22459-57-0

Basic information

• Product Name: 2,4,6-triphenyl-1,2,3,4-tetrahydro-1,2,4,5-tetrazine
• CAS NO: 22459-57-0
• Molecular Formula: C₂₀H₁₈N₄
• Molecular Weight: 314.3837
• Mol File: 22459-57-0.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 447.6°C at 760 mmHg
• Flash Point: 224.5°C
• Density: 1.15g/cm³
• Vapor Pressure: 3.31E-08mmHg at 25°C
• Refractive Index: 1.646
• CAS DataBase Reference: 2,4,6-triphenyl-1,2,3,4-tetrahydro-1,2,4,5-tetrazine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6-triphenyl-1,2,3,4-tetrahydro-1,2,4,5-tetrazine(22459-57-0)
• EPA Substance Registry System: 2,4,6-triphenyl-1,2,3,4-tetrahydro-1,2,4,5-tetrazine(22459-57-0)

Safety Data

• Hazardous Substances Data: 22459-57-0(Hazardous Substances Data)

Usage

General Description

2,4,6-triphenyl-1,2,3,4-tetrahydro-1,2,4,5-tetrazine, also known as TAT, is a synthetic compound with a tetrazine backbone. It is a high-energy, highly reactive compound that has received interest for its potential applications in the field of organic chemistry and materials science. TAT can participate in a range of chemical reactions, including cycloaddition reactions with strained alkenes, as well as bioorthogonal chemistry. These properties make it a valuable tool for the development of new materials and bioconjugation techniques. TAT has potential applications in drug delivery, bioimaging, click chemistry, and polymer synthesis. However, its high reactivity and energetic nature also require careful handling and storage.

Upstream product

• 103-82-2 phenylacetic acid 
• 2154-65-6 1,3,5-triphenylverdazyl 
• 936-49-2 2-phenyl-2-imidazoline 
• 51940-11-5 2,4,6-triphenylverdazylium bromide 
• 3637-11-4 1-hydroxy-2,2,6,6-tetramethyl-piperidin-4-one 
• 13623-52-4 2-(4-chlorophenyl)-2-imidazoline 
• 6302-84-7 2-(4-methoxyphenyl)-4,5-dihydro-1H-imidazole 
• 71-55-6 1,1,1-trichloroethane 
• 27852-61-5 2-bromo-2-methyladamantane 
• 141-97-9 ethyl acetoacetate 
• 104-15-4 toluene-4-sulfonic acid 
• 108-98-5 thiophenol 
• 79-11-8 chloroacetic acid 
• 16200-57-0 Toluene-4-sulfonic acid adamantan-1-yl ester 

Downstream Products

• 3637-11-4 1-hydroxy-2,2,6,6-tetramethyl-piperidin-4-one 
• 2154-65-6 1,3,5-triphenylverdazyl 
• 103-82-2 phenylacetic acid 
• 69-72-7 salicylic acid 
• 79-11-8 chloroacetic acid 
• 51940-11-5 2,4,6-triphenylverdazylium bromide 
• 2154-65-6 2,4,6-triphenylverdazyl radical 

Relevant articles and documents

Kinetics and mechanism of monomolecular heterolysis of commercial organohalogen compounds: XXXII. Solvent effects on activation parameters of heterolysis of 1-chloro-1-methylcyclopentane. Correlation analysis of solvation effects

Kinetics of heterolysis of 1-chloro-1-methylcyclopentane in MeOH, BuOH, cyclohexane, i-PrOH, t-BuOH, tert-C5H11OH, γ-butyrolactone, MeCN, PhCN, PhNO2, acetone, PhCOMe, cyclohexanone, and 1,2-dichloroethane at 25-50°C were studied by the verdazyl method. Correlation analysis of solvent effects on activation parameters of the reaction in 8 protic (additionally, AcOH and CF 3CH2OH) and 8 aprotic solvents together and separately in either group of solvents was performed. In all the solvents studied, two ΔH≠-ΔS≠ compensation effects were revealed.

Triarylverdazyl radicals as promising redox-active components of rechargeable organic batteries

A novel design of electroactive components of rechargeable organic batteries based on stable verdazyl radicals bearing various substituents is proposed. 3-Positioned aromatic substituents at the verdazyl moiety affect the reduction potentials and almost do not affect the oxidation potential, while 1-positioned aromatic substituents affect contrariwise the oxidation potential of this radical without any influence on the reduction potential. The acquired electrochemical data allowed us to reveal the structure—potential relationship for the cathodic and anodic processes, which provided the design of triarylverdazyl radicals possessing record-breaking parameters of the “electrochemical gap”.

Kinetics and mechanism of monomolecular heterolysis of commercial halogenated organic compounds: XXVI. Correlation analysis of solvation effects in dehydrobromination of 1-bromo-1-methylcyclohexane and tert-butyl bromide

The dehydrobromination rate of 1-bromo-1-methylcyclohexane and tert-butyl bromide increases with increasing polarity, electrophilicity, and cohesiveness of a solvent, and decreases with increasing solvent nucleophilicity and polarizability; a negative effect of nucleophilic solvation is observed.