Thiirane

Thiirane

Chembox new
Name = Thiirane
ImageFile = Ethylene-sulfide-2D.png ImageSize = 200px
ImageName = Structure formula of thiirane
ImageFileL1 = Ethylene-sulfide-2D-skeletal.png ImageSizeL1 = 100px
ImageNameL1 = Skeletal formula of thiirane
ImageFileR1 = Ethylene-sulfide-3D-vdW.png ImageSizeR1 = 100px
ImageNameR1 = Space-filling model of thiirane
IUPACName = Thiirane
OtherNames = Ethylene sulfide
Section1 = Chembox Identifiers
SMILES = C1CS1
CASNo = 420-12-2
RTECS = KX3500000
Section2 = Chembox Properties
Formula = C2H4S
MolarMass = 60.12 g mol−1
Appearance = liquid,
usually pale yellow
Density = 1.01 g cm−3, liquid
Solubility = low
MeltingPt =
BoilingPt = 54.0–54.5 °C
Section3 = Chembox Structure
MolShape = C2v symmetry
Dipole =
Section7 = Chembox Hazards
ExternalMSDS =
MainHazards = toxic, stench
FlashPt =
RPhrases = 11-23/25-41
SPhrases = 16-36/37/39-45
Section8 = Chembox Related
Function = heterocycles
OtherFunctn = ethylene oxide
aziridine

Thiirane, more commonly known as ethylene sulfide, is the cyclic chemical compound with the formula C2H4S. [cite journal
author= Warren Chew; David N. Harpp
title = Recent aspects of thiirane chemistry
journal = Journal of Sulfur Chemistry
year = 1993
volume = 15
issue = 1
pages = 1–39
doi = 10.1080/01961779308050628] 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.

Preparation

It is prepared by the reaction of ethylene carbonate and KSCN. [Searles, S.; Lutz, E. F.; Hays, H. R.; Mortensen, H. E. "Ethylenesulfide" Organic Syntheses, 1973, Collective Volume 5, page 562.] 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, [R. J. Cremlyn “An Introduction to Organosulfur Chemistry” John Wiley and Sons: Chichester (1996). ISBN 0-471-95512-4.] which are good chelating ligands.:C2H4S + R2NH → R2NCH2CH2SH

References


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