Thiirane

Thiirane
Identifiers
CAS number 420-12-2 Y
PubChem 9865
ChemSpider 9481 N
EC number 206-993-9
UN number 1992
KEGG C19419 Y
MeSH ethylene+sulfide
ChEBI CHEBI:30977 N
RTECS number KX3500000
Beilstein Reference 102379
Gmelin Reference 1278
Jmol-3D images Image 1
Properties
Molecular formula C2H4S
Molar mass 60.12 g mol−1
Exact mass 60.003370818 g mol−1
Appearance Pale, yellow liquid
Density 1.01 g cm−3
Melting point

-109 °C, 164 K, -164 °F

Boiling point

56 °C, 329 K, 133 °F

Vapor pressure 28.6 kPa (at 20 °C)
Thermochemistry
Std enthalpy of
formation
ΔfHo298
51-53 kJ mol-1
Std enthalpy of
combustion
ΔcHo298
-2.0126 MJ mol-1
Hazards
GHS pictograms
GHS signal word DANGER
GHS hazard statements H225, H301, H318, H331
GHS precautionary statements P210, P261, P280, P301+310, P305+351+338, P311
EU classification F T
R-phrases R11, R23/25, R41
S-phrases S16, S36/37/39, S45
NFPA 704
4
3
2
Flash point 10 °C
Related compounds
Related heterocycles Ethylene oxide
Aziridine
Borirane
 N (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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. 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

References

  1. ^ a b c d "thiirane (CHEBI:30977)". Chemical Entities of Biological Interest (ChEBI). UK: European Bioinformatics Institute. http://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:30977. 
  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. "Ethylenesulfide" Organic Syntheses, 1973, Collective Volume 5, page 562.
  4. ^ R. J. Cremlyn “An Introduction to Organosulfur Chemistry” John Wiley and Sons: Chichester (1996). ISBN 0-471-95512-4.