Thiirane

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.

Thiirane
Skeletal formula of thiirane
Spacefill model of thiirane
Names
Preferred IUPAC name
Thiirane
Systematic IUPAC name
Thiacyclopropane
Other names
2,3-Dihydrothiirene[1]
Ethylene sulfide[1]
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference
 102379
ChEBI
ChemSpider
ECHA InfoCard 100.006.359
EC Number
  • 206-993-9
Gmelin Reference
 1278
KEGG
MeSH ethylene+sulfide
PubChem CID
RTECS number
  • KX3500000
UNII
UN number 1992
CompTox Dashboard (EPA)
Properties
Chemical formula
 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⦵298)
 51-53 kJ mol−1
Std enthalpy of
combustion (ΔcH⦵298)
 -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
NFPA 704 (fire 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).
N verify (what is YN ?)
Infobox references

Structure

According to electron diffraction, the C-C and C-S distances in ethylene sulfide are respectively 1.473 and 1.811 Å. The C-C-S and C-S-C angles are respectively 66.0 and 48.0°.[3]

Preparation and reactions

It can be prepared by the reaction of ethylene carbonate and KSCN.[4] For this purpose the KSCN is first melted under vacuum to remove water.

KSCN + C2H4O2CO → KOCN + C2H4S + CO2

Ethylenesulfide adds to amines to afford 2-mercaptoethylamines,[5] which are good chelating ligands.

C2H4S + R2NH → R2NCH2CH2SH

This process is often called mercaptoethylation.[6]

Oxidation of thiirane with periodate gives ethylene episulfoxide.

References
  1. "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. Wataru Ando Nami Choi Norihiro Tokitoh (1996). "Thiiranes and Thiirenes: Monocyclic". Comprehensive Heterocyclic Chemistry II. 1A. pp. 173–240. doi:10.1016/B978-008096518-5.00005-8.CS1 maint: uses authors parameter (link)
  4. Searles, S.; Lutz, E. F.; Hays, H. R.; Mortensen, H. E. (1962). "Ethylene Sulfide". 42: 59. doi:10.15227/orgsyn.042.0059. Cite journal requires |journal= (help)
  5. R. J. Cremlyn “An Introduction to Organosulfur Chemistry” John Wiley and Sons: Chichester (1996). ISBN 0-471-95512-4.
  6. Gunars Zelans, Jacquelyn Gervay-Hague, Ivy Maulie (2010). "Ethylene Sulfide". Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons. doi:10.1002/047084289X.re079.pub2.CS1 maint: uses authors parameter (link)
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