1618-26-4

Basic information

• Product Name: Bis(methylthio)methane
• Synonyms: 2,4-DITHIAPENTANE;FEMA 3878;FORMALDEHYDE DIMETHYL MERCAPTAL;DIMETHYLTHIOMETHANE;BIS(METHYLMERCAPTO)METHANE;BIS(METHYLTHIO)METHANE;METHYLENEBIS(METHYL SULFIDE);Bis(methylsulfanyl)methane
• CAS NO: 1618-26-4
• Molecular Formula: C₃H₈S₂
• Molecular Weight: 108.23
• EINECS: 216-577-9
• Product Categories: Industrial/Fine Chemicals;sulfide Flavor;Building Blocks;Chemical Synthesis;Organic Building Blocks;Sulfides/Disulfides;Sulfur Compounds
• Mol File: 1618-26-4.mol

Chemical Properties

• Melting Point: 148 °C
• Boiling Point: 147 °C(lit.)
• Flash Point: 111 °F
• Appearance: APHA: ≤100/
• Density: 1.059 g/mL at 25 °C(lit.)
• Vapor Pressure: 5.71mmHg at 25°C
• Refractive Index: n20/D 1.53(lit.)
• Storage Temp.: Flammables area
• Solubility: IMMISCIBLE
• Water Solubility: IMMISCIBLE
• Merck: 14,1256
• BRN: 1731143
• CAS DataBase Reference: Bis(methylthio)methane(CAS DataBase Reference)
• NIST Chemistry Reference: Bis(methylthio)methane(1618-26-4)
• EPA Substance Registry System: Bis(methylthio)methane(1618-26-4)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 16-26-36/37/39
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• F: 13
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 1618-26-4(Hazardous Substances Data)

Usage

Uses

1. Used in Odor Control Applications:
Bis(methylthio)methane is used as an odor control agent for reducing unpleasant smells in rooms during remodeling work. It achieves this by removing the causative substances responsible for the odors, providing a fresher and more pleasant environment.
2. Used in Food Industry:
Given its natural occurrence in various food items, Bis(methylthio)methane may also be used in the food industry to enhance or modify the flavor profiles of certain products, contributing to their unique taste and aroma.
3. Used in Chemical Research:
The liquid structure of bis(methylthio)methane at room temperature has been studied using bonding and non-bonding interatomic potential functions (FMP-RMC) simulation. This makes it a subject of interest in chemical research, potentially leading to new discoveries and applications in the field of chemistry.

Flammability and Explosibility

Notclassified

Purification Methods

Work in an efficient fume cupboard as the substance may contain traces (or more) of methylmercaptan which has a very bad odour. Dissolve the mercaptal in Et2O, shake it with aqueous alkalis then dry it over anhydrous K2CO3, filter and distil it over K2CO3 under a stream of N2. If the odour is very strong, then allow all gas efluents to bubble through 5% aqueous NaOH solution which is then treated with dilute KMnO4 in order to oxidise MeSH to odourless products. UV: max 238 nm (log 2.73) [Fehnel & Carmack J Am Chem Soc 71 90 1949, Fehér & Vogelbruch Chem Ber 91 996 1958, B.hme & Marz Chem Ber 74 1672 1941]. Oxidation with aqueous KMnO4 yields bis-(methylsulfonyl)methane which has m 142-143o [Fiecchi et al. Tetrahedron Lett 1681 1967]. [Beilstein 1 IV 3088.]

InChI:InChI=1/C3H8S2/c1-4-3-5-2/h3H2,1-2H3

Upstream product

• 50-00-0 formaldehyd 
• 74-93-1 methylthiol 
• 20044-28-4 2-(Methylthiomethyl)-1H-isoindole-1,3(2H)-dione 
• 75-09-2 dichloromethane 
• 60-29-7 diethyl ether 
• 2373-51-5 chloro-methylsulfanyl-methane 
• 108-59-8 malonic acid dimethyl ester 
• 110-88-3 1,3,5-Trioxan 
• 532-32-1 sodium benzoate 
• 67-68-5 dimethyl sulfoxide 
• 186581-53-3 diazomethane 
• 29414-47-9 formaldehyde methyldithiohemiacetal 
• 109-87-5 Dimethoxymethane 
• 2568-90-3 di-n-butyloxymethane 

