60779-24-0

Basic information

• Product Name: Disulfide, butyl methyl
• Synonyms: Disulfide, butyl methyl;Butylmethyl persulfide;Methyl(butyl) persulfide
• CAS NO: 60779-24-0
• Molecular Formula: C₅H₁₂S₂
• Molecular Weight: 136.28
• Mol File: 60779-24-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Disulfide, butyl methyl(CAS DataBase Reference)
• NIST Chemistry Reference: Disulfide, butyl methyl(60779-24-0)
• EPA Substance Registry System: Disulfide, butyl methyl(60779-24-0)

Safety Data

• Hazardous Substances Data: 60779-24-0(Hazardous Substances Data)

Upstream product

• 624-92-0 Dimethyldisulphide 
• 629-45-8 dibutyl disulfide 
• 109-79-5 n-butanethiol 
• 118087-46-0 2-methylpropanedithioperoxy acid methyl ester 
• 3658-80-8 dimethyltrisulfane 

Downstream Products

• 624-92-0 Dimethyldisulphide 
• 629-45-8 dibutyl disulfide 

Relevant articles and documents

The energy-transfer-enabled biocompatible disulfide–ene reaction

Sulfur-containing molecules participate in many essential biological processes. Of utmost importance is the methylthioether moiety, present in the proteinogenic amino acid methionine and installed in tRNA by radical-S-adenosylmethionine methylthiotransferases. Although the thiol–ene reaction for carbon–sulfur bond formation has found widespread applications in materials or medicinal science, a biocompatible chemo- and regioselective hydrothiolation of unactivated alkenes and alkynes remains elusive. Here, we describe the design of a general chemoselective anti-Markovnikov hydroalkyl/aryl thiolation of alkenes and alkynes—also allowing the biologically important hydromethylthiolation—by triplet–triplet energy transfer activation of disulfides. This fast disulfide–ene reaction shows extraordinary functional group tolerance and biocompatibility. Transient absorption spectroscopy was used to study the sensitization process in detail. The hereby gained mechanistic insights were successfully employed for optimization of the catalytic system. This photosensitized transformation should stimulate bioimaging applications and carbon–sulfur bond-forming late-stage functionalization chemistry, especially in the context of metabolic labelling.

Crack healing and reclaiming of vulcanized rubber by triggering the rearrangement of inherent sulfur crosslinked networks

CuCl2 has been shown to effectively catalyze reshuffling of the inherent sulfur crosslinked networks of vulcanized rubber. Once activated, CuCl2-based complex catalysis enables disulfide metathesis through circulated crossover reactions among disulfide and polysulfide bonds without forming radicals and ionic intermediates. By taking advantage of this mechanism, the model material of this study, vulcanized polybutadiene rubber, acquires thermal remendability as characterized by repeated restoration of mechanical properties. Moreover, it can be reprocessed like thermoplastics. The compositions and fabrication of the model material simulate those of industrial vulcanized rubber, so as to facilitate formulation optimization under the circumstances close to the actual situation for possible future practical applications. It is hoped that the results of the present preliminary exploration would provide the basis for extending the service life and developing new recycling techniques of vulcanized rubber, which is produced, used and scrapped in large quantities every day.

Cleavage of S-S bond by nitric oxide (NO) in the presence of oxygen: A disproportionation reaction of two disulfides

Disulfide bond was cleaved by a catalytic amount of nitric oxide in the presence of oxygen, which was confirmed by experiments employing two symmetrical disulfides. The reaction resulted in the formation of unsymmetrical disulfides in nearly 50% yields. The steric hindrance of alkyl disulfide slowed the reaction rate, and an electron-donating group on the aryl disulfide promoted the reaction. The substituent and S-nitrosothiol effects suggested that the reaction was initialized with an oxidative process by NO+.

Disproportionation reaction of disulfides promoted by nitric oxide (NO) in the presence of oxygen

Two disulfides brought about disproportionation reaction to afford an unsymmetrical disulfide in 50% yield with a catalytic amount of nitric oxide in the presence of oxygen. The reaction proceeded faster when alkyl disulfides were employed for the reaction, and the substituent effects suggested that the reaction commenced with an oxidative process.

Selective thiophilic addition of alkyl- and aryllithiums to dithio esters and a sulfine in the pyridine series

Reaction of two dithio esters and a new sulfine (S-thiocarbonyl oxide) with various aryl- and alkyllithiums at -78°C afforded dithio acetals or their oxides, arising from a thiophilic addition. The intermediate carbanions can be trapped by alkyl halides or an aldehyde. This provides a new entry to pyridyl acyl anions, "Umpolung" synthons.

The Reaction of Ph3P+SR with Thiols: A Simple, Efficient Synthesis of Unsymmetrical Disulphides

Reaction of Ph3P+SRClO4-, prepared electrochemically from RSSR and Ph3P, with thiols in n-hexane at room temperature gave unsymmetrical disulphides in excellent yields with recovery of Ph3P.

NEW SIMPLE SYNTHESIS OF UNSYMMETRICAL DISULFIDE

Unsymmetrical disulfides from the co-photolysis of mixtures of symmetrical alkyl disulfides is reported.Rates have been obtained for 35 combinations of C2 to C10 alkyl disulfides and their isomers.An equilibrium is attained after relatively short irradiation periods in cyclohexane.

Reaction of thiyl radicals. XIII. Photochemically induced exchange reactions of liquid alkyl disulfides

The liquid phase photolysis of some 35 liquid alkyl disulfide mixtures has been studied.The corresponding unsymmetrical disulfide is the only significant product of the reaction and the system attains a photo-equilibrium state at longer exposure times.Product formation is completely eliminated by the addition of nitric oxide.Quantum yields have been redetermined for the methyl disulfide- ethyl disulfide system using four different light sources.Initial rates have been measured for each of the 35 combinations and have been shown to be a function of total molecular weight of the disulfide mixture and to be strongly influenced by steric factors.These effects are most pronounced for mixtures wherein the exchange reaction between thiyl radical and a symmetrical disulfide is important as indicated by quantum yields above unity.Combinations of isodisulfides give rise to anomalously high rates.