6224-55-1

Usage

InChI:InChI=1/C9H8O2S/c1-7-6-8-4-2-3-5-9(8)12(7,10)11/h2-6H,1H3

Upstream product

• 1195-14-8 2-Methylbenzothiophene 
• 88050-71-9 2-methyl-(8H)-cycloheptathiophen-8-one 
• 95-15-8 Benzo[b]thiophene 
• 33945-86-7 2-Methylbenzothiophene sulfoxide 
• 446-52-6 2-Fluorobenzaldehyde 

Downstream Products

• 6224-56-2 1,1-Dioxo-2-methyl-2,3-dihydro-1-benzothiophen 
• 86559-04-8 4,4-dioxo-3a-methyl-3-(2,4,6-trimethylphenyl)-2,3-dihydrobenzothiopheno<2,3-d>isoxazoline 
• 89911-99-9 8,8-dioxo-8a-methyl-2,3-diphenyl-2,3-dihydrobenzothieno<3,2-d>isoxazolidine 
• 86558-95-4 4,4-dioxo-3a-methyl-2,3-diphenyl-2,3-dihydrobenzothieno<2,3-d>isoxazolidine 

Relevant academic research and scientific papers

Niobium(V) oxido tris-carbamate as easily available and robust catalytic precursor for the selective sulfide to sulfone oxidation

The oxidation of the sulfide function promoted by a variety of vanadium compounds has been largely explored, whereas the use of homogeneous catalytic systems based on the heavier group 5 metals remains less explored. We report the use of easily available niobium and tantalum carbamates, i.e. [M(O2CNMe2)5] (M = Nb, 1; M = Ta, 2), [Nb(O2CNMe2)4], 3, [NbO(O2CNEt2)3], 4, and [NbCl3(O2CNEt2)2], 5, as effective catalysts for the conversion of a series of alkyl aryl and aromatic sulfides into the corresponding sulfones. NMR investigations on the performant niobium catalyst 4 unexpectedly revealed the substantial stability of this compound in the protic catalytic environment, and a plausible catalytic cycle was obtained by DFT studies. The two active catalytic species, i.e. 4 and its minor mono-methoxide derivative, presumably interconvert to each other exploiting the versatile coordination of the carbamato ligand.

Highly Efficient Enantioselective Synthesis of Chiral Sulfones by Rh-Catalyzed Asymmetric Hydrogenation

A highly efficient and enantioselective Rh-(R,R)-f-spiroPhos complex catalyzed hydrogenation of a series of unsaturated sulfones has been developed. With Rh-(R,R)-f-spiroPhos catalyst under mild conditions, not only the asymmetric hydrogenation of both the 3,3-diaryl and exocyclic α,β-unsaturated sulfones was first realized with up to 99.9% ee but also 3-alkyl-3-aryl and benzo[b]thiophene-1,1-dioxides were successfully hydrogenated to the corresponding chiral sulfones with excellent enantioselectivities (up to 99.4% ee) regardless of the steric hindrance, electronic property, and geometry of the substrates. Moreover, this reaction offers a route to (S)-(+)-ar-turmerone as a spice flavor, which is an important synthetic intermediate of pharmaceuticals.

Method for preparing aromatic ring thiophthene-1,1-dioxide

The invention provides a method for preparing aromatic ring thiophthene-1,1-dioxide. The method comprises the following steps: carrying out one-step cyclization on an ortho-position substituted aromatic ring and sodium alkylsulfinate, and carrying out a dehydration reaction, thereby obtaining the aromatic ring thiophthene-1,1-dioxide. The ortho-position substituted aromatic ring is of a structureof a compound of formula (I) as shown in the description. Compared with synthesis routes of a conventional method, the method for preparing the aromatic ring thiophthene-1,1-dioxide, which is providedby the invention, is easy in raw material obtaining, low in cost, gentle in reaction, easy to control, small in waste generation, small in pollution, simple in aftertreatment and in addition applicable to preparation of all types of aromatic ring thiophthene-1,1-dioxide, novel strategies are provided for the aromatic ring thiophthene-1,1-dioxide, and high production and application values can bemade.

Iridium-Catalyzed Asymmetric Hydrogenation of Benzo[b]thiophene 1,1-Dioxides

An efficient iridium-catalyzed asymmetric hydrogenation of substituted benzothiophene 1,1-dioxides is described. The use of iridium complexes with chiral pyridyl phosphinite ligands provides access to highly enantiomerically enriched sulfones with substituents at the 2- and 3-position. Sulfones of this type are of interest as core structures of agrochemicals and pharmaceuticals. Moreover, they can be further reduced to chiral 2,3-dihydrobenzothiophenes.

A Mn(III) polyoxotungstate in the oxidation of organosulfur compounds by H2O2 at room temperature: An environmentally safe catalytic approach

The tetrabutylammonium (TBA) salt of a Keggin-type polyoxometalate (POM), with the chemical formula TBA4H2[BW11Mn(H2O)O39]·H2O, TBABW11Mn, was evaluated as a catalyst in the oxidation by hydrogen peroxide of several organosulfur compounds, namely benzothiophene (BT), 2-methylbenzothiophene (2-MBT), 3-methylbenzothiophene (3-MBT), dibenzothiophene (DBT), 4-methyldibenzothiophene (4-MDBT) and 4,6-diethyldibenzothiophene (4,6-DEDBT), in acetonitrile at room temperature. All compounds were oxidized to their corresponding sulfones with high conversion and selectivity. Following the excellent results achieved, the BW11Mn/H2O2 in CH3CN system was tested in the oxidation of model fuels (MFs) consisting of a mixture of BTs and DBTs in hexane (MF1 containing mainly BTs and MF2 containing predominantly DBTs). In both cases, the organosulfur compounds from the model fuels were fully converted into their corresponding sulfones. Envisaging the development of a promising desulfurization procedure, the extraction of sulfur compounds from MF2 was attempted after the catalytic oxidation process. More than 98 mol% was removed using an ethanol/H2O mixture.

Biomimetic oxidation of organosulfur compounds with hydrogen peroxide catalyzed by manganese porphyrins

A biomimetic and environmentally benign approach, with potential application in the oxidative desulfurization procedure for several organosulfur compounds (thioanisol, diphenylsulfide, benzothiophene, 2-methylbenzothiophene, 3-methylbenzothiophene, benzothiophene-2-methanol and dibenzothiophene), is presented. The current methodology involves manganese porphyrins as catalysts, which are well-known biomimetic models of cytochrome P450 enzymes, and hydrogen peroxide as the oxygen source. [Mn(TDCPP)Cl] and [Mn(TPFPP)Cl], the manganese porphyrin complexes used in this study, proved to be very efficient catalysts, affording high conversions of all the substrates tested into the corresponding sulfones. The conversion of benzothiophene reaches 99.9% in 90 min, whereas the conversion of dibenzothiophene attains 99.9% after 120 min of reaction, both for a catalyst/substrate molar ratio of 150. The substituted benzothiophenes give rise to similar results, being the best conversions obtained for a catalyst/substrate molar ratio of 150. The oxidation of a model fuel (solution of benzothiophene, 3-methylbenzothiophene, 2-methylbenzothiophene, and dibenzothiophene in hexane) was performed using hydrogen peroxide and [Mn(TDCPP)Cl] as catalyst, achieving total conversion into the corresponding sulfones.