Tetrahydrothiophene

Tetrahydrothiophene

Names
IUPAC name Thiolane
Other names Tetrahydrothiophene, thiophane, tetramethylene sulfide
Identifiers
Abbreviations	THT
CAS Registry Number	110-01-0 Y
ChEBI	CHEBI:48458 Y
ChEMBL	ChEMBL1379 Y
ChemSpider	1095 Y
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
Jmol-3D images	Image
SMILES S1CCCC1
Properties
Molecular formula	C4H8S
Molar mass	88.17 g·mol−1
Density	0.999 g/mL[1]
Melting point	−96 °C (−141 °F; 177 K)
Boiling point	119 °C (246 °F; 392 K)
Except where noted otherwise, data is 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 consists of a five-membered ring containing 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

It 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.

Applications

Because of its smell, tetrahydrothiophene has been used as an odorant in LPG,^[3] although, 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