4-Toluenesulfonyl chloride

• Toluene-4 -sulfonyl chloride
• Toluene - 4-sulfonic acid
• 4- methylbenzene -1 -sulfonyl chloride
• P- toluenesulfonyl chloride
• Tosyl chloride
• P-toluenesulfonyl
• Toluene - 4-sulphonyl chloride
• TosCl
• TsCl

White to gray solid

Fixed

1.49 g · cm -3

67 ° C

135 ° C ( 13 hPa)

1.3 hPa at 88 ° C.

Decomposition with water

Risk

4680 mg · kg -1 ( LD50, rat, oral)

Template: Infobox chemical / molecular formula search available

Para- toluenesulfonic acid chloride is a chemical compound from the group of sulfonic acids. It is the acid chloride of para- toluenesulfonic acid, and is colloquially, often written as tosyl chloride TsCl, respectively. In this case, the abbreviation " Ts " for a tosyl group.

Representation

The compound can be prepared by a reaction similar to a Friedel -Crafts alkylation of toluene. This toluene with sulfuryl chloride, and aluminum chloride is placed as a catalyst.

A further possibility consists in the reaction of para- methylaniline in a Sandmeyer -type reaction. For this purpose, the amine is initially diazotized with sodium nitrite. The resulting diazonium salt is then reacted with sulfur dioxide in the presence of copper ( I) chloride and magnesium chloride to the reaction.

Tosyl chloride is a by- product of the manufacture of saccharin. This is where the next required for this o -toluenesulfonyl chloride and p -toluenesulfonyl chloride which is sold from each other after the separation as fine chemical.

Properties

Para- toluenesulfonyl chloride is a corrosive solid with a characteristic peculiar smell, which melts at 67 ° C and boils at 135 ° C at a pressure of 13 hPa. Above a temperature of 220 ° C it decomposes.

Use

Tosylates may be prepared by deprotonation of an alcohol and subsequent reaction with p-toluenesulfonyl chloride, with one equivalent of hydrogen chloride, which is bound by a base as the hydrochloride is formed:

Due to their property as a leaving group tosylates are used as intermediates in preparative organic chemistry. The conversion of alcohols to tosylates the poor leaving group HO- transferred in a good leaving group, thereby substitution reactions are made possible at this position of the carbon skeleton. The anion of p- toluenesulfonic acid occurs as a leaving group.