5000-46-4

Usage

Uses

Used in Organic Synthesis:
METHYLSULFONYLACETONE is used as a reactant for the stereoselective preparation of chiral cyclic ketones, which are important building blocks in the synthesis of complex organic molecules and pharmaceuticals. It is used as a reactant in the preparation of poly-substituted pyridines, a class of nitrogen-containing heterocycles with diverse applications in medicinal chemistry and materials science.
METHYLSULFONYLACETONE aids in the gold-catalyzed Friedlander cyclocondensation reaction, a key process for the synthesis of quinolines, which are significant structures in various biologically active compounds and pharmaceuticals.
Additionally, METHYLSULFONYLACETONE is used as a reactant in radical homoallylation reactions, which are crucial for the formation of carbon-carbon bonds and the synthesis of complex organic molecules. It is also employed in multicomponent cyclocondensation with aldehydes and aminoazoles, a reaction that leads to the formation of diverse heterocyclic compounds with potential applications in pharmaceuticals and agrochemicals.

InChI:InChI=1/C4H8O3S/c1-4(5)3-8(2,6)7/h3H2,1-2H3

Upstream product

• 14109-72-9 methylsulfanyl-acetone 
• 666-15-9 methyl methanesulfinate 
• 78-95-5 chloroacetone 
• 408350-81-2 3-methanesulfonyl-pentane-2,4-dione 
• 7732-18-5 water 
• 20277-69-4 sodium methansulfinate 
• 124-63-0 methanesulfonyl chloride 
• 598-31-2 1-bromoacetone 

Downstream Products

• 631898-83-4 4-(2',4'-dichlorophenyl)-3-methylsulfonyl-but-3-en-2-one 
• 837425-59-9 3-methanesulfonyl-2-methyl-4-phenyl-1H-pyrrole 
• 58741-04-1 2,6-dimethyl-3-carbomethoxy-5-methylsulphonyl-4-(2-trifluoromethylphenyl)-1,4-dihydro-pyridine 
• 58741-08-5 2,6-Dimethyl-3-carbotert.-butoxy-4-(2-nitrophenyl)-5-methylsulphonyl-1,4-dihydro pyridine 
• 58741-05-2 methyl 1,4-dihydro-2,6-dimethyl-5-methylsulphonyl-4-(2-nitrophenyl)pyridine-3-carboxylate 
• 58741-07-4 2,6-Dimethyl-3-(2-dimethylamino)-carboethoxy-4-(2-nitrophenyl)-5methylsulphonyl-1,4-dihydropyridine 
• 58741-09-6 2,6-Dimethyl-3-piperidinocarbonyl-4-(2-nitrophenyl)-5-methylsulphonyl-1,4-dihydropyridine 
• 1007091-59-9 C₁₉H₁₉N₃O₂S 
• 1007091-60-2 C₁₈H₁₆FN₃O₂S 
• 1007091-61-3 C₁₉H₁₉N₃O₃S 
• 1007091-80-6 6-methyl-5-methylsulfonyl-2-methylsulfonylmethyl-4-(4-methylphenyl)-1,4-dihydropyridine 
• 1007091-78-2 C₁₅H₁₈ClNO₄S₂ 

Relevant academic research and scientific papers

Facile One-Pot Access to α-Diazo-β-ketosulfones from Sulfonyl Chlorides and α-Haloketones

A convenient one-pot approach to the preparation of α-diazo-β-ketosulfones from sulfonyl chlorides is described. It involves the conversion of the sulfonyl chloride to sodium sulfinate, alkylation of the latter with α-haloketones followed by diazo transfer using the 'sulfonyl-azide-free' ('SAFE') protocol in aqueous medium. The simple and expedient method relies on readily available starting materials and provides facile access to a wide variety of valuable diazo reagents for organic synthesis.

α-Diazo-β-oxosulfones as Partners in the Wolff 1,2,3-Triazole Synthesis and the Wolff Rearrangement in the Presence of Aromatic Amines

The readily available α-diazo-β-oxosulfones have been employed, for the first time, in the Wolff cyclocondensation with aromatic amines promoted by 1.5-fold excess of TiCl4. The reaction was found to be general (as illustrated by 15 product examples) and resulted in moderate yields of medicinally relevant sulfonyl 1,2,3-triazoles. Excluding the Lewis acid promoter resulted in a clean and high-yielding formation of α-sulfonyl acetanilides resulting from the thermal Wolff rearrangement and trapping of the ketene intermediate with an aniline molecule.

METHOD FOR PRODUCING PYRIDAZINONE COMPOUNDS AND INTERMEDIATE THEREOF

The present invention relates to a novel method for producing a pyridazinone compound and an intermediate thereof as shown in the following scheme: wherein the symbols are as defined in the specification.

Tetra-(tetraalkylammonium)octamolybdate catalysts for selective oxidation of sulfides to sulfoxides with hydrogen peroxide

Tetra-(tetraalkylammonium)octamolybdate catalysts are successfully applied in the selective oxidation of various sulfides to sulfoxides with 30% aqueous hydrogen peroxide as oxidant under mild reaction conditions in 94-100% yield and 95-100% selectivity. The octamolybdate catalysts show high catalytic activity in a high ratio of substrate to catalyst (up to 10000:1) and are recyclable, with actively functional groups, including hydroxyl group and CC bonds, tolerated in the oxidation. The Royal Society of Chemistry 2009.

Multicomponent cyclocondensations of β-ketosulfones with aldehydes and aminoazole building blocks

The multicomponent reaction of methylsulfonylacetone (or α-methylsulfonylacetophenone) with aromatic aldehydes and aminoazoles (or urea) under microwave irradiation to yield 5,8-dihydroimidazolo[1,2-a]pyrimidines and 4,7-dihydro[1,2,4]triazolo[l,5-a]pyrimidines was studied. The influence of the type of aminoazole building block on the reactivity was established. In addition, an unusual reaction pathway for the Biginelli-type condensation of methylsulfonylacetone with aldehydes and urea leading to non-classical Hantzsch-type dihydropyridines was found.

Facile polyethylene glycol (PEG-400) promoted synthesis of β-ketosulfones

An efficient and convenient synthesis of β-ketosulfones is described. Reaction of an α-haloketone with sodium alkyl/aryl sulphinate yields the corresponding β-ketosulfone promoted by polyethylene glycol (PEG-400) as an efficient reaction medium.

PREFERRED CONFORMATIONS OF METHYLTHIO-ACETONE AND -ACETOPHENONE, METHYLSULPHONYL-ACETONE AND -ACETOPHENONE, FROM MOLECULAR-MECHANICS AND DIPOLE-MOMENT TECHNIQUES

Preferred conformations for the title compounds are determined from calculated molecular-mechanics energies in the gaseous phase and analysis of the dipole moments measured in solvents of low dielectric permittivity.In all cases, the gauche conformer having the Me-S bond situated far away from the Me(-C) (or Ph(-C)) group, and nearly bisecting one of the C(=O)-C-H valleys, is predominant.