Thiirane

Thiirane
Names
Systematic IUPAC name
Thiirane[1]
Other names
2,3-Dihydrothiirene[1]

Ethylene sulfide[1]

Thiacyclopropane[1]
Identifiers
420-12-2 YesY
102379
ChEBI CHEBI:30977 YesY
ChemSpider 9481 YesY
EC Number 206-993-9
1278
Jmol interactive 3D Image
KEGG C19419 N
MeSH ethylene+sulfide
PubChem 9865
RTECS number KX3500000
UN number 1992
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
51-53 kJ mol−1
-2.0126 MJ mol−1
Hazards
GHS pictograms
GHS signal word DANGER
H225, H301, H318, H331
P210, P261, P280, P301+310, P305+351+338, P311
F T
R-phrases R11, R23/25, R41
S-phrases S16, S36/37/39, S45
NFPA 704
Flammability code 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g., propane Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g., phosphorus Special hazards (white): no codeNFPA 704 four-colored diamond
4
3
2
Flash point 10 °C (50 °F; 283 K)
Related compounds
Related heterocycles
 Ethylene oxide
Aziridine
Borirane
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

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

Ethylenesulfide adds to amines to afford 2-mercaptoethylamines,[4] which are good chelating ligands.

C2H4S + R2NH → R2NCH2CH2SH

Dithiiranes

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

  1. 1 2 3 4 "thiirane (CHEBI:30977)". Chemical Entities of Biological Interest (ChEBI). UK: European Bioinformatics Institute.
  2. ↑ Warren Chew; David N. Harpp (1993). "Recent aspects of thiirane chemistry". Journal of Sulfur Chemistry 15 (1): 1–39. doi:10.1080/01961779308050628.
  3. ↑ Searles, S.; Lutz, E. F.; Hays, H. R.; Mortensen, H. E. (1973). "Ethylene Sulfide". Org. Synth.; Coll. Vol. 5, p. 562
  4. ↑ R. J. Cremlyn “An Introduction to Organosulfur Chemistry” John Wiley and Sons: Chichester (1996). ISBN 0-471-95512-4.
  5. ↑ 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
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