Sulfolane

• Catalog No.: A13466
• CAS Number: 126-33-0
• M. F.: C4H8O2S
• M. W.: 120.17012
• Purity: 99%

SYNONYMS

• Title: 环丁砜
• IUPAC name: 1λ^6-thiolane-1,1-dione
• IUPAC Traditional name: sulfolane
• Synonyms: tetramethylene sulfone; Tetrahydrothiophene 1,1-dioxide

DATABASE IDS

• Merck Index: 148955
• Beilstein Number: 107765
• CAS Number: 126-33-0
• EC Number: 204-783-1
• MDL Number: MFCD00005484

PROPERTIES

• Purity: 99%
• Boiling Point: 285°C
• Density: 1.261
• Flash Point: 166°C(330°F)
• Melting Point: 25-28°C
• Refractive Index: 1.4825
• GHS Hazard statements: H302
• European Hazard Symbols: X
• GHS Precautionary statements: P262-P308+P313-P330
• Risk Statements: 22
• RTECS: XN0700000
• Safety Statements: 25
• Storage Warning: Hygroscopic
• TSCA Listed: 是

REFERENCES

• Solvent for nitrations using Nitronium tetrafluoroborate, B20167.
• 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).
• 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.
• 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).