17733-22-1

Basic information

• Product Name: 2-CHLOROTHIOANISOLE
• Synonyms: 2-CHLORO THIOANISOLE 99%;(2-chlorophenyl)(methyl)sulfane;1-(Methylthio)-2-chlorobenzene;1-Methylthio-2-chlorobenzene;Methyl (2-chlorophenyl) sulfide;Methyl [2-chlorophenyl] sulfide;Methyl 2-chlorophenyl sulfide;2-Chlorobenzyl thioalcohol
• CAS NO: 17733-22-1
• Molecular Formula: C₇H₇ClS
• Molecular Weight: 158.65
• EINECS: 254-602-5
• Product Categories: Building Blocks;Chemical Synthesis;Organic Building Blocks;Sulfides/Disulfides;Sulfur Compounds;Boron, Nitrile, Thio,& TM-Cpds
• Mol File: 17733-22-1.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 239-240 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1,22 g/cm3
• Vapor Pressure: 0.00216mmHg at 25°C
• Refractive Index: n20/D 1.608(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Sensitive: Stench
• CAS DataBase Reference: 2-CHLOROTHIOANISOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLOROTHIOANISOLE(17733-22-1)
• EPA Substance Registry System: 2-CHLOROTHIOANISOLE(17733-22-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: UN 3334
• WGK Germany: 3
• HazardClass: STENCH
• Hazardous Substances Data: 17733-22-1(Hazardous Substances Data)

Usage

Uses

2-Chlorothioanisole may be used to synthesize 2-chlorophenyl methyl sulfone.

Synthesis Reference(s)

The Journal of Organic Chemistry, 48, p. 3114, 1983 DOI: 10.1021/jo00166a040

General Description

2-Chlorothioanisole can be prepared from the reaction between N,N-dimethylformamide, 1,2-dichlorobenzene, finely ground KOH and methyl mercaptan. Benzene dipole moment value analysis of 2-chlorothioanisole indicates that it exists predominantly in trans- form. 1H NMR spectrum of 2-chlorothioanisole has been studied in acetone-d6 solution.

InChI:InChI=1/C7H7ClOS/c1-9-6-4-2-3-5-7(6)10-8/h2-5H,1H3

Upstream product

• 6320-03-2 2-chlorothiphenol 
• 74-93-1 methylthiol 
• 95-50-1 1,2-dichloro-benzene 
• 5188-07-8 sodium thiomethoxide 
• 616-38-6 carbonic acid dimethyl ester 
• 2905-23-9 2-chlorophenylsulfonyl chloride 
• 624-92-0 Dimethyldisulphide 
• 348-51-6 1-chloro-2-fluorobenzene 
• 615-41-8 2-iodochlorobenzene 
• 124-38-9 carbon dioxide 
• 110-05-4 di-tert-butyl peroxide 
• 31121-19-4 bis(2-chlorobenzene)disulfide 
• 3900-89-8 2-Chlorobenzeneboronic acid 
• 139696-88-1 2-chlorophenyl methyl sulfoxide 

Downstream Products

• 312612-67-2 1-(2-(methylthio)phenyl)-2-phenylacetylene 
• 134749-78-3 1-Methylsulfanyl-2-((E)-styryl)-benzene 
• 870195-94-1 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-chlorobenzene 
• 53897-91-9 S-methyl-S-(2-chlorophenyl)-N-p-tosylsulfilimine 
• 17482-05-2 o-chlorophenyl methyl sulfone 
• 7321-57-5 (R)-(+)-o-chlorophenyl methyl sulfoxide 
• 172338-47-5 (R)-(+)-2-chlorophenyl methyl sulfoxide 
• 1207-95-0 2-phenylbenzo[b]thiophene 
• 147917-81-5 2-chlorophenyl chloromethyl sulfide 
• 1402581-96-7 2-(3-chloro-4-methylsulfonyl-phenyl)-N-[[2-(3-chlorophenyl)-5-(trifluoromethyl)-2H-pyrazol-3-yl]methyl]propionamide 
• 1072429-72-1 2-(3-chloro-4-(methylsulfonyl)phenyl)propanoic acid 
• 1402586-39-3 methyl 2-(3-chloro-4-(methylsulfonyl)phenyl)propanoate 

Relevant articles and documents

Synthesis of Aryl Methyl Sulfides from Arysulfonyl Chlorides with Dimethyl Carbonate as the Solvent and C1 Source

A new procedure for the synthesis of aryl methyl sulfides from dimethyl carbonate (DMC) and arylsulfonyl chlorides has been achieved. In this strategy, DMC plays a dual role as both, C1 building block and green solvent. Arylsulfonyl chlorides served as the sulfur precursors, and a variety of aryl methyl sulfides were obtained in moderate to excellent yields with good functional group tolerance. Additionally, alkylsulfonyl chloride and dibenzyl carbonate are proven to be suitable substrates as well.

Copper-Catalyzed Methylthiolation of Aryl Iodides and Bromides with Dimethyl Disulfide in Water

An efficient route to aryl methyl sulfides through the copper-catalyzed coupling reaction of aryl iodides or bromides with dimethyl disulfide in water is described. Electron-donating and electron-withdrawing functional groups in the substrates were tolerated, and the corresponding products were obtained in moderate to good yields.

Metal-free S-methylation of diaryl disulfides with di-tert-butyl peroxide

An efficient approach for S-methylation of diaryl disulfides with di-tert-butyl peroxide under metal-free and neutral conditions was established. The present protocol shows good functional group tolerance to afford aryl methyl sulfides in moderate to good