696-63-9

Usage

Uses

Used in Electronics Industry:
4-Methoxybenzenethiol is used as a precursor in the preparation of self-assembled monolayers (SAMs) for the characterization of SAMs and to study their effect on both nand p-channel organic thin film transistors. The formation of SAMs on various substrates can improve the performance and stability of organic thin film transistors by providing a well-ordered and functional interface.
Used in Chemical Synthesis:
4-Methoxybenzenethiol is used as a reagent in the cesium fluoride-Celite catalyzed preparation of thioethers and thioesters. Thioethers and thioesters are important functional groups in organic chemistry, and their synthesis can lead to the development of new compounds with potential applications in various fields, such as pharmaceuticals, agrochemicals, and materials science.

Synthesis Reference(s)

The Journal of Organic Chemistry, 49, p. 2637, 1984 DOI: 10.1021/jo00188a028

InChI:InChI=1/C7H8OS/c1-8-6-2-4-7(9)5-3-6/h2-5,9H,1H3/p-1

Upstream product

• 17333-79-8 p-methoxybenzenediazonium 
• 1709-60-0 4-methoxybenzenesulfinic acid 
• 100-66-3 methoxybenzene 
• 123-75-1 pyrrolidine 
• 99186-33-1 O-ethyl S-(4-methoxyphenyl) dithiocarbonate 
• 110-85-0 piperazine 
• 103-76-4 1-(2-hydroxyethyl)piperazine 
• 67-56-1 methanol 
• 53492-47-0 3-<2-<(4-methylphenyl)thio>ethyl>-4-methylsydnone 
• 108-85-0 1-bromocyclohexane 
• 26971-83-5 4-methoxybenzenethiolate 
• 7755-92-2 piperazine-1-carbaldehyde 
• 5335-87-5 4,4'-dimethoxyphenyl disulfide 
• 1879-16-9 1-methoxy-4-methylsulfanyl-benzene 

Downstream Products

• 100618-00-6 1-[(4-methoxy-phenylsulfanyl)-methyl]-piperidine 
• 132752-95-5 (Z)-1,2-bis(p-methoxyphenylsulfanyl)ethylene 
• 132752-96-6 trans-1,2-bis-(4-methoxy-phenylsulfanyl)-ethene 
• 13739-36-1 β-(4-methoxyphenylmercapto)propionic acid 
• 78597-95-2 1-(butylsulfanyl)-4-methoxybenzene 
• 7205-89-2 1-chloromethylsulfanyl-4-methoxy-benzene 
• 7205-58-5 ethyl (4-methoxyphenyl) sulfide 
• 858816-12-3 (4-methoxy-phenylsulfanyl)-acetaldehyde dimethylacetal 
• 714-31-8 3t-(4-methoxy-phenylsulfanyl)-acrylic acid 
• 873386-98-2 (4-methoxyphenyl) (pentyl) sulfane 
• 59693-90-2 n-hexyl 4-methoxyphenyl sulfide 
• 109047-48-5 1-((E)-1,2-dichloro-vinylmercapto)-4-methoxy-benzene 
• 347356-46-1 1-methoxy-3-[(4-methoxyphenyl)thio]benzene 
• 14065-23-7 1-methoxy-2-[(4-methoxyphenyl)thio]benzene 

Relevant academic research and scientific papers

Spontaneous substitution of azulene-derived benzylic alcohols by thiols and its application to labeling/protection of biothiols

By mixing guaiazulene-3-methanol derivatives and thiols at room temperature, benzylic substitution of the alcohol proceeded to yield the corresponding sulfide. Because of the blue color of the guaiazulene derivative, this spontaneous reaction was used for labeling of paper-immobilized biothiols. By treatment with tris(2-carboxyethyl)phosphine hydrochloride, the guaiazulene-3-ylmethyl part of the sulfide could be removed and the original thiol recovered. Based on these findings, a guaiazulene-3-methanol derivative was used as a protective group for the synthesis of cysteine derivatives.

Sulfur Incorporation Using Disulfanes as the Sulfur Atom Source Enabled Metal-Free Heteroannulation of 1,7-Enynes

A new oxidative [2+2+1] heteroannulation of 1,7-enynes with disulfanes promoted by Et3N, producing 3,3a-dihydro-thieno[3,4-c]quinolin-4(5H)-ones, is described. This reaction is achieved by using equivalent amounts of 1,7-enynes, sulfur atoms (disulfanes), tert-butyl peroxybenzoate (TBPB) as an oxidant and Et3N as the base, and represents an unprecedented strategy to applications of disulfanes as sulfur atom sources in synthesis. (Figure presented.).

