Thiirane
From Wikipedia, the free encyclopedia
| Thiirane | |
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| IUPAC name | Thiirane |
| Other names | Ethylene sulfide |
| Identifiers | |
| CAS number | [420-12-2] |
| RTECS number | KX3500000 |
| SMILES | C1CS1 |
| Properties | |
| Molecular formula | C2H4S |
| Molar mass | 60.12 g mol−1 |
| Appearance | liquid, usually pale yellow |
| Density | 1.01 g cm−3, liquid |
| Boiling point |
54.0–54.5 °C |
| Solubility in water | low |
| Structure | |
| Molecular shape | C2v symmetry |
| Hazards | |
| Main hazards | toxic, stench |
| R-phrases | 11-23/25-41 |
| S-phrases | 16-36/37/39-45 |
| Related compounds | |
| Related heterocycles | ethylene oxide aziridine |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Thiirane, more commonly known as ethylene sulfide, is the cyclic chemical compound with the formula C2H4S.[1] 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.[2] 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,[3] which are good chelating ligands.
- C2H4S + R2NH → R2NCH2CH2SH
[edit] References
- ^ Warren Chew; David N. Harpp (1993). "Recent aspects of thiirane chemistry". Journal of Sulfur Chemistry 15 (1): 1–39. doi:.
- ^ 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.
