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

• 696-63-9 4-Methoxybenzenethiol 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 15436-21-2 S-Methyl-S-p-methoxyphenyl-N-p-tosylsulfylimin 
• 13882-12-7 S-methyl methanethiosulfinate 
• 100-66-3 methoxybenzene 
• 407-25-0 trifluoroacetic anhydride 
• 24197-73-7 S-4-methoxyphenyl benzothioate 
• 132381-65-8 S-4-methoxyphenyl 2,2-dimethylpropanethioate 
• 637-89-8 4-sulfanylphenol 
• 616-38-6 carbonic acid dimethyl ester 
• 127022-75-7 methoxy(diphenyl)-λ⁶-sulfanenitrile 
• 1073-72-9 4-hydroxythioanisole 
• 141-52-6 sodium ethanolate 

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 
• 76030-62-1 10-(2,6-Dimethyl-phenyl)-5-ethyl-4a-hydroxy-3-methyl-5,10-dihydro-4aH-benzo[g]pteridine-2,4-dione 
• 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 
• 15436-21-2 S-Methyl-S-p-methoxyphenyl-N-p-tosylsulfylimin 
• 4816-23-3 5-(Ethylthio)-2-methoxybenzoic acid 
• 50390-78-8 4-methoxy-3-methylphenyl methyl sulphide 
• 7205-58-5 ethyl (4-methoxyphenyl) sulfide 
• 7205-61-0 1-methoxy-4-<(1-methylethyl)thio>-benzene 

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).

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.

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.

Aryl or heteroaryl methoxylation reaction method

The invention discloses an aryl or heteroaryl methoxylation reaction method. The method comprises the following steps: preparing a substrate. The coupling agent, ligand, solvent, catalyst and base are mixed homogeneously in an inert gas to give the aryl or heteroaryl methoxy compounds. Compared with a methoxylation reaction method in the prior art, the method has the advantages that the reaction system conditions are mild, the usage amount of the catalyst and the ligand is low to 5% of the amount of the substrate material, and the catalytic efficiency is improved. The method has better compatibility to different substrate expansion and discovery of aryl halides or heteroaryl halides with different functional groups. The yield of aryl or heteroaryl methoxy compounds prepared by the method disclosed by the invention is 36% - 89%.