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 Y

3D model (JSmol)

* Interactive image

Beilstein Reference

| 1696909
ChEBI |

* CHEBI:27710 Y

ChEMBL |

* ChEMBL117181 Y

ChemSpider |

* 9233 Y

EC Number |

* 206-526-9

Gmelin Reference

| 1915
KEGG |

* C14706 Y

PubChem CID

* 9609

RTECS number |

* LC7200000

UNII |

* 9191Y76OTC Y

InChI

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

Key: LJSQFQKUNVCTIA-UHFFFAOYSA-N Y

* 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

| (CH
3CH

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[1]
Main hazards | Skin and eye irritant. Highly flammable liquid and vapor
Safety data sheet | External MSDS
GHS pictograms |
GHS Signal word | Danger

GHS hazard statements

| H225, H315, H319

GHS precautionary statements

| 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

* Dimethyl sulfide
* Diphenyl sulfide

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

Y verify (what is YN ?)
Infobox references

Tracking categories (test):

* SizeSet

Diethyl sulfide (British English: diethyl sulphide) is an organosulfur compound with the chemical formula (CH
3CH

2S. It is a colorless, malodorous liquid. Although a common thioether, it has few applications.

## Contents

* 1 Preparation
* 2 Occurrence
* 3 Reactions
* 4 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]

(CH
3CH

2S + Br
2 → [(CH
3CH

2SBr]+
Br−

A typical coordination complex is cis-PtCl
2(S(CH
2CH

2, one of many transition metal thioether complexes.

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

## References

1. ↑ "GESTIS-Stoffdatenbank" (in de). https://gestis.dguv.de/data?name=031980.
2. ↑ 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.
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. Bibcode: 1964JAFC...12..404G.
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. Bibcode: 2007AcCrC..63M.361H.

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*[CID]: Compound ID
*[H225]: Highly flammable liquid and vapour
*[H315]: Causes skin irritation
*[H319]: Causes serious eye irritation
*[P210]: Keep away from heat/sparks/open flames/hot surfaces – No smoking
*[P233]: Keep container tightly closed
*[P264]: Wash … thoroughly after handling
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P303+361+353]: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower
*[P370+378]: In case of fire: Use … for extinction