| Revision as of 12:41, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,084 edits Saving copy of the {{chembox}} taken from revid 457178245 of page Tetrahydrothiophene for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 19:19, 10 December 2024 edit 129.62.48.155 (talk)No 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.}} |
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|verifiedrevid = 470604441 |
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|ImageFileL1_Ref = {{chemboximage|correct|??}} |
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| verifiedrevid = 416016603 |
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|ImageFileL1=Tetrahydrothiophene.svg |
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| ImageFileL1_Ref = {{chemboximage|correct|??}} |
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|ImageFileR1=Tetrahydrothiophene3d.png |
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| ImageFileL1=Tetrahydrothiophene.svg |
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|PIN=Thiolane |
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| ImageSizeL1=100px |
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|OtherNames=Tetrahydrothiophene,<br />thiophane, tetramethylene sulfide |
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| ImageFileR1=Tetrahydrothiophene3d.png |
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|Section1={{Chembox Identifiers |
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|Abbreviations = THT |
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| IUPACName=Thiolane |
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|InChI = 1/C4H8S/c1-2-4-5-3-1/h1-4H2 |
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| OtherNames=Tetrahydrothiophene,<br />thiophane, tetramethylene sulfide |
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|InChIKey = RAOIDOHSFRTOEL-UHFFFAOYAY |
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| Section1= {{Chembox Identifiers |
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|ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| Abbreviations = THT |
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|ChEMBL = 1379 |
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| InChI = 1/C4H8S/c1-2-4-5-3-1/h1-4H2 |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| InChIKey = RAOIDOHSFRTOEL-UHFFFAOYAY |
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|StdInChI = 1S/C4H8S/c1-2-4-5-3-1/h1-4H2 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| ChEMBL = 1379 |
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|StdInChIKey = RAOIDOHSFRTOEL-UHFFFAOYSA-N |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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| StdInChI = 1S/C4H8S/c1-2-4-5-3-1/h1-4H2 |
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|CASNo=110-01-0 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| StdInChIKey = RAOIDOHSFRTOEL-UHFFFAOYSA-N |
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|ChemSpiderID = 1095 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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|PubChem= 1127 |
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| CASNo=110-01-0 |
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|Beilstein = 102392 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChemSpiderID = 1095 |
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|ChEBI = 48458 |
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|SMILES = S1CCCC1 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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|EC_number = 203-728-9 |
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| ChEBI = 48458 |
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|RTECS = XN0370000 |
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| SMILES = S1CCCC1 |
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|UNNumber = 2412 |
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|UNII = 744EHT13FM |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=4|H=8|S=1 |
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| C=4 | H=8 | S=1 |
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| Appearance= |
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|Appearance=colorless liquid |
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|Density= 0.997 g/mL<ref name="ArmaregoChai2003">{{cite book|vauthors = Armarego WF,Chai CL|title=Purification of Laboratory Chemicals|chapter=Purification of Organic Chemicals|year=2003|pages=361|doi=10.1016/B978-075067571-0/50008-9|isbn=9780750675710}}</ref> |
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| Density= 0.999 g/mL <ref>, Alfa Aesar</ref> |
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| MeltingPtC=-96 |
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|MeltingPtC=-96 |
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| BoilingPtC=119 |
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|BoilingPtC=119 |
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|Section3= {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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|ExternalSDS= |
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|MainHazards= Stench, flammable, irritant |
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|FlashPtC=12 |
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|AutoignitionPtC = 200 |
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|GHSPictograms = {{GHS02}}{{GHS07}} |
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|GHSSignalWord = Danger |
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|HPhrases = {{H-phrases|225|302|312|315|319|332|412}} |
