4526-41-4

Basic information

• Product Name: O-[(METHYLTHIO)METHYL]PHENOL
• Synonyms: O-[(METHYLTHIO)METHYL]PHENOL;2-(METHYLTIOMETHYL)PHENOL,97%
• CAS NO: 4526-41-4
• Molecular Formula: C₈H₁₀OS
• Molecular Weight: 154.23
• Mol File: 4526-41-4.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 257.1°C at 760 mmHg
• Flash Point: 125.6°C
• Appearance: /
• Density: 1.145g/cm³
• Vapor Pressure: 0.00919mmHg at 25°C
• Refractive Index: 1.593
• PKA: 9.78±0.30(Predicted)
• CAS DataBase Reference: O-[(METHYLTHIO)METHYL]PHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: O-[(METHYLTHIO)METHYL]PHENOL(4526-41-4)
• EPA Substance Registry System: O-[(METHYLTHIO)METHYL]PHENOL(4526-41-4)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 4526-41-4(Hazardous Substances Data)

Usage

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

Upstream product

• 13165-73-6 phenyl chlorosulphinate 
• 67-68-5 dimethyl sulfoxide 
• 108-95-2 phenol 
• 90-01-7 salicylic alcohol 
• 50450-21-0 dimethylbromosulphonium bromide 
• 75-18-3 dimethylsulfide 
• 37873-98-6 N-(2,4-dinitro-phenyl)-S,S-dimethyl-sulfimide 

Downstream Products

• 1246811-27-7 (Ph₃P)2(platinum)(OC₆H₄CH₂) 
• 10419-35-9 2-ethoxy-3,4-dihydro-2H-chromene 
• 124313-15-1 2-<2-(methylthiomethyl)phenoxymethyl>phenol 
• 494-12-2 flavan 

Relevant articles and documents

A new synthesis of o-quinonemethides and their inter- and intramolecular cyclization reactions

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Selective ortho-Alkylation of Phenols with Sulphoxides via Sigmatropic Rearrangement: Synthesis of Coumarins

ortho-Alkylphenols have been prepared from phenol and dialkyl sulphoxides via sigmatropic rearrangement, using thionyl chloride or phenyl chlorosulphinate as an activator of sulphoxides.In the same manner, ortho-phenylthiomethylphenol has been prepared in good yields.When ethyl phenyl sulphoxide, diallyl sulphoxide, and methyl methylsulphinylacetate were used as sulphoxides, none of the expected products were obtained.Salicylaldehyde has been prepared in moderate yield, when methyl methylthiomethyl sulphoxide was used as a sulphoxide. 3-(2-Hydroxyphenyl)propionic acid derivatives, which were obtained from substituted phenols and dimethyl 3,3'-sulphynyldipropionate, have been cyclized to give the corresponding coumarins in good yields.

Selective ortho-Methylthiomethylation of Phenols with Dimethyl Sulphoxide and Thionyl Chloride

Thionyl chloride and phenyl chlorosulphinate have been shown to be useful activators for dimethyl sulphoxide in the selective preparation of ortho-methylthiomethylphenol via a sigmatropic rearrangement.By this process, ortho-methylthiomethylated phenols having a variety of 2- or 4-substituents (Me, Cl, OMe, NO2, and CO2Me) have been prepared in good yields.In contrast, similar reactions of 3-substituted phenols were affected by the electronic characters of the substituents.With more electron-donating groups such as OH and OMe in the 3-position, none of the expected products were obtained, but in the case of other 3-substituted phenols, two possible rearrangement products were obtained in moderate yields.