CAS 126-33-0|SULFOLANE|sulfolane|1$l^{6}-thiolane-1,1-dione|四亚甲基砜|tetramethylene sulfone|环丁砜|Sulfolane|四氢噻吩-1,1-二氧化物|Tetrahydrothiophene 1,1-dioxide|Sulpholane|Thiolane 1,1-dioxide|1...

General Information

Structure

Molecular Formula

C₄H₈O₂S

Molecular Mass

120.17012

Exact Mass

120.0245005

Charge

InChI

InChI=1S/C4H8O2S/c5-7(6)3-1-2-4-7/h1-4H2

InChIKey

HXJUTPCZVOIRIF-UHFFFAOYSA-N

Canonic Smiles

O=S1(=O)CCCC1

Isomeric Smiles

S1(=O)(=O)CCCC1

Calculated Properties

JChem

LogD (pH = 7.4)

-0.59

LogD (pH = 5.5)

-0.59

Log P

-0.59

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Polar Surface Area

34.14

Polarizability

11.48

Molar Refractivity

27.91

LOG S

-0.44

Data Source

Names and Identifiers

Synonyms

SULFOLANE四亚甲基砜tetramethylene sulfone环丁砜Sulfolane四氢噻吩-1,1-二氧化物Tetrahydrothiophene 1,1-dioxideSulpholaneThiolane 1,1-dioxideTetrahydrothiophene 1,1-dioxidesulfolane1,1-dioxothiolanthiacyclopentane dioxidesulfolane(CH2)4SO2thiophane dioxidethiolane-1,1-dioxidecyclotetramethylene sulfone1,1-dioxidetetrahydrothiophene1,1-dioxidetetrahydrothiofurandioxothiolanthiophan sulfonesulfolan2,3,4,5-tetrahydrothiophene-1,1-dioxidetetrahydrothiophene 1-dioxidetetramethylene sulfonecyclic tetramethylene sulfone

IUPAC Traditional name

sulfolane 1-oxo-1λ⁴-thiolan-1-ium-1-olate 1lambda6-thiolane-1,1-dione

IUPAC name

1$l^{6}-thiolane-1,1-dione 1λ⁶-thiolane-1,1-dione 1-oxo-1λ⁴-thiolan-1-ium-1-olate 1λ⁶-thiolane-1,1-dione

Names and Identifiers

Registration numbers

CAS Number

MDL Number

EC Number

Beilstein Number

PubChem SID

2490002316207642524889157163725547

Merck Index

PubChem CID

Wikipedia Title

Chemspider ID

Unique Ingredient Identifier

MetaCyc Database

NMRShiftDB Database

Patent number

PubMed Citation Links

2291853622219044370950240715601187859622936336

Reaxys Registry

CHEMBL

SureChEMBL Database

CompTox Database

CHEBI ID

ACToR Database

Protein Data Bank

Registration numbers

Properties

Related Proteins

PDB Bank

7A3X

Related Proteins

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

Wikipedia

Sulfolane

Sigma Aldrich

T22209

Packaging
5, 100, 500 g in glass bottle

ChEBI

CHEBI:74794

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 (285degreeC) 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.

Molecule Details

References

PubChem Literature

From Data Sources

• High-boiling dipolar aprotic solvent. Compare Dimethyl sulfoxide, A13280, N,N-Dimethylacetamide, A10924 and 1-Methyl-2-pyrrolidinone, A12260.

• Widely used as solvent in the nucleophilic displacement of chloroaromatics with F^- (Halex fluorination). For example, chlorinated benzaldehydes were converted to their fluoro-analogues by heating with KF in tetramethylene sulfone at 220^o: J. Fluorine Chem., 46, 529 (1990). Nitro groups have also been displaced by F^- by heating in the presence of tetramethylammonium chloride and phthaloyl chloride as a nitrite trap: J. Org. Chem., 56, 6406 (1991). See, however, Tetrahydrothiophene 1-oxide, A17502 and Potassium fluoride, 14130.

• Solvent for nitrations using Nitronium tetrafluoroborate, B20167.

• Can be doubly metallated at the ɑ-positions with strong bases such as NaNH₂, LiNH₂ or n-BuLi, and the resulting dianion reacted with one or two equivalents of benzophenone to give the mono- or bis-adduct respectively: J. Org. Chem., 35, 1834 (1970); J. Organomet. Chem., 59, 53 (1973). For alkylation of the monolithio-derivative, see: Synth. Commun., 18, 583 (1988).

• Use of this solvent makes possible the reduction of alkyl bromides to alkanes by NaBH₄: Tetrahedron Lett., 3495 (1969).

• Solvent for the Baylis-Hillman reaction, using 1,4-Diazabicyclo[2.2.2]octane, A14003, which enables short reaction times at room temperature: Tetrahedron Lett., 45, 1183 (2004).

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC Traditional name

sulfolane 1-oxo-1λ⁴-thiolan-1-ium-1-olate 1lambda6-thiolane-1,1-dione

IUPAC name

1$l^{6}-thiolane-1,1-dione 1λ⁶-thiolane-1,1-dione 1-oxo-1λ⁴-thiolan-1-ium-1-olate 1λ⁶-thiolane-1,1-dione

Registration numbers

CAS Number

MDL Number

EC Number

Beilstein Number

PubChem SID

2490002316207642524889157163725547

Merck Index

PubChem CID

Wikipedia Title

Chemspider ID

Unique Ingredient Identifier

MetaCyc Database

NMRShiftDB Database

Patent number

PubMed Citation Links

2291853622219044370950240715601187859622936336

Reaxys Registry

CHEMBL

SureChEMBL Database

CompTox Database

CHEBI ID

ACToR Database

Protein Data Bank

Related Proteins

Molecule Details

T22209

Packaging
5, 100, 500 g in glass bottle

ChEBI

CHEBI:74794

References

PubChem Literature

From Data Sources

• High-boiling dipolar aprotic solvent. Compare Dimethyl sulfoxide, A13280, N,N-Dimethylacetamide, A10924 and 1-Methyl-2-pyrrolidinone, A12260.

• Solvent for nitrations using Nitronium tetrafluoroborate, B20167.

• Use of this solvent makes possible the reduction of alkyl bromides to alkanes by NaBH₄: Tetrahedron Lett., 3495 (1969).

• Solvent for the Baylis-Hillman reaction, using 1,4-Diazabicyclo[2.2.2]octane, A14003, which enables short reaction times at room temperature: Tetrahedron Lett., 45, 1183 (2004).

Bioactivity

PubChem BioAssay

Properties

Molecule

ID:89548