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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.
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. It consists of a tolyl group , −C 6 H 4 −CH 3 , joined to a sulfonyl group, −SO 2 − , with the open valence on sulfur .
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
C 6 H 5 SO 3 H + HOSO 2 Cl → C 6 H 5 SO 2 Cl + H 2 SO 4. The intermediate benzenesulfonic acid can be chlorinated with thionyl chloride as well. Benzenesulfonyl chloride, the most important sulfonyl halide, can also be produced by treating sodium benzenesulfonate with phosphorus pentachlorides. [5]
Tosyl chloride (p-toluenesulfonyl chloride) CH 3 C 6 H 4 SO 2 Cl Brosyl: p-bromobenzenesulfonyl Bs Nosyl o- or p-nitrobenzenesulfonyl Ns Mesyl: methanesulfonyl Ms Mesyl chloride (methanesulfonyl chloride) CH 3 SO 2 Cl Triflyl: trifluoromethanesulfonyl Tf Tresyl: 2,2,2-trifluoroethyl-1-sulfonyl Dansyl: 5-(dimethylamino)naphthalene-1-sulfonyl Ds ...
For example, 2,6-dichlorotoluene can be prepared by chlorination of 4-toluenesulfonyl chloride followed by desulfonation. [1] Some dichlorotoluenes are precursors to commercial pesticides. 2,4-Dichlorotoluene is the precursor to pyrifenox, butafenacil, and the pyrazole derivatives pyrazoxyfen and [pyrazolynate]].
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.
Structures of the three isomers of tolyl group. In organic chemistry, tolyl groups are functional groups related to toluene. [1] They have the general formula CH 3 C 6 H 4 −R, the change of the relative position of the methyl and the R substituent on the aromatic ring can generate three possible structural isomers 1,2 (ortho), 1,3 (meta), and 1,4 (para).