Downstream Products

• 3084-53-5 trimethylsulphonium bromide 
• 2373-51-5 chloro-methylsulfanyl-methane 
• 54267-12-8 bis(methylsulfinyl)methane 
• 36678-00-9 3,3-bis-methylsulfanyl-propan-1-ol 
• 37891-79-5 bis(methylsulfanyl)trimethylsilylmethane 
• 20163-71-7 methyl((methylsulfonyl)methyl)sulfane 
• 33577-16-1 methyl methylsulfinylmethyl sulfide 
• 766-92-7 [(methylthio)methyl]-benzene 
• 14252-44-9 bis(methylthio)phenylmethane 
• 1534-08-3 S-methyl thiolacetate 
• 80283-43-8 dimethyl-4-methoxyphenylphosphonotrithioate 
• 88790-44-7 3-formyl-5-methyl-2-cyclohexen-1-one 
• 140658-49-7 2,3,4,6-Tetra-O-benzyl-1-C--α-D-glucopyranose 
• 53369-94-1 3-(Bis-methylsulfanyl-methyl)-cyclohexanone 

Relevant articles and documents

Stereoelectronic Effects in the Gas Phase. 2. Negative Ion Reactions of 1,3-Dithianes and 1,3-Dithiane 1-Oxides

Reactions of gaseous anions (methoxide, hydroxide, and thermal electrons) with cis-4,6-dimethyl-1,3-dithiane and the corresponding axial and equatorial 1-oxides have been investigated using the techniques of ion cyclotron resonance (ICR) spectroscopy and pulsed positive-negative ion chemical ionization (PPNICI) spectroscopy.Deprotonation to (M-H)(1-) ions and extensive fragmentation to ions m/z 99 and 101 were observed for all three compounds with all three reactant anions.When compounds labeled with deuterium specifically at the C2 position were used, it was foundthat deprotonation occurred at C2 and elsewhere in the molecule.The axial hydrogen at C2 was removed as readily or more so than the equatorial hydrogen, depending on the reactants and conditions of ion generation. (These results differ from the corresponding condensed-phase reactions, which show strong selectivity for C2 equatorial deprotonation).Deuterium isotope effects were estimated to be 1.2 and 1.3 for ions generated by MeO(1-) and e, respectively.Exchange (H/D) between hydroxide and cis-4,6-dimethyl-1,3-dithiane-2-d2 was insignificant, although exchange was observed in comparable reactions of hydroxide with 1,3-dithiane-d2 and bis(methylthio)methane-d2.Stereoelectronic effects that may contribute to selectivity in solution do not account for the gas-phase results.Ab initio calculations at the 3-21G(*) level applied to methanedithiol and the anion (HS)2CH(1-) (as models for the 1,3-dithiane system) provide insight into the nature of the gas-phase reactions.Possible reaction pathways are discussed.

Formation of Dithioacetals by Treatment of Sulfoxides Carrying α-Hydrogens with Magnesium Amides

Sulfoxides carrying α-hydrogens were allowed to react with magnesium amides generated in situ by the treatment of ethylmagnesium bromide with secondary amines such as 2,2,6,6-tetramethylpiperidine or diisopropylamine in diethyl ether to give the corresponding dithioacetals in moderate to good yields.

Static and dynamic structures of pentacarbonyl-chromium(0) and -tungsten(0) complexes of dithioether ligands I. Symmetrical dithioether complexes and X-ray crystal structure of

The complexes (M=Cr, R=Et, iPr, t-Bu; M=W, R=Me, Et, iPr, t-Bu) were synthesised.Total bandshape NMR analysis was used to measure energies of inversion of the coordinated S atom in the tungsten complexes. ΔG (298.15 K) values were in the range 34-42 kJ mol-1.An X-ray structure of was obtained.

Effect of Zinc Oxide on the Thermal Decomposition of Dimethyl Sulfoxide

Dimethyl sulfoxide (DMSO) is widely used in the chemical industry. However, it has a non-neglectful thermal runaway risk due to the nature of self-accelerating decomposition near the boiling point. Under the background that zinc oxide (ZnO) may extend the isothermal induction period of thermal decomposition of DMSO, this article conducts an in-depth study for the phenomenon with the techniques such as differential scanning calorimetry (DSC), accelerating rate calorimetry (ARC), gas chromatography-mass spectrometry (GC-MS), X-ray photoelectron spectroscopy (XPS), and X-ray diffractometry (XRD). After being mixed with ZnO, the maximum decomposition rate of DMSO was significantly reduced and the adiabatic induction period of DMSO decomposition was extended by 3.27 times, indicating that the thermal decomposition intensity of DMSO was obviously reduced. It was experimentally demonstrated that ZnO did not change the decomposition pathways of DMSO, but it could promote the decomposition of methanethiol, which was a decomposition intermediate of DMSO and could potentially serve as a promoter on the decomposition of DMSO.

