4867-37-2

Basic information

• Product Name: 3-CHLOROTHIOANISOLE
• Synonyms: M-CHLOROTHIOANISOLE;1-CHLORO-3-(METHYLTHIO)BENZENE;3-CHLOROTHIOANISOLE;3-CHLOROPHENYL METHYL SULFIDE;1-Chloro-3-(methylsulfanyl)benzene;3-Chlorophenyl methyl sulphide;3-Chlorothioanisole,99%;3-Chloro
• CAS NO: 4867-37-2
• Molecular Formula: C₇H₇ClS
• Molecular Weight: 158.65
• EINECS: -0
• Product Categories: Organic Building Blocks;Sulfides/Disulfides;Sulfur Compounds;Building Blocks;Chemical Synthesis;Organic Building Blocks;Sulfur Compounds
• Mol File: 4867-37-2.mol

Chemical Properties

• Boiling Point: 120°C 20mm
• Flash Point: 106
• Appearance: /
• Density: 1.206 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.19mmHg at 25°C
• Refractive Index: 1.6
• BRN: 1931485
• CAS DataBase Reference: 3-CHLOROTHIOANISOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CHLOROTHIOANISOLE(4867-37-2)
• EPA Substance Registry System: 3-CHLOROTHIOANISOLE(4867-37-2)

Safety Data

• Hazard Codes: Xi
• Statements: 22-36/37/38
• Safety Statements: 23-36/37-36-26
• RIDADR: 3334
• HazardClass: STENCH
• Hazardous Substances Data: 4867-37-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Chlorothioanisole is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its unique chemical properties make it a valuable component in the development of new drugs and medications.
Used in Dye Industry:
In the dye industry, 3-Chlorothioanisole is utilized as a chemical intermediate in the production of dyes. Its ability to react with other compounds allows for the creation of a wide range of colorants used in textiles, plastics, and other materials.
Used in Perfume Industry:
3-Chlorothioanisole is employed as a chemical intermediate in the formulation of perfumes. Its strong odor can be modified and combined with other compounds to create unique and complex fragrances.
Used as a Chemical Reagent in Organic Synthesis:
3-Chlorothioanisole serves as a chemical reagent in organic synthesis, facilitating various chemical reactions and transformations. Its versatility in this capacity makes it an essential tool in the development of new organic compounds and materials.
Environmental Considerations:
Due to its persistence and low solubility in water, 3-Chlorothioanisole has been identified as a potential environmental pollutant. As a result, it is crucial to implement proper handling, storage, and disposal methods to minimize its impact on the environment.

InChI:InChI=1/C7H7ClS/c1-9-7-4-2-3-6(8)5-7/h2-5H,1H3

Upstream product

• 2037-31-2 3-chlorophenylthiol 
• 127022-75-7 methoxy(diphenyl)-λ⁶-sulfanenitrile 
• 5188-07-8 sodium thiomethoxide 
• 2888-06-4 3-chlorophenylsulfonyl chloride 
• 616-38-6 carbonic acid dimethyl ester 
• 13150-73-7 3-chlorophenyl methyl sulfoxide 
• 624-92-0 Dimethyldisulphide 
• 541-73-1 1,3-Dichlorobenzene 
• 625-98-9 3-chlorofluorobenzene 
• 5271-38-5 2-methylmercapto-ethanol 
• 625-99-0 3-iodochlorobenzene 
• 110-05-4 di-tert-butyl peroxide 
• 19742-92-8 bis(3-chlorophenyl) disulfide 
• 67-68-5 dimethyl sulfoxide 

Downstream Products

• 103860-95-3 3-<2-Chlor-4-methylmercapto-benzoyl>-propionsaeure 
• 13150-73-7 3-chlorophenyl methyl sulfoxide 
• 64-19-7 acetic acid 
• 21383-00-6 3-chlorophenyl methyl sulfone 
• 710348-63-3 4,4,5,5‐tetramethyl‐2‐[3‐(methylsulfanyl)phenyl]‐1,3,2‐dioxaborolane 
• 38695-76-0 S-methyl-S-(3-chlorophenyl)-N-p-tosylsulfilimine 
• 635305-47-4 2-(3-chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 22133-00-2 (3-chlorophenyl)(imino)(methyl)-λ⁶-sulfanone 
• 1256360-24-3 2-(3-chloro-5-(methylthio)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

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.

