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Contents

   



(Top)
  


1 Preparation  




2 Occurrence  




3 Reactions  




4 References  













Diethyl sulfide






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From Wikipedia, the free encyclopedia
  

Diethyl sulfide
diethyl sulfide
diethyl sulfide 3D
Names
Preferred IUPAC name

(Ethylsulfanyl)ethane

Other names
  • 1,1-Thiobisethane
  • Diethyl thioether
  • Ethyl sulfide
  • Thioethyl ether
    • Identifiers

    CAS Number

    3D model (JSmol)

    Beilstein Reference

    		 1696909
    ChEBI
    ChEMBL
    ChemSpider
    ECHA InfoCard 100.005.934 Edit this at Wikidata
    EC Number
    • 206-526-9

    Gmelin Reference

    		 1915
    KEGG

    PubChem CID
    RTECS number
    • LC7200000
    UNII

    CompTox Dashboard (EPA)

    • InChI=1S/C4H10S/c1-3-5-4-2/h3-4H2,1-2H3 checkY

      Key: LJSQFQKUNVCTIA-UHFFFAOYSA-N checkY

    • InChI=1/C4H10O4S/c1-3-7-9(5,6)8-4-2/h3-4H2,1-2H3

      Key: DENRZWYUOJLTMF-UHFFFAOYAR

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

      Key: LJSQFQKUNVCTIA-UHFFFAOYAZ

    • S(CC)CC

    Properties

    Chemical formula

    		 (CH3CH2)2S
    Molar mass 90.18 g·mol−1
    Appearance Colorless liquid
    Odor Unpleasant
    Density 0.837 g/cm3
    Melting point −103.8 °C (−154.8 °F; 169.3 K)
    Boiling point 92 °C (198 °F; 365 K)

    Solubility in water

    		 insoluble
    Solubilityinethanol miscible
    Solubilityindiethyl ether miscible

    Magnetic susceptibility (χ)

    		 −67.9·10−6cm3/mol

    Refractive index (nD)

    		 1.44233
    Hazards[1]
    Occupational safety and health (OHS/OSH):

    Main hazards

    		 Skin and eye irritant. Highly flammable liquid and vapor
    GHS labelling:

    Pictograms

    		 GHS02: FlammableGHS07: Exclamation mark

    Signal word

    		 Danger

    Hazard statements

    		 H225, H315, H319

    Precautionary statements

    		 P210, P233, P264, P280, P303+P361+P353, P370+P378
    NFPA 704 (fire diamond)
    NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
    2
    3
    1
    Flash point −10 °C (14 °F; 263 K)
    Safety data sheet (SDS) External MSDS
    Related compounds

    Related thioethers
  • Diphenyl sulfide

    • Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

    checkY verify (what is checkY☒N ?)

    Infobox references

    Diethyl sulfide (British English: diethyl sulphide) is an organosulfur compound with the chemical formula (CH3CH2)2S. It is a colorless, malodorous liquid. Although a common thioether, it has few applications.

    Preparation[edit]

    Diethyl sulfide is a by-product of the commercial production of ethanethiol, which is prepared by the reaction of ethylene with hydrogen sulfide over an alumina-based catalyst. The amount of diethyl sulfide produced can be controlled by varying the ratio of hydrogen sulfide to ethylene.

    Occurrence[edit]

    Diethyl sulfide has been found to be a constituent of the odor of durian fruit[2] and as a constituent found in volatiles from potatoes.[3]

    Reactions[edit]

    Diethyl sulfide is a Lewis base, classified as a soft ligand (see also ECW model). Its relative donor strength toward a series of acids, versus other Lewis bases, can be illustrated by C-B plots.[4][5]

    With bromine, it forms a salt called diethylbromosulfonium bromide:[6]

    (CH3CH2)2S + Br2 → [(CH3CH2)2SBr]+Br−

    A typical coordination complexiscis-PtCl2(S(CH2CH3)2)2.

    Structure of cis-PtCl2(SEt2)2.[7]

    References[edit]

    1. ^ "GESTIS-Stoffdatenbank". gestis.dguv.de (in German).
  • ^ Baldry, Jane; J. Dougan; G. E. Howard (1972). "Volatile Flavouring Constituents of Durian". Phytochemistry. 11 (6): 2081–2084. Bibcode:1972PChem..11.2081B. doi:10.1016/s0031-9422(00)90176-6.
  • ^ Gumbmann, M. R.; H. K. Burr (1964). "Food Flavors and Odors, Volatile Sulfur Compounds in Potatoes". Journal of Agricultural and Food Chemistry. 12 (5): 404–408. doi:10.1021/jf60135a004.
  • ^ Laurence, C. and Gal, J-F. Lewis Basicity and Affinity Scales, Data and Measurement, (Wiley 2010) pp 50-51 ISBN 978-0-470-74957-9
  • ^ Cramer, R. E.; Bopp, T. T. (1977). "Graphical display of the enthalpies of adduct formation for Lewis acids and bases". Journal of Chemical Education. 54: 612–613. doi:10.1021/ed054p612. The plots shown in this paper used older parameters. Improved E&C parameters are listed in ECW model.
  • ^ Scott A. Snyder, Daniel S. Treitler (2011). "Synthesis of Et2SBrSbCl5Br and Its Use in Biomimetic Brominative Polyene Cyclizations". Organic Syntheses. 88: 54. doi:10.15227/orgsyn.088.0054.
  • ^ C.Hansson (2007). "cis-Dichloridobis(diethyl sulfide-κS)platinum(II) at 295 and 150 K". Acta Crystallographica Section C. 63 (Pt 8): m361-3. doi:10.1107/S0108270107030417. PMID 17675684.

    • Retrieved from "https://en.wikipedia.org/w/index.php?title=Diethyl_sulfide&oldid=1168726521"
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