29627-34-7

Basic information

• Product Name: Disulfide, 4-methylphenyl phenyl
• CAS NO: 29627-34-7
• Molecular Formula: C13H12S2
• Molecular Weight: 232.37
• Mol File: 29627-34-7.mol

Chemical Properties

• CAS DataBase Reference: Disulfide, 4-methylphenyl phenyl(CAS DataBase Reference)
• NIST Chemistry Reference: Disulfide, 4-methylphenyl phenyl(29627-34-7)
• EPA Substance Registry System: Disulfide, 4-methylphenyl phenyl(29627-34-7)

Safety Data

• Hazardous Substances Data: 29627-34-7(Hazardous Substances Data)

Upstream product

• 933-00-6 p-methylbenzenesulfenyl chloride 
• 536-57-2 p-toluene sulfinic acid 
• 64-17-5 ethanol 
• 108-98-5 thiophenol 
• 106-45-6 para-thiocresol 
• 67-56-1 methanol 
• 26974-30-1 S-phenyl p-toluenethiosulfinate 
• 10557-67-2 N-nitroso-p-methyl-acetanilide 
• 949-00-8 phenyl dithiobenzoate 
• 83078-46-0 2-Methyl-dithiopropionsaeure-phenylester 
• 104411-45-2 phenyl phenyldithioacetate 
• 3561-67-9 bis(phenylthio)methane 
• 17241-04-2 bis(p-tolylthio)methane 
• 100-68-5 methyl-phenyl-thioether 

Downstream Products

• 106-45-6 para-thiocresol 
• 3541-14-8 phenyl toluene-4-thiosulfonate 
• 1433204-83-1 2-((4-methylphenyl)thio)benzofuran 
• 1451371-30-4 (2-(1,4-dioxane))(4-methylphenyl)sulfide 
• 1889-58-3 O,O-diethyl S-phenyl phosphorothioate 
• 4143-38-8 thiophosphoric acid O,O'-diethyl ester S-p-tolyl ester 
• 17041-81-5 p-tolyl benzenethiosulfonate 
• 82211-05-0 1-phenyl-2-(phenylsulfonyl)-2-(phenylthio)ethan-1-one 

Relevant articles and documents

Rewiring Chemical Networks Based on Dynamic Dithioacetal and Disulfide Bonds

The control of the connectivity between nodes of synthetic networks is still largely unexplored. To address this point we take advantage of a simple dynamic chemical system with two exchange levels that are mutually connected and can be activated simultan

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.

Mapping mechanisms in glycosylation reactions with donor reactivity: Avoiding generation of side products

The glycosylation reaction, which is key for the studies on glycoscience, is challenging due to its complexity and intrinsic side reactions. Thioglycoside is one of the most widely used glycosyl donors in the synthesis of complex oligosaccharides. However, one of the challenges is its side reactions, which lower its yield and limits its efficiency, thereby requiring considerable effort in the optimization process. Herein, we reported a multifaceted experimental approach that reveals the behaviors of side reactions, such as the intermolecular thioaglycon transformation and N-glycosyl succinimides, via the glycosyl intermediate. Our mechanistic proposal was supported by low temperature NMR studies that can further be mapped by utilizing relative reactivity values. Accordingly, we also presented our findings to suppress the generation of side products in solving this particular problem for achieving high-yield glycosylation reactions.

Phthalimide-Carried Disulfur Transfer to Synthesize Unsymmetrical Disulfanes via Copper Catalysis

A versatile Cu-catalyzed cross-coupling reaction to various unsymmetrical disulfanes has been presented, from phthalimide-carried disulfur transfer reagents and commercially available boronic acids under mild and practical conditions. The method features the unprecedented use of phthalimide-carried disulfurating reagents (Harpp reagent) in cross-coupling chemistry and is highlighted by the broad substrate scopes, even applicable for the transfer of aryl-disulfur moieties (ArSS-). Notably, the robustness of this methodology is shown by the late-stage modification of bioactive scaffolds of coumarin, estrone, and captopril.

A Novel Method for the Direct Synthesis of Symmetrical and Unsymmetrical Sulfides and Disulfides from Aryl Halides and Ethyl Potassium Xanthogenate

An efficient and new method for the synthesis of disulfides and sulfides via the reaction of aryl halides with ethyl potassium xanthogenate in the presence of MOF-199 is described. O -Ethyl- S -aryl carbonodithioate has a key role as an intermediate in this procedure; it was converted into symmetrical diaryl disulfides in DMF. Additionally, this could be applied to the synthesis of unsymmetrical aryl alkyl(aryl′) disulfides by the reaction with S -alkyl(aryl) sulfurothioates (Bunte salts) as well as unsymmetrical aryl alkyl(aryl′) sulfides in DMSO.

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.

Catalyst-Free S–S Bond Insertion Reaction of a Donor/Acceptor-Free Carbene by a Radical Process: A Combined Experimental and Computational Study

Herein, a donor/acceptor-free carbene insertion reaction of an S–S bond through a radical process is presented. This catalyst-free reaction was thermally induced and provided the dithioketal products in moderate to high yields. A mechanism involving radical intermediates was proposed according to the computational study, and these intermediates were verified experimentally and intercepted for the first time by using a cross-coupling reaction.

Heterogeneously catalyzed direct C-H thiolation of heteroarenes

The first general methodology for the direct thiolation of electron-rich heteroarenes was developed by employing Pd/Al2O3, a recoverable and commercially available heterogeneous catalyst, and CuCl2. This method represents an operationally simple approach for the synthesis of these valuable compounds. Preliminary mechanistic studies indicate a heterogeneous catalytic system, in which both metals play a complementary role in the formation of the thiolated products. (Hetero)genius: A general method for the direct thiolation of electron-rich heteroarenes was developed by employing Pd/Al2O3, a recoverable and commercially available heterogeneous catalyst, and CuCl2. Preliminary mechanistic studies indicate a heterogeneous active catalytic species, with the two metals playing complementary roles in the formation of the thiolated products.

Mechanistic insight into the photoredox catalysis of anti-markovnikov alkene hydrofunctionalization reactions

We describe our efforts to understand the key mechanistic aspects of the previously reported alkene hydrofunctionalization reactions using 9-mesityl-10-methylacridinium (Mes-Acr+) as a photoredox catalyst. Importantly, we are able to detect alk

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.