Tosyl chloride is an important intermediate dyes in organic synthesis and raw materials for pesticides, there are three kinds of isomers, namely o-toluenesulfonyl chloride, m-toluenesulfonyl chloride and p-toluenesulfonyl chloride. Relative molecular mass is 190.65. All three stimulate skin and mucous membranes, commonly used is adjacent toluenesulfonyl chloride and p-toluenesulfonyl chloride.O-toluenesulfonyl chloride, also known as 2-methyl-benzenesulfonyl chloride, 2-toluene-sulfonyl chloride, is colorless oily liquid. The relative density is 1.3383. Melting point is 10.2 ℃. Boiling point is 154 ℃ (4.800 × 103Pa), 126 ℃ (1.333 × 103Pa). The refractive index is 1.5565. It is insoluble in water, soluble in ether, benzene and ethanol.
M-toluenesulfonyl chloride, also known as 3-methyl-benzenesulfonyl chloride, 3-toluenesulfonyl chloride, is colorless oily liquid. Melting point is 11.7 ℃. Boiling point is 146 ℃ (2.933 × 103Pa). It is insoluble in water, soluble in alcohol, ether and benzene.
P-toluenesulfonyl chloride is also known as 4-methyl-benzenesulfonyl chloride, 4-toluenesulfonyl chloride. Precipitation from ether or petroleum ether is triclinic white flaky crystal. The relative density is 1.26. Melting point is 11. 7 ℃. Boiling point is 164 ℃ (4.4 × 103Pa), 151.6 ℃ (2.666 × 103Pa), 145~146 ℃ (2.000 × 103Pa), 134.5 ℃ (1.333 × 103Pa). It is insoluble in water, soluble in alcohol, benzene and ether.
Toluenesulfonyl chloride is called "TsCl", with strong nucleophilicity and substitution reaction with nucleophilic reagent. For example, reaction with the alcohol into the ester:
ROH + TsCl-Py → ROTs + Py + HCl-, reaction with amine and hydrazine respectively to generate the sulfonamide and sulfonyl hydrazide:
The above information were edited and collated by Xiaonan of Chemicalbook.