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Thiirane

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Thiirane
Skeletal formula of thiirane
Skeletal formula of thiirane
Spacefill model of thiirane
Spacefill model of thiirane
Ball-and-stick model of thiirane
Names
Preferred IUPAC name Thiirane
Systematic IUPAC name Thiacyclopropane
Other names 2,3-Dihydrothiirene
Ethylene sulfide
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 102379
ChEBI
ChemSpider
ECHA InfoCard 100.006.359 Edit this at Wikidata
EC Number
  • 206-993-9
Gmelin Reference 1278
KEGG
MeSH ethylene+sulfide
PubChem CID
RTECS number
  • KX3500000
UNII
UN number 1992
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C2H4S/c1-2-3-1/h1-2H2Key: VOVUARRWDCVURC-UHFFFAOYSA-N
SMILES
  • C1CS1
Properties
Chemical formula C2H4S
Molar mass 60.11 g·mol
Appearance Pale, yellow liquid
Density 1.01 g cm
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 (ΔfH298) 		51-53 kJ mol
Std enthalpy of
combustion (ΔcH298) 		-2.0126 MJ mol
Hazards
GHS labelling:
Pictograms GHS02: Flammable GHS05: Corrosive GHS06: Toxic
Signal word Danger
Hazard statements H225, H301, H318, H331
Precautionary statements 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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound For the class of compounds known as thiiranes, see Episulfide.

Thiirane, more commonly known as ethylene sulfide, is the cyclic chemical compound with the formula C2H4S. 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°.

Preparation and reactions

It can be prepared by the reaction of ethylene carbonate and KSCN. 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, which are good chelating ligands.

C2H4S + R2NH → R2NCH2CH2SH

This process is often called mercaptoethylation.

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. 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.
Sulfur compounds
Sulfides and
disulfides
Sulfur halides
Sulfur oxides
and oxyhalides
Sulfites
Sulfates
Sulfur nitrides
Thiocyanates
Organic compounds
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