2388-73-0

Usage

Uses

Used in Perfumery and Cosmetics Industry:
2-Methoxythioanisole is used as a fragrance and flavoring agent for its ability to impart a unique and pleasant scent to perfumes and cosmetics. Its distinct thioether odor adds depth and complexity to the final product, making it a valuable component in the creation of scents and fragrances.
Used in Food and Beverage Industry:
In the food and beverage sector, 2-Methoxythioanisole is utilized as a flavoring agent to enhance the taste and aroma of various products. Its ability to add a distinct flavor profile makes it a sought-after ingredient in the formulation of food products, contributing to their overall sensory appeal.
Used in Organic Synthesis:
2-Methoxythioanisole also serves as a key intermediate in organic synthesis, where it is used to produce a variety of chemical compounds. Its unique chemical structure allows it to participate in various reactions, making it a versatile building block in the synthesis of new molecules.
Used as a Solvent in Chemical Reactions:
Furthermore, 2-Methoxythioanisole is employed as a solvent in chemical reactions due to its ability to dissolve a wide range of substances. Its solubility properties make it an effective medium for carrying out various chemical processes, facilitating the formation of desired products.
It is crucial to handle 2-Methoxythioanisole with care, as it can be harmful if ingested or inhaled, and may cause skin irritation upon contact. Proper safety measures should be taken to minimize potential risks associated with its use.

InChI:InChI=1/C8H10OS/c1-9-7-5-3-4-6-8(7)10-2/h3-6H,1-2H3

Upstream product

• 7217-59-6 2-Methoxybenzenethiol 
• 77-78-1 dimethyl sulfate 
• 17733-22-1 2-chlorothioanisole 
• 124-41-4 sodium methylate 
• 1073-29-6 2-(methylsulfenyl)phenol 
• 74-88-4 methyl iodide 
• 75-15-0 carbon disulfide 
• 578-57-4 2-bromoanisole 
• 624-92-0 Dimethyldisulphide 
• 100-66-3 methoxybenzene 
• 5188-07-8 sodium thiomethoxide 
• 529-28-2 4-iodoanisol 
• 95-50-1 1,2-dichloro-benzene 
• 38452-13-0 1-methylsulfinyl-2-methoxybenzene 

Downstream Products

• 38452-13-0 1-methylsulfinyl-2-methoxybenzene 
• 876497-01-7 2-methanesulfinyl-1-methoxy-4-nitro-benzene 
• 18619-21-1 <(2-Methoxyphenyl)thio>acetic acid 
• 107832-70-2 3-Carboxymethylsulfanyl-2-methoxy-benzoic acid 
• 15436-19-8 S-Methyl-S-<2-methoxy-phenyl>-N-p-tolyl-sulfonyl-sulfilimin 
• 1121-24-0 ortho-mercaptophenol 
• 1073-29-6 2-(methylsulfenyl)phenol 
• 7217-59-6 2-Methoxybenzenethiol 
• 13736-79-3 1-methanesulfonyl-2-methoxy-benzene 
• 84413-74-1 (R)-1-methoxy-2-(methylsulfinyl)benzene 
• 84413-73-0 (S)-(-)-2-methoxyphenyl methyl sulfoxide 
• 73891-69-7 (2-Methoxy-phenyl)-methyl-sulfonium 
• 73953-50-1 C₈H₁₂OS⁽²⁺⁾ 
• 578-58-5 2-methylmethoxybenzene 

Relevant academic research and scientific papers

The Aryl Sulfide Synthesis via Sulfide Transfer

Aryl sulfides are in great demands in drugs and materials sciences. To avoid using nucleophilic and noxious thiols, many efforts have been focused on exploring novel sulfide resources. Herein, a reductive Pd-catalyzed, Ni-mediated method to synthesize aryl sulfides via a sulfide transfer reaction is developed. The utility and scope of this reaction is exemplified by various aryl electrophiles and aryl sulfides. Mechanistic studies reveal two competing catalytic cycles of sulfide transfer and aryl transfer in this reaction, where the former one is favored over the later one because of the large energy barrier difference during the transmetalation. Moreover, two important chemicals are late-stage functionalized by this method, exhibiting the potential applications in drugs and materials science.

