Tetrahydrothiophene: Difference between revisions
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==Synthesis and reactions== |
==Synthesis and reactions== |
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Tetrahydrothiophene is prepared by the reaction of [[tetrahydrofuran]] with [[hydrogen sulfide]]. 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| |
Tetrahydrothiophene is prepared by the reaction of [[tetrahydrofuran]] with [[hydrogen sulfide]]. 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 [[ligand]] in [[coordination chemistry]], an example being the complex [[chloro(tetrahydrothiophene)gold(I)]].<ref name="UsonLaguna2007">{{cite journal|vauthors = Uson R, Laguna A, Laguna M, Briggs DA, Murray HH, Fackler JP|title=(Tetrahydrothiophene)Gold(I) or Gold(III) Complexes|year=2007|pages=85–91|issn=19344716|doi=10.1002/9780470132579.ch17}}</ref> |
This compound is a [[ligand]] in [[coordination chemistry]], an example being the complex [[chloro(tetrahydrothiophene)gold(I)]].<ref name="UsonLaguna2007">{{cite journal|vauthors = Uson R, Laguna A, Laguna M, Briggs DA, Murray HH, Fackler JP|title=(Tetrahydrothiophene)Gold(I) or Gold(III) Complexes|year=2007|pages=85–91|issn=19344716|doi=10.1002/9780470132579.ch17}}</ref> |
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Revision as of 09:48, 15 February 2019
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| Names | |||
|---|---|---|---|
| IUPAC name
Thiolane
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| Other names
Tetrahydrothiophene,
thiophane, tetramethylene sulfide | |||
| Identifiers | |||
3D model (JSmol)
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| Abbreviations | THT | ||
| 102392 | |||
| ChEBI | |||
| ChEMBL | |||
| ChemSpider | |||
| ECHA InfoCard | 100.003.391 | ||
| EC Number |
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PubChem CID
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| RTECS number |
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| UNII | |||
| UN number | 2412 | ||
CompTox Dashboard (EPA)
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| Properties | |||
| C4H8S | |||
| Molar mass | 88.17 g·mol−1 | ||
| Density | 0.997 g/mL[1] | ||
| Melting point | −96 °C (−141 °F; 177 K) | ||
| Boiling point | 119 °C (246 °F; 392 K) | ||
| Hazards | |||
| Occupational safety and health (OHS/OSH): | |||
Main hazards
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Stench, flammable, irritant | ||
| GHS labelling: | |||
 
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| Danger | |||
| H225, H302, H312, H315, H319, H332, H412 | |||
| P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P370+P378, P403+P235, P501 | |||
| Flash point | 12 °C (54 °F; 285 K) | ||
| 200 °C (392 °F; 473 K) | |||
| Safety data sheet (SDS) | Oakwood | ||
| Related compounds | |||
Related compounds
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Tetrahydrofuran, Thiophene, Selenolane, Thiazolidine, Dithiolane, Thiane | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Tetrahydrothiophene is an organosulfur compound with the formula (CH2)4S. It contains a five-membered ring consisting of four carbon atoms and a sulfur atom. It is the saturated analog of thiophene. It is a volatile, colorless liquid with an intensely unpleasant odor. It is also known as thiophane, thiolane, or THT.
Synthesis and reactions
Tetrahydrothiophene is prepared by the reaction of tetrahydrofuran with hydrogen sulfide. This vapor-phase reaction is catalyzed by alumina and other heterogenous acid catalysts.[2][3]
This compound is a ligand in coordination chemistry, an example being the complex chloro(tetrahydrothiophene)gold(I).[4]
Oxidation of THT gives the solvent called sulfolane, a polar solvent with almost no odor. Sulfolane is more conventionally prepared from butadiene.
Natural occurrence
Both unsubstituted and substituted tetrahydrothiophenes are reported to occur in nature. For example, tetrahydrothiophene occurs as a volatile from Eruca sativa Mill. (salad rocket)[5] while monocyclic substituted tetrahydrothiophenes have been isolated from Allium fistulosum 'Kujou'[6], Allium sativum (garlic)[7], Allium cepa (onion)[8], and Salacia prinoides.[9] Albomycins are a group of tetrahydrothiophene-ring containing antibiotics from streptomyces while biotin and neothiobinupharidine are examples of bicyclic and polycyclic tetrahydrothiophene-ring containing natural products, respectively.
Applications
Because of its smell, tetrahydrothiophene has been used as an odorant in LPG,[3] albeit no longer in North America. It is also used as an odorant for natural gas, usually in mixtures containing tert-butylthiol.
See also
References
- ^ Armarego WF, Chai CL (2003). "Purification of Organic Chemicals": 361. doi:10.1016/B978-075067571-0/50008-9.
{{cite journal}}: Cite journal requires|journal=(help) - ^ Loev, B; Massengale, JT U. S. Patent 2,899,444, "Synthesis of Tetrahydrothiophene", 8/11/1959
- ^ a b Jonathan Swanston (2006). "Thiophene". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a26_793.pub2. ISBN 978-3527306732.
- ^ Uson R, Laguna A, Laguna M, Briggs DA, Murray HH, Fackler JP (2007). "(Tetrahydrothiophene)Gold(I) or Gold(III) Complexes": 85–91. doi:10.1002/9780470132579.ch17. ISSN 1934-4716.
{{cite journal}}: Cite journal requires|journal=(help) - ^ Aissani, N; et al. (2006). "Nematicidal Activity of the Volatilome of Eruca sativa on Meloidogyne incognita". Journal of Agricultural and Food Chemistry. 63 (27): 6120–6125. doi:10.1021/acs.jafc.5b02425. PMID 26082278.
{{cite journal}}: Cite has empty unknown parameter:|1=(help) - ^ Fukaya, M; et al. (2018). "Rare Sulfur-Containing Compounds, Kujounins A1 and A2 and Allium Sulfoxide A1, from Allium fistulosum 'Kujou'". Organic Letters. 20 (1): 28–31. doi:10.1021/acs.orglett.7b03234. PMID 29227665.
{{cite journal}}: Cite has empty unknown parameter:|1=(help) - ^ Block, E; et al. (2018). "Ajothiolanes: 3,4-Dimethylthiolane Natural Products from Garlic (Allium sativum)". Journal of Agricultural and Food Chemistry. 66 (39): 10193–10204. doi:10.1021/acs.jafc.8b03638. PMID 30196701.
{{cite journal}}: Cite has empty unknown parameter:|1=(help) - ^ Aoyagi, M; et al. (2011). "Structure and Bioactivity of Thiosulfinates Resulting from Suppression of Lachrymatory Factor Synthase in Onion". Journal of Agricultural and Food Chemistry. 59 (20): 10893–10900. doi:10.1021/jf202446q. PMID 21905712.
{{cite journal}}: Cite has empty unknown parameter:|1=(help) - ^ Tanabe, G; et al. (2008). "Synthesis and Elucidation of Absolute Stereochemistry of Salaprinol, another Thiosugar Sulfonium Sulfate from the Ayurvedic Traditional Medicine Salacia prinoides". Tetrahedron. 64: 10080–10086. doi:10.1016/j.tet.2008.08.010.