13865-50-4

Usage

Uses

Used in Chemical Synthesis:
Methoxymethyl phenyl sulfide is used as a precursor in the chemical synthesis of methoxymethyl phenyl sulfoxide. METHOXYMETHYL PHENYL SULFIDE serves as an intermediate in the production of various organic compounds, contributing to the development of new materials and chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, methoxymethyl phenyl sulfide is used as a key component in the synthesis of methoxymethyl phenyl sulfoxide, which can be further transformed into methoxymethyl benzenesulfenate through the Meisenheimer rearrangement. This rearrangement is a significant chemical reaction in the synthesis of various pharmaceutical compounds, making methoxymethyl phenyl sulfide an essential building block in drug development.
Used in Solvent-Free Oxidation Processes:
Methoxymethyl phenyl sulfide is also used in solvent-free permanganate oxidation processes to yield methoxymethyl phenyl sulfone. This oxidation reaction is important in the production of sulfone derivatives, which have a wide range of applications in the chemical and pharmaceutical industries, including the synthesis of dyes, agrochemicals, and pharmaceuticals.

Synthesis Reference(s)

The Journal of Organic Chemistry, 51, p. 879, 1986 DOI: 10.1021/jo00356a025

InChI:InChI=1/C8H10OS/c1-9-7-10-8-5-3-2-4-6-8/h2-6H,7H2,1H3

Upstream product

• 426218-81-7 bis-methoxymethyl-disulfane 
• 930-69-8 sodium thiophenolate 
• 107-30-2 chloromethyl methyl ether 
• 67-56-1 methanol 
• 100-68-5 methyl-phenyl-thioether 
• 109-87-5 Dimethoxymethane 
• 108-98-5 thiophenol 
• 13057-17-5 bromethyl methyl ether 
• 66080-23-7 4,4,5,5-tetramethyl-2-((phenylsulfanyl)methyl)-1,3,2-dioxaborolane 
• 591-50-4 iodobenzene 
• 17873-08-4 (phenylsulfanylmethyl)trimethylsilane 

Downstream Products

• 37559-63-0 Methoxymethyl phenyl sulfoxide 
• 65756-04-9 trans-(±)-2-(phenylthio)cyclopentanol 
• 133030-42-9 4--1-methylpiperidin-4-ol 
• 124666-70-2 1-((3aR,5S,6aR)-2,2-Dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-methoxy-2-phenylsulfanyl-ethanol 
• 124666-70-2 1-((3aR,5R,6aR)-2,2-Dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-methoxy-2-phenylsulfanyl-ethanol 
• 111-71-7 heptanal 
• 86290-33-7 threo-2,3-dimethylpentanal 
• 86290-35-9 erythro-2,3-dimethylpentanal 
• 22092-54-2 2-ethylpentanal 
• 22198-58-9 1-methoxy-1-phenylthiopropan-2-one 
• 89171-36-8 1-Methoxy-1-phenylsulfanyl-tridecan-2-one 
• 99706-73-7 3-cyclohex-2-en-1-one 
• 128590-06-7 2-[1-Butylsulfanyl-meth-(E)-ylidene]-1-(methoxy-phenylsulfanyl-methyl)-cyclohexanol 
• 114701-23-4 6-[1-Butylsulfanyl-meth-(E)-ylidene]-1-(methoxy-phenylsulfanyl-methyl)-2,2-dimethyl-cyclohexanol 

Relevant academic research and scientific papers

Electrochemical Properties and Reactions of Sulfur-Containing Organoboron Compounds

Electrochemical analyses of 4,4,5,5-tetramethyl-2-phenylsulfanylmethyl-[1,3,2]dioxaborolane and tetra-n-butylammonium phenylthiomethyltrifluoroborate were comparatively studied by cyclic voltammetry measurements and we found for the first time the β-effect of organoborate, which was indicated by experimental and theoretical aspects. The organoborate was found to have a much lower oxidation potential compared to the organoborane. Anodic substitution reaction of organoboronate ester and organoborate was successfully carried out in the presence of nucleophiles to afford the selectively substituted products in good yields.

