Substance
ID:716363
Names and Identifiers
IUPAC Traditional name
sulfolane
Synonyms
Sulfolanetetramethylene sulfone环丁砜Tetrahydrothiophene 1,1-dioxide
IUPAC name
1λ6-thiolane-1,1-dione
Registration numbers
MDL Number
CAS Number
Beilstein Number
EC Number
Merck Index
Properties
Safety Information
European Hazard Symbols
Harmful (X)GHS Pictograms
Acute toxicity (oral, dermal, inhalation), category 4
Skin irritation, category 2
Eye irritation, category 2
Skin sensitisation, category 1
Specific Target Organ Toxicity – Single exposure, category 3
GHS Precautionary statements
P262-P308+P313-P330
Risk Statements
22
GHS Hazard statements
H302
Storage Warning
Hygroscopic
Safety Statements
25
RTECS
XN0700000
TSCA Listed
是
Product Information
Purity
99%
Physical Property
Boiling Point
285°C
Flash Point
166°C(330°F)
Melting Point
25-28°C
Refractive Index
1.4825
Density
1.261
Molecule Details
No Data Available
Click here to submit data
Molecular Spectra
No Data Available
Click here to submit data
References
• Solvent for nitrations using Nitronium tetrafluoroborate, B20167.
• 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 220o: 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 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).
• 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).