13865-50-4

Basic information

• Product Name: METHOXYMETHYL PHENYL SULFIDE
• Synonyms: ALPHA-METHOXYTHIOANISOLE;[(METHOXYMETHYL)THIO]BENZENE;METHOXYMETHYL PHENYL SULFIDE;METHYL PHENYLTHIOMETHYL ETHER;Methoxy(phenylthio)methane;Phenylthiomethylmethyl ether;alpha-Methoxythioanisole Methyl Phenylthiomethyl Ether;(MethoxyMethyl)(phenyl)sulfane
• CAS NO: 13865-50-4
• Molecular Formula: C₈H₁₀OS
• Molecular Weight: 154.23
• Product Categories: Sulfur Compounds (for Synthesis);Synthetic Organic Chemistry
• Mol File: 13865-50-4.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 113-114 °C18 mm Hg(lit.)
• Flash Point: 203 °F
• Appearance: /
• Density: 1.047 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0942mmHg at 25°C
• Refractive Index: n20/D 1.5632(lit.)
• CAS DataBase Reference: METHOXYMETHYL PHENYL SULFIDE(CAS DataBase Reference)
• NIST Chemistry Reference: METHOXYMETHYL PHENYL SULFIDE(13865-50-4)
• EPA Substance Registry System: METHOXYMETHYL PHENYL SULFIDE(13865-50-4)

Safety Data

• RIDADR: UN 3334
• WGK Germany: 3
• Hazardous Substances Data: 13865-50-4(Hazardous Substances Data)

Usage

Uses

Methoxymethyl phenyl sulfide has been used in the preparation of methoxymethyl phenyl sulfoxide.

Synthesis Reference(s)

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

General Description

Meisenheimer rearrangement of methoxymethyl phenyl sulfoxide to methoxymethyl benzenesulfenate has been reported. Methoxymethyl phenyl sulfide undergoes solvent free permanganate oxidation to yield methoxymethyl phenyl sulfone.

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

Upstream product

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

Downstream Products

• 65756-04-9 trans-(±)-2-(phenylthio)cyclopentanol 
• 144632-21-3 3-(Methoxy-phenylsulfanyl-methyl)-1-aza-bicyclo[2.2.2]octan-3-ol 
• 22198-58-9 1-methoxy-1-phenylthiopropan-2-one 
• 78614-65-0 2-ethyl-1-methoxy-1-(phenylthio)-2-butanol 
• 99369-47-8 1-Methoxy-2-methyl-1-phenylsulfanyl-butan-2-ol 
• 670-98-4 methyl benzenesulfinate 
• 42919-47-1 3-Phenylthio-3-methoxy-2-hydroxy-propan 
• 116204-90-1 (1-Methoxy-4-methyl-pent-3-enylsulfanyl)-benzene 
• 73188-45-1 2-ethyl-2-(phenylthio)butanal 
• 57768-35-1 1-(phenylthio)-1-cyclohexanecarboxaldehyde 
• 108139-15-7 1-(phenylthio)-2-cyclohexene-1-carboxaldehyde 
• 133030-42-9 4--1-methylpiperidin-4-ol 
• 99706-77-1 2,2-bis<2-(carbomethoxy)ethyl>-3--5,5-dimethylcyclohexan-1-one 
• 99706-83-9 8,8-dimethyl-10-<(Z)-methoxy(phenylthio)methylene>spiro<4,5>decan-6-one 

Relevant articles and documents

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.

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.

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.