CHEBI:74794 - sulfolane

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ChEBI Name sulfolane
ChEBI ID CHEBI:74794
Definition A member of the class of tetrahydrothiophenes that is tetrahydrothiophene in which the sulfur has been oxidised to give the corresponding sulfone. A colourless, high-boiling (285°C) liquid that is miscible with both water and hydrocarbons, it is used as an industrial solvent, particularly for the purification of hydrocarbon mixtures by liquid-vapour extraction.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C4H8O2S
Net Charge 0
Average Mass 120.17000
Monoisotopic Mass 120.025
InChI InChI=1S/C4H8O2S/c5-7(6)3-1-2-4-7/h1-4H2
InChIKey HXJUTPCZVOIRIF-UHFFFAOYSA-N
SMILES O=S1(=O)CCCC1
Roles Classification
Chemical Role(s): polar aprotic solvent
A solvent with a comparatively high relative permittivity (or dielectric constant), greater than ca. 15, and a sizable permanent dipole moment, that cannot donate suitably labile hydrogen atoms to form strong hydrogen bonds.
Application(s): polar aprotic solvent
A solvent with a comparatively high relative permittivity (or dielectric constant), greater than ca. 15, and a sizable permanent dipole moment, that cannot donate suitably labile hydrogen atoms to form strong hydrogen bonds.
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ChEBI Ontology
Outgoing sulfolane (CHEBI:74794) has parent hydride tetrahydrothiophene (CHEBI:48458)
sulfolane (CHEBI:74794) has role polar aprotic solvent (CHEBI:48358)
sulfolane (CHEBI:74794) is a sulfone (CHEBI:35850)
sulfolane (CHEBI:74794) is a tetrahydrothiophenes (CHEBI:48224)
IUPAC Name
tetrahydrothiophene 1,1-dioxide
Synonyms Sources
(CH2)4SO2 ChEBI
1,1-dioxidetetrahydrothiofuran ChemIDplus
1,1-dioxidetetrahydrothiophene NIST Chemistry WebBook
1,1-dioxidetetrahydrothiophene ChemIDplus
1,1-dioxothiolan ChemIDplus
2,3,4,5-tetrahydrothiophene-1,1-dioxide ChemIDplus
cyclic tetramethylene sulfone NIST Chemistry WebBook
cyclotetramethylene sulfone ChemIDplus
dioxothiolan ChemIDplus
sulfolan NIST Chemistry WebBook
tetrahydrothiophene 1-dioxide ChemIDplus
tetramethylene sulfone ChemIDplus
thiacyclopentane dioxide ChemIDplus
thiolane-1,1-dioxide ChemIDplus
thiophan sulfone ChemIDplus
thiophane dioxide ChemIDplus
Database Links Databases
CPD-3747 MetaCyc
Sulfolane Wikipedia
US2360859 Patent
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Registry Numbers Types Sources
107765 Reaxys Registry Number Reaxys
126-33-0 CAS Registry Number NIST Chemistry WebBook
126-33-0 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
11878596 PubMed citation Europe PMC
22219044 PubMed citation Europe PMC
22918536 PubMed citation Europe PMC
22936336 PubMed citation Europe PMC
3709502 PubMed citation Europe PMC
4071560 PubMed citation Europe PMC
Last Modified
19 July 2013