52143-11-0

Basic information

• Product Name: 1,3,6-triphenyl-1,2-dihydro-1,2,4,5-tetrazine
• CAS NO: 52143-11-0
• Molecular Formula: C₂₀H₁₆N₄
• Molecular Weight: 312.3678
• Mol File: 52143-11-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 451.4°C at 760 mmHg
• Flash Point: 226.8°C
• Density: 1.17g/cm³
• Vapor Pressure: 2.44E-08mmHg at 25°C
• Refractive Index: 1.657
• CAS DataBase Reference: 1,3,6-triphenyl-1,2-dihydro-1,2,4,5-tetrazine(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,6-triphenyl-1,2-dihydro-1,2,4,5-tetrazine(52143-11-0)
• EPA Substance Registry System: 1,3,6-triphenyl-1,2-dihydro-1,2,4,5-tetrazine(52143-11-0)

Safety Data

• Hazardous Substances Data: 52143-11-0(Hazardous Substances Data)

Usage

Abbreviation

TPDHT

Type of compound

Tetrazine derivative

Usage

Crosslinking agent in the preparation of energetic materials

Applications

Propellants, explosives, organic synthesis, and materials science

Thermal stability

High

Sensitivity to impact

Low

Suitability

Energetic formulations for military and industrial applications

Structure

Unique chemical structure that contributes to its properties and applications

Upstream product

• 14478-73-0 3,6-diphenyl-1,4-dihydro-1,2,4,5-tetrazine 
• 95309-27-6 1,4-dihydro-1-(4-methylphenyl)-3,6-diphenyl-s-tetrazine 
• 95309-30-1 1,4-dihydro-1-isopropyl-3,6-diphenyl-s-tetrazine 
• 6830-78-0 3,6-diphenyl-1,2,4,5-tetrazine 
• 100-58-3 phenylmagnesium bromide 
• 108-86-1 bromobenzene 
• 787-84-8 N'-benzoylbenzohydrazide 

Downstream Products

• 725-12-2 2,5-bis-(phenyl)-1,3,4-oxadiazole 
• 55134-96-8 4-anilino-3,5-diphenyl-1,2,4-triazole 
• 2039-06-7 3,5-diphenyl-1,2,4-triazole 
• 31730-65-1 2,4-diphenylquinazoline 
• 106910-89-8 1-anilino-3,5-diphenyl-1H-1,2,4-triazole 

Relevant articles and documents

Rearrangement Reactions of 1,3,6-Triaryl-1,4-dihydro-s-tetrazines leading to 2,4-Diarylquinazolines, 1-Anilino-3,5-diaryl-1H-1,2,4-triazoles, 1,3,5-Triaryl-1H-1,2,4-triazoles, and 2,5-Diaryl-1H-1,3,4-oxadiazoles. X-ray Structure Determination of 6-Isopropyl-2,4-diphenylquinazoline

1,3,6-Triaryl-1,4-dihydro-s-tetrazines (2c-g) rearrange on heating at ca. 200 deg C to 2,4-diarylquinazolines (for which an X-ray determination was carried out on the 6-isopropyl compound) and 1-anilino-3,5-diaryl-1H-1,2,4-triazoles as major products.Hydrolysis in chloroform solution of the title compounds (2) and their 1-alkyl analogues gives rise to 1-aryl (or alkyl)-3,5-diaryl-1H-1,2,4-triazoles and 2,5-diaryl-1,3,4-oxadiazoles.

Thermal Rearrrangement of 1-Alkyl-3,6-diaryl-1,4-dihydro-s-tetrazines to 1-Alkylamino-3,5-diaryl-1,2,4-triazoles

s-Tetrazines having aryl substituents in either the 3- or 3,6-positions react readily with alkyl or aryl Grignard reagents to give 1-alkyl(or aryl)-1,4-dihydro-s-terazines.The 1-alkyl-1,4-dihydro-s-tetrazines rearrange in methanolic hydrogen chloride to 4-alkylamino-1,2,4-triazoles, but thermolyse readily to the less well known, isomeric 1-alkylamino-1,2,4-triazoles.Possible reaction pathways involving breakdown to nitrile and reactive intermediates such as 1,3-dipolar species are discussed.