Thiirane
From Wikipedia, the free encyclopedia
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Names | |||
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Systematic IUPAC name
Thiirane[1]
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Other names | |||
Identifiers | |||
420-12-2 ![]() |
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3D model (Jmol) | Interactive image | ||
102379 | |||
ChEBI | CHEBI:30977 ![]() |
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ChemSpider | 9481 ![]() |
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ECHA InfoCard | 100.006.359 | ||
EC Number | 206-993-9 | ||
1278 | |||
KEGG | C19419 ![]() |
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MeSH | ethylene+sulfide | ||
PubChem | 9865 | ||
RTECS number | KX3500000 | ||
UN number | 1992 | ||
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Properties | |||
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 (ΔfH |
51-53 kJ mol−1 | ||
Std enthalpy of
combustion (ΔcH |
-2.0126 MJ mol−1 | ||
Hazards | |||
GHS pictograms | ![]() ![]() ![]() |
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GHS signal word | DANGER | ||
H225, H301, H318, H331 | |||
P210, P261, P280, P301+310, P305+351+338, P311 | |||
EU classification (DSD)
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R-phrases | R11, R23/25, R41 | ||
S-phrases | S16, S36/37/39, S45 | ||
NFPA 704 | |||
Flash point | 10 °C (50 °F; 283 K) | ||
Related compounds | |||
Related heterocycles
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Ethylene oxide Aziridine Borirane |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 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 and the simplest episulfide. Like many organosulfur compounds, this species has a stench. Thiirane is also used to describe any derivative of the parent ethylene sulfide.
Preparation[edit]
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
Reactions[edit]
Ethylenesulfide adds to amines to afford 2-mercaptoethylamines,[4] which are good chelating ligands.
- C2H4S + R2NH → R2NCH2CH2SH
Dithiiranes[edit]
Dithiiranes are three membered rings containing two sulfur atoms and one carbon. One example was prepared by oxidation of a 1,3-dithietane.[5]
References[edit]
- ^ a b c d "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.
- ^ Searles, S.; Lutz, E. F.; Hays, H. R.; Mortensen, H. E. (1973). "Ethylene Sulfide". Org. Synth.; Coll. Vol., 5, p. 562
- ^ R. J. Cremlyn “An Introduction to Organosulfur Chemistry” John Wiley and Sons: Chichester (1996). ISBN 0-471-95512-4.
- ^ Ahhiko Ishii, Masamatsu Hoshino, and Juzo Nakayama "Recent Advances in Chemistry of Dithiirane and Small Ring Compounds Containing Two Chalcogen Atoms" Pure & Appl. Chem., 1996, volume 68, pp. 869-874.doi:10.1002/chin.199650272