6830-78-0

Basic information

• Product Name: 3,6-DIPHENYL-1,2,4,5-TETRAZINE
• Synonyms: 2,6-diphenyl-s-tetrazin;3,6-Diphenyl-1,2,4,5-tetraazine;3,6-Diphenyl-sym-tetrazine;3,6-Diphenyltetrazine;4,5-tetrazine,3,6-diphenyl-2;Diphenyl-s-tetrazine;s-Tetrazine, 3,6-diphenyl-;1,2,4,5-Tetrazine, 3,6-diphenyl-
• CAS NO: 6830-78-0
• Molecular Formula: C₁₄H₁₀N₄
• Molecular Weight: 234.26
• Product Categories: Heterocyclic Building Blocks;N-Containing;Others
• Mol File: 6830-78-0.mol
• Article Data: 36

Chemical Properties

• Melting Point: 198 °C (dec.)(lit.)
• Boiling Point: 446 °C at 760 mmHg
• Flash Point: 208.7 °C
• Appearance: white crystalline powder
• Density: 1.214 g/cm³
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility: chloroform: soluble25mg/mL, clear, very dark red
• PKA: 0.36±0.10(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: 3,6-DIPHENYL-1,2,4,5-TETRAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,6-DIPHENYL-1,2,4,5-TETRAZINE(6830-78-0)
• EPA Substance Registry System: 3,6-DIPHENYL-1,2,4,5-TETRAZINE(6830-78-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: XF6863300
• Hazardous Substances Data: 6830-78-0(Hazardous Substances Data)

Usage

Uses

3,6-Diphenyl-1,2,4,5-tetrazine may be used in the preparation of dihydropyridazine derivatives, via reaction with cis,cis-cycloocta-1,5-diene.

General Description

3,6-Diphenyl-1,2,4,5-tetrazine is an an electron-deficient heteroaromatic azadiene. It participates in inverse electron demand cycloaddition reactions with various dienophiles. It is reported to participate in facile inverse electron demand Diels-Alder reactions with “tunable” reaction rates. The electron transport characteristics of 3,6-diphenyl-1,2,4,5-tetrazine (DPT) single molecular conductor have been studied by density functional theory (DFT) method. Basicity of 3,6-diphenyl-1,2,4,5-tetrazine in aqueous solutions of sulfuric acid (pKBH+) is -4.8. It undergoes thermal Diels-Alder reaction with C60 to afford monoadducts, possessing a diaryldihydropyridazine function nested atop the fullerene.

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

• 62-53-3 aniline 
• 140-29-4 phenylacetonitrile 
• 100-47-0 benzonitrile 
• 104-47-2 p-methoxybenzylnitrile 
• 140-53-4 p-chlorobenzyl cyanide 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 58106-82-4 3-(methylthio)-6-phenyl-1,2,4,5-tetrazine 
• 98-80-6 phenylboronic acid 
• 17224-04-3 2-[(tetrahydro-2H-pyran-2-yl)oxy]propionitrile 
• 729-44-2 1,2-bis[chloro(phenyl)methylidene]hydrazone 
• 98-88-4 benzoyl chloride 
• 787-84-8 N'-benzoylbenzohydrazide 
• 1666-17-7 benzaldehyde p-toluenesulfonylhydrazone 
• 69374-62-5 3,6-diphenyl-1,4-di(p-tolylsulfonyl)-1,4-dihydro-1,2,4,5-tetrazine 

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 
• 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 
• 125256-67-9 4a,5,6,7,8,9,10,10a-Octahydro-4a-morpholino-1,4-diphenylcyclooctapyridazine 
• 68629-76-5 5,6,7,8,9,10-Hexahydro-1,4-diphenylcycloocta<1,2-d>pyridazin 
• 82488-99-1 1,4-Diphenyl-5,6-dihydro<1,2,4>triazino<5,4-a>isochinolin 
• 2272-60-8 4a,6,7,7a-Tetrahydro-4a-morpholino-1,4-diphenyl-5H-cyclopentapyridazine 
• 2272-61-9 6,7-Dihydro-1,4-diphenyl-5H-cyclopentapyridazine 

Relevant articles and documents

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.

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

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.