Scalable electrochemical reduction of sulfoxides to sulfides

A scalable reduction of sulfoxides to sulfides in a sustainable way remains an unmet challenge. This report discloses an electrochemical reduction of sulfoxides on a large scale (>10 g) under mild reaction conditions. Sulfoxides are activated using a substoichiometric amount of the Lewis acid AlCl3, which could be regeneratedviaa combination of inexpensive aluminum anode with chloride anion. This deoxygenation process features a broad substrate scope, including acid-labile substrates and drug molecules.

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.

Palladium-catalyzed intermolecular transthioetherification of aryl halides with thioethers and thioesters

Functional group transfer reactions are an important synthetic tool in modern organic synthesis. Herein, we developed a new palladium-catalyzed intermolecular transthioetherification reaction of aryl halides with thioethers and thioesters. The synthetic utility and practicality of this catalytic protocol are demonstrated in a wide range of successful transformations (>70 examples). This catalytic protocol is applicable in carbonylative coupling processes as well, and the first example of carbonylative methylthioesterification of aryl halides has been achieved. Notably, this work also provides an approach to using natural products, such as methionine and selenomethionine, as the functional group sources.

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

A visible-light photocatalytic thiolation of aryl, heteroaryl and vinyl iodides

The general catalytic synthesis of aryl and vinyl thioethers from readily available halides remains a challenge. Herein we report a unified method for the thiolation of aryl and vinyl iodides with dialkyl disulfides using visible light photoredox catalysis. A range of thioether products bearing diverse functional groups can be accessed in high yield and with excellent chemoselectivity. We demonstrate the versatility of this method through the expedient synthesis of a family of thioether-rich natural products. A detailed investigation of the photocatalytic mechanism is presented from both steady-state and time-resolved luminescent quenching as well as transient absorption spectroscopy experiments.

N-Imidazolylation of Sulfoximines from N-Cyano Sulfoximines, 1-Alkynes, and N-Sulfonyl Azides

The rhodium-catalyzed N-imidazolylation of N-sulfonyl-1,2,3-triazoles with a variety of N-cyano sulfoximines has been developed for the synthesis of N-imidazolyl sulfoximines via elimination of molecular nitrogen. Copper-catalyzed [3+2] cycloaddition followed by rhodium-catalyzed N-imidazolylation from 1-alkynes, N-sulfonyl azides, and N-cyano sulfoximines is also demonstrated for the synthesis of N-imidazolyl sulfoximines in a one-pot procedure.

Copper(II)-Catalyzed Single-Step Synthesis of Aryl Thiols from Aryl Halides and 1,2-Ethanedithiol

A highly efficient transition metal-catalyzed single-step synthesis of aryl thiols from aryl halides has been developed employing copper(II) catalyst and 1,2-ethanedithiol. The key features are use of readily available reagents, a simple operation, and relatively mild reaction conditions. This new protocol shows a broad substrate scope with excellent functional group compatibility. A variety of aryl thiols are directly prepared from aryl halides in high yields. Furthermore, the aryl thiols are used in situ for the synthesis of more advanced molecules such as diaryl sulfides and benzothiophenes.

Organocatalytic visible light mediated synthesis of aryl sulfides

Photo-sensitized synthesis of arylsulfides from arenediazonium salts in the presence of eosin Y has been developed. This protocol exhibits high functional group tolerance and a wide substrate scope and is an attractive alternative to the thermal reaction that involves explosive intermediates.