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Thiirane



Thiirane

General
Systematic name Thiirane
Other names Ethylene sulfide
Molecular formula C2H4S
SMILES C1CS1
Molar mass 60.12 g mol−1
Appearance liquid,
usually pale yellow
CAS number [420-12-2]
Properties
Density and phase 1.01 g cm−3, liquid
Solubility in water low
Melting point  ? °C
Boiling point 54.0–54.5 °C
Structure
Molecular shape C2v symmetry
Dipole moment  ? D
Hazards
MSDS External MSDS
Main hazards toxic, stench
NFPA 704
Flash point  ? °C
R/S statement R: 11-23/25-41
S: 16-36/37/39-45
RTECS number KX3500000
Supplementary data page
Structure and
properties
n (20/D) = 1.495
Thermodynamic
data
Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
Related compounds
Related heterocycles ethylene oxide
aziridine
Except where noted otherwise, data are given for
materials in their standard state (at 25 °C, 100 kPa)
Infobox disclaimer and references

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

Additional recommended knowledge

Preparation

It is prepared by the reaction of ethylenecarbonate and KSCN.[1] 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,[2] which are good chelating ligands.

C2H4S + R2NH → R2NCH2CH2SH

References

  1. ^ Searles, S.; Lutz, E. F.; Hays, H. R.; Mortensen, H. E. "Ethylenesulfide" Organic Syntheses, 1973, Collective Volume 5, page 562.
  2. ^ R. J. Cremlyn “An Introduction to Organosulfur Chemistry” John Wiley and Sons: Chichester (1996). ISBN 0-471-95512-4.
  • Warren Chew; David N. Harpp (1993). "Recent aspects of thiirane chemistry". Journal of Sulfur Chemistry 15 (1): 1 - 39. doi:10.1080/01961779308050628.
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Thiirane". A list of authors is available in Wikipedia.
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