Thiirane
From Wikipedia, the free encyclopedia
| Thiirane | |
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Thiirane[1] |
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| Identifiers | |
| CAS number | 420-12-2  |
| PubChem | 9865 |
| ChemSpider | 9481 |
| EC number | 206-993-9 |
| UN number | 1992 |
| KEGG | C19419  |
| MeSH | ethylene+sulfide |
| ChEBI | CHEBI:30977 |
| RTECS number | KX3500000 |
| Beilstein Reference | 102379 |
| Gmelin Reference | 1278 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C2H4S |
| Molar mass | 60.12 g mol−1 |
| Exact mass | 60.003370818 g mol−1 |
| Appearance | Pale, yellow liquid |
| Density | 1.01 g cm−3 |
| Melting point |
-109 °C, 164 K, -164 °F |
| Boiling point |
56 °C, 329 K, 133 °F |
| Vapor pressure | 28.6 kPa (at 20 °C) |
| Thermochemistry | |
| Std enthalpy of formation ΔfH |
51-53 kJ mol-1 |
| Std enthalpy of combustion ΔcH |
-2.0126 MJ mol-1 |
| Hazards | |
| GHS pictograms |    |
| GHS signal word | DANGER |
| GHS hazard statements | H225, H301, H318, H331 |
| GHS precautionary statements | P210, P261, P280, P301+310, P305+351+338, P311 |
| EU classification |  F  T |
| R-phrases | R11, R23/25, R41 |
| S-phrases | S16, S36/37/39, S45 |
| NFPA 704 |
 4
3
2
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| Flash point | 10 °C |
| Related compounds | |
| Related heterocycles | Ethylene oxide Aziridine Borirane |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Thiirane, more commonly known as ethylene sulfide, is the cyclic chemical compound with the formula C2H4S.[2] It is the smallest sulfur-containing heterocycle. Like many organosulfur compounds, this species has a stench. Thiirane is also used to describe any derivative of the parent ethylene sulfide.
[edit] Preparation
It is prepared by the reaction of ethylene carbonate and KSCN.[3] For this purpose the KSCN is first melted under vacuum to remove water.
- KSCN + C2H4O2CO → KOCN + C2H4S + CO2
[edit] Reactions
Ethylenesulfide adds to amines to afford 2-mercaptoethylamines,[4] which are good chelating ligands.
- C2H4S + R2NH → R2NCH2CH2SH
[edit] References
- ^ a b c d "thiirane (CHEBI:30977)". Chemical Entities of Biological Interest (ChEBI). UK: European Bioinformatics Institute. http://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:30977.
- ^ Warren Chew; David N. Harpp (1993). "Recent aspects of thiirane chemistry". Journal of Sulfur Chemistry 15 (1): 1–39. doi:10.1080/01961779308050628.
- ^ Searles, S.; Lutz, E. F.; Hays, H. R.; Mortensen, H. E. "Ethylenesulfide" Organic Syntheses, 1973, Collective Volume 5, page 562.
- ^ R. J. Cremlyn “An Introduction to Organosulfur Chemistry” John Wiley and Sons: Chichester (1996). ISBN 0-471-95512-4.