Anodic Dehydrogenative Cyanamidation of Thioethers: Simple and Sustainable Synthesis of N-Cyanosulfilimines

A novel and very simple to perform electrochemical approach for the synthesis of several N-cyanosulfilimines in good to excellent yields was established. This method provides access to biologically relevant sulfoximines by consecutive oxidation using electro-generated periodate. This route can be easily scaled-up to gram quantities. The S,N coupling is carried out at an inexpensive carbon anode by direct oxidation of sulfide. Therefore, the designed process is atom economic and represents a new “green route” for the synthesis of sulfilimines and sulfoximines.

Synthesis of dithioacetals and oxathioacetals with chiral auxiliaries

One-pot synthesis of dithioacetals as well as an efficient method for oxathioacetal is reported. Additionally, some chiral auxiliaries were used to synthesize enantiomerically pure dithioacetals and oxathioacetals.

Spectral and Thermodynamic Characteristics of Complexes of Seleno- and Thioacetals with Iodine

Seleno- and thioacetal complexes of iodine were studied spectrophotometrically. The spectral and thermodynamic parameters of the complexes are compared with the special features of the electronic and steric structure of the donor molecules and with the characteristics of tetracyanoethylene complexes of the same compounds.

Electrooxidative Inter- and Intramolecular Carbon-Carbon Bond Formation Using Organothio Groups as Electroauxiliaries

The introduction of an organothio group to an α-carbon of ethers results in significant decrease of the oxidation potentials. Anodic oxidation of α-organothioethers gives rise to facile cleavage of the C-S bond and the introduction of carbon nucleophiles on the carbon. Allylsilanes, silyl enol ethers, and trimethylsilyl cyanide serve as effective carbon nucleophiles. The anodic oxidation of the α-organothioethers having a carbon-carbon double bond in an appropriate position using Bu4-NBF4 as the supporting electrolyte leads to the effective cyclization and the introduction of the fluoride to one of the formal olefinic carbon. The present study demonstrates the effectiveness of organothio groups as electroauxiliaries in electrooxidative inter- and intramolecular carbon-carbon bond formation.

Ketone homologation to produce α-methoxyketones: Application to conduritol synthesis

The scope of Trost's sulfone homologation procedure for the conversion of ketones into their α-methoxylated higher homologues has been dramatically expanded. The use of zirconium (or hafnium) tetrachloride in the hydroxy sulfone rearrangement step gives g

Cross Aldol Products from α-Haloalkoxysilanes and Silyl Enol Ethers

α-Haloalkoxysilanes have been prepared by cleavage of the C-S bond in O,S-acetals with sulfuryl chloride, and by cleavage of C-Sn bond in α-silyloxystannanes by bromine.The α-haloalkoxysilanes, both after isolation or after preparation in situ react with silyl enol ethers to yield silyl-protected cross aldol products.The reaction is catalyzed by Lewis acids.

Fluoride Ion Promoted Anodic Substitutions of Chalcogeno Compounds. 1. Regioselective Anodic Alkoxylation of Sulfides

Anodic α-alkoxylation of sulfides was remarkably promoted in the presence of fluoride ions: When Et3N*3HF was used as a supporting electrolyte, simple alkyl phenyl sulfides and sulfides bearing weak electron-withdrawing groups underwent anodic alkoxylatio

Anodic Oxidation of (Trimethylsilyl)methanes with ?-Electron Substituents in the Presence of Nucleophiles

It was found that oxidation potentials of methanes with ?-electron substituents were decreased by introduction of a trimethylsilyl group.The anodic oxidation of benzyl-, allyl-, aryl(or alkyl)thiomethyl-, and aryloxymethyl-substituted trimethylsilanes smoothly proceeded in the presence of nucleophiles, e.g. alcohols and carboxylic acids, to eliminate the trimethylsilyl groups giving the corresponding alkoxylated and carboxylated products in moderate or high yields without full optimization of electrolytic conditions, while aminomethylsilanes did not undergo such a kind of anodic oxidation.

Indirect Electrooxidation Mediated by an Ni(III)/(II) Redox Couple with a Cyclam Ligand

The first example of an Ni(III)-mediated indirect electrolysis was found in the oxidation of silicon compounds using an Ni(III)/(II) redox couple having a macrocyclic polyamine (cyclam) as a ligand.