Diethyl sulfide

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.

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
3D model (JSmol)
1696909
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.934
EC Number
  • 206-526-9
1915
KEGG
RTECS number
  • LC7200000
UNII
  • 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
(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)
insoluble
Solubility in ethanol miscible
Solubility in diethyl ether miscible
−67.9·10−6 cm3/mol
1.44233
Hazards[1]
Occupational safety and health (OHS/OSH):
Main hazards
 Skin and eye irritant. Highly flammable liquid and vapor
GHS labelling:
GHS02: FlammableGHS07: Exclamation mark
Danger
H225, H315, H319
P210, P233, P264, P280, P303+P361+P353, P370+P378
NFPA 704 (fire diamond)
NFPA 704 four-colored diamond
2
3
1
Flash point −10 °C (14 °F; 263 K)
Safety data sheet (SDS) External MSDS
Related compounds
Related thioethers
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

Preparation

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

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

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 complex is cis-PtCl2(S(CH2CH3)2)2.

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

References
  1. "GESTIS-Stoffdatenbank". gestis.dguv.de (in German).
  2. 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.
  3. 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.
  4. 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
  5. 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.
  6. 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.
  7. 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.
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