1672-34-0

Basic information

• Product Name: 1,2,4,5-Tetrazine, 3,6-bis(methylthio)-
• CAS NO: 1672-34-0
• Molecular Formula: C4H6N4S2
• Molecular Weight: 174.25
• Mol File: 1672-34-0.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1,2,4,5-Tetrazine, 3,6-bis(methylthio)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,4,5-Tetrazine, 3,6-bis(methylthio)-(1672-34-0)
• EPA Substance Registry System: 1,2,4,5-Tetrazine, 3,6-bis(methylthio)-(1672-34-0)

Safety Data

• Hazardous Substances Data: 1672-34-0(Hazardous Substances Data)

Usage

General Description

1,2,4,5-Tetrazine, 3,6-bis(methylthio)- is a chemical compound that is a derivative of tetrazine. It consists of a tetrazine ring with two methylthio (–SCH3) groups attached at the 3 and 6 positions. 1,2,4,5-Tetrazine, 3,6-bis(methylthio)- has potential applications in the field of organic synthesis and materials science, particularly in the development of high-energy materials and pharmaceuticals. Its unique molecular structure and reactivity make it a promising candidate for various research and industrial applications. As a result, there is ongoing interest in studying the properties and potential uses of 1,2,4,5-Tetrazine, 3,6-bis(methylthio)- in different scientific fields.

Upstream product

• 1672-33-9 3,6-bis(methylthio)-1,4-dihydro-1,2,4,5-tetrazine 
• 37839-01-3 1H(+)-S-methylisothiocarbonohydrazidium iodide 
• 74-88-4 methyl iodide 
• 1672-33-9 3,6-bis(methylsulfanyl)-1,2-dihydro-1,2,4,5-tetrazine 

Downstream Products

• 37813-54-0 3,6-bis(methylthio)pyridazine 
• 75328-93-7 N-<(3,4-dichlorophenyl)methyl>-6-(methylthio)-1,2,4,5-tetrazin-3-amine 
• 75328-85-7 N-<3-<(diethylamino)methyl>-4-methoxyphenyl>-6-(methylthio)-1,2,4,5-tetrazin-3-amine 
• 112740-80-4 3,6-bis(methylthio)-4-phenyl-1,2-diazine 
• 138373-19-0 3,5-Bis(methylthio)-4-(N-benzylidenamino)pyrazol 
• 75328-84-6 N-(3,4-dichlorophenyl)-6-(methylthio)-1,2,4,5-tetrazin-3-amine 
• 181364-00-1 N¹⁰-acetyl-N¹⁰-[6-methylthio-3-(1,2,4,5-tetrazinyl)]-N¹-benzyltryptamine 
• 69466-83-7 5-(p-methoxyphenyl)-3-methylsulfanyl-1,2,4-triazine 
• 28735-27-5 3-methylthio-5-phenyl-1,2,4-triazine 
• 67642-94-8 5-(4-chlorophenyl)-3-(methylthio)-1,2,4-triazine 
• 71347-48-3 5-(4-fluorophenyl)-3-(methylthio)-1,2,4-triazine 

Relevant articles and documents

Selective N1/N4 1,4-Cycloaddition of 1,2,4,5-Tetrazines Enabled by Solvent Hydrogen Bonding

An unprecedented 1,4-cycloaddition (vs 3,6-cycloaddition) of 1,2,4,5-tetrazines is described with preformed or in situ generated aryl-conjugated enamines promoted by the solvent hydrogen bonding of hexafluoroisopropanol (HFIP) that is conducted under mild reaction conditions (0.1 M HFIP, 25 °C, 12 h). The reaction constitutes a formal [4 + 2] cycloaddition across the two nitrogen atoms (N1/N4) of the 1,2,4,5-tetrazine followed by a formal retro [4 + 2] cycloaddition loss of a nitrile and aromatization to generate a 1,2,4-triazine derivative. The factors that impact the remarkable change in the reaction mode, optimization of reaction parameters, the scope and simplification of its implementation through in situ enamine generation from aldehydes and ketones, the reaction scope for 3,6-bis(thiomethyl)-1,2,4,5-tetrazine, a survey of participating 1,2,4,5-tetrazines, and key mechanistic insights into this reaction are detailed. Given its simplicity and breath, the study establishes a novel method for the simple and efficient one-step synthesis of 1,2,4-triazines under mild conditions from readily accessible starting materials. Whereas alternative protic solvents (e.g., MeOH vs HFIP) provide products of the conventional 3,6-cycoladdition, the enhanced hydrogen bonding capability of HFIP uniquely results in promotion of the unprecedented formal 1,4-cycloaddition. As such, the studies represent an example of not just an enhancement in the rate or efficiency of a heterocyclic azadiene cycloaddition by hydrogen bonding catalysis but also the first to alter the mode (N1/N4 vs C3/C6) of cycloaddition.

Radical Cations and Anions of 1,2,4,5-Tetrazines: an Electron Spin Resonance and Cyclic Voltammetric Study

Exposure to (60)Co γ-ray of dilute solutions of a range of s-tetrazines in fluorotrichloromethane at 77 K gave the corresponding radical cations, identified by their e.s.r. spectra.Two distinct types of spectra were obtained, one showing large hyperfine coupling to four equivalent (14)N nuclei is assigned to n(?)-radical cations, and the other, only found for -NR2 substituents, with strong coupling to two nitrogen nuclei, is assigned to ?-radical cations.The former include the parent s-tetrazine and the 3,6-dimethyl, -diphenyl, dichloro, dimethoxy, bis(methylthio), and di(aziridin-1-yl) derivatives.The latter were also prepared in fluid solution, and showed reversible behaviour in their cyclic voltammograms, in contrast with the former group.The corresponding radical anions have been studied in both fluid and solid solution, all derivatives showing major hyperfine coupling to the four ring (14)N nuclei.Total spin densities have been estimated for both types of radical cations and for the radical anions, and in all cases the total is in the 1.05-1.2 range.This deviation from unity is interpreted in terms of spin polarisation giving rise to considerable negative spin densities.

Synthesis of 6-(arylthio)- and 6-[(arylmethyl)thio]-1,2,4,5-tetrazin-3-amines and N-phenyl- and N-(phenylmethyl)-1,2,4,5-tetrazine-3,6-diamines (1) as potential antimalarial agents

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