Thiirane
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Names | |||
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Preferred IUPAC name
Thiirane | |||
Systematic IUPAC name
Thiacyclopropane | |||
Other names | |||
Identifiers | |||
3D model (
JSmol ) |
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102379 | |||
ChEBI | |||
ChemSpider | |||
ECHA InfoCard
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100.006.359 | ||
EC Number |
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1278 | |||
KEGG | |||
MeSH | ethylene+sulfide | ||
PubChem CID
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RTECS number
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UNII | |||
UN number | 1992 | ||
CompTox Dashboard (EPA)
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Properties | |||
C2H4S | |||
Molar mass | 60.11 g·mol−1 | ||
Appearance | Pale, yellow liquid | ||
Density | 1.01 g cm−3 | ||
Melting point | −109 °C (−164 °F; 164 K) | ||
Boiling point | 56 °C; 133 °F; 329 K | ||
Vapor pressure | 28.6 kPa (at 20 °C) | ||
Thermochemistry | |||
Std enthalpy of (ΔfH⦵298)formation |
51-53 kJ mol−1 | ||
Std enthalpy of (ΔcH⦵298)combustion |
-2.0126 MJ mol−1 | ||
Hazards | |||
GHS labelling: | |||
Danger | |||
H225, H301, H318, H331 | |||
P210, P261, P280, P301+P310, P305+P351+P338, P311 | |||
NFPA 704 (fire diamond) | |||
Flash point | 10 °C (50 °F; 283 K) | ||
Related compounds | |||
Related
heterocycles |
Ethylene oxide Aziridine Borirane | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Thiirane, more commonly known as ethylene sulfide, is the cyclic
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
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°.[3]
Preparation and reactions
It can be prepared by the reaction of ethylene carbonate and KSCN.[4] 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,[5] which are good chelating ligands.
- C2H4S + R2NH → R2NCH2CH2SH
This process is often called mercaptoethylation.[6]
Oxidation of thiirane with periodate gives ethylene episulfoxide.
References
- ^ a b "thiirane (CHEBI:30977)". Chemical Entities of Biological Interest (ChEBI). UK: European Bioinformatics Institute.
- .
- ISBN 978-0-08-096518-5.
- .
- ISBN 0-471-95512-4.
- ISBN 978-0-471-93623-7.