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

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

Used in Chemical Synthesis:
2-Chlorothioanisole is used as a chemical intermediate for the synthesis of 2-chlorophenyl methyl sulfone, which can be utilized in various chemical reactions and applications.

Synthesis Reference(s)

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

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 
• 110-05-4 di-tert-butyl peroxide 
• 31121-19-4 bis(2-chlorobenzene)disulfide 
• 624-92-0 Dimethyldisulphide 
• 348-51-6 1-chloro-2-fluorobenzene 
• 616-38-6 carbonic acid dimethyl ester 
• 2905-23-9 2-chlorophenylsulfonyl chloride 
• 615-41-8 2-iodochlorobenzene 
• 124-38-9 carbon dioxide 
• 3900-89-8 2-Chlorobenzeneboronic acid 
• 139696-88-1 2-chlorophenyl methyl sulfoxide 
• 34560-81-1 ortho-chlorophenyl n-propyl sulfide 
• 32503-27-8 tetra(n-butyl)ammonium hydrogensulfate 
• 63451-08-1 2-Chloro-benzenediazonium; hydrogen sulfate 

Downstream Products

• 7321-57-5 (R)-(+)-o-chlorophenyl methyl sulfoxide 
• 1251954-90-1 S-(2-chlorophenyl)-S-methyl-N-(trifluoromethanesulfonyl)sulfilimine 
• 1207-95-0 2-phenylbenzo[b]thiophene 
• 17482-05-2 o-chlorophenyl methyl sulfone 
• 172338-47-5 (R)-(+)-2-chlorophenyl methyl sulfoxide 
• 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 
• 1402586-38-2 methyl 2-(3-chloro-4-(methylthio)phenyl)propanoate 
• 1072429-71-0 2-(3-chloro-4-(methylthio)phenyl)propanoic acid 
• 300356-07-4 (E)-2-(3-chloro-4-methylsulfanylphenyl)-3-cyclopentyl acrylic acid ethyl ester 
• 588941-45-1 RO 0505082 
• 300356-14-3 (R)-2-(3-chloro-4-(methylsulfonyl)phenyl)-3-cyclopentylpropanoic acid 

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.

t-BuOK-promoted methylthiolation of aryl fluorides with dimethyldisulfide under transition-metal-free and mild conditions

In the presence of potassium tert-butoxide (t-BuOK), the cross-coupling reaction between aryl fluorides and dimethyldisulfide was developed. A series of aryl methyl sulfides were obtained in moderate to good yields under transition-metal-free and mild conditions.

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.

Reduction of CO2 with NaBH4/I2 for the Conversion of Thiophenols to Aryl Methyl Sulfides

We report a tandem reaction to realize reduction of carbon dioxide with thiophenols to generate aryl methyl sulfides under the NaBH4/I2 system with 18-crown-6 as the solvent. Thiophenols bearing electron-donating and electron-withdrawing groups are feasible in this reaction. Controlled experiment results indicate that 18-crown-6 plays a critical role in six-electron reduction of carbon dioxide.

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

Metal-Free, DTBP-Mediated Methylthiolation of Arylboronic Acids with Dimethyldisulfide

An efficient method for the C-S bond formation via the coupling reaction of arylboronic acids with dimethyldisulfide has been developed under the metal-free conditions. This novel protocol provides an attractive route for the synthesis of aryl methyl sulf

Development of the large-scale preparation of 2-(Methanesulfonyl) benzenesulfonyl chloride

A practical and scalable process is described for the preparation of 2-(methansulfonyl)benzenesulfonyl chloride, a key building block used in the synthesis of several drug candidates. The material is prepared by an efficient four-step sequence from inexpe

Mild and efficient deoxygenation of sulfoxides to sulfides using HFCL 4/KBH4 system

HfCl4/KBH4 was found to be a facile, efficient, convenient, and chemoselective system for the deoxygenation of dialkyl, diaryl, and aryl alkyl sulfoxides, especially for the reduction of dibenzyl sulfoxide to the corresponding sulfides under mild conditions. In addition, the HfCl 4/KBH4 system could be used in reduction of some other sulfur-bearing substrates to the corresponding sulfides, such as 2,2'-dibenzothiazolyl disulfide, but this reducing system could not reduce sulfolane, diphenyl sulfone, p-toluenesulfonic acid, and p-toluenesulfonyl chloride to their corresponding thiophenols. Copyright

Sulfur containing compounds

This invention is directed to novel and known stufur containing compounds and pharmaceutically acceptable salts thereof that have utility as antifungals and as antiproliferative agents against mammalian cells, in particular cancer cells and most particularly leukemia-derived cells. The invention provides a method for synthesizing certain of the sulfur containing compounds that is more efficient than previously known methods.

Alkyl- and Arylthiodediazoniations of Dry Arenediazonium o-Benzenedisulfonimides. Efficient and Safe Modifications of the Stadler and Ziegler Reactions to Prepare Alkyl Aryl and Diaryl Sulfides

The reaction between dry arenediazonium o-benzenedisulfonimides 1 and sodium thiolates in anhydrous methanol represents an efficient and safe procedure, of general validity, for the preparation of unfunctionalized or variously functionalized alkyl aryl and diaryl sulfides. As a rule, the reaction temperature was maintained at 0-5°C for the alkylthiodediazoniations and at room temperature (20-25°C) for the arylthiodediazoniations. The sulfide yields are generally high; of the 63 considered examples, 43 gave yields greater than 80% and 13 were between 70% and 80%. Lower yields were obtained only when sterically hindered diazonium salts or thiols were used. A good amount of the o-benzenedisulfonimide (8) was always recovered from the reactions and could be reused to prepare salts 1. The copious experimental data collected in homogeneous conditions have offered several starting points for the study of the mechanism of these reactions.