Thiirane

Thiirane
Skeletal formula of thiirane source ↗	Spacefill model of thiirane source ↗
	Ball-and-stick model of thiirane source ↗
Names
	Preferred IUPAC name Thiirane
	Systematic IUPAC name Thiacyclopropane
	Other names 2,3-Dihydrothiirene; Ethylene sulfide
Identifiers
CAS Number	420-12-2 Y;
3D model (JSmol)	Interactive image;
Beilstein Reference	102379
ChEBI	CHEBI:30977 Y;
ChemSpider	9481 Y;
ECHA InfoCard	100.006.359
EC Number	206-993-9;
Gmelin Reference	1278
KEGG	C19419 N;
MeSH	ethylene+sulfide
PubChem CID	9865;
RTECS number	KX3500000;
UNII	A2W5165740 Y;
UN number	1992
CompTox Dashboard (EPA)	DTXSID3049411 ;
	InChI InChI=1S/C2H4S/c1-2-3-1/h1-2H2 Y Key: VOVUARRWDCVURC-UHFFFAOYSA-N Y;
	SMILES C1CS1;
Properties
Chemical formula	C2H4S
Molar mass	60.11 g·mol−1
Appearance	Pale, yellow liquid
Odor	Sulfurous
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
Std enthalpy of; formation (ΔfH⦵298)	51–53 kJ mol−1
Std enthalpy of; combustion (ΔcH⦵298)	−2.0126 MJ mol−1
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H301, H318, H331
Precautionary statements	P210, P261, P280, P301+P310, P305+P351+P338, P311
NFPA 704 (fire diamond)	source ↗ 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 [77 °F], 100 kPa). N verify (what is YN ?) 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 highly unpleasant odour. Thiirane is also used to describe any derivative of the parent ethylene sulfide.

Structure and properties

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°.³ The microwave and infrared spectra were studied experimentally and computationally.⁴

Preparation and reactions

It can be prepared by the reaction of ethylene carbonate and KSCN.⁵ 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,⁶ which are good chelating ligands.

C₂H₄S + R₂NH → R₂NCH₂CH₂SH

This process is often called mercaptoethylation.⁷

Oxidation of thiirane with periodate gives ethylene episulfoxide.

References

"thiirane (CHEBI:30977)". Chemical Entities of Biological Interest (ChEBI). UK: European Bioinformatics Institute.
Warren Chew; David N. Harpp (1993). "Recent aspects of thiirane chemistry". Journal of Sulfur Chemistry. 15 (1): 1–39. doi:10.1080/01961779308050628.
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.
De Vos, John; Schröder, Benjamin; Rauhut, Guntram (2023-12-05). "Comprehensive quantum chemical analysis of the (ro)vibrational spectrum of thiirane and its deuterated isotopologue". Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 302 123083. Bibcode:2023AcSpA.30223083D. doi:10.1016/j.saa.2023.123083. hdl:1854/LU-01HP1F40851T3MX6QGN9QBHR4E. ISSN 1386-1425. PMID 37423098.
Searles, S.; Lutz, E. F.; Hays, H. R.; Mortensen, H. E. (1962). "Ethylene Sulfide". Organic Syntheses. 42: 59. doi:10.15227/orgsyn.042.0059.
R. J. Cremlyn "An Introduction to Organosulfur Chemistry" John Wiley and Sons: Chichester (1996). ISBN 0-471-95512-4.
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.

[thiirane_(CHEBI:30977)-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] De Vos, John; Schröder, Benjamin; Rauhut, Guntram (2023-12-05). "Comprehensive quantum chemical analysis of the (ro)vibrational spectrum of thiirane and its deuterated isotopologue". Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 302 123083. Bibcode:2023AcSpA.30223083D. doi:10.1016/j.saa.2023.123083. hdl:1854/LU-01HP1F40851T3MX6QGN9QBHR4E. ISSN 1386-1425. PMID 37423098.

[5] Searles, S.; Lutz, E. F.; Hays, H. R.; Mortensen, H. E. (1962). "Ethylene Sulfide". Organic Syntheses. 42: 59. doi:10.15227/orgsyn.042.0059.

[6] R. J. Cremlyn "An Introduction to Organosulfur Chemistry" John Wiley and Sons: Chichester (1996). ISBN 0-471-95512-4.

[7] 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.

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