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126-33-0 - Sulfolane, 99% - Tetramethylene sulfone - Tetrahydrothiophene 1,1-dioxide - A13466 - Alfa Aesar

A13466 Sulfolane, 99%

CAS Number
126-33-0
Synonyms
Tetramethylene sulfone
Tetrahydrothiophene 1,1-dioxide

Size Price ($) Quantity Availability
250g 27.03
1000g 75.92
5000g 290.46
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Sulfolane, 99%

MDL
MFCD00005484
EINECS
204-783-1

Chemical Properties

Formula
C4H8O2S
Formula Weight
120.17
Melting point
25-28°
Boiling Point
285°
Flash Point
166°(330°F)
Density
1.261
Refractive Index
1.4825
Sensitivity
Hygroscopic
Solubility
Miscible with alcohol, water, acetone, toluene and dilute mineral acids. Slightly miscible with octanes, olefins and naphthenes.

Applications

Sulfolane is used as an industrial solvent utilized for the extraction of aromatic hydrocarbons from hydrocarbon mixtures and to purify natural gas. Further, it is used in refineries and the petrochemical industry.

Notes

Miscible with water, acetone, tolueneIncompatible with strong oxidizing agents.

Literature References

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.

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.

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

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).

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).

Vergaelen, M.; Verbraeken, B.; Monnery, B. D.; Hoogenboom, R. Sulfolane as Common Rate Accelerating Solvent for the Cationic Ring-Opening Polymerization of 2-Oxazolines. ACS Macro Lett. 2015, 4 (8), 825-828.

Raghuram, N.; Suresh, R.; Ramesh, G.; Sowjanya, G.; Jyostna, T. S. Excess parameters for the binary mixtures of sulfolane with chloroethanes at different temperatures. J. Therm. Anal. Calorim. 2015, 119 (3), 2107-2117.

GHS Hazard and Precautionary Statements

Hazard Statements: H302

Harmful if swallowed.

Precautionary Statements: P262-P308+P313-P330

Do not get in eyes, on skin, or on clothing. IF exposed or concerned: Get medical advice/attention. Rinse mouth.

Other References

Merck
14,8955
Beilstein
107765
Harmonized Tariff Code
2934.99
TSCA
Yes
RTECS
XN0700000

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