[67-71-0] · C2H6O2S · Dimethyl Sulfone · (MW 94.15)
((methanesulfonyl)methylation agent; may be used as a dipolar aprotic solvent)
Physical Data: mp 108-110 °C; bp 238 °C; d 1.1707 g cm-3 (110 °C); pK
Solubility: sol in hot H2O, EtOH, benzene.
Form Supplied in: white solid; commercially available.
Purification: recrystallized from CHCl3 or H2O and then dried over P2O5.
Handling, Storage, and Precautions: stable indefinitely at rt.
Because of its high boiling point, dimethyl sulfone is a convenient solvent for high-temperature reactions, e.g. treatment of 2-chloropyridine with Potassium Fluoride in dimethyl sulfone at 110 °C for 21 days results in the displacement of the chlorine by fluorine.1
Dimethyl sulfone can be deprotonated by organolithium compounds, Grignard reagents, or alkali metal alkoxides,2 amides,3,4 or hydrides5 to give (methanesulfonyl)methyllithium or (methanesulfonyl)methyldilithium, depending upon the amount of base added.3 The choice of the solvent (THF, DMSO, or liquid ammonia) is dictated by the nature of the base. The resultant carbanions react with halides, aldehydes,4 ketones, esters, nitriles,3 or amides. Under phase transfer catalysis, condensation of dimethyl sulfone with aldehydes occurs without dehydration to give the corresponding b-hydroxysulfones.6 The acidity of dimethyl sulfone (pK Methyl Phenyl Sulfone;
Georges Hareau & Philip Kocienski Southampton University, UK
Methyl Phenyl Sulfone;
Georges Hareau & Philip Kocienski
Southampton University, UK