Chemistry:Diethyl sulfide
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| Names | |
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| Preferred IUPAC name
(Ethylsulfanyl)ethane | |
Other names
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| Identifiers | |
3D model (JSmol)
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| 1696909 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| EC Number |
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| 1915 | |
| KEGG | |
PubChem CID
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| RTECS number |
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| UNII | |
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| Properties | |
| (CH 3CH 2) 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 | |
Refractive index (nD)
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1.44233 |
| Hazards[1] | |
| Main hazards | Skin and eye irritant. Highly flammable liquid and vapor |
| Safety data sheet | External MSDS |
| GHS pictograms |  
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| GHS Signal word | Danger |
| H225, H315, H319 | |
| P210, P233, P264, P280, P303+361+353, P370+378 | |
| NFPA 704 (fire diamond) | |
| Flash point | −10 °C (14 °F; 263 K) |
| Related compounds | |
Related thioethers
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
 verify (what is   ?)
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| Infobox references | |
Diethyl sulfide (British English: diethyl sulphide) is an organosulfur compound with the chemical formula (CH
3CH
2)
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]
- (CH
3CH
2)
2S + Br
2 → [(CH
3CH
2)
2SBr]+
Br−
A typical coordination complex is cis-PtCl
2(S(CH
2CH
3)
2)
2.
References
- ↑ "GESTIS-Stoffdatenbank" (in de). https://gestis.dguv.de/data?name=031980.
- ↑ Baldry, Jane; J. Dougan; G. E. Howard (1972). "Volatile Flavouring Constituents of Durian". Phytochemistry 11 (6): 2081–2084. doi:10.1016/s0031-9422(00)90176-6. Bibcode: 1972PChem..11.2081B.
- ↑ 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.
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