6258-60-2

Usage

Uses

Used in Chemical Synthesis:
4-Methoxybenzyl mercaptan is used as a key intermediate in the synthesis of numerous ω-mercapto amino acids. These amino acids possess side-chain lengths ranging from 3-5 methylene units, which are essential for various applications in the chemical and pharmaceutical industries.
Used in Wine Industry:
In the wine industry, 4-Methoxybenzyl mercaptan serves as an internal standard for the quantitative determination of polyfunctional mercaptans at the nanogram per liter level. This application is crucial for maintaining the quality and consistency of wines, as these compounds contribute to the overall aroma and flavor profile of the final product.
Chemical Properties:
As a light yellow oil, 4-Methoxybenzyl mercaptan exhibits specific chemical properties that make it suitable for use in various synthesis processes and analytical applications. Its physical state and reactivity contribute to its effectiveness in the mentioned uses.

InChI:InChI=1/C8H10OS/c1-9-8-4-2-7(6-10)3-5-8/h2-5,10H,6H2,1H3

Upstream product

• 2746-25-0 p-Methoxybenzyl bromide 
• 17356-08-0 thiourea 
• 824-94-2 p-methoxybenzyl chloride 
• 76950-80-6 1-(4-Methoxy-benzyl)-2-methylsulfanyl-4,6-diphenyl-pyridinium; iodide 
• 102607-00-1 S-(4-methoxybenzyl) ethanethioate 
• 19927-28-7 p-methoxybenzyl thiocyanate 
• 17049-73-9 4-methoxybenzyl carbamate 
• 123-11-5 4-methoxy-benzaldehyde 
• 27877-42-5 S-(4-methoxybenzyl) N,N-dimethylthiocarbamate 
• 18357-78-3 S-(4-methoxybenzyl) N,N-diethylthiocarbamate 
• 51956-88-8 O-(4-methoxybenzyl) N,N-dimethylthiocarbamate 
• 105-13-5 4-Methoxybenzyl alcohol 
• 17004-42-1 1,2-bis(4-methoxybenzyl)disulfide 

Downstream Products

• 239127-35-6 1-ethanesulfonylmethyl-4-methoxy-benzene 
• 4705-34-4 1,2-bis(4-methoxyphenyl)ethene 
• 61830-24-8 5-(4-methoxy-benzylsulfanyl)-thiazole-4-carboxylic acid ethyl ester 
• 526212-40-8 dithiooxalodiimidic acid bis-(4-methoxy-benzyl) ester 
• 110057-63-1 5-p-Methoxy-phenyl-3,4-dithia-pentansaeure-methylester 
• 100171-58-2 <4-Methoxy-benzyl>-diphenylthiocarbamat 
• 72326-28-4 (E)-4-[4-(4-Trifluoromethyl-phenoxy)-phenoxy]-pent-2-enethioic acid S-(4-methoxy-benzyl) ester 
• 53636-22-9 3-(4-methoxybenzylthio)pyridine 
• 100393-16-6 4-[(4-methoxybenzyl)thio]pyridine 
• 155222-26-7 2-<(4-methoxyphenyl)methylthio>pyridine 
• 147032-16-4 2-(4-Methoxybenzylthio)pyrazine 
• 147032-13-1 2-Methyl-3-(4-methoxybenzylthio)pyrazine 
• 147032-14-2 2-(4-Methoxybenzylthio)-5-methylpyrazine 
• 147032-15-3 2-(4-Methoxybenzylthio)-6-methylpyrazine 

Relevant academic research and scientific papers

Benzylic Thio and Seleno Newman-Kwart Rearrangements

The thermally induced OBn → SBn and OBn → SeBn migration reactions facilitate the rearrangement of O-benzyl thio- and selenocarbamates [BnOC(=X)NMe2] (X = S or Se) into their corresponding S-benzyl thio- and Se-benzyl selenocarbamates [BnXC(=O)NMe2] (X = S or Se). A series of substituted O-benzyl thio- and selenocarbamates were synthesized and rearranged in good yields of 33-88%. The reaction rates are higher for substrates with electron-donating groups in the 2 or 4 position of the aromatic ring, but the rearrangement also proceeds with electron-withdrawing substituents. The rearrangement follows first-order reaction kinetics and proceeds via a tight ion pair intermediate consisting of the benzylic carbocation and the thio- or selenocarbamate moiety. Computational studies support these findings.

Nonenzymatic Dynamic Kinetic Resolution of in situ Generated Hemithioacetals: Access to 1,3-Disubstituted Phthalans

The first nonenzymatic DKR reaction of hemithioacetals is developed. Hemithioacetals were formed in situ via thiol addition and subsequently underwent an intramolecular oxa-Michael reaction. The scope of the reaction was quite broad ranging from aliphatic to aromatic substituents and 1,3-disubstituted-1,3-dihyroisobenzofuran products were obtained in good yields with moderate diastereoselectivities and high enantioselectivities. (Figure presented.).

