Thiirane

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Thiirane

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Template:Longitem	Template:Unbulleted list
Template:Longitem	102379
ChEBI	Template:Unbulleted list
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EC Number	Template:Unbulleted list
Template:Longitem	1278
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MeSH	ethylene+sulfide
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UN number	1992
Template:Longitem	Template:Chembox Elements/molecular formula
Molar mass	Template:Chem molar mass
Appearance	Pale, yellow liquid
Density	1.01 g cm−3
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Vapor pressure	28.6 kPa (at 20 °C)
Template:Longitem	51–53 kJ mol−1
Template:Longitem	−2.0126 MJ mol−1
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Template:Longitem	Ethylene oxide Aziridine Borirane

Thiirane, more commonly known as ethylene sulfide, is the cyclic chemical compound with the formula C₂H₄S. It is the smallest sulfur-containing heterocycle and the simplest episulfide. Like many organosulfur compounds, this species has a highly unpleasant odour. Thiirane is also used to describe any derivative of the parent ethylene sulfide.

Structure and properties

According to electron diffraction, the C-C and C-S distances in ethylene sulfide are respectively 1.473 and 1.811 Å. The C-C-S and C-S-C angles are respectively 66.0 and 48.0°. The microwave and infrared spectra were studied experimentally and computationally.

Preparation and reactions

It can be prepared by the reaction of ethylene carbonate and KSCN. For this purpose the KSCN is first melted under vacuum to remove water.

KSCN + C₂H₄O₂CO → KOCN + C₂H₄S + CO₂

Ethylenesulfide adds to amines to afford 2-mercaptoethylamines, which are good chelating ligands.

C₂H₄S + R₂NH → R₂NCH₂CH₂SH

This process is often called mercaptoethylation.

Oxidation of thiirane with periodate gives ethylene episulfoxide.