83180-92-1

Upstream product

• 103-19-5 di(p-tolyl) disulfide 
• 1153-43-1 4,4'-dimethoxyphenyl thiosulfonate 
• 80472-59-9 S-(4-methoxyphenyl) (4-methylbenzene)thiosulfonate 
• 74-88-4 methyl iodide 
• 696-63-9 4-Methoxybenzenethiol 
• 1068439-06-4 4-[(5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)disulfanyl]toluene 
• 1068439-10-0 4-[(5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)disulfanyl]anisole 
• 106-45-6 para-thiocresol 
• 696-62-8 para-iodoanisole 
• 15199-26-5 N-((4-methylphenyl)thio)phthalimide 
• 88683-45-8 2-((4-methoxyphenyl)thio)isoindoline-1,3-dione 
• 2943-42-2 di(4-methyl)phenylthiosulfonate 
• 5335-87-5 4,4'-dimethoxyphenyl disulfide 
• 10436-83-6 S-(4-methylphenyl) ethanethioate 

Downstream Products

• 103-19-5 di(p-tolyl) disulfide 
• 5335-87-5 4,4'-dimethoxyphenyl disulfide 
• 95348-47-3 S-4-methoxyphenyl 4-methylbenzenesulfinothioate 
• 121955-58-6 S-4-tolyl 4-methoxybenzenesulfinothioate 
• 6013-47-4 4-methylphenyl 4-methoxyphenyl sulfide 

Relevant academic research and scientific papers

NFSI-catalyzed S[sbnd]S bond exchange reaction for the synthesis of unsymmetrical disulfides

The metal-free S[sbnd]S bond exchange reaction of symmetrical disulfides catalyzed by NFSI is described. This novel protocol provides a facile and efficient approach to accessing important unsymmetrical disulfides. Furthermore, this strategy could also be utilized in the late-stage functionalization of amino acids, drugs, and natural products. The broad substrate scope, good functional group tolerance and easy accessibility of catalyst indicate that this strategy affords a green and practical complementary method to various unsymmetrical disulfides.

Alternating Current Electrolysis for the Electrocatalytic Synthesis of Mixed Disulfide via Sulfur–Sulfur Bond Metathesis towards Dynamic Disulfide Libraries

A novel approach of electrolysis using alternating current was applied in the sulfur–sulfur bond metathesis of symmetrical disulfides towards unsymmetrical disulfides. As initially expected, a statistical distribution in disulfides was obtained. Furthermore, the influence of electrode polarisation by alternating current was investigated on a two-disulfide matrix. The highly dynamic nature of this chemistry resulted in the creation of dynamic disulfide libraries by expansion of the matrices, consisting of up to six symmetrical disulfides. In addition, mixing of matrices and stepwise expanding of a matrix by using alternating current electrolysis were realised.

Synthesis of unsymmetrical disulfides: Via PPh3-mediated reductive coupling of thiophenols with sulfonyl chlorides

A facile and rapid synthesis of unsymmetrical aryl disulfides using PPh3-mediated reductive coupling of thiophenols with aryl sulfonyl chlorides was described. Good functional group tolerance and scalability were achieved in this strategy. More importantl

Preparation of Unsymmetrical Disulfides from Thioacetates and Thiosulfonates

A method for the transformation of organic thioacetates, a widely used functionality for the preparation of self-assembled monolayers on gold surfaces, into unsymmetrical disulfides is reported. Disulfides are readily immobilized on gold in contrast to thioacetates, which usually require a deprotection step prior to bonding to the metal surface. The potential of the method for the controlled preparation of unsymmetrical disulfides has been demonstrated with model compounds comprising several thioacetates, which were readily converted into the corresponding unsymmetrical disulfides.

