1879-16-9

Basic information

• Product Name: 1-METHOXY-4-(METHYLTHIO)BENZENE
• Synonyms: 1-Methoxy-4-(methylsulfanyl)benzene;Anisole, p-(methylthio)-;Benzene,1-methoxy-4-(methylthio)-;Methyl 4-methoxyphenyl sulfide;Methyl p-methoxyphenyl sulfide;p-(Methylthio)anisole;p-Anisyl methyl sulfide;p-Methoxyphenyl methyl sulfide
• CAS NO: 1879-16-9
• Molecular Formula: C₈H₁₀OS
• Molecular Weight: 154.23
• Mol File: 1879-16-9.mol
• Article Data: 97

Chemical Properties

• Melting Point: 22-23 °C
• Boiling Point: 99 °C (4 mmHg)
• Flash Point: 107 °C
• Appearance: colorless to yellow liquid after melting
• Density: 1.11 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0415mmHg at 25°C
• Refractive Index: 1.5785-1.5805
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 1-METHOXY-4-(METHYLTHIO)BENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-METHOXY-4-(METHYLTHIO)BENZENE(1879-16-9)
• EPA Substance Registry System: 1-METHOXY-4-(METHYLTHIO)BENZENE(1879-16-9)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 37/39-26
• RIDADR: UN 3335
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 1879-16-9(Hazardous Substances Data)

Usage

Chemical Properties

colorless to yellow liquid after melting

Synthesis Reference(s)

Journal of the American Chemical Society, 79, p. 717, 1957 DOI: 10.1021/ja01560a059

InChI:InChI=1/C8H10O2S/c1-9-7-3-5-8(6-4-7)11-10-2/h3-6H,1-2H3

Upstream product

• 624-92-0 Dimethyldisulphide 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 696-63-9 4-Methoxybenzenethiol 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 1073-72-9 4-hydroxythioanisole 
• 141-52-6 sodium ethanolate 
• 127022-75-7 methoxy(diphenyl)-λ⁶-sulfanenitrile 
• 544-40-1 Dibutyl sulfide 
• 3517-99-5 1-methoxy-4-(methylsulfinyl)benzene 
• 24658-23-9 (4-methoxyphenyl)(methyl)sulfane-d₃ 
• 123-09-1 4-chlorophenyl methyl sulfide 
• 124-41-4 sodium methylate 
• 3406-77-7 (4-methoxy-phenylsulfanyl)-acetic acid 

Downstream Products

• 7205-89-2 1-chloromethylsulfanyl-4-methoxy-benzene 
• 3517-90-6 p-anisyl methyl sulfone 
• 1073-72-9 4-hydroxythioanisole 
• 3517-99-5 1-methoxy-4-(methylsulfinyl)benzene 
• 56403-23-7 1,4-Bis-chloromethyl-2-ethoxy-5-methylsulfanyl-benzene 
• 38278-08-9 4-methoxyphenyl bis(carbomethoxy) 3-methylylide 
• 76030-62-1 10-(2,6-Dimethyl-phenyl)-5-ethyl-4a-hydroxy-3-methyl-5,10-dihydro-4aH-benzo[g]pteridine-2,4-dione 
• 5285-90-5 4-thiocyanatoanisole 
• 1445-91-6 (S)-1-phenylethanol 
• 1517-69-7 (R)-1-phenylethanol 
• 3517-99-5 (S)-p-methoxyphenyl methyl sulfoxide 
• 3517-99-5 (R)-4-methoxyphenyl methyl sulfoxide 
• 107832-68-8 5-carboxymethylsulfanyl-2-methoxy-benzoic acid 
• 15436-21-2 S-Methyl-S-p-methoxyphenyl-N-p-tosylsulfylimin 

Relevant articles and documents

Alkaline oxidation by perpropionic acid of aryl-methyl sulfoxide formation. Experimental studies and theories of nucleophilic oxidation of p-substituted thioanisole by perpropionate anion in micellar medium

The reaction of perpropionic acid CH3CH3CO 3H (1) with thioanisole (4) and p-substituted thioanisoles [p-methoxy (2), p-methyl (3), p-bromo (5), and p-nitro (6)] in stoechiometric proportion has been carried out in micellar medium (cetyl trimethyl ammonium chloride, CTACl). Studies of the influence of the pH, the temperature and the substitution of the thioanisole, provide a better understanding of the sulfoxides (2a-6a) formation. Ab initio calculations have been achieved and the oxidation reaction has been studied in detail in aqueous medium (pH = 11).

Catalytic Chemoselective Sulfimidation with an Electrophilic [CoIII(TAML)]?-Nitrene Radical Complex**

The cobalt species PPh4[CoIII(TAMLred)] is a competent and stable catalyst for the sulfimidation of (aryl)(alkyl)-substituted sulfides with iminoiodinanes, reaching turnover numbers up to 900 and turnover frequencies of 640 min?1 under mild and aerobic conditions. The sulfimidation proceeds in a highly chemoselective manner, even in the presence of alkenes or weak C?H bonds, as supported by inter- and intramolecular competition experiments. Functionalization of the sulfide substituent with various electron-donating and electron-withdrawing arenes and several alkyl, benzyl and vinyl fragments is tolerated, with up to quantitative product yields. Sulfimidation of phenyl allyl sulfide led to [2,3]-sigmatropic rearrangement of the initially formed sulfimide species to afford the corresponding N-allyl-S-phenyl-thiohydroxylamines as attractive products. Mechanistic studies suggest that the actual nitrene transfer to the sulfide proceeds via (previously characterized) electrophilic nitrene radical intermediates that afford the sulfimide products via electronically asynchronous transition states, in which SET from the sulfide to the nitrene radical complex precedes N?S bond formation in a single concerted process.

N-bromosuccinimide/HCl mediated reduction of sulfoxides to sulfides

An efficient reduction of sulfoxides to sulfides mediated by N-bromosuccinimide (NBS)/HCl system has been developed. This protocol shows good functional group compatibility as well as broad substrates scope with operational simplicity.

Production of Alkyl Aryl Sulfides from Aromatic Disulfides and Alkyl Carboxylates via a Disilathiane–Disulfide Interchange Reaction

The results of this study show that disilathiane is an effective mediator in the synthesis of alkyl aryl sulfides with disulfides and alkyl carboxylates. Mechanistic studies suggest that disilathiane promotes cleavage of the sulfur–sulfur bond of disulfides to generate thiosilane as a key intermediate. Diselenides were also applicable to this transformation to produce the corresponding selenides.