39539-67-8

Usage

Uses

Used in Pharmaceutical Industry:
3-Amino-6-methylthiopyridazine is used as a building block for the synthesis of pharmaceuticals, contributing to the development of new drugs with potential therapeutic applications.
Used in Agricultural Chemical Industry:
In the agricultural chemical industry, 3-Amino-6-methylthiopyridazine is employed as a precursor in the production of various agrochemicals, such as pesticides and herbicides, to enhance crop protection and yield.
Used as a Reagent in Chemical Reactions:
3-Amino-6-methylthiopyridazine is utilized as a reagent in chemical reactions to facilitate the formation of new carbon-sulfur and carbon-nitrogen bonds, which is crucial for the synthesis of complex organic molecules and compounds with specific properties and applications.

InChI:InChI=1/C5H7N3S/c1-9-5-3-2-4(6)7-8-5/h2-3H,1H3,(H2,6,7)

Upstream product

• 5788-46-5 6-amino-2H-pyridazine-3-thione 
• 77-78-1 dimethyl sulfate 
• 109-92-2 ethyl vinyl ether 
• 213320-11-7 6-[(tert-butyloxycarbonyl)-amino]-3-(methylthio)-1,2,4,5-tetrazine 
• 99844-36-7 6-(toluene-4-sulfonyl)-pyridazin-3-ylamine 
• 5469-69-2 6-chloro-pyridazin-3-ylamine 
• 5188-07-8 sodium thiomethoxide 

Downstream Products

• 99845-60-0 4-nitro-N-(6-methylsulfanyl-pyridazin-3-yl)-benzenesulfonamide 
• 113121-32-7 6-methylthio-2-phenylimidazo<1,2-b>pyridazin-3-(5H)-one 
• 141409-15-6 2-(4'-methylphenyl)-6-methylthioimidazo<1,2-b>pyridazine 
• 113121-34-9 3-methoxy-6-methylsulfonyl-2-phenylimidazo<1,2-b>pyridazine 
• 113121-33-8 3-methoxy-6-methylthio-2-phenylimidazo<1,2-b>pyridazine 
• 142074-17-7 3-benzamidomethyl-2-methyl-6-methylthioimidazo<1,2-b>pyridazine 

Relevant academic research and scientific papers

A revision of the alcoholysis and alkanethiolysis of 3-amino-6-chloropyridazine

The synthesis of 3-amino-6-alkoxy- and 3-amino-6-alkylthiopyridazines via nucleophilic aromatic substitution on 3-amino-6-chloropyridazine is described. In contrast to literature reports, no pressure tube is required to perform these reactions.

Regioselective Inverse Electron Demand Diels-Alder Reactions of N-Acyl 6-Amino-3-(methylthio)-1,2,4,5-tetrazines

The regioselective inverse electron demand Diels-Alder reactions of 6-[(tert-butyloxycarbonyl)-amino]-3-(methylthio)-1,2,4,5-tetrazine (2), 6-(acetylamino)-3-(methylthio)-1,2,4,5-tetrazine (3), and 6-(benzyloxycarbonyl)amino-3-(methylthio)-1,2,4,5-tetrazine (4) are disclosed. All three underwent regioselective [4 + 2] cycloaddition with electron-rich dienophiles to form the corresponding functionalized 1,2-diazines in excellent yields. An order of reactivity with electron-rich dienophiles was observed with both 2 and 3 being more reactive than 3,6-bis(methylthio)-1,2,4,5-tetrazine (1, i.e. 3 > 2 > 1), and both 3 and 4 were shown to be more robust than 2 at the higher temperatures necessary for [4 + 2] cycloaddition with less reactive dienophiles. The cycloaddition regioselectivity is consistent with the polarization of the diene and the ability of the methylthio group to stabilize a partial negative charge at C-3, and the N-acylamino group to stabilize a partial positive charge at C-6. While intermolecular reactions of unactivated alkynes either did not proceed or required high temperatures and long reaction times, intramolecular Diels-Alder reactions utilizing tethered unactivated acetylenes led to five- and six-membered bicyclic 1,2-diazines under mild conditions.