Thiirane
Skeletal formula of thiirane
Skeletal formula of thiirane
Spacefill model of thiirane
Spacefill model of thiirane
Ball and model of thiirane
Names
Preferred IUPAC name
Thiirane
Systematic IUPAC name
Thiacyclopropane
Other names
2,3-Dihydrothiirene[1]
Ethylene sulfide[1]
Identifiers
3D model (JSmol)
102379
ChEBI
ChemSpider
ECHA InfoCard 100.006.359 Edit this at Wikidata
EC Number
  • 206-993-9
1278
KEGG
MeSH ethylene+sulfide
RTECS number
  • KX3500000
UNII
UN number 1992
  • InChI=1S/C2H4S/c1-2-3-1/h1-2H2 checkY
    Key: VOVUARRWDCVURC-UHFFFAOYSA-N checkY
  • C1CS1
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 labelling:
GHS02: Flammable GHS05: Corrosive GHS06: Toxic
Danger
H225, H301, H318, H331
P210, P261, P280, P301+P310, P305+P351+P338, P311
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 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. propaneInstability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorusSpecial hazards (white): no code
3
4
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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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 highly unpleasant odour. Thiirane is also used to describe any derivative of the parent ethylene sulfide.

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. ^ a b "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. Vol. 1A. pp. 173–240. doi:10.1016/B978-008096518-5.00005-8. ISBN 978-0-08-096518-5.
  4. ^ Searles, S.; Lutz, E. F.; Hays, H. R.; Mortensen, H. E. (1962). "Ethylene Sulfide". Organic Syntheses. 42: 59. doi:10.15227/orgsyn.042.0059.
  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. ISBN 978-0-471-93623-7.
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