352-93-2

Usage

Uses

Used in Chemical Synthesis:
1,1'-Thiobisethane is used as a solvent for anhydrous mineral salts and in plating baths for coating metals with gold or silver. It serves as a starting material for the synthesis of various chemicals, including platinum ethynyl dimers and polymers with pendant ferrocenyl groups.
Used in Flavoring Industry:
Diethyl sulfide is employed as a flavoring agent, adding a unique garlic-like aroma to different products.
Used in Analytical Chemistry:
1,1'-Thiobisethane may be used as an analytical standard for the determination of the analyte in wastewater, wines, and beer by gas chromatography (GC) based techniques. This application aids in the quantification procedure of volatile sulfur compounds by solid-phase microextraction.
Used in the Preparation of Other Compounds:
Diethyl sulfide is used in the preparation of triethylsulfoniuim ethylsulfate by reaction with sulfuric acid diethyl ester, further expanding its utility in chemical synthesis and various industrial applications.

Synthesis Reference(s)

Tetrahedron Letters, 14, p. 3853, 1973 DOI: 10.1016/S0040-4039(01)87056-8

Air & Water Reactions

Highly flammable. Slightly soluble in water.

Reactivity Profile

Organosulfides, such as 1,1'-Thiobisethane, are incompatible with acids, diazo and azo compounds, halocarbons, isocyanates, aldehydes, alkali metals, nitrides, hydrides, and other strong reducing agents. Reactions with these materials generate heat and in many cases hydrogen gas. Many of these compounds may liberate hydrogen sulfide upon decomposition or reaction with an acid.

Health Hazard

May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Fire Hazard

HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

Safety Profile

Mildly toxic by ingestion. A skin and eye irritant. A very dangerous fire hazard when exposed to heat, flame, or sparks; can react vigorously with oxidizers. Reacts with water, steam, acids, or acid fumes to produce toxic and flammable vapors. To fight fire, use water spray or mist, dry chemical, CO2, foam. When heated to decomposition it yields highly toxic fumes of SOx. See also SULFIDES.

Purification Methods

Wash the sulfide with aqueous 5% NaOH, then water, dry with CaCl2 and distil it from sodium. It can also be dried with MgSO4 or silica gel. Alternative purification is via the Hg(II) chloride complex [(Et)2S.2HgCl2] (see dimethyl sulfide). [Beilstein 1 IV 1394.]

InChI:InChI=1/C4H10S/c1-3-5-4-2/h3-4H2,1-2H3

Upstream product

• 10467-10-4 ethylmagnesium iodide 
• 74-96-4 ethyl bromide 
• 64-67-5 diethyl sulfate 
• 60-29-7 diethyl ether 
• 625-01-4 ethyl chlorosulfate 
• 925-90-6 ethylmagnesium bromide 
• 64-17-5 ethanol 
• 56-89-3 cysteine disulfide 
• 74-85-1 ethene 
• 13730-34-2 diethyltetrasulfane 
• 75-00-3 chloroethane 
• 70-29-1 diethyl sulphide 
• 2314-49-0 diethyl trithiocarbonate 
• 857822-02-7 pentathiodicarbonic acid diethyl ester 

Downstream Products

• 624-89-5 Ethyl methyl sulfide 
• 625-60-5 ethyl thioacetate 
• 1829-92-1 triethylsulfonium iodide 
• 1613-45-2 ethyl isobutyl sulfide 
• 75-08-1 ethanethiol 
• 188290-36-0 thiophene 
• 925-93-9 ethyl [2]alcohol 
• 594-45-6 ethanesulfonic acid 
• 597-35-3 diethylsulfone 
• 527-72-0 2-thiophenylcarboxylic acid 
• 25569-97-5 thiophen-2-carboxylic anhydride 
• 109405-98-3 diethyl-(4-nitro-benzyl)-sulfonium ; picrate 
• 126-68-1 O,O,O-triethyl phosphorothioate 
• 70064-34-5 2-Ethylsulfanyl-1,1-diphenyl-propan-1-ol 

Relevant academic research and scientific papers

Catalytic synthesis of dialkyl sulfides from dialkyl disulfides

Dialkyl disulfides R2S2 where R = Me, Et, or Pr, both as individual compounds and as their mixtures, isolated from petroleum products can turn into alkanethiols and dialkyl sulfides under the action of catalysts having strong acid sites and medium-strength basic sites on their surface. In a helium atmosphere, the main conversion products are alkanethiols, while dialkyl sulfides form in low yield at a selectivity of no higher than 20%. A much higher dialkyl sulfide selectivity is attained in the reaction involving methanol. The most efficient catalyst for this reaction is alumina, with which the dialkyl sulfide selectivity is up to 99%.

