methods of their synthesis are provided. Formulations and medicaments are also provided that are directed to the treatment of disease, such as, for example, neoplasms, cancers, and other diseases. Therapeutics are also provided containing a therapeutically effective dose of one or more small molecule compounds, present either as pharmaceutically effective salt or in pure form, including, but not limited to, formulations for oral, intravenous, or intramuscular administration.

Redox potential tuning of s-tetrazine by substitution of electron-withdrawing/donating groups for organic electrode materials

Herein, we tune the redox potential of 3,6-diphenyl-1,2,4,5-tetrazine (DPT) by introducing various electron-donating/withdrawing groups (methoxy, t-butyl, H, F, and trifluoromethyl) into its two peripheral benzene rings for use as electrode material in a

Synthetic Sphingolipids with 1,2-Pyridazine Appendages Improve Antiproliferative Activity in Human Cancer Cell Lines

A synthetic sphingolipid related to a ring-constrained hydroxymethyl pyrrolidine analog of FTY720 that was known to starve cancer cells to death was chemically modified to include a series of alkoxy-tethered 3,6-substituted 1,2-pyridazines. These derivati

Iridium complex and organic electroluminescence device using the same

Provided are: an iridium complex represented by formula (1); and an organic electroluminescent element which uses the iridium complex as a phosphorescent dopant material. The organic electroluminescent element can exhibit good performance, such as reduced driving voltage, improved current efficiency, or a long half-life period.

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.

Installation of Minimal Tetrazines through Silver-Mediated Liebeskind-Srogl Coupling with Arylboronic Acids

Described is a general method for the installation of a minimal 6-methyltetrazin-3-yl group via the first example of a Ag-mediated Liebeskind-Srogl cross-coupling. The attachment of bioorthogonal tetrazines on complex molecules typically relies on linkers that can negatively impact the physiochemical properties of conjugates. Cross-coupling with arylboronic acids and a new reagent, 3-((p-biphenyl-4-ylmethyl)thio)-6-methyltetrazine (b-Tz), proceeds under mild, PdCl2(dppf)-catalyzed conditions to introduce minimal, linker-free tetrazine functionality. Safety considerations guided our design of b-Tz which can be prepared on decagram scale without handling hydrazine and without forming volatile, high-nitrogen tetrazine byproducts. Replacing conventional Cu(I) salts used in Liebeskind-Srogl cross-coupling with a Ag2O mediator resulted in higher yields across a broad library of aryl and heteroaryl boronic acids and provides improved access to a fluorogenic tetrazine-BODIPY conjugate. A covalent probe for MAGL incorporating 6-methyltetrazinyl functionality was synthesized in high yield and labeled endogenous MAGL in live cells. This new Ag-mediated cross-coupling method using b-Tz is anticipated to find additional applications for directly introducing the tetrazine subunit to complex substrates.

CLEAVABLE TETRAZINE USED IN BIO-ORTHOGONAL DRUG ACTIVATION

Disclosed is an advancement in provoked chemical cleavage. Thereby the invention provides the use of a diene as a chemically cleavable group attached to a Construct, and the use of a dienophile to provoke the release of the Construct by allowing the diene to react with a dienophile capable of undergoing an inverse electron demand Diels Alder reaction with the diene. The invention includes a kit for releasing a Construct CA bound to a Trigger TR, the kit comprising a tetrazine and a dienophile, wherein the Trigger is the tetrazine. The invention also includes the use of the formation of a pyridazine by reacting a tetrazine comprising a Construct CA bound thereto and a dienophile, as a chemical tool for the release, in a chemical, biological or physiological environment, of said Construct.

PROCESS FOR PREPARING FUNCTIONALIZED 1,2,4,5-TETRAZINE COMPOUNDS

The present invention relates to a process for the synthesis of 3,6 functionalized 1,2,4,5-tetrazine compounds of formula (I); wherein A and B being the same; and wherein at least one of R1, R1', R2 and R2' and at least one of R10 and R10' is a halogen atom or acetate group; said process comprising reacting the corresponding 1,2,4,5-tetrazine compounds wherein at least one of R1, R1', R2 and R2' and at least one of R10 and R10' is a hydrogen atom with an oxidative reagent in presence of a catalyst.

Ortho-Functionalized Aryltetrazines by Direct Palladium-Catalyzed C-H Halogenation: Application to Fast Electrophilic Fluorination Reactions

A general catalyzed direct C-H functionalization of s-tetrazines is reported. Under mild reaction conditions, N-directed ortho-C-H activation of tetrazines allows the introduction of various functional groups, thus forming carbon-heteroatom bonds: C-X (X=I, Br, Cl) and C-O. Based on this methodology, we developed electrophilic mono- and poly-ortho-fluorination of tetrazines. Microwave irradiation was optimized to afford fluorinated s-aryltetrazines, with satisfactory selectivity, within only ten minutes. This work provides an efficient and practical entry for further accessing highly substituted tetrazine derivatives (iodo, bromo, chloro, fluoro, and acetate precursors). It gives access to ortho-functionalized aryltetrazines which are difficult to obtain by classical Pinner-like syntheses.