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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.
Tosyl group (blue) with a generic "R" group attached Tosylate group with a generic "R" group attached. Note the extra oxygen, compared to plain tosyl. In organic chemistry, a toluenesulfonyl group (tosyl group, abbreviated Ts or Tos [nb 1]) is a univalent functional group with the chemical formula −SO 2 −C 6 H 4 −CH 3.
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.
Sulfonic acids are strong acids. They are commonly cited as being around a million times stronger than the corresponding carboxylic acid. For example, p-Toluenesulfonic acid and methanesulfonic acid have pK a values of −2.8 and −1.9, respectively, while those of benzoic acid and acetic acid are 4.20 and 4.76, respectively
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p-Toluenesulfonyl hydrazide is the organic compound with the formula CH 3 C 6 H 4 SO 2 NHNH 2. It is a white solid that is soluble in many organic solvents but not water or alkanes. It is a white solid that is soluble in many organic solvents but not water or alkanes.
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