Thiirane
title: "Thiirane" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["episulfides"] topic_path: "general/episulfides" source: "https://en.wikipedia.org/wiki/Thiirane" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 470606690
| ImageFile2 = Ethylene-sulfide-3D-balls.png
| ImageFile2_Ref =
| ImageSize2 = 121
| ImageName2 = Ball-and-stick model of thiirane
| ImageFileL1 = Ethylene-sulfide-2D-skeletal.png
| ImageFileL1_Ref =
| ImageSizeL1 = 121
| ImageNameL1 = Skeletal formula of thiirane
| ImageFileR1 = Ethylene-sulfide-3D-vdW.png
| ImageFileR1_Ref =
| ImageSizeR1 = 121
| ImageNameR1 = Spacefill model of thiirane
| PIN = Thiirane
| SystematicName = Thiacyclopropane
| OtherNames = 2,3-Dihydrothiirene
Ethylene sulfide
|Section1={{Chembox Identifiers
| CASNo = 420-12-2
| CASNo_Ref =
| UNII_Ref =
| UNII = A2W5165740
| PubChem = 9865
| ChemSpiderID = 9481
| ChemSpiderID_Ref =
| EINECS = 206-993-9
| UNNumber = 1992
| KEGG = C19419
| KEGG_Ref =
| MeSHName = ethylene+sulfide
| ChEBI_Ref =
| ChEBI = 30977
| RTECS = KX3500000
| Beilstein = 102379
| Gmelin = 1278
| SMILES = C1CS1
| StdInChI = 1S/C2H4S/c1-2-3-1/h1-2H2
| StdInChI_Ref =
| StdInChIKey = VOVUARRWDCVURC-UHFFFAOYSA-N
| StdInChIKey_Ref =
|Section2={{Chembox Properties
| C=2 | H=4 | S=1
| Appearance = Pale, yellow liquid
| Density = 1.01 g cm−3
| MeltingPtC = -109
| BoilingPtK = 329
| VaporPressure = 28.6 kPa (at 20 °C)
|Section4={{Chembox Thermochemistry
| DeltaHf = 51–53 kJ mol−1
| DeltaHc = −2.0126 MJ mol−1
|Section5={{Chembox Hazards
| GHSPictograms =
| GHSSignalWord = DANGER
| HPhrases =
| PPhrases =
| NFPA-F = 4
| NFPA-H = 3
| NFPA-R = 2
| FlashPtC = 10
|Section6={{Chembox Related
| OtherFunction_label = heterocycles
| OtherFunction = Ethylene oxide
Aziridine
Borirane
Thiirane, more commonly known as ethylene sulfide, is the cyclic chemical compound with the formula C2H4S.{{cite journal
| author= Warren Chew |author2=David N. Harpp
| title = Recent aspects of thiirane chemistry
| journal = Journal of Sulfur Chemistry
| year = 1993
| volume = 15
| issue = 1
| pages = 1–39
| doi = 10.1080/01961779308050628}} 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.
References
References
- "thiirane (CHEBI:30977)". European Bioinformatics Institute.
- Wataru Ando. (1996). "Thiiranes and Thiirenes: Monocyclic".
- (2023-12-05). "Comprehensive quantum chemical analysis of the (ro)vibrational spectrum of thiirane and its deuterated isotopologue". Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy.
- (1962). "Ethylene Sulfide". Organic Syntheses.
- R. J. Cremlyn "An Introduction to Organosulfur Chemistry" John Wiley and Sons: Chichester (1996). {{ISBN. 0-471-95512-4.
- Gunars Zelans. (2010). "Ethylene Sulfide". John Wiley & Sons.
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