2905-17-1

Basic information

• Product Name: di(2,6-xylyl) disulphide
• Synonyms: di(2,6-xylyl) disulphide;1,1'-Dithiobis(2,6-dimethylbenzene);Bis(2,6-xylyl) persulfide
• CAS NO: 2905-17-1
• Molecular Formula: C₁₆H₁₈S₂
• Molecular Weight: 274.44412
• EINECS: 220-806-8
• Mol File: 2905-17-1.mol

Chemical Properties

• Boiling Point: 345.9°Cat760mmHg
• Flash Point: 148.1°C
• Appearance: /
• Density: 1.13g/cm³
• Vapor Pressure: 0.00012mmHg at 25°C
• Refractive Index: 1.628
• CAS DataBase Reference: di(2,6-xylyl) disulphide(CAS DataBase Reference)
• NIST Chemistry Reference: di(2,6-xylyl) disulphide(2905-17-1)
• EPA Substance Registry System: di(2,6-xylyl) disulphide(2905-17-1)

Safety Data

• Hazardous Substances Data: 2905-17-1(Hazardous Substances Data)

Usage

Uses

Used in Rubber Industry:
DIDS is used as a cross-linking agent for enhancing the strength and durability of rubber compounds. It helps to improve the physical properties and stability of the material.
Used in Anti-corrosive Applications:
DIDS is used as an anti-corrosive agent to protect materials from corrosion and extend their lifespan.
Used in Vulcanization Process:
DIDS is used as a vulcanization accelerator in the production of rubber, speeding up the process and improving the quality of the final product.
Used in Polymer Synthesis:
DIDS is used as a cross-linking agent in the synthesis of polymers, where it helps to enhance the strength and durability of the resulting materials.
Used in Manufacturing of Industrial and Consumer Products:
Due to its versatile applications, DIDS is widely used in the manufacturing of various industrial and consumer products, contributing to their improved performance and quality.
However, it is important to handle DIDS with care, as it can be harmful if ingested or inhaled, and it may cause skin and eye irritation upon contact.

InChI:InChI=1/C16H18S2/c1-11-7-5-8-12(2)15(11)17-18-16-13(3)9-6-10-14(16)4/h5-10H,1-4H3

Upstream product

• 118-72-9 2,6-dimethylbenzene-1-thiol 
• 109404-65-1 Bis-<2,6-dimethyl-phenyl>-dithiolcarbonat 
• 66713-28-8 tert-Butyl 2,6-xylyl sulfoxide 
• 24010-54-6 Natrium-2,6-dimethylbenzolsulfonat 
• 78-79-5 isoprene 
• 68191-56-0 Triphenylmethyl-2,6-dimethylphenylsulfid 
• 100379-00-8 2,6-dimethylbenzene boronic acid 
• 106-95-6 allyl bromide 
• 608-28-6 2,6-dimethyliodobenzene 
• 2905-29-5 2,6-dimethyl-benzene-sulfonyl chloride 
• 85518-80-5 2,6-Dimethylphenyl diazonium chloride 
• 16463-11-9 2,6-dimethylphenyl 2-methyl-2-propyl sulfide 
• 129225-67-8 2,6-dimethylbenzenesulfenyl chloride 
• 2192-33-8 2,6-dimethylbenzenediazonium tetrafluoroborate 

Downstream Products

• 118-72-9 2,6-dimethylbenzene-1-thiol 
• 4143-34-4 Monothiophosphorsaeure-O,O-dimethylester-S-(2,6-dimethyl-phenylester) 
• 100058-48-8 Ethylxanthogensaeure-(2,6-dimethyl-phenylester) 
• 1270110-52-5 3-(2,6-dimethylphenylthio)benzonitrile 
• 52805-90-0 2,2',6,6'-tetramethyldiphenyl sulfide 

Relevant articles and documents

Reaction of organic disulfides with cobalt-centered metal radicals. Use of the E- and C-based dual-parameter substituent model and quantitative solvent effect analyses to compare outer-sphere and inner-sphere electron- transfer processes

Treatment of isolable, paramagnetic Cp2Ta(μ-CH2)2CoCp (1, Cp = η5- C5H5) with aromatic disulfides RSSR affords diamagnetic monothiolate complexes Cp2Ta(μ-CH2)2Co(SR)Cp in quantitative yield. The structure of Cp2Ta(μ-CH2)2Co(SC6H3(CH3)2)Cp (2a) has been characterized by X-ray crystallography. The mechanism of this disulfide S-S bond cleavage reaction has been probed using kinetic, substituent effect, and solvent effect techniques. A Hammett σ/ρ substituent constant analysis yields a nonlinear correlation. In contrast, application of the E- and C-based dual-parameter substituent model gives a good fit of the data and demonstrates that the reaction is sensitive to both the electrostatic and the covalent characteristics of the entering disulfide. All substituents examined (excluding p-(trifluoromethyl)phenyl) exhibited a solvent effect consistent with a modest amount of charge separation in the transition state. The reaction of 1 with the strongly electron withdrawing substituted bis[p- (trifluoromethyl)phenyl] disulfide is much more sensitive to solvent polarity changes. As a comparison system expected to proceed via a limiting outer- sphere electron-transfer mechanism, the reaction of aromatic disulfides with the 19-electron complex cobaltocene (CoCp2, 3), which leads to salts [CoCp2][SR] (4), was investigated using methods parallel to those employed in the study of Ta/Co complex 1. In the cobaltocene system, the kinetic, solvent effect, and substituent effect data showed that the reaction is especially sensitive to the electrostatic character of the disulfide and relatively insensitive to its Covalent character and steric bulk. The comparison of cobaltocene with Ta/CO complex 1 shows that the latter reacts with most diaryl disulfides (perhaps with the exception of p-CF3 compound 2f, which may be a borderline case) via a transition state with substantially more covalent character, and correspondingly less charge separation. than that involved in the outer-sphere reactions of Cp2Co.

