In organic chemistry, a toluenesulfonyl group (tosyl group, abbreviated Ts or Tos[nb 1]) is a univalent functional group with the chemical formula −SO2−C6H4−CH3. It consists of a tolyl group, −C6H4−CH3, joined to a sulfonyl group, −SO2−, with the open valence on sulfur.

Chlorides, bromides, and tosylate / mesylate groups are excellent leaving groups in nucleophilic substitution reactions, due to resonance delocalization of the developing negative charge on the leaving oxygen.

Mar 10, 2015 · Another popular option is using the conjugate base of p-toluenesulfonic acid, (“p-toluenesulfonate”) commonly called “tosylate” and abbreviated OTs. These groups have essentially identical leaving group ability and for our purposes are interchangeable.

Tosylate | C7H7O3S- | CID 85570 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities, safety/hazards/toxicity information, supplier lists, and more.

Para-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.

Tosylate Ester Formation. We can transform an alcohol group into a sulfonic ester using para-toluene sulfonyl chloride (Ts-Cl) or methanesulfonyl chloride (Ms-Cl), creating what is termed an organic tosylate or mesylate:

Mesylate and tosylate groups are excellent leaving groups in nucleophilic substitution reactions because the negative charge on the leaving group is stabilized by resonance.

Unlike alcohols, mesylates and tosylates are always reacted with a salt such as NaCl or NaBr and not the acids. The use of salts is to ensures the halogens are in a form of good nucleophiles as they are not suppressed by the protons and the reaction goes by S N 2 mechanism.

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A tosylate is a functional group or a salt derived from tosylic acid, which is a sulfonic acid. Tosylates are commonly used as leaving groups in $\text{S}_\text{N}2$ reactions, a key topic in organic chemistry.