3517-90-6

Basic information

• Product Name: 4-METHOXYPHENYLMETHYLSULFONE
• Synonyms: 4-METHOXYPHENYLMETHYLSULFONE;1-METHANESULFONYL-4-METHOXY-BENZENE;4-methoxyphenyl methyl sulphone;NSC87355;1-(Methylsulfonyl)-4-methoxybenzene;1-Methoxy-4-(methylsulfonyl)benzene;1-Methoxy-4-methylsulfonylbenzene;4-Methoxy-1-(methylsulfonyl)benzene
• CAS NO: 3517-90-6
• Molecular Formula: C₈H₁₀O₃S
• Molecular Weight: 186.23
• Mol File: 3517-90-6.mol

Chemical Properties

• Melting Point: 120-121.5°C
• Boiling Point: 341.1 °C at 760 mmHg
• Flash Point: 160.1 °C
• Appearance: /
• Density: 1.199 g/cm³
• Vapor Pressure: 0.000163mmHg at 25°C
• Refractive Index: 1.511
• Storage Temp.: Room temperature.
• CAS DataBase Reference: 4-METHOXYPHENYLMETHYLSULFONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-METHOXYPHENYLMETHYLSULFONE(3517-90-6)
• EPA Substance Registry System: 4-METHOXYPHENYLMETHYLSULFONE(3517-90-6)

Safety Data

• Hazardous Substances Data: 3517-90-6(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 28, p. 1945, 1963 DOI: 10.1021/jo01042a536

InChI:InChI=1/C8H10O3S/c1-11-7-3-5-8(6-4-7)12(2,9)10/h3-6H,1-2H3

Upstream product

• 1879-16-9 1-methoxy-4-methylsulfanyl-benzene 
• 3517-99-5 1-methoxy-4-(methylsulfinyl)benzene 
• 33599-22-3 (4-methanesulfonylphenyl)-N,N-dimethyl-amine 
• 3466-32-8 4-bromoohenyl methyl sulfone 
• 38050-71-4 9-methoxy-9-BBN 
• 1129-26-6 4-methoxybenzene sulfonamide 
• 74-88-4 methyl iodide 
• 18836-84-5 1-[(4-methoxyphenyl)sulfonyl]-1H-pyrrole 
• 1950-68-1 4-methoxybenzenesulfonyl hydrazide 
• 868-85-9 Dimethyl phosphite 
• 616-42-2 dimethylsulfite 
• 696-62-8 para-iodoanisole 
• 512-56-1 trimethyl phosphite 
• 20277-69-4 sodium methansulfinate 

Downstream Products

• 140-67-0 Estragole 
• 613-37-6 4-methoxylbiphenyl 
• 100-66-3 methoxybenzene 
• 1047974-45-7 (E)-1-(4-methoxyphenylsulfonyl)-4-phenylbut-3-en-2-ol 
• 108485-22-9 1-((bromomethyl)sulfonyl)-4-methoxybenzene 
• 108545-54-6 1-methoxy-4-((4-methylbenzyl)sulfonyl)benzene 
• 203247-70-5 1-methoxy-4-(phenethylsulfonyl)benzene 
• 14223-10-0 1-(benzylsulfonyl)-4-methoxybenzene 

Relevant articles and documents

High Chemoselectivity in the Construction of Aryl Methyl Sulfones via an Unexpected C-S Bond Formation between Sulfonylhydrazides and Dimethyl Phosphite

A highly chemoselective route to aryl methyl sulfones via an unexpected C S bond formation between sulfonylhydrazides and dimethyl phosphite catalyzed by NaI under mild conditions has been established. This transformation provides an alternative and metal-free pathway to acquire various aryl methyl sulfones in good to excellent yields. Notably, dimethyl phosphite was employed as a stable and readily available alkyl source.

Polyoxometalate-Based Organic-Inorganic Hybrids as Heterogeneous Catalysts for Cycloaddition of CO2with Epoxides and Oxidative Desulfurization Reactions

Self-assembly of polyoxometalates, transition metal salts, and 2,6-bis(2′-pyridyl)-4-hydroxypyridine (LOH) obtained four organic-inorganic hybrids [Co2.5(LOH)(LO)2(H2O)2(PW12O39)]·3CH3CN·2OH (1), [Zn1.5(LOH)3]·(PMo12O40)·CH3OH·2H2O (2), [Cd1.5(LOH)3]·(PW12O40)·2CH3OH·1.5H2O (3), and [Mn(LOH)2]·(PW12O40)·2CH3CN·H3O (4). Hybrid 1 exhibits an extended chain, which could be further connected into a 3D supramolecular architecture by H-bonds. Hybrids 2-4 feature monomolecular structures, which are further bridged via H-bonds to yield charming 3D supramolecular structures. Noteworthy, 1 and 2 can be employed as recyclable and highly efficient heterogeneous catalysts. The activated 1 displays a high catalytic activity for the cycloaddition reaction of CO2 and epoxides. Hybrid 2 exhibits an excellent catalytic performance for the oxidative desulfurization reaction.

