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
• Article Data: 20

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

General Description

Di(2,6-xylyl) disulphide, also known as DIDS, is a chemical compound that consists of two 2,6-xylyl groups linked by a disulphide bond. It is commonly used as a cross-linking agent, particularly in rubber compounds, where it helps to improve the physical properties and stability of the material. DIDS is also used as an anti-corrosive agent and as a vulcanization accelerator in the production of rubber. Additionally, it can act as a cross-linking agent in the synthesis of polymers, where it helps to enhance the strength and durability of the resulting materials. Due to its versatile applications, DIDS is widely used in the manufacturing of various industrial and consumer products. 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 
• 87-62-7 2,6-dimethylaniline 
• 2192-33-8 2,6-dimethylbenzenediazonium tetrafluoroborate 
• 129225-67-8 2,6-dimethylbenzenesulfenyl chloride 
• 68191-56-0 Triphenylmethyl-2,6-dimethylphenylsulfid 
• 16463-11-9 2,6-dimethylphenyl 2-methyl-2-propyl sulfide 
• 85518-80-5 2,6-Dimethylphenyl diazonium chloride 
• 2905-29-5 2,6-dimethyl-benzene-sulfonyl chloride 
• 608-28-6 2,6-dimethyliodobenzene 
• 106-95-6 allyl bromide 

Downstream Products

• 118-72-9 2,6-dimethylbenzene-1-thiol 
• 16463-11-9 2,6-dimethylphenyl 2-methyl-2-propyl sulfide 
• 133620-57-2 bis(2-bromomethyl-6-methylphenyl)disulfide 
• 133620-52-7 bis<2,6-bis(bromomethyl)phenyl>disulfide 
• 4143-34-4 Monothiophosphorsaeure-O,O-dimethylester-S-(2,6-dimethyl-phenylester) 
• 92876-65-8 methyl 2,6-dimethylbenzenesulfinate 
• 66713-28-8 tert-Butyl 2,6-xylyl sulfoxide 
• 66713-30-2 Methyl trans-<(2,6-xylyl)sulfinyl>acrylate 
• 66713-32-4 2,6-Xylyl 2,6-xylenethiosulfinate 
• 66713-33-5 2,6-Xylyl 2,5-xylenethiosulfonate 
• 133620-54-9 2-Mercaptomethyl-6-methyl-benzenethiol 
• 133620-56-1 2,6-Bis-mercaptomethyl-benzenethiol 
• 100058-48-8 Ethylxanthogensaeure-(2,6-dimethyl-phenylester) 
• 4163-79-5 (2,6-dimethylphenyl)(methyl)sulfane 

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.

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.

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.

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.