Diethyl sulfide

Diethyl sulfide
Names
	Preferred IUPAC name (Ethylsulfanyl)ethane
	Other names 1,1-Thiobisethane; Diethyl thioether; Ethyl sulfide; Thioethyl ether;
Identifiers
CAS Number	352-93-2 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1696909
ChEBI	CHEBI:27710 ;
ChEMBL	ChEMBL117181 ;
ChemSpider	9233 ;
ECHA InfoCard	100.005.934
EC Number	206-526-9;
Gmelin Reference	1915
KEGG	C14706 ;
PubChem CID	9609;
RTECS number	LC7200000;
UNII	9191Y76OTC ;
CompTox Dashboard (EPA)	DTXSID5027146 ;
	InChI InChI=1S/C4H10S/c1-3-5-4-2/h3-4H2,1-2H3 Key: LJSQFQKUNVCTIA-UHFFFAOYSA-N ; 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;
	SMILES 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
Solubility in ethanol	miscible
Solubility in diethyl ether	miscible
Magnetic susceptibility (χ)	−67.9·10−6 cm3/mol
Refractive index (nD)	1.44233
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Skin and eye irritant. Highly flammable liquid and vapor
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H315, H319
Precautionary statements	P210, P233, P264, P280, P303+P361+P353, P370+P378
NFPA 704 (fire diamond)	2 3 1
Flash point	−10 °C (14 °F; 263 K)
Safety data sheet (SDS)	External MSDS
Related compounds
Related thioethers	Dimethyl sulfide; Diphenyl sulfide;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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

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.

References

^ "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. Bibcode:1964JAFC...12..404G. 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. Bibcode:2007AcCrC..63M.361H. doi:10.1107/S0108270107030417. PMID 17675684.

[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. Bibcode:1964JAFC...12..404G. 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. Bibcode:2007AcCrC..63M.361H. doi:10.1107/S0108270107030417. PMID 17675684.

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