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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	C_2v 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.

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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

^ Searles, S.; Lutz, E. F.; Hays, H. R.; Mortensen, H. E. "Ethylenesulfide" Organic Syntheses, 1973, Collective Volume 5, page 562.
^ 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.

Categories: Thioethers | Sulfur heterocycles