Copper-Catalyzed Direct Synthesis of Aryl Thiols from Aryl Iodides Using Sodium Sulfide Aided by Catalytic 1,2-Ethanedithiol

A copper-catalyzed direct and effective synthesis of aryl thiols from aryl iodides using readily available Na 2 S·9H 2 O and 1,2-ethanedithiol was described. A variety of aryl thiols were readily obtained in yields of 76-99%. In this protocol, Na 2 S·9H 2 O was used as ultimate sulfur source, and 1,2-ethanedithiol functioned as an indispensable catalytic reagent.

Nitromethane as a cyanating reagent for the synthesis of thiocyanates

Nitromethane has been developed to be an effective cyanating reagent for the synthesis of thiocyanates. In the presence of iodine and base, a wide range of disulfides were reacted with nitromethane smoothly to give diverse thiocyanates in moderate to good yields.

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.

Tris(3-hydroxypropyl)phosphine (THPP): A mild, air-stable reagent for the rapid, reductive cleavage of small-molecule disulfides

Tris(3-hydroxypropyl)phosphine (THPP) is demonstrated to be a versatile, water-soluble and air-stable reducing agent, allowing for the rapid, irreversible reductive cleavage of disulfide bonds in both aqueous and buffered aqueous-organic media. The reagent shows exceptional stability at biological pH under which condition it permits the rapid reduction of a wide range of differentially functionalized small-molecule disulfides.

Development of selective colorimetric probes for hydrogen sulfide based on nucleophilic aromatic substitution

Hydrogen sulfide is an important biological signaling molecule and an important environmental target for detection. A major challenge in developing H2S detection methods is separating the often similar reactivity of thiols and other nucleophiles from H2S. To address this need, the nucleophilic aromatic substitution (SNAr) reaction of H2S with electron-poor aromatic electrophiles was developed as a strategy to separate H2S and thiol reactivity. Treatment of aqueous solutions of nitrobenzofurazan (7-nitro-1,2,3-benzoxadiazole, NBD) thioethers with H 2S resulted in thiol extrusion and formation of nitrobenzofurazan thiol (λmax = 534 nm). This reactivity allows for unwanted thioether products to be converted to the desired nitrobenzofurazan thiol upon reaction with H2S. The scope of the reaction was investigated using a Hammett linear free energy relationship study, and the determined ρ = +0.34 is consistent with the proposed SN2Ar reaction mechanism. The efficacy of the developed probes was demonstrated in buffer and in serum with associated submicromolar detection limits as low as 190 nM (buffer) and 380 nM (serum). Furthermore, the sigmoidal response of nitrobenzofurazan electrophiles with H2S can be fit to accurately quantify H2S. The developed detection strategy offers a manifold for H2S detection that we foresee being applied in various future applications.

Novel one-pot synthesis of thiophenols from related triazenes under mild conditions

In this work, at first, triazenes were synthesized from primary aryl amines. Afterwards, triazenes were converted into the corresponding thiophenols in one-pot using sodium sulfide in acidic media, by in situ generation of diazonium counterion beside hydrogen sulfide as anionic sulfur nucleophile at room temperature. The procedure can be a convenient shortcut for the preparation of thiophenols from primary aryl amines. Georg Thieme Verlag Stuttgart · New York.

A study of the kinetics of La3+-promoted methanolysis of S-aryl methylphosphonothioates: Possible methodology for decontamination of EA 2192, the toxic byproduct of VX hydrolysis

The kinetics of the La3+-catalyzed methanolysis of a series of S-aryl methylphosphonothioates (4a-e, phenyl substituents = 3,5-dichloro, 4-chloro, 4-fluoro, 4-H, 4-methoxy) were studied at 25 °C with ss pH control. The reaction involves saturation binding of the anionic substrates to dimeric La3+/methoxide catalysts formulated as La2 3+(-OCH3)x, where x = 2-5 depending on the solution ss pH. Cleavage of the La3+-bound methylphosphonothioates is fast, ranging from 5 × 10-3 s -1 to 5.5 × 10-5 s-1 for substrates 4a-e at a ss pH of 8.4 and 1.6 × 10-1 s-1 to 4 × 10-3s-1 at a ss pH of 11.7. The rate accelerations for the methanolysis of substrates 4a-e, relative to their background methoxide-promoted reactions, average 7 × 1010 and 1.5 × 109, respectively, at sspH's of 8.4 and 11.7. The catalytic system is predicted to cleave EA 2192 (S-2(N,N-di-iso-propylaminoethyl) methylphosphonothioate), a toxic byproduct of the hydrolysis of VX, with a t1/2 between 4 and 8 min at a ss pH of 8.4, and 27 min at a ss pH of 11.7.

CuI-nanoparticles-catalyzed selective synthesis of phenols, anilines, and thiophenols from aryl halides in aqueous solution

CuI-nanoparticles-catalyzed selective synthesis of phenols, anilines, and thiophenols from aryl halides was developed in the absence of both ligands and organic solvents. Anilines were formed selectively with ammonia competing with hydroxylation and thiophenols were generated selectively with sulfur powder after subsequent reduction competing with hydroxylation and amination.