Tetrahydrothiophene

Tetrahydrothiophene

Names
IUPAC name Thiolane
Other names Tetrahydrothiophene, thiophane, tetramethylene sulfide
Identifiers
CAS Number	110-01-0 Y
3D model (Jmol)	Interactive image
Abbreviations	THT
ChEBI	CHEBI:48458 Y
ChEMBL	ChEMBL1379 Y
ChemSpider	1095 Y
ECHA InfoCard	100.003.391
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 S1CCCC1
Properties
Chemical formula	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
Main hazards	Stench, flammable, irritant
Safety data sheet	Oakwood
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 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] 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