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Revision as of 13:00, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 465715899 of page Thiirane for the Chem/Drugbox validation project (updated: 'KEGG').  Latest revision as of 21:05, 23 November 2024 edit TheZacher5645 (talk | contribs)26 editsmNo edit summary 
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{Chembox {{Chembox
| Verifiedfields = changed | Verifiedfields = changed
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 433987901 | verifiedrevid = 470606690
| ImageFile2 = Ethylene-sulfide-3D-balls.png | ImageFile2 = Ethylene-sulfide-3D-balls.png
| ImageFile2_Ref = {{chemboximage|correct|??}} | ImageFile2_Ref = {{chemboximage|correct|??}}
| ImageSize2 = 121 | ImageSize2 = 121
| ImageName2 = Ball and model of thiirane | ImageName2 = Ball-and-stick model of thiirane
| ImageFileL1 = Ethylene-sulfide-2D-skeletal.png | ImageFileL1 = Ethylene-sulfide-2D-skeletal.png
| ImageFileL1_Ref = {{chemboximage|correct|??}} | ImageFileL1_Ref = {{chemboximage|correct|??}}
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| ImageSizeR1 = 121 | ImageSizeR1 = 121
| ImageNameR1 = Spacefill model of thiirane | ImageNameR1 = Spacefill model of thiirane
| PIN = Thiirane
⚫ | SystematicName = Thiirane<ref name = "thiirane (CHEBI:30977)" >{{Cite web|url = http://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:30977|title = thiirane (CHEBI:30977)|work = Chemical Entities of Biological Interest (ChEBI)|location = UK|publisher = European Bioinformatics Institute}}</ref>
| SystematicName = Thiacyclopropane
| OtherNames = 2,3-Dihydrothiirene<ref name = "thiirane (CHEBI:30977)" /><br />
⚫ | OtherNames = 2,3-Dihydrothiirene<ref name = "thiirane (CHEBI:30977)" >{{Cite web|url = http://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:30977|title = thiirane (CHEBI:30977)|work = Chemical Entities of Biological Interest (ChEBI)|location = UK|publisher = European Bioinformatics Institute}}</ref><br />Ethylene sulfide<ref name = "thiirane (CHEBI:30977)" />
Ethylene sulfide<ref name = "thiirane (CHEBI:30977)" /><br />
⚫ |Section1={{Chembox Identifiers
Thiacyclopropane<ref name = "thiirane (CHEBI:30977)" />
⚫ | CASNo = 420-12-2
⚫ | Section1 = {{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
⚫ | CASNo = 420-12-2
| CASNo_Ref = {{cascite|correct|CAS}} | UNII_Ref = {{fdacite|correct|FDA}}
| PubChem = 9865 | UNII = A2W5165740
| PubChem = 9865
| PubChem_Ref = {{Pubchemcite|correct|pubchem}}
| ChemSpiderID = 9481 | ChemSpiderID = 9481
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| EINECS = 206-993-9 | EINECS = 206-993-9
| UNNumber = 1992 | UNNumber = 1992
| KEGG = <!-- blanked - oldvalue: C19419 --> | KEGG = C19419
| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|changed|kegg}}
| MeSHName = ethylene+sulfide | MeSHName = ethylene+sulfide
| ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 30977 | ChEBI = 30977
| RTECS = KX3500000 | RTECS = KX3500000
| Beilstein = 102379 | Beilstein = 102379
| Gmelin = 1278 | Gmelin = 1278
| SMILES = C1CS1 | SMILES = C1CS1
| StdInChI = 1S/C2H4S/c1-2-3-1/h1-2H2 | StdInChI = 1S/C2H4S/c1-2-3-1/h1-2H2
| StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = VOVUARRWDCVURC-UHFFFAOYSA-N | StdInChIKey = VOVUARRWDCVURC-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C = 2 | C=2 | H=4 | S=1
⚫ | Appearance = Pale, yellow liquid
⚫ | H = 4
⚫ | Density = 1.01 g cm<sup>−3</sup>
⚫ | S = 1
⚫ | MeltingPtC = -109
| ExactMass = 60.003370818 g mol<sup>−1</sup>
⚫ | BoilingPtK = 329
⚫ | Appearance = Pale, yellow liquid
⚫ | VaporPressure = 28.6 kPa (at 20&nbsp;°C)
⚫ | Density = 1.01 g cm<sup>−3</sup>
⚫ | MeltingPtC = -109
⚫ | BoilingPtK = 329
⚫ | VaporPressure = 28.6 kPa (at 20 °C)
}} }}
| Section4 = {{Chembox Thermochemistry |Section4={{Chembox Thermochemistry
| DeltaHf = 51-53 kJ mol<sup>-1</sup> | DeltaHf = 51-53 kJ mol<sup>−1</sup>
| DeltaHc = -2.0126 MJ mol<sup>-1</sup> | DeltaHc = -2.0126 MJ mol<sup>−1</sup>
}} }}
| Section5 = {{Chembox Hazards |Section5={{Chembox Hazards
| GHSPictograms = {{GHS flame}} {{GHS corrosion}} {{GHS skull and crossbones}} | GHSPictograms = {{GHS flame}} {{GHS corrosion}} {{GHS skull and crossbones}}
| GHSSignalWord = '''DANGER''' | GHSSignalWord = '''DANGER'''
| HPhrases = {{H-phrases|225|301|318|331}} | HPhrases = {{H-phrases|225|301|318|331}}
| PPhrases = {{P-phrases|210|261|280|301+310|305+351+338|311}} | PPhrases = {{P-phrases|210|261|280|301+310|305+351+338|311}}
⚫ | NFPA-F = 4
| EUClass = {{Hazchem F}} {{Hazchem T}}
⚫ | NFPA-H = 3
| RPhrases = {{R11}}, {{R23/25}}, {{R41}}
⚫ | NFPA-R = 2
| SPhrases = {{S16}}, {{S36/37/39}}, {{S45}}
| NFPA-F = 4 | FlashPtC = 10
⚫ | NFPA-H = 3
⚫ | NFPA-R = 2
| FlashPt = 10 °C
}} }}
| Section6 = {{Chembox Related |Section6={{Chembox Related
| Function = ] | OtherFunction_label = ]
| OtherFunctn = ]<br />]<br />] | OtherFunction = ]<br />]<br />]
}} }}
}} }}
{{for|the class of compounds known as thiiranes|Episulfide}}
'''Thiirane''', more commonly known as '''ethylene sulfide''', is the cyclic ] with the formula C<sub>2</sub>H<sub>4</sub>S.<ref>{{cite journal
| author= Warren Chew |author2=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}}</ref> It is the smallest sulfur-containing ] and the simplest ]. 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==
According to ], 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°.<ref>{{cite encyclopedia|encyclopedia=Comprehensive Heterocyclic Chemistry II|volume=1A|year=1996|pages=173–240|title=Thiiranes and Thiirenes: Monocyclic |author=Wataru Ando |author2=Nami Choi |author3=Norihiro Tokitoh |doi=10.1016/B978-008096518-5.00005-8|isbn=978-0-08-096518-5}}</ref>