Self-Assembled Polyoxometalate-Based Metal-Organic Polyhedra as an Effective Heterogeneous Catalyst for Oxidation of Sulfide

Two polyoxovanadate-based metal-organic polyhedra with octahedral (oct) and rhombic dodecahedral (rdo) geometries have been constructed from a concave molecular building block and linear and triangular carboxylate ligands. VMOP-7 is constructed from {V5O9Cl} SBU and a linear anthracene-9,10-dicarboxylic acid ligand in which all the anthracene groups are perpendicular to the edge of the octahedron. Such an arrangement mode can effectively reduce the steric hindrance between ligands. VMOP-8 is constructed from {V5O9Cl} SBU and a triangular biphenyl 3,4,5-tricarboxylate ligand, which exhibits an elongated rhombic dodecahedral configuration due to the geometry of the ligand. Furthermore, VMOP-8 can serve as a heterogeneous catalyst and exhibits efficient and common catalytic activity for oxidative desulfurization.

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.

Assembly of polyoxometalate-thiacalix[4]arene-based inorganic-organic hybrids as efficient catalytic oxidation desulfurization catalysts

Self-assembly of polyoxometalates, Ni(ii)/Ag(i) cations and tetra-[5-(mercapto)-1-methyltetrazole]-thiacalix[4]arene (L) yielded three inorganic-organic hybrids, namely, [Ni3L2(CH3OH)6(H2O)4][PMo12O40]2·3CH3OH·2H2O (1), [Ni3L2(CH3OH)6(H2O)4][PW12O40]2·3CH3OH·2H2O (2) and [Ag3L(PMo12O40)] (3). In hybrids (1) and (2), Ni(ii) cations are linked by L ligands to produce layered frameworks, and H bonds among the [PMo12O40]3?/[PW12O40]3?anions and L ligands lengthen the structures to form 3D supramolecular architectures. Hybrid (3) exhibits a 3D architecture, of which Ag(i) cations not only coordinated with the N and O atoms of L ligands and [PMo12O40]3?anions simultaneously, but also connected each other by Ag-Ag interactions. It is worth mentioning that1and3as recyclable catalysts show excellent heterogeneous catalytic activity in oxidation desulfurization reactions.

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.

Magneli-type tungsten oxide nanorods as catalysts for the selective oxidation of organic sulfides

Selective oxidation of thioethers is an important reaction to obtain sulfoxides as synthetic intermediates for applications in the chemical industry, medicinal chemistry and biology or the destruction of warfare agents. The reduced Magneli-type tungsten oxide WO3?xpossesses a unique oxidase-like activity which facilitates the oxidation of thioethers to the corresponding sulfoxides. More than 90% of the model system methylphenylsulfide could be converted to the sulfoxide with a selectivity of 98% at room temperature within 30 minutes, whereas oxidation to the corresponding sulfone was on a time scale of days. The concentration of the catalyst had a significant impact on the reaction rate. Reasonable catalytic effects were also observed for the selective oxidation of various organic sulfides with different substituents. The WO3?xnanocatalysts could be recycled at least 5 times without decrease in activity. We propose a metal oxide-catalyzed route based on the clean oxidant hydrogen peroxide. Compared to other molecular or enzyme catalysts the WO3?xsystem is a more robust redox-nanocatalyst, which is not susceptible to decomposition or denaturation under standard conditions. The unique oxidase-like activity of WO3?xcan be used for a wide range of applications in synthetic, environmental or medicinal chemistry.

Copper-Catalyzed Methoxylation of Aryl Bromides with 9-BBN-OMe

A Cu-catalyzed cross-coupling reaction between aryl bromides and 9-BBN-OMe to provide aryl methyl ethers under mild conditions is reported. The oxalamide ligand BHMPO plays a key role in the transformation. Various functional groups on bromobenzenes are well tolerated, providing the desired anisole products in moderate to high yields.

Method for synthesizing aryl alkyl sulfone compound by promoting oxidation of aryl alkyl thioether compound through visible light

The invention discloses a method for synthesizing an aryl alkyl sulfone compound by promoting oxidation of an aryl alkyl thioether compound through visible light. The method comprises the following steps of: performing one-pot reaction on an aryl alkyl thioether compound and sodium trifluoromethanesulfinate in a diethylene glycol dibutyl ether solution system under the conditions of oxygen-containing atmosphere and 385-390 nm purple light irradiation to generate the aryl alkyl sulfone compound. The method has the advantages of mild conditions, simple operation, environmental protection, easilyavailable raw materials, excellent compatibility of substrate functional groups, high reaction yield and the like.

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