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4-Toluenesulfonyl chloride

Chemical compound From Wikipedia, the free encyclopedia

4-Toluenesulfonyl chloride
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4-Toluenesulfonyl chloride (p-toluenesulfonyl chloride, toluene-p-sulfonyl chloride) is an organic compound with the formula CH3C6H4SO2Cl. This white, malodorous solid is a reagent widely used in organic synthesis.[2] Abbreviated TsCl or TosCl, it is a derivative of toluene and contains a sulfonyl chloride (−SO2Cl) functional group.

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Uses

As typical for Sulfonyl halides, TsCl converts alcohols (abbreviated ROH) into the corresponding toluenesulfonate esters, or tosyl derivatives ("tosylates"):

CH3C6H4SO2Cl + ROH → CH3C6H4SO2OR + HCl

Tosylates can be cleaved with lithium aluminium hydride:

4 CH3C6H4SO2OR + LiAlH4 → LiAl(O3SC6H4CH3)4 + 4 RH

Thus, tosylation followed by reduction allows for removal of a hydroxyl group.

Likewise, TsCl is used to prepare sulfonamides from amines:[3]

CH3C6H4SO2Cl + R2NH → CH3C6H4SO2NR2 + HCl

The resulting sulfonamides are non-basic and, when derived from primary amines, are even acidic.

TsCl reacts with hydrazine to give p-toluenesulfonyl hydrazide.

The preparation of tosyl esters and amides are conducted in the presence of a base, which absorbs hydrogen chloride. The selection of the base is often crucial to the efficiency of tosylation. Typical bases include pyridine and triethylamine. Unusual bases are also used; for example, catalytic amounts of trimethylammonium chloride in the presence of triethylamine is highly effective by virtue of the trimethylamine.[2]

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Other reactions

Being a widely available reagent, TsCl has been heavily examined from the perspective of reactivity. It is used in dehydrations to make nitriles, isocyanides and diimides.[2] In an unusual reaction focusing on the sulfur center, zinc reduces TsCl to the sulfinate, CH3C6H4SO2Na.[4]

Manufacture

This reagent 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:[5]

CH3C6H5 + SO2Cl2 → CH3C6H4SO2Cl + HCl

Hazards

Tosyl chloride is "a corrosive lachrymator."[2]

References

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