934-72-5

Usage

Uses

Used in Catalyst Applications:
1-METHYL-4-(METHYLSULFINYL)BENZENE is used as a catalyst in the preparation of homoallylic alcohols by the allylation of aldehydes with allyltrichlorosilane. It facilitates the reaction by lowering the activation energy and enhancing the reaction rate, leading to the formation of the desired product.
Used in Ligand Applications:
1-METHYL-4-(METHYLSULFINYL)BENZENE is used as a ligand in the synthesis of molybdenum chlorocomplexes. As a ligand, it plays a crucial role in stabilizing the metal center and influencing the properties and reactivity of the resulting complex. This application is particularly relevant in coordination chemistry and the development of new catalysts and materials.

Synthesis Reference(s)

Chemistry Letters, 15, p. 967, 1986Synthetic Communications, 19, p. 1569, 1989 DOI: 10.1080/00397918908051052Tetrahedron Letters, 19, p. 3415, 1978

InChI:InChI=1S/C8H10OS/c1-7-3-5-8(6-4-7)10(2)9/h3-6H,1-2H3

Upstream product

• 26910-35-0 1-[(bromomethyl)-sulfinyl]-4-methylbenzene 
• 20414-85-1 S-methyl-S-(p-tolyl)sulfoximine 
• 75-16-1 methylmagnesium bromide 
• 91378-37-9 S,S-diphenyl-(N-p-tolylfulfinyl)sulfoximine 
• 126218-83-5 1-bromo-2-(methylsulfinyl)benzene 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 623-13-2 4-methylphenyl methylsulfide 
• 127-65-1 chloroamine-T 
• 7601-90-3 perchloric acid 
• 64-17-5 ethanol 
• 7722-84-1 dihydrogen peroxide 
• 109-72-8 n-butyllithium 
• 100-39-0 benzyl bromide 
• 184377-59-1 E-2-carbomethoxyethenyl p-tolyl sulfoxide 

Downstream Products

• 13372-58-2 N-(N'-butyl-carbamoyl)-methyl-(4-tolyl)-sulfoxim 
• 4235-12-5 C₁₅H₁₇NO₂S₂ 
• 24824-93-9 chloromethyl p-tolyl sulfoxide 
• 26910-35-0 1-[(bromomethyl)-sulfinyl]-4-methylbenzene 
• 1600-44-8 1-oxothiolane 
• 623-13-2 4-methylphenyl methylsulfide 
• 109-03-5 1,4-oxathiane-4-oxide 
• 52154-24-2 (R)-p-tolylsulfinylacetophenone 
• 68326-61-4 1-Cyclohexyl-2-((S)-toluene-4-sulfinyl)-ethanone 
• 700-58-3 2-Adamantanone 
• 29186-07-0 bisadamantylidene epoxide 
• 3185-99-7 Methyl p-tolyl sulfone 
• 131137-82-1 1-(2-Methoxyphenyl)-2-<(4-methylphenyl)sulphinyl>ethanone 
• 71899-71-3 (R)-(+)-3,3-dimethyl-1-(4-methylphenylsulfinyl)-2-butanone 

Relevant academic research and scientific papers

Unexpected nucleophilic participation and rearrangement of DBU in reactions with saccharin derivatives

DBU attacks saccharin derivatives with subsequent rearrangement to give rise to 3-[3′-(1″-azepin-2″-onyl)propylamino]-1, 2-benzisothiazole-1,1-dioxide 2 after work-up.

Organocatalytic sulfoxidation

Treatment of a sulfide with a catalytic amount of a 1,3-diketone in the presence of silica sulfuric acid as a co-catalyst and hydrogen peroxide (50% aq) as the stoichiometric oxidant leads to the corresponding sulfoxide product. The reaction is effective for diaryl, aryl-alkyl and dialkyl sulfides and is tolerant of oxidisable and acid sensitive functional groups. Investigations have shown that the tris-peroxide 2, formed on reaction of pentane-2,4-dione with hydrogen peroxide under acidic reaction conditions, can oxidise two equivalents of sulfide using the exocyclic peroxide groups whereas the endocyclic peroxide remains intact. Calculations provide a mechanism consistent with experimental observations and suggest the reaction proceeds via an initial acid catalysed ring opening of a protonated tris-peroxide prior to oxygen transfer to a sulfur nucleophile.

