Thiirane

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Thiirane
Skeletal formula of thiirane
Spacefill model of thiirane
Ball and model of thiirane
Names
Systematic IUPAC name
Thiirane[1]
Other names
2,3-Dihydrothiirene[1]

Ethylene sulfide[1]

Thiacyclopropane[1]
Identifiers
102379
420-12-2 YesY
ChEBI CHEBI:30977 YesY
ChemSpider 9481 YesY
EC number 206-993-9
1278
Jmol-3D images Image
KEGG C19419 N
MeSH ethylene+sulfide
PubChem 9865
RTECS number KX3500000
UN number 1992
Properties
C2H4S
Molar mass 60.12 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 The flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The corrosion pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The skull-and-crossbones pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
H225, H301, H318, H331
P210, P261, P280, P301+310, P305+351+338, P311
EU classification Highly Flammable F Toxic 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
Flash point 10 °C (50 °F; 283 K)
Related compounds
Related heterocycles
Ethylene oxide
Aziridine
Borirane
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N verify (what isYesY/N?)
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[edit]

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[edit]

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

C2H4S + R2NH → R2NCH2CH2SH

Dithiiranes[edit]

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[edit]

  1. ^ a b c d "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