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Thiirane
| Thiirane |
|
| General |
| Systematic name |
Thiirane |
| Other names |
Ethylene sulfide |
| Molecular formula |
C2H4S |
| SMILES |
C1CS1 |
| Molar mass |
60.12 g mol−1 |
| Appearance |
liquid,
usually pale yellow |
| CAS number |
[420-12-2] |
| Properties |
| Density and phase |
1.01 g cm−3, liquid |
| Solubility in water |
low |
| Melting point |
? °C |
| Boiling point |
54.0–54.5 °C |
| Structure |
| Molecular shape |
C2v symmetry |
| Dipole moment |
? D |
| Hazards |
| MSDS |
External MSDS |
| Main hazards |
toxic, stench |
| NFPA 704 |
|
| Flash point |
? °C |
| R/S statement |
R: 11-23/25-41
S: 16-36/37/39-45 |
| RTECS number |
KX3500000 |
| Supplementary data page |
Structure and
properties |
n (20/D) = 1.495 |
Thermodynamic
data |
Phase behaviour
Solid, liquid, gas |
| Spectral data |
UV, IR, NMR, MS |
| 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 |
Thiirane, more commonly known as ethylene sulfide, is the cyclic chemical compound with the formula C2H4S. 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.
Preparation
It is prepared by the reaction of ethylenecarbonate and KSCN.[1] For this purpose the KSCN is first melted under vacuum to remove water.
- KSCN + C2H4O2CO → KOCN + C2H4S + CO2
Reactions
Ethylenesulfide adds to amines to afford 2-mercaptoethylamines,[2] which are good chelating ligands.
- C2H4S + R2NH → R2NCH2CH2SH
References
- ^ 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.
- Warren Chew; David N. Harpp (1993). "Recent aspects of thiirane chemistry". Journal of Sulfur Chemistry 15 (1): 1 - 39. doi:10.1080/01961779308050628.
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This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Thiirane". A list of authors is available in Wikipedia.
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