Vapor generation of inorganic anionic species after aqueous phase alkylation with trialkyloxonium tetrafluoroborates

Aqueous phase reaction of trialkyloxonium tetrafluoroborates, R 3O+BF4- (R=Me, Et) has been tested in the alkylation of simple inorganic anionic substrates such as halogen ions, cyanide, thiocyanate, sulphide an

Process and catalyst for synthesis of mercaptans and sulfides from alcohols

A process and catalyst blend for selectively producing mercaptans and sulfides from alcohols. The alcohol is reacted with hydrogen sulfide, in the presence of a catalyst blend containing a hydrotreating catalyst and a dehydration catalyst to convert the alcohol to mercaptan or sulfide in one-pass. The alcohols can include primary and secondary alcohols. The mercaptan or sulfide having less than about 30% unreacted alcohol contained therein.

Semi-continuous photochemical method and device therefor

In the photochemical synthetic process in semi-continuous mode according to the invention, a reactor comprising two zones is used, the radiating portion of the lamp(s) being totally immersed in a first zone which is completely filled with reaction medium and spills off via an overflow into a second zone whose volume is sufficient to contain the volume of reaction medium originating from the first zone and corresponding substantially to the volume of the reagent(s) gradually introduced.

Nucleophilic substitution by Grignard reagents on sulfur mustards

With proper activation of the leaving group, sulfur mustards react with Grignard reagents with neighboring group participation of the sulfur atom. 2,6-Dichloro-9-thiabicyclo[3.3.1]nonane is especially useful in this regard, providing clean reactivity with organomagnesium nucleophiles on a topologically constrained scaffold.

A catalytic synthesis of thiosilanes and silthianes: Palladium nanoparticle-mediated cross-coupling of silanes with thio phenyl and thio vinyl ethers through selective carbon-sulfur bond activation

Palladium nanoparticles generated in situ from N, N-dimethyl-acetamide (DMA) solutions of PdX2 (X = Cl-, OAc-, OCOCF3-) or Pd2(dba)3 by reduction with alkyl silanes R3SiH (R = Me, Et, i-Pr, t-Bu) are selective catalysts for the cross-coupling of the silanes R3SiH with phenyl and vinyl thioethers forming the corresponding thiosilanes and silthianes in high yields and under mild conditions. The method is applicable to phenyl thioglycosides, giving access to thiosilyl glycosides a new class of sugar derivatives.

Reaction of Mono- and Dihaloalkanes with Mixed Solutions of Chalcogens in Alkaline Reductive Systems

Sufur-selenium, sulfur-tellurium, selenium-tellurium, and sulfur-selenium-tellurium mixtures readily dissolve in the hydrazine hydrate-alkali system to form chalcogenide anions. Alkylation of the latter with ethyl bromide results in preferential formation

Hydrosulfurization of methanol on Y2O3-TiO2-ZrO2 catalysts

Y2O3-TiO2-ZrO2 catalysts, where the contribution of oxide components ranges from 0 to 100 mol %, have been studied for their catalytic performance in methanol hydrosulfurization. Their activity and selectivity have shown a strong dependence on acid-base properties which, in turn, changed with catalyst composition. High yttria content favors selectivity to methanethiol, while catalysts highly active for the formation of dimethyl-sulfide were those containing 8 mol % Y2O3. The latter composition, which boosted selectivity to (CH3)2S, has created favorable conditions for the generation of acid centers in chemically mixed oxides as concluded on the ground of ESR studies and acidity measurements.

Inactivation of mitochondrial monoamine oxidase B by methylthio-substituted benzylamines

Mitochondrial monoamine oxidase was inactivated by o-mercaptobenzylamine (1) and o- (2) and p-methylthiobenzylamine (5). Experiments were carried out to provide evidence for possible mechanisms of inactivation. The corresponding o- (3) and p-hydroxybenzylamine (4) are not inactivators. Four radiolabeled analogues of 2 and 5, having radioactivity at either the methyl or benzyl groups, were synthesized, and all were shown to incorporate multiple equivalents of radioactivity into the enzyme. Inactivation in the presence of an electrophile scavenger decreased the number of molecules incorporated, but still multiple molecules became incorporated; catalase did not further reduce the number of inactivator molecules bound. Two inactivation mechanisms are proposed, one involving a nucleophilic aromatic substitution (SNAr) mechanism and the other a dealkylation mechanism. Evidence for both mechanisms is that inactivation leads to reduction of the flavin (oxidation of the inactivator), but upon denaturation the flavin is reoxidized, indicating that attachment is not at the flavin. A cysteine titration indicates the loss of four cysteines after inactivation and denaturation. Support for the S NAr mechanism was obtained by showing that o- and p-chlorobenzylamine also inactivate MAO. Chemical model studies were carried out that also support both SNAr and dealkylation mechanisms.

New Routes to Poly(Alkylene Sulfidoselenides)

A procedure was developed for preparing mixed poly(alkylene sulfidoselenides) by simultaneous dissolution of sulfur and selenium in basic reducing systems NaOH (KOH)-N2H4 * H2O-H2O, followed by alkylation of the resulting solutions with bielectrophilic agents.