20193-94-6

Basic information

• Product Name: bis[(p-tolyl)methyl] disulphide
• Synonyms: bis[(p-tolyl)methyl] disulphide;Bis(4-methylbenzyl) persulfide;Bis[(4-methylphenyl)methyl] persulfide;Einecs 243-576-0
• CAS NO: 20193-94-6
• Molecular Formula: C₁₆H₁₈S₂
• Molecular Weight: 274.44412
• EINECS: 243-576-0
• Mol File: 20193-94-6.mol

Chemical Properties

• Boiling Point: 398.6°Cat760mmHg
• Flash Point: 220.7°C
• Appearance: /
• Density: 1.127g/cm³
• CAS DataBase Reference: bis[(p-tolyl)methyl] disulphide(CAS DataBase Reference)
• NIST Chemistry Reference: bis[(p-tolyl)methyl] disulphide(20193-94-6)
• EPA Substance Registry System: bis[(p-tolyl)methyl] disulphide(20193-94-6)

Safety Data

• Hazardous Substances Data: 20193-94-6(Hazardous Substances Data)

Upstream product

• 18991-39-4 p-methylbenzyl thiocyanate 
• 4498-99-1 4-methylbenzylthiol 
• 127-65-1 chloroamine-T 
• 81067-95-0 4-Methyl-thiobenzylchlorid 
• 104-82-5 4-Methylbenzyl chloride 
• 104-81-4 4-Methylbenzyl bromide 
• 72209-88-2 S-(4-methylbenzyl)isothiouronium bromide 
• 65094-22-6 diethyl (bromodifluoromethyl)phosphonate 
• 73789-86-3 4-i-propylbenzyl bromide 
• 589-18-4 4-Methylbenzyl alcohol 
• 68-12-2 N,N-dimethyl-formamide 
• 17356-08-0 thiourea 
• 124-41-4 sodium methylate 
• 3111-52-2 potassium thiophenolate 

Downstream Products

• 13250-88-9 bis(4-methylbenzyl)sulfane 
• 73975-48-1 (α-acetylthio)-p-methylbenzyl p-methylbenzyl sulphoxide 
• 76625-88-2 p-methylbenzyl α-disulfone 
• 104-88-1 4-chlorobenzaldehyde 
• 104-87-0 4-methyl-benzaldehyde 
• 15563-46-9 4-chloro-N,N-dimethylbenzenecarbothioamide 
• 5977-80-0 O-methyl 4-methylbenzenecarbothioate 
• 5925-49-5 O-methyl 4-chlorobenzenecarbothioate 
• 62926-06-1 4-chloro-N-propylbenzenecarbothioamide 
• 1126-46-1 Methyl 4-chlorobenzoate 
• 21011-44-9 4-(4-chloro-thiobenzoyl)-morpholine 
• 99-75-2 4-methyl-benzoic acid methyl ester 

Relevant articles and documents

SULFUR EXTRUSION FROM DISULFIDES BY CARBENES

The present invention relates to a method for preparing a compound T having a thioether group from a compound D having a disulfide group in the presence of a carbene.

Synthesis of difluoromethyl and deuterium-labeled difluoromethyl thioethers from aliphatic electrophiles

A one-pot difluoromethylthiolation of alkyl electrophiles with thiourea and diethyl bromodifluoromethylphosphonate is described. The transition-metal-free approach, readily available reagents, and mild conditions provide a practical way for the synthesis of difluoromethyl thioethers. By changing the "H" source to the most commonly used "D" sources CD3OD and D2O, this strategy enables efficient synthesis of SCF2D-substituted molecules in good yields with high levels of D incorporation.

Trisulfides over disulfides: Highly selective synthetic strategies, anti-proliferative activities and sustained H2S release profiles

Temperature-and solvent-induced selective synthesis of trisulfides and disulfides is demonstrated. A remarkable selectivity was achieved using Na2S as a sulfur-Transfer agent under mild, greener, catalyst-free and additive-free conditions. This study reveals trisulfides as a better model than disulfides in general for a sustained release of H2S and potent anti-cancer activities.

