Thiirane (original) (raw)
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Thiirane
 Skeletal formula of thiirane  Spacefill model of thiirane |
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| Names | |
| Preferred IUPAC name Thiirane | |
| Systematic IUPAC name Thiacyclopropane | |
| Other names2,3-Dihydrothiirene[1]Ethylene sulfide[1] | |
| Identifiers | |
| CAS Number | 420-12-2  Y |
| 3D model (JSmol) | Interactive image |
| Beilstein Reference | 102379 |
| ChEBI | CHEBI:30977 Y |
| ChemSpider | 9481 Y |
| ECHA InfoCard | 100.006.359  |
| EC Number | 206-993-9 |
| Gmelin Reference | 1278 |
| KEGG | C19419  N |
| MeSH | ethylene+sulfide |
| PubChem CID | 9865 |
| RTECS number | KX3500000 |
| UNII | A2W5165740 Y |
| UN number | 1992 |
| CompTox Dashboard (EPA) | DTXSID3049411 |
| InChI InChI=1S/C2H4S/c1-2-3-1/h1-2H2 YKey: VOVUARRWDCVURC-UHFFFAOYSA-N Y |
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| SMILES C1CS1 | |
| Properties | |
| Chemical formula | 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 formation (Δf_H_⦵298) | 51-53 kJ mol−1 |
| Std enthalpy of combustion (Δc_H_⦵298) | -2.0126 MJ mol−1 |
| Hazards | |
| GHS labelling: | |
| Pictograms |    |
| Signal word | Danger |
| Hazard statements | H225, H301, H318, H331 |
| Precautionary statements | P210, P261, P280, P301+P310, P305+P351+P338, P311 |
| NFPA 704 (fire diamond) |  3 4 2 |
| Flash point | 10 °C (50 °F; 283 K) |
| Related compounds | |
| Related heterocycles | Ethylene oxideAziridineBorirane |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).  N verify (what is YN ?) Infobox references |
Chemical compound
For the class of compounds known as thiiranes, see Episulfide.
Thiirane, more commonly known as ethylene sulfide, is the cyclic chemical compound with the formula C2H4S.[2] 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.
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
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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.
- ^ a b "thiirane (CHEBI:30977)". Chemical Entities of Biological Interest (ChEBI). UK: European Bioinformatics Institute.
- ^ Warren Chew; David N. Harpp (1993). "Recent aspects of thiirane chemistry". Journal of Sulfur Chemistry. 15 (1): 1–39. doi:10.1080/01961779308050628.
- ^ Wataru Ando; Nami Choi; Norihiro Tokitoh (1996). "Thiiranes and Thiirenes: Monocyclic". Comprehensive Heterocyclic Chemistry II. Vol. 1A. pp. 173–240. doi:10.1016/B978-008096518-5.00005-8. ISBN 978-0-08-096518-5.
- ^ Searles, S.; Lutz, E. F.; Hays, H. R.; Mortensen, H. E. (1962). "Ethylene Sulfide". Organic Syntheses. 42: 59. doi:10.15227/orgsyn.042.0059.
- ^ R. J. Cremlyn "An Introduction to Organosulfur Chemistry" John Wiley and Sons: Chichester (1996). ISBN 0-471-95512-4.
- ^ Gunars Zelans; Jacquelyn Gervay-Hague; Ivy Maulie (2010). "Ethylene Sulfide". Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons. doi:10.1002/047084289X.re079.pub2. ISBN 978-0-471-93623-7.