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
CAS Number	352-93-2 Y
3D model (JSmol)	Interactive image
Beilstein Reference	1696909
ChEBI	CHEBI:27710 Y
ChEMBL	ChEMBL117181 Y
ChemSpider	9233 Y
ECHA InfoCard	100.005.934
EC Number	206-526-9
Gmelin Reference	1915
KEGG	C14706 Y
PubChem CID	9609
RTECS number	LC7200000
UNII	9191Y76OTC Y
CompTox Dashboard (EPA)	DTXSID5027146
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	(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[1]
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). Y verify (what is YN ?) 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, one of many transition metal thioether complexes.

Structure of cis-PtCl₂(SEt₂)₂.^[7]