Thermal conversion of primary alcohols to disulfides: Via xanthate intermediates: An extension to the Chugaev elimination

Primary alcohols are converted into dialkyl disulfides via heating in situ generated O-alkyl S-difluoro(ethoxycarbonyl)methyl xanthates from ethyl bromodifluoroacetate and potassium xanthates, prepared from primary alcohols and carbon disulfide in the presence of KOH. The reaction mechanism is suggested as an alkyl C[1,3] shift followed by a radical mechanism. This extends to the Chugaev elimination which yields olefins. The current research provides easy access to dialkyl disulfides from commercially available primary alkanols.

Conversion of organic halides to disulfanes using KCN and CS2

A sulfur transfer reagent was produced in situ upon stirring a mixture of KCN and CS2 in DMF at r.t. for 15 min, which after heating with an alkyl halide or aryl halide and CuI gave the corresponding symmetric dialkyl or diaryl disulfide, respectively, in high to excellent yields.

Europhtal (8020) efficiently catalyzes the aerobic oxidation of in situ generated thiols to symmetric disulfides (disulfanes)

Efficient, odorless and scalable synthetic protocols have been introduced for the preparation of symmetric alkyl disulfides by treatment of the corresponding organic halides with thiourea and NaHCO3in the presence of commercially available Europhtal catalyst (8020) in both H2O and poly ethylene glycol (PEG-200) media at 80–90 °C. Structurally diverse primary, secondary, allylic and benzylic halides were examined successfully whereas, the result with tert-butyl bromide was not satisfactory. Also, another procedure has been introduced for achieving symmetric aryl disulfides in high yields by reacting aryl halides, thiourea and NaHCO3in PEG-200 at 115–120 °C using CuI along with Europhtal catalysts. The results showed that the aerobic oxidation of in situ generated thiols proceeded efficiently in the presence of Europhtal catalyst giving the symmetric disulfide without contamination by symmetric sulfide side-product.

Diarylmethylene disulfide compound as well as preparation method and application thereof

The invention relates to the technical field of medicines and in particular relates to a diarylmethylene disulfide compound as well as a preparation method and application thereof. An experiment result shows that on a cell model, the diarylmethylene disulfide compound provided by the invention has an effect of inhibiting neurotoxicity caused by excessive glutamic acid and an effect of inhibiting neurotoxicity caused by hydrogen peroxide; the diarylmethylene disulfide compound also has a platelet aggregation resisting effect and can be used for reducing a cerebral infarct area in a mouse MCAO (Middle Cerebral Artery Occlusion) model. The results show that the diarylmethylene disulfide compound provided by the invention can have prevention and/or treatment effects on cerebral stroke.

Catalyst-Free, Regioselective Ring Opening of Donor-Acceptor Cyclopropanes: Synthesis of Functionalized Mono- and Disulfides

Interesting sulfur compounds such as monosulfides, symmetrical disulfides, unsymmetrical disulfides, and other 1,3-bifunctionalized compounds were synthesized using benzyltriethylammonium tetrathiomolybdate, [BnNEt3]2MoS4, as the sulfur transfer reagent via regioselective ring opening of donor-acceptor cyclopropanes without the addition of any catalyst.

Alternative Protocol for the Synthesis of Symmetrical Dibenzyl Diselenides and Disulfides

A one-pot protocol for the preparation of symmetrical dibenzyl diselenides and disulfides from the corresponding benzyl alcohols employing NaBH2Se3 and NaBH2S3 as selenium-transfer and sulfur-transfer reagent, respectively, is described. Structurally diverse substituted benzyl alcohols afforded the corresponding diselenides and disulfides in good to excellent yields. The protocol is simple and mild, and the products were obtained within a short reaction time.

One-pot conversion of alkyl halides to organic disulfides (disulfanes) using thiourea and hexamethyldisilazane (HMDS) in DMSO

A practical method to synthesize symmetric disulfides from alkyl halides has been developed. Using this procedure primary, secondary, benzylic and allylic disulfides were prepared by treating the corresponding alkyl halides with thiourea and HMDS in DMSO at 50 °C within 10-24 h in high yields.