Description
Methyl benzenesulfonate is used as a raw material for the dye and pharmaceutical industries, used as an alkylating agent in organic synthesis for the production of some synthetic dye. It can also be used for the manufacturing the thin-cation exchanger film.
Preparation
Methyl benzenesulfonate is the effective methylating reagent of synthetic multiple organic intermediate, and industry is at present gone up and mainly adopted Phenylsulfonic acid and methyl alcohol to carry out after the esterification essence to steam, this technology starting material costliness, and reaction time is long, and product yield is low. How to get Methyl benzenesulfonate with high yield, scientists have lots of researcher.
Photolysis
Irradiation of methyl benzenesulfonate in methanol causes photolysis, yielding benzene (5–34%), biphenyl (9–15%), and phenethyl ether (trace amounts). The quantum yield of extinction at a wavelength of 254 nm at room temperature is estimated to be 0.07 ± 0.005 [1].
Genotoxicity
Methyl benzenesulfonate is a sulfonate ester which acts as a potential genotoxic impurity in drug substances. Further, it exerts genotoxic effects in bacterial and mammalian cell systems. Incompatible with strong oxidizing agents, strong acids and strong bases.
Reaction
V. M. Nesterov and I. E. Chubova prepared theobromine from 3-methylxanthine, methyl benzenesulfonate, which has been used as the methylating agent. To obtain theobromine, 3-methylxanthine is generally methylated with dimethyl sulfate in an aqueous ethanolic solution of caustic potash. However, if in the reaction the pH exceeds 8.0, the methylation of 3-methylxanthine leads to caffeine, which forms a by-product.
Chemical Properties
clear colourless to slightly brown liquid
Uses
A sulfonate ester as potential genotoxic impurity in drug substances.
Uses
Methyl benzenesulfonate is a sulfonate ester which acts as a potential genotoxic impurity in drug substances. Further, it exerts genotoxic effects in bacterial and mammalian cell systems.
References
[1] Y. Izawa, Naoki K. (1975). Photolysis of Methyl Benzenesulfonate in Methanol. Bulletin of the Chemical Society of Japan, 48 1, 3197–3199.
https://doi.org/10.1246/bcsj.48.3197
