23853-95-4

Usage

Molar Mass

268.4 g/mol

Structure

A naphthalene ring with two phenyldisulfanyl groups attached at the 1 and 2 positions.

Usage

Building block for the synthesis of various organic compounds, including biologically active molecules and materials for organic electronics. Reagent in organic chemistry reactions, particularly in the construction of sulfur-containing compounds.

Potential Applications

Development of new materials with specific electronic and optical properties.

Upstream product

• 60-29-7 diethyl ether 
• 15515-55-6 2-naphthalenesulfenyl thiocyanate 
• 108-98-5 thiophenol 
• 1212-08-4 S-Phenyl benzenethiosulfonate 
• 91-60-1 2-Naphthalenethiol 
• 931-59-9 benzenesulfenyl chloride 
• 13865-50-4 methoxymethyl phenyl sulfide 
• 64-17-5 ethanol 
• 6667-19-2 benzenenesulfenyl dimethylamine 
• 3153-52-4 benzenesulfenyl thiocyanate 
• 882-33-7 diphenyldisulfane 
• 17527-60-5 C₂₄H₁₈OS 
• 1068439-08-6 [(5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)disulfanyl]benzene 
• 1068439-09-7 2-[(5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)disulfanyl]naphthalene 

Relevant academic research and scientific papers

Fenton-Inspired C-H Functionalization: Peroxide-Directed C-H Thioetherification

Substoichiometric iron mediates the thioetherification of unactivated aliphatic C-H bonds directed by resident silylperoxides. Upon exposure to a catalytic amount of iron(II) triflate, TIPS-protected peroxides bearing primary, secondary, and tertiary C-H sites undergo chemoselective thioetherification of remote C-H bonds with diaryl disulfides. The reaction demonstrates a broad substrate scope and functional group tolerance without the use of any noble metal additives. Mechanistic experiments suggest that the reaction proceeds through 1,5-H atom abstraction by a hydroxyl radical generated with iron.

A versatile and convenient preparation of unsymmetrical diaryl disulfides

We have developed a convenient method for the synthesis of unsymmetrical diaryl disulfides under mild conditions in excellent yields. The described method is based on the straightforward preparation of 5,5-dimethyl-2-thioxo-1,3, 2-dioxaphosphorinane-2-sulfenyl bromide from readily available 5,5-dimethyl-2-sulfanyl-2-thioxo-l,3,2-dioxaphosphorinane or bis(5,5-dimethyl-2-thioxo-l,3,2-dioxaphosphorinan-2-yl) disulfide. The unsymmetrical diaryl disulfides can be obtained from aromatic thiol derivatives bearing electron-withdrawing or electron-donating groups. Thieme Stuttgart.

One-pot synthesis using the supported reagent system Na2CO 3/SiO2-PPA/SiO2: Synthesis of Benzo[b]thiophenes and naphthothiophenes

A simple and efficient method has been developed for the synthesis of benzo[b]thiophenes and naphtho[2,l-6]thiophenes from arenethiols and α-halo ketones using Na2CO3/SiO2-PPA/ SiO2. Reaction of a-halo ketones with arenethiols is promoted by Na2CO3/SiO2 to afford α-sulfanyl ketones, which cyclize in the presence of PPA/SiO2 to give the corresponding thiophene-fused arenes in one-pot. The reaction using α-bromo acetals instead of α-halo ketones also gave the corresponding naphtho[2,l-b] thiophenes via a three-step reaction in one-pot. Thieme Stuttgart.

Extremely Reactive C=C-Double Bonds, IV. Unusual Reactions with Thiophenol, 1,2-Ethanedithiol, and other Sulfur Compounds

Reactions of thiophenol and 1,2-ethanedithiol with imidazolidine derivatives lead to solvolysis with opening or conversion of the imidazolidine system as well as to hydrogenation, partly without a change in the ring system .Benzophenone diaryl dithioacetals are reduced to aryl benzhydryl sulfides by thiophenol . 1,1',3,3'-Tetraphenyl-Δ2,2'-biimidazolidine (9) desulfurates thioacetic acid, dibenzoyl disulfide, and dixanthogen .