Methyl phenyl sulfone, a versatile building block for the construction of chemicals with diverse functionalities
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
Methyl phenyl sulfone, a versatile building block for the construction of chemicals with diverse functionalities
Solubility
Soluble in methanol, ethanol, benzene, and chloroform. Partly miscible in water.
Notes
Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Store away from oxidizing agent.
RUO – Research Use Only
General References:
- Marc Julia; Dominique Deprez. Syntheses a l'aide de sulfones XIII. Transpositions stereoselectives des alcools α-allyliques β'-sulfones. Tetrahedron Letters. 1976, 17 (4), 277-280.
- Gerald W. Buchanan; Cesar Reyes-Zamora; Douglas E. Clarke. A Carbon-13 Nuclear Magnetic Resonance Investigation of Some Substituted Methyl Phenyl Sulfides, Sulfoxides, and Sulfones. Canadian Journal of Chemistry. 1974, 52 (23), 3895-3904.
- Factors governing the selective alkylation have been studied. Lithium bases favor dialkylation. For monoalkylation, a potassium base, e.g. KH in THF, should be used: J. Org. Chem., 55, 2234 (1990).
- Adds to aldehydes and ketones in the presence of base, e.g. n-BuLi, to give ß-hydroxy sulfones. Conversion of the OH to, e.g. to mesylate, and elimination/desulfurative reduction with sodium amalgam provides a 1-substitued or 1,1-disubstituted alkene by the Julia olefination reaction: Tetrahedron Lett., 4833 (1973); J. Chem. Soc., Perkin 1, 829 (1978). For reaction scheme, see Ethyl phenyl sulfone, A10710. The adducts with aldehydes can also be rearranged to give the dimethyl acetals of the homologous aldehydes: J. Chem. Soc., Perkin 1, 1646 (1978). Reaction with acyl halides gives ß-keto sulfones: J. Org. Chem., 53, 906 (1988).