Nickel-Catalyzed Reversible Functional Group Metathesis between Aryl Nitriles and Aryl Thioethers

We describe a new functional group metathesis between aryl nitriles and aryl thioethers. The catalytic system nickel/dcype is essential to achieve this fully reversible transformation in good to excellent yields. Furthermore, the cyanide- and thiol-free reaction shows high functional group tolerance and great efficiency for the late-stage derivatization of commercial molecules. Finally, synthetic applications demonstrate its versatility and utility in multistep synthesis.

A Nickel-Doped Dehydrobenzoannulene-Based Two-Dimensional Covalent Organic Framework for the Reductive Cleavage of Inert Aryl C-S Bonds

The development of metalated covalent organic frameworks (COFs) is useful for generating recyclable catalytic systems for practical applications. Herein, we report the synthesis, characterization, and catalytic properties of an azine-linked two-dimensional (2D) COF containing nickel-doped dehydrobenzoannulene (DBA) units. We demonstrate that Ni-DBA-2D-COF can be used to reductively cleave the aryl C-S bonds of several organosulfur compounds utilizing dimethylethylsilane as the reducing agent. The Ni-DBA-2D-COF catalytic system displays excellent recyclability and good yields. This work highlights a rare example of utilizing metalated DBA complexes to perform catalytic transformations.

Iridium-Catalyzed ortho-C-H Borylation of Thioanisole Derivatives Using Bipyridine-Type Ligand

A simple iridium catalytic system was developed that allows for a variety of 2-borylthioanisoles to be easily synthesized via ortho-selective C-H borylation of thioanisole derivatives. Once introduced, boryl and methylthio groups were converted by palladium-catalyzed transformations. Density functional theory calculations revealed that weak interactions, such as hydrogen bonding between the C-H bond of the SCH3 group and the oxygen atom of the boryl ligand, control the ortho-selectivity.

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.

Photocatalytic Deoxygenation of Sulfoxides Using Visible Light: Mechanistic Investigations and Synthetic Applications

The photocatalytic deoxygenation of sulfoxides to generate sulfides facilitated by either Ir[(dF(CF3)ppy)2(dtbbpy)]PF6 or fac-Ir(ppy)3 is reported. Mechanistic studies indicate that a radical chain mechanism operates, which proceeds via a phosphoranyl radical generated from a radical/polar crossover process. Initiation of the radical chain was found to proceed via two opposing photocatalytic quenching mechanisms, offering complementary reactivity. The mild nature of the radical deoxygenation process enables the reduction of a wide range of functionalized sulfoxides, including those containing acid-sensitive groups, in typically high isolated yields.

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.

Lewis Acid–Base Interaction-Controlled ortho-Selective C?H Borylation of Aryl Sulfides

An iridium/bipyridine-catalyzed ortho-selective C?H borylation of aryl sulfides was developed. High ortho-selectivity was achieved by a Lewis acid–base interaction between a boryl group of the ligand and a sulfur atom of the substrate. This is the first example of a catalytic and regioselective C?H transformation controlled by a Lewis acid–base interaction between a ligand and a substrate. The C?H borylation reaction could be conducted on a gram scale, and with a bioactive molecule as a substrate, demonstrating its applicability to late-stage regioselective C?H borylation. A bioactive molecule was synthesized from an ortho-borylated product by converting the boryl and methylthio groups of the product.

Copper-mediated methylthiolation of aryl halides with DMSO

A copper-mediated methylthiolation of aryl halides with the widely available DMSO is described. The procedure tolerates a series of functional groups such as methoxy, nitro, chloro, fluoro, trifluoromethyl, formyl and methoxycarbonyl groups. Thus, it represents a simple and facile methylthiolation procedure.

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