==Preparation and reactions==
It can be prepared by the reaction of ] and ].<ref>{{cite journal| author1 = Searles, S. | author2 = Lutz, E. F. | author3 = Hays, H. R. | author4 = Mortensen, H. E. | title = Ethylene Sulfide | year = 1962| volume = 42 | page = 59 | doi= 10.15227/orgsyn.042.0059|journal=Organic Syntheses|doi-access=free}}</ref> For this purpose the KSCN is first melted under vacuum to remove water.
:KSCN + C<sub>2</sub>H<sub>4</sub>O<sub>2</sub>CO → KOCN + C<sub>2</sub>H<sub>4</sub>S + CO<sub>2</sub>

Ethylenesulfide adds to amines to afford 2-mercaptoethylamines,<ref>R. J. Cremlyn "An Introduction to Organosulfur Chemistry" John Wiley and Sons: Chichester (1996). {{ISBN|0-471-95512-4}}.</ref> which are good chelating ligands.
:C<sub>2</sub>H<sub>4</sub>S + R<sub>2</sub>NH → R<sub>2</sub>NCH<sub>2</sub>CH<sub>2</sub>SH
This process is often called '''mercaptoethylation'''.<ref>{{cite encyclopedia|title=Ethylene Sulfide|author=Gunars Zelans |author2=Jacquelyn Gervay-Hague |author3=Ivy Maulie |encyclopedia= Encyclopedia of Reagents for Organic Synthesis|year=2010|publisher= John Wiley & Sons|doi=10.1002/047084289X.re079.pub2|isbn=978-0-471-93623-7}}</ref>

Oxidation of thiirane with ] gives ].

==References==
{{reflist}}
{{sulfur compounds}}

]