In characteristic manner, TsCl converts alcohols (abbreviated ROH) into the corresponding toluenesulfonate esters, or tosyl derivatives ("tosylates"):
: CHCHSOCl  +  ROH  →  CHCHSOOR  +  HCl
Tosylates can be cleaved with lithium aluminium hydride:
: 4 CHCHSOOR  +  LiAlH  →  LiAl(OSCHCH)  + 4 RH
Thus, tosylation followed by reduction allows for removal of a hydroxyl group.
Likewise, TsCl is used to prepare sulfonamides from amines:
:CHCHSOCl  +  RNH   →   CHCHSONR  +  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.