Photocatalytic Deoxygenation of Sulfoxides Using Visible Light: Mechanistic Investigations and Synthetic Applications

The photocatalytic deoxygenation of sulfoxides to generate sulfides facilitated by either Ir[(dF(CF3)ppy)2(dtbbpy)]PF6 or fac-Ir(ppy)3 is reported. Mechanistic studies indicate that a radical chain mechanism operates, which proceeds via a phosphoranyl radical generated from a radical/polar crossover process. Initiation of the radical chain was found to proceed via two opposing photocatalytic quenching mechanisms, offering complementary reactivity. The mild nature of the radical deoxygenation process enables the reduction of a wide range of functionalized sulfoxides, including those containing acid-sensitive groups, in typically high isolated yields.

Nickel phosphide nanoalloy catalyst for the selective deoxygenation of sulfoxides to sulfides under ambient H2pressure

Exploring novel catalysis by less common, metal-non-metal nanoalloys is of great interest in organic synthesis. We herein report a titanium-dioxide-supported nickel phosphide nanoalloy (nano-Ni2P/TiO2) that exhibits high catalytic activity for the deoxygenation of sulfoxides. nano-Ni2P/TiO2 deoxygenated various sulfoxides to sulfides under 1 bar of H2, representing the first non-noble metal catalyst for sulfoxide deoxygenation under ambient H2 pressure. Spectroscopic analyses revealed that this high activity is due to cooperative catalysis by nano-Ni2P and TiO2. This journal is

Rh-Catalyzed Hydrogenation of CO2 to Formic Acid in DMSO-based Reaction Media: Solved and Unsolved Challenges for Process Development

Process concepts have been conceived and evaluated for the amine-free homogeneous catalyzed hydrogenation of CO2 to formic acid (FA). Base-free DMSO-mediated production of FA has been shown to avoid the formation of stable intermediates and presumably the energy-intensive FA recovery strategies. Here, we address the challenges in the development of an overall process: from catalyst immobilization to the FA isolation. The immobilization of the homogeneous catalyst was achieved using a multiphasic approach (n-heptane/DMSO) ensuring high retention of the catalyst (>99%) and allowing facile separation of the catalyst-free product phase. We show that the strong molecular interactions between DMSO and FA on the one hand shift the equilibrium towards the product side, on the other hand, lead to the formation of an azeotrope preventing a simple isolation step by distillation. Thus, we devised an isolation strategy based on the use of co-solvents and computed the energy demands. Acetic acid was identified as best co-solvent and its compatibility with the catalyst system was experimentally verified. Overall, the outlined process involving DMSO and acetic acid as co-solvent has a computed energy demand on a par with state-of-the art amine-based processes. However, the insufficient chemical stability of DMSO poses major limitations on processes based on this solvent. (Figure presented.).

Deoxygenation of sulfoxides to sulfides in the presence of zinc catalysts and boranes as reducing reagents

In the present study, the zinc-catalyzed deoxygenation of aliphatic and aromatic sulfoxides in the presence of boranes as reducing reagent has been explored. After investigation of different reaction parameters the abilities of catalytic amounts of Zn(OTf)2 has been demonstrated in the deoxygenation of various sulfoxides. Moreover, various experiments have been performed to shed light on the underlying reaction mechanism.

Zinc-catalyzed deoxygenation of sulfoxides to sulfides applying [B(Pin)]2 as deoxygenation reagents

In the present study, the zinc-catalyzed deoxygenation of aliphatic and aromatic sulfoxides in the presence of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi-1, 3, 2-dioxaborolane [B(Pin)]2 as reducing reagent to produce the corresponding sulfides has been investigated. After examination of various reaction parameters the abilities of catalytic amounts of Zn(OTf)2 has been proven in the deoxygenation of various sulfoxides. Especially, a high functional group tolerance was noticed for the Zn(OTf)2/ B(Pin) 2 system. Springer Science+Business Media, LLC 2012.

Reduction of sulfoxides to sulfides in the presence of copper catalysts

Copper complexes catalyze the reduction of aliphatic and aromatic sulfoxides in the presence of silanes as reducing reagent. The influence of different reaction parameters on the catalytic activity is investigated in detail. The scope and limitations of the described catalyst is demonstrated in the reduction of various sulfoxides. In most cases, high conversion and excellent chemoselectivity are obtained. Graphical Abstract: [Figure not available: see fulltext.]