Thiirane
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| Thiirane | |
|---|---|
| Image:Ethylene-sulfide-2D.png Image:Ethylene-sulfide-2D-skeletal.png Image:Ethylene-sulfide-3D-vdW.png | |
| 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,[1] which are good chelating ligands.
- C2H4S + R2NH → R2NCH2CH2SH
References
- Warren Chew; David N. Harpp (1993). "Recent aspects of thiirane chemistry". Journal of Sulfur Chemistry 15 (1): 1 - 39. doi:10.1080/01961779308050628.
External links
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