Phosphorus Pentasulfide Mediated Conversion of Primary Carbamates into Thiols

In this paper, we report a method for the conversion of primary carbamates into thiols in the presence of phosphorus pentasulfide (P 2 S 5) in refluxing toluene. Presently, no method exists in the literature for conversion of carbamates into thiols and, to the best of our knowledge, it is the first report for this type of conversion. This method presents an indirect route for the conversion of alcohols into thiols via their carbamate derivatives that may be useful in the total synthesis of compounds containing a thiol functionality.

Phosphorus pentasulfide mediated conversion of organic thiocyanates to thiols

In this paper we report an efficient and mild procedure for the conversion of organic thiocyanates to thiols in the presence of phosphorus pentasulfide (P2S5) in refluxing toluene. The method avoids the use of expensive and hazardous transition metals and harsh reducing agents, as required by reported methods, and provides an attractive alternative to the existing methods for the conversion of organic thiocyanates to thiols.

A metal-free and recyclable synthesis of benzothiazoles using thiourea as a sulfur surrogate

Using odorless thiourea as the S source, benzothiazoles and asymmetric disulfides could be obtained from thioformanilides through the tandem cyclization/nucleophilic addition/hydrolysis/nucleophilic substitution reaction. Furthermore, the obtained asymmetric disulfides could readily transfer to benzothiazoles after nitro-reduction and amide formation reaction. This metal-free and recyclable synthetic methodology offered a time-efficient, less expensive, and environmentally friendly alternative to multifunctional benzothiazoles.

Electron transfer to sulfides and disulfides: Intrinsic barriers and relationship between heterogeneous and homogeneous electron-transfer kinetics

The electron-acceptor properties of series of related sulfides and disulfides were investigated in N,N-dimethylformamide with homogeneous (redox catalysis) and/or heterogeneous (cyclic voltammetry and convolution analysis) electrochemical techniques. The electron-transfer rate constants were determined as a function of the reaction free energy and the corresponding intrinsic barriers were determined. The dependence of relevant thermodynamic and kinetic parameters on substituents was assessed. The kinetic data were also analyzed in relation to corresponding data pertaining to reduction of diaryl disulfides. All investigated reductions take place by stepwise dissociative electron transfer (DET) which causes cleavage of the Calkyl-S or S-S bond. A generalized picture of how the intrinsic electron-transfer barrier depends on molecular features, ring substituents, and the presence of spacers between the frangible bond and aromatic groups was established. The reduction mechanism was found to undergo a progressive (and now predictable) transition between common stepwise DET and DET proceeding through formation of loose radical anions. The intrinsic barriers were compared with available results for ET to several classes of dissociative- and nondissociative-type acceptors, and this led to verification that the heterogeneous and the homogeneous data correlate as predicted by the Hush theory.

A Ramberg-Baecklund route to the stilbenoid anti-cancer agents combretastatin A-4 and DMU-212

A concise route to combretastatin A-4, a potent inhibitor of tubulin polymerisation, using a Ramberg-Baecklund reaction to form the key (Z)-stilbene unit has been developed; this Ramberg-Baecklund approach has also been extended to prepare the (E)-stilbene DMU-212, which also possesses interesting growth inhibitory properties. The Royal Society of Chemistry.

Chemoselective protection of thiols versus alcohols and phenols. The Tosvinyl group

The conjugate addition of aliphatic and aromatic thiols to ethynyl p-tolyl sulphone (tosylacetylene) has been managed to afford Tosvinyl derivatives chemoselectively (in the presence of oxygen nucleophiles) and stereoselectively (isomers Z) in practically quantitative yields. The conditions of choice are: catalytic amounts of Et3N (only 0.5-1.0 mol%), a reaction temperature around 0°C and, for the less acidic thiols, CF3CH2OH or CH3CN/CF3CH2OH as the solvent. Thus, N-Boc-Cys-OMe has been quantitatively protected as its S-Tosvinyl derivative in the presence of N-Boc-Ser-OMe and N-Boc-Tyr-OMe. This novel protecting group is stable to several basic and acidic conditions; its removal is achieved at rt by treatment with an excess of pyrrolidine or at 0°C with alkanethiolate ions.

Synthesis of 9-methyl-1H-[1,4]thiazino[3,2-g]quinoline-2,5,10(3H)-trione, the B,C,D ring core of the shermilamine alkaloids

The synthesis of 9-methyl-1H-[1,4]thiazino[3,2-g]quinoline-2,5,10(3H)-trione(4), from N-(4-bromo-2,5-dimethoxyphenyl)acetamide was discussed. Oxidative cyclisation of 2,2′-disulfanediylbis[N-2,5-dimethoxyphenyl)acetamide] to 5,8-dimethoxy-2H-1,4-benzothiazin-3(4H)-one(7b) was reported. It was found that the reaction proceeded through the disulfide and iodine acted as an oxidizing agent, enabling the cyclization.

One pot rapid synthesis of thiols from alcohols under mild conditions

Thiols are prepared in high yields from corresponding alcohols using Ph3P, NBS in acetone and followed by addition of polymer supported hydrosulfide under mild condition.