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p-Toluenesulfonic acid (PTSA, pTSA, or pTsOH) or tosylic acid (TsOH) is an organic compound with the formula CH 3 C 6 H 4 SO 3 H. It is a white extremely hygroscopic solid that is soluble in water, alcohols, and other polar organic solvents. [6] The CH 3 C 6 H 4 SO 2 group is known as the tosyl group and is often abbreviated as Ts or Tos.
The simplest examples are methanesulfonic acid, CH 3 SO 2 OH and p-toluenesulfonic acid, which are regularly used in organic chemistry as acids that are lipophilic (soluble in organic solvents). Polymeric sulfonic acids are also useful. Dowex resin are sulfonic acid derivatives of polystyrene and is used as catalysts and for ion exchange (water ...
Sodium p-toluenesulfonate is an organic compound with the formula CH 3 C 6 H 4 SO 3 Na. It is white, water-soluble solid. It is produced by the neutralization toluenesulfonic acid with sodium hydroxide. It is also a common product from the reactions of sodium-based reagents with toluenesulfonates. [1]
In organic synthesis, PPTS is used as a weakly acidic catalyst, providing an organic soluble source of pyridinium (C 5 H 5 NH +) ions.For example, PPTS is used to deprotect silyl ethers or tetrahydropyranyl ethers when a substrate is unstable to stronger acid catalysts.
This group is usually derived from the compound tosyl chloride, CH 3 C 6 H 4 SO 2 Cl (abbreviated TsCl), which forms esters and amides of toluenesulfonic acid, CH 3 C 6 H 4 SO 2 OH (abbreviated TsOH). The para orientation illustrated (p-toluenesulfonyl) is most common, and by convention tosyl without a prefix refers to the p-toluenesulfonyl group.
4-Toluenesulfonyl chloride (p-toluenesulfonyl chloride, toluene-p-sulfonyl chloride) is an organic compound with the formula CH 3 C 6 H 4 SO 2 Cl. 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 (−SO 2 Cl) functional group.
It undergoes sulfonation to give p-toluenesulfonic acid, and chlorination by Cl 2 in the presence of FeCl 3 to give ortho and para isomers of chlorotoluene. Nitration of toluene gives mono-, di-, and trinitrotoluene, all of which are widely used.
Alternatively p-toluenesulfonic acid or various Lewis acids can be used with chlorinated solvents. The aldehyde and pyrrole are heated in this medium to afford modest yields of the meso tetrasubstituted porphyrins [RCC 4 H 2 N] 4 H 2 .