34733-85-2

Basic information

• Product Name: 5-phenyl-1,2,3,4-thiatriazole
• Synonyms: 5-Phenyl-1,2,3,4-thiatriazole; Phenyl-1,2,3,4-thiatriazol
• CAS NO: 34733-85-2
• Molecular Formula: C₇H₅N₃S
• Molecular Weight: 163.1997
• Mol File: 34733-85-2.mol

Chemical Properties

• Boiling Point: 279.6°C at 760 mmHg
• Flash Point: 124.5°C
• Density: 1.317g/cm³
• Vapor Pressure: 0.00676mmHg at 25°C
• Refractive Index: 1.619
• CAS DataBase Reference: 5-phenyl-1,2,3,4-thiatriazole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-phenyl-1,2,3,4-thiatriazole(34733-85-2)
• EPA Substance Registry System: 5-phenyl-1,2,3,4-thiatriazole(34733-85-2)

Safety Data

• Hazardous Substances Data: 34733-85-2(Hazardous Substances Data)

Upstream product

• 121-68-6 dithiobenzoic acid 
• 3335-22-6 thiobenzoyl chloride 
• 129256-80-0 2-benzenethiocarbonylthio-1-methylpyridinium iodide 
• 100-47-0 benzonitrile 
• 39969-91-0 piperidinium dithiobenzoate 
• 65-85-0 benzoic acid 
• 10364-94-0 1-benzoylimidazole 
• 463962-26-7 thiobenzoyl 2-(5,5-dimethyl-2-thiono-1,3,2-dioxaphosphorinanyl)sulfide 
• 942-91-6 Carboxymethyl dithiobenzoate 
• 20605-40-7 thiobenzoylhydrazine 

Downstream Products

• 57529-16-5 5-phenyl-[1,2,3,4]thiatriazole 3-oxide 
• 103-72-0 phenyl isothiocyanate 
• 56400-02-3 dinitrogen sulfide 
• 100-47-0 benzonitrile 
• 99939-18-1 N,N,N',N'-Tetraethyl-3,5-dimethyl-7-(thiobenzoyl)-1,2,7-triazabicyclo<2.2.1>hepta-2,5-dien-4,6-diamin 

Relevant articles and documents

Convenient One-Pot Synthesis of 1,2,3,4-Thiatriazoles Towards a Novel Electron Acceptor for Highly-Efficient Thermally-Activated Delayed-Fluorescence Emitters

A novel and unexpected convenient one-pot synthesis of 1,2,3,4-thiatriazoles has been discovered while investigating the classical tetrazine “Pinner synthesis”. The synthetic route starts from commercially-available nitrile derivatives and gives good to high yields (51–80 %) with no need to isolate any thioacylating agents. The crucial impact of the solvent on the outcome of the modified “Pinner synthesis” is moreover examined and discussed. Using this new synthetic route, a novel donor-acceptor thiatriazole derivative has been prepared, which exhibits prominent thermally-activated delayed fluorescence (TADF) in both solution and film. The photoluminescence quantum yield (PLQY) in methylcyclohexane (MCH) and Zeonex (a cyclo olefin polymer) in oxygen-free conditions were determined to be 76 and 99 %, respectively. This work provides an efficient and practical synthetic approach to functionalized 1,2,3,4-thiatriazole derivatives, and will noticeably facilitate the application of 1,2,3,4-thiatriazole as an electron acceptor in organic electronics.

Synthesis of S-thioacyl dithiophosphates, efficient and chemoselective thioacylating agents

Easily available acyl dithiophosphates are not stable and isomerise reversibly to O-thioacyl monothiophosphates, especially when subjected to heating. Much slower but probably irreversible isomerisation to S-thioacyl monothiophosphates occurs. Since equilibrium states are established and S-thioacyl (mono)thiophosphates form slowly, reaction mixtures contain generally both thioacylating and acylating agents, and consequently cannot be used for efficient thioacylation. On the other hand, treatment of a mixture of isomeric anhydrides with an excess of a dithiophosphoric acid leads to exclusive formation of S-thioacyl dithiophosphates. They appear to be excellent thioacylating agents: relatively stable, inert towards water and oxygen and therefore easy to handle. Reactions with nitrogen or sulfur nucleophiles proceed very rapidly under ambient conditions, yielding respective thioacyl derivatives. Isolation of the products is very simple. Due to the low reactivity of S-thioacyl dithiophosphates towards oxygen nucleophiles they can be used for direct thioacylation of multifunctional nucleophiles with unprotected hydroxy groups. Respective thioacyl derivatives cannot readily be obtained using other methods.

A Convenient Synthesis of 5-Alkyl- and 5-Aryl-1,2,3,4-thiatriazoles

1-Methyl-2-thioacylthiopyridinium salts react with sodium azide to afford 5-alkyl- and 5-aryl-1,2,3,4-thiatriazoles in good yields.