Indolylarylsulfones carrying a heterocyclic tail as very potent and broad spectrum HIV-1 non-nucleoside reverse transcriptase inhibitors

We synthesized new indolylarylsulfone (IAS) derivatives carrying a heterocyclic tail at the indole-2-carboxamide nitrogen as potential anti-HIV/AIDS agents. Several new IASs yielded EC50 values 1.0 nM against HIV-1 WT and mutant strains in MT-4 cells. The (R)-11 enantiomer proved to be exceptionally potent against the whole viral panel; in the reverse transcriptase (RT) screening assay, it was remarkably superior to NVP and EFV and comparable to ETV. The binding poses were consistent with the one previously described for the IAS non-nucleoside reverse transcriptase inhibitors. Docking studies showed that the methyl group of (R)-11 points toward the cleft created by the K103N mutation, different from the corresponding group of (S)-11. By calculating the solvent-accessible surface, we observed that the exposed area of RT in complex with (S)-11 was larger than the area of the (R)-11 complex. Compounds 6 and 16 and enantiomer (R)-11 represent novel robust lead compounds of the IAS class.

Metal-free chalcogenation of cycloketone oxime esters with dichalcogenides

We report the metal-free chalcogenation of cycloketone oxime esters with dichalcogenides via a radical process. Because of the metal-free condition and use of readily accessible dichalcogenides, this method is an effective and green strategy for the synthesis of chalcogen-substituted butyronitrile.

Sequential C-H activation enabled expedient delivery of polyfunctional arenes

Modular construction of polyfunctional arenes from abundant feedstocks stands as an unremitting pursue in synthetic chemistry, accelerating the discovery of drugs and materials. Herein, using the multiple C-H activation strategy with versatile imidate esters, the expedient delivery of molecular libraries of densely functionalized sulfur-containing arenes was achieved, which enabled the concise construction of biologically active molecules, such as Bipenamol.

Transformation of arylboronic acids with sodium thiosulfate into organodisulfides catalyzed by a recyclable polyoxometalate-based Cr(iii) catalyst

Organo disulfides represent an abundant class of compounds in chemical biology, pharmaceutical fields, and industry. They are traditionally synthesized by the oxidation of mercaptan in the presence of an organic ligand supported metal catalyst or toxic oxidants under harsh conditions. Here, we disclose a highly-efficient pathway in which disulfide is synthesized by organic boric acid and Na2S2O3 using the catalyst (NH4)3[CrMo6O18(OH)6], demonstrating a high activity and excellent selectivity. Various boric acid derivatives have been successfully transformed into the corresponding disulfides. Mechanistic insights have been furnished based on the observation of intermediate and control experiments.

Chemoselective synthesis of diaryl disulfides via a visible light-mediated coupling of arenediazonium tetrafluoroborates and CS2

A highly efficient and chemoselective method for the synthesis of diaryl disulfides is developed via a visible light-promoted coupling of readily accessible arenediazonium tetrafluoroborates and CS2. This practical and convenient protocol provides a direct pathway for the assembly of a series of disulfides in an environmentally friendly manner with good to excellent yields.

Diacetoxyiodobenzene mediated oxidative transformation of thione to disulfides

We have developed an efficient oxidative transformation of thione to disulfides using diacetoxyiodobenzene (DIB) in acetonitrile at room temperature. This strategy is suited for oxidation of thiols to disulfide also. The present oxidation protocol is mild reaction condition, column free, and a new route for disulfide formation.

Silica: An efficient catalyst for one-pot regioselective synthesis of dithioethers

The development of a silica-promoted highly selective synthesis of 1,2 or 1,3-dithioethers via solvent-free one-pot tandem reactions of an allyl bromide with excess thiol at room temperature is described. The choice of silica gel, either pre-calcined or moistened with water, exhibited notable regioselectivity in the formation of dithioethers. Plausible mechanistic routes were explored and postulated.

Aerobic oxidation of thiols to disulfides under ball-milling in the absence of any catalyst, solvent, or base

An efficient aerobic chemoselective oxidation of thiols to disulfides has been achieved under ball-milling over neutral aluminium oxide (grinding auxiliary) in the absence of any catalyst, co-oxidant, solvent, or base. A wide variety of functionalized diaryl, diheteroaryl and dialkyl disulfides have been obtained in high yields. The Royal Society of Chemistry 2013.

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.