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|PPhrases = {{P-phrases|210|233|240|241|242|243|261|264|270|271|273|280|301+312|302+352|303+361+353|304+312|304+340|305+351+338|312|321|322|330|332+313|337+313|362|363|370+378|403+235|501}} |
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| OtherCompounds = ], ], ], ], ], ] |
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'''Tetrahydrothiophene''' is an ] with the formula (CH<sub>2</sub>)<sub>4</sub>S. The molecule consists of a five-membered saturated ring with four ] groups and a ] atom. It is the ] ] of ] and is therefore the sulfur analog of ]. It is a volatile, colorless liquid with an intensely unpleasant ]. It is also known as '''thiophane''', '''thiolane''', or '''THT'''. |
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==Synthesis and reactions== |
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Tetrahydrothiophene is prepared by the reaction of ] with ]. This vapor-phase reaction is catalyzed by alumina and other heterogenous acid catalysts.<ref>Loev, B; Massengale, JT U. S. Patent 2,899,444, "Synthesis of Tetrahydrothiophene", 8/11/1959</ref><ref name="Ullmann">{{Ullmann|author=Jonathan Swanston|title=Thiophene|year=2006|doi=10.1002/14356007.a26_793.pub2}}</ref> |
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This compound is a ] in ], an example being the complex ].<ref>{{cite book|vauthors = Uson R, Laguna A, Laguna M, Briggs DA, Murray HH, Fackler JP|author6-link=John P. Fackler Jr.|title=Inorganic Syntheses|chapter=(Tetrahydrothiophene)Gold(I) or Gold(III) Complexes|year=2007|volume=26 |pages=85–91|issn=1934-4716|doi=10.1002/9780470132579.ch17|isbn=9780470132579}}</ref> |
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Oxidation of THT gives the sulfone ], which is of interest as a polar, odorless solvent: |
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:{{chem2|C4H8S + 2 O -> C4H8SO2}} |
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Sulfolane is, however, more conventionally prepared from ]. |
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==Natural occurrence== |
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Both unsubstituted and substituted tetrahydrothiophenes are reported to occur in nature. For example, tetrahydrothiophene occurs as a volatile from '']'' Mill. (salad rocket)<ref>{{cite journal|last=Aissani|first=N|year=2006|title=Nematicidal Activity of the Volatilome of ''Eruca sativa'' on ''Meloidogyne incognita''|journal=]|volume=63|issue=27|pages=6120–6125|doi=10.1021/acs.jafc.5b02425|pmid=26082278|display-authors=etal }}</ref> while monocyclic substituted tetrahydrothiophenes have been isolated from '']'' 'Kujou',<ref>{{cite journal|last=Fukaya|first=M|year=2018|title=Rare Sulfur-Containing Compounds, Kujounins A1 and A2 and Allium Sulfoxide A1, from ''Allium fistulosum'' 'Kujou'|journal=]|volume=20|issue=1|pages=28–31|doi=10.1021/acs.orglett.7b03234|pmid=29227665|display-authors=etal}}</ref> '']'' (garlic),<ref>{{cite journal |last=Block |first=E |display-authors=etal |year=2018 |title=Ajothiolanes: 3,4-Dimethylthiolane Natural Products from Garlic (''Allium sativum''). |url=https://www.osti.gov/servlets/purl/1490686 |journal=] |volume=66 |issue=39 |pages=10193–10204 |doi=10.1021/acs.jafc.8b03638 |osti=1490686 |pmid=30196701 |bibcode=2018JAFC...6610193B |s2cid=52178061}}</ref> '']'' (onion),<ref>{{cite journal|last=Aoyagi|first=M|year=2011|title=Structure and Bioactivity of Thiosulfinates Resulting from Suppression of Lachrymatory Factor Synthase in Onion|journal=]|volume=59|issue=20|pages=10893–10900|doi=10.1021/jf202446q|pmid=21905712|bibcode=2011JAFC...5910893A|display-authors=etal}}</ref> '']'' (chives),<ref>{{cite journal|last=Fukaya|first=M|year=2019|title=Cyclic Sulfur Metabolites from ''Allium schoenoprasum'' var. ''foliosum''|journal=]|volume=29|pages=125–128|doi=10.1016/j.phytol.2018.11.018|bibcode=2019PChL...29..125F|s2cid=104387714|display-authors=etal}}</ref> and ''].''<ref>{{cite journal|last=Tanabe|first=G|year=2008|title=Synthesis and Elucidation of Absolute Stereochemistry of Salaprinol, another Thiosugar Sulfonium Sulfate from the Ayurvedic Traditional Medicine ''Salacia prinoides''|journal=]|volume=64|issue=43|pages=10080–10086|doi=10.1016/j.tet.2008.08.010|display-authors=etal}}</ref> ]s are a group of tetrahydrothiophene-ring containing antibiotics from ] while ] and ] (and other ] alkaloids |
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<ref>{{cite journal|last=Korotkov|first=A|year=2015|title=Total Syntheses and Biological Evaluation of Both Enantiomers of Several Hydroxylated Dimeric Nuphar Alkaloids|journal=]|volume=54|issue=36|pages=10604–10607|doi=10.1002/anie.201503934|pmid=26205039|display-authors=etal|pmc=4691328}}</ref>), are examples of bicyclic and polycyclic tetrahydrothiophene-ring containing natural products, respectively. |
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==Applications== |
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Because of its smell, tetrahydrothiophene has been used as an ] in ],<ref name="Ullmann"/> albeit no longer in North America. It is also used as an odorant for ], usually in mixtures containing ]. |
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Tetrahydrothiophene is a Lewis base classified as a ] and its donor properties are discussed in the ]. |
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==See also== |
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*] |
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*] |
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== References == |
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{{reflist}} |
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