Tetrahydrothiophene

Tetrahydrothiophene

Names
IUPAC name Thiolane
Other names Tetrahydrothiophene, thiophane, tetramethylene sulfide
Identifiers
CAS Number	110-01-0 Y
3D model (JSmol)	Interactive image
Abbreviations	THT
Beilstein Reference	102392
ChEBI	CHEBI:48458 Y
ChEMBL	ChEMBL1379 Y
ChemSpider	1095 Y
ECHA InfoCard	100.003.391
EC Number	203-728-9
PubChem CID	1127
RTECS number	XN0370000
UNII	744EHT13FM1
UN number	2412
InChI InChI=1S/C4H8S/c1-2-4-5-3-1/h1-4H2 Y Key: RAOIDOHSFRTOEL-UHFFFAOYSA-N Y InChI=1/C4H8S/c1-2-4-5-3-1/h1-4H2 Key: RAOIDOHSFRTOEL-UHFFFAOYAY
SMILES S1CCCC
Properties
Chemical formula	C4H8S
Molar mass	7001881700000000000♠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
Main hazards	Stench, flammable, irritant
Safety data sheet	Oakwood
GHS pictograms
GHS signal word	Danger
GHS hazard statements	H225, H302, H312, H315, H319, H332, H412
GHS precautionary statements	P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P273, P280, P301+312, P302+352, P303+361+353, P304+312, P304+340, P305+351+338, P312, P321, P322, P330, P332+313, P337+313, P362
Flash point	12 °C (54 °F; 285 K)
Autoignition temperature	200 °C (392 °F; 473 K)
Related compounds
Related compounds	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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Infobox references

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.

Contents

• 
  1 Synthesis and reactions
  


• 
  2 Natural occurrence
  


• 
  3 Applications
  


• 
  4 See also
  


• 
  5 References
  

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], Allium schoenoprasum (chives)^[9], and Salacia prinoides.^[10]Albomycins are a group of tetrahydrothiophene-ring containing antibiotics from streptomyces while biotin and neothiobinupharidine (and other nuphar alkaloids
^[11]), 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

• Tetrahydrofuran


• Thiophene

References

1. 
   ^ Armarego WF, Chai CL (2003). "Purification of Organic Chemicals": 361. doi:10.1016/B978-075067571-0/50008-9..mw-parser-output cite.citation{font-style:inherit}.mw-parser-output .citation q{quotes:"""""""'""'"}.mw-parser-output .citation .cs1-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/9px-Lock-green.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .citation .cs1-lock-limited a,.mw-parser-output .citation .cs1-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Lock-gray-alt-2.svg/9px-Lock-gray-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .citation .cs1-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Lock-red-alt-2.svg/9px-Lock-red-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration{color:#555}.mw-parser-output .cs1-subscription span,.mw-parser-output .cs1-registration span{border-bottom:1px dotted;cursor:help}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Wikisource-logo.svg/12px-Wikisource-logo.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output code.cs1-code{color:inherit;background:inherit;border:inherit;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;font-size:100%}.mw-parser-output .cs1-visible-error{font-size:100%}.mw-parser-output .cs1-maint{display:none;color:#33aa33;margin-left:0.3em}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration,.mw-parser-output .cs1-format{font-size:95%}.mw-parser-output .cs1-kern-left,.mw-parser-output .cs1-kern-wl-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right,.mw-parser-output .cs1-kern-wl-right{padding-right:0.2em}
   


2. 
   ^ Loev, B; Massengale, JT U. S. Patent 2,899,444, "Synthesis of Tetrahydrothiophene", 8/11/1959
   


3. 
   ^ ^ab Jonathan Swanston (2006), "Thiophene", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a26_793.pub2
   


4. 
   ^ 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.
   


5. 
   ^ 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.
   


6. 
   ^ 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.
   


7. 
   ^ 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.
   


8. 
   ^ 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.
   


9. 
   ^ Fukaya, M; et al. (2019). "Cyclic Sulfur Metabolites from Allium schoenoprasum var. foliosum". Phytochemistry Letters. 29: 125–128. doi:10.1016/j.phytol.2018.11.018.
   


10. 
    ^ 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.
    


11. 
    ^ Korotkov, A; et al. (2015). "Total Syntheses and Biological Evaluation of Both Enantiomers of Several Hydroxylated Dimeric Nuphar Alkaloids". Angewandte Chemie International Edition. 54 (36): 10604–10607. doi:10.1002/anie.201503934. PMID 26205039.
    

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