Luminescent cis-Bis(bipyridyl)ruthenium(II) Complexes with 1,2-Azolylamidino Ligands: Photophysical, Electrochemical Studies, and Photocatalytic Oxidation of Thioethers

New 1,2-azolylamidino complexes cis-[Ru(bipy)2(NH=C(R)az*-κ2N,N)](OTf)2 (R = Me, Ph; az? = pz, indz, dmpz) are synthesized via chloride abstraction after a subsequent base-catalyzed coupling of a nitrile with the previously coordinated 1,2-azole. The synt

Electrochemical oxygenation of sulfides with molecular oxygen or water: Switchable preparation of sulfoxides and sulfones

A practical and eco-friendly method for the controllable aerobic oxygenation of sulfides by electrochemical catalysis was developed. The switchable preparation of sulfoxides and sulfones was effectively controlled by reaction time, in which both molecular oxygen and water can be used as the oxygen source under catalyst and external oxidant-free conditions. The electrochemical protocol features a broad substrate scope and excellent site selectivity and is successfully applied to the modification of some sulfide-containing pharmaceuticals and their derivatives. This journal is

Synergistic cooperative effect of CF3SO2Na and bis(2-butoxyethyl)ether towards selective oxygenation of sulfides with molecular oxygen under visible-light irradiation

A safe, practical and eco-friendly method for the switchable synthesis of sulfoxides and sulfones through visible-light-initiated oxygenation of sulfides at ambient temperature under transition-metal-, additives-free and minimal solvent conditions. The synergistic catalytic efforts between CF3SO2Na and 2-butoxyethyl ether represents the key promoting factor for the reaction. This journal is

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.

Synthesis of a light-harvesting ruthenium porphyrin complex substituted with BODIPY units. Implications for visible light-promoted catalytic oxidations

A light-harvesting ruthenium porphyrin substituted covalently with four boron-dipyrrin (BODIPY) moieties has been synthesized and studied. The resulting complex showed an efficient decarbonylation reaction predominantly due to a photo-induced energy transfer process. Chemical oxidation of the ruthenium(ii) BODIPY-porphyrin afforded a high-energytrans-dioxoruthenium(vi) species that is one order of magnitude more reactive towards alkene oxidation than those analogues supported by conventional porphyrins. In the presence of visible light, the ruthenium(ii) BODIPY-porphyrin displayed remarkable catalytic activity toward sulfide oxidation and alkene epoxidation using iodobenzene diacetate [PhI(OAc)2] and 2,6-dichloropyridineN-oxide (Cl2pyNO) as terminal oxidants, respectively. The findings in this work highlight that porphyrin-BODIPY conjugated metal complexes are potentially useful for visible light-promoted catalytic oxidations.

Air atmospheric photocatalytic oxidation by ultrathin C,N-TiO2nanosheets

Herein, we demonstrate the highly efficient photocatalytic sulfide oxidation reaction under mild conditions,i.e.in air, at room temperature and in the absence of a sacrificial reagent, co-catalyst or redox mediator, by using ultrathin C,N-TiO2nanosheets as a photocatalyst.

Preparation method and application of metal organic cage compound

The invention belongs to the technical field of fine chemical engineering, and relates to a preparation method and application of a metal organic cage compound. According to the preparation method, Zn in transition metal salt is used as a node, L is u

Synthesis and characterization of VO–vanillin complex immobilized on MCM-41 and its facile catalytic application in the sulfoxidation reaction, and synthesis of 2,3-dihydroquinazolin-4(1H)-ones and disulfides in green media

In this work, a vanillin complex is immobilized onto MCM-41 and characterized by FT-IR, X-ray diffraction, scanning electron microscopy, energy dispersive spectroscopy, thermogravimetric analysis, and BET techniques. This supported Schiff base complex was found to be an efficient and recoverable catalyst for the chemoselective oxidation of sulfides into sulfoxides and thiols into their corresponding disulfides (using hydrogen peroxide as a green oxidant) and also a suitable catalyst for the preparation of 2,3-dihydroquinazolin-4(1H)-one derivatives in water at 90°C. Using this protocol, we show that a variety of disulfides, sulfoxides, and 2,3-dihydroquinazolin-4(1H)-one derivatives can be synthesized in green conditions. The catalyst can be recovered and recycled for further reactions without appreciable loss of catalytic performance.