Disulfide-Catalyzed Iodination of Electron-Rich Aromatic Compounds

Herein, a disulfide-catalyzed electrophilic iodination of aromatic compounds using 1,3-diiodo-5,5-dimethylhydantoin (DIH) has been developed. The disulfide activates DIH as a Lewis base to promote the iodination reaction in acetonitrile under mild conditions. This system is applicable to a wide range of electron-rich aromatic compounds, including acetanilide, anisole, imidazole, and pyrazole derivatives.

Transition Metal-Free Oxidative Coupling of Primary Amines in Polyethylene Glycol at Room Temperature: Synthesis of Imines, Azobenzenes, Benzothiazoles, and Disulfides

A transition metal-free protocol has been developed for the oxidative coupling of primary amines to imines and azobenzenes, thiols to disulfides, and 2-aminothiophenols to benzothiazoles, offering excellent yields. The advantageous features of the present environmentally benign methodology include the usage of biocompatible and green reaction conditions such as, solvent, room temperature reactions and transition metal-free approach. Moreover, it offers a broader substrate scope.

Synthesis and in vitro biological evaluation of thiosulfinate derivatives for the treatment of human multidrug-resistant breast cancer

Organosulfur compounds derived from Allium vegetables have long been recognized for various therapeutic effects, including anticancer activity. Allicin, one of the main biologically active components of garlic, shows promise as an anticancer agent; however, instability makes it unsuitable for clinical application. The aim of this study was to investigate the effect of stabilized allicin derivatives on human breast cancer cells in vitro. In this study, a total of 22 stabilized thiosulfinate derivatives were synthesized and screened for their in vitro antiproliferative activities against drug-sensitive (MCF-7) and multidrug-resistant (MCF-7/Dx) human adenocarcinoma breast cancer cells. Assays for cell death, apoptosis, cell cycle progression and mitochondrial bioenergetic function were performed. Seven compounds (4b, 7b, 8b, 13b, 14b, 15b and 18b) showed greater antiproliferative activity against MCF-7/Dx cells than allicin. These compounds were also selective towards multidrug-resistant (MDR) cells, a consequence attributed to collateral sensitivity. Among them, 13b exhibited the greatest anticancer activity in both MCF-7/Dx and MCF-7 cells, with IC50 values of 18.54±0.24 and 46.50±1.98 μmol/L, respectively. 13b altered cellular morphology and arrested the cell cycle at the G2/M phase. Additionally, 13b dose-dependently induced apoptosis, and inhibited cellular mitochondrial respiration in cells at rest and under stress. MDR presents a significant obstacle to the successful treatment of cancer clinically. These results demonstrate that thiosulfinate derivatives have potential as novel anticancer agents and may offer new therapeutic strategies for the treatment of chemoresistant cancers.

Unsymmetrical disulfide and sulfenamide synthesis via reactions of thiosulfonates with thiols or amines

The reactivity of thiosulfonates with nucleophilic reagents was investigated. When reactions of thiosulfonates with thiols were performed, unsymmetrical disulfides were obtained in excellent yields. This procedure could employ numerous aryl or alkyl thiols. On the other hand, reactions of thiosulfonates with amines proceeded in the presence of a copper catalyst. The procedure was performed efficiently in air, and afforded the corresponding sulfenamides.

Microwave-assisted synthesis of disulfides

A new microwave-assisted synthesis methodology for the preparation of substituted disulfide derivatives is presented. 4-Substituted sulfenimides were reacted with 4-substituted thiols under neat (to right doughy consistency) conditions in chloroform, with both microwave heating and conventional methods. The resulting 4-substituted disulfide derivatives were obtained at higher yields and in shorter reaction times with microwave heating. Their chemistry was confirmed by 1H-NMR, 13C-NMR, infrared (IR), and elemental analysis.

Ligand-free palladium-catalyzed C-S coupling reactions using water as solvent and microwaves

Herein we demonstrate for the first time a rapid and efficient method for the synthesis of aryl sulfides by the direct substitution reaction of aromatic thiols with aryl halides using water as solvent under microwave irradiation. This procedure offers a high yield in shorter reaction time as compared to conventional methods.