4-Toluenesulfonyl chloride is a white, malodorous solid, with the formula CH3C6H4SO2Cl. It is widely used in organic synthesis as a reagent. Abbreviated TsCl, it is a derivative of toluene and contains a sulfonyl chloride (?SO2Cl) functional group.

Uses

Being a widely available reagent, TsCl is used in dehydrations to make nitriles, isocyanides, and diimides. In an unusual reaction focusing on the sulfur center, zinc reduces TsCl to the sulfinate, CH3C6H4SO2Na.

Synthesis

TsCl is inexpensively available for laboratory use. It is a by-product from the production of ortho-toluenesulfonyl chloride (a precursor for the synthesis of the common food additive and catalyst saccharin), via the chlorosulfonation of toluene:

CH3C6H5 + SO2Cl2 → CH3C6H4SO2Cl + HCl

Toxicity

TsCl is considered to be a toxic and corrosive substance.

Like many chemical reagents, TsCl should be handled with care and appropriate safety precautions. It is important to wear protective equipment, such as gloves and goggles, and work in a well-ventilated area when using TsCl.

Effects of short-term exposure

TsCl is severely irritating to the eyes.TsCl is irritating to the skin and respiratory tract.