Tosyylikloridi

Tosylikloridi, also known as p-toluenesulfonyl chloride, is an organic compound with the chemical formula CH3C6H4SO2Cl. It is a white solid that is soluble in many organic solvents but reacts with water. Tosylikloridi is a derivative of toluenesulfonic acid, where the hydroxyl group has been replaced by a chlorine atom. Its molecular structure consists of a toluene group attached to a sulfonyl chloride group.

The compound is primarily used as a reagent in organic synthesis. It is a common tosylating agent, meaning it is used to introduce the tosyl (p-toluenesulfonyl) group into other molecules. This tosyl group is an excellent leaving group in nucleophilic substitution reactions, making alcohols and amines more reactive. For example, tosylikloridi reacts with alcohols to form tosylates, which can then be easily displaced by nucleophiles. It is also used to protect hydroxyl and amino groups during multi-step syntheses.

Tosylikloridi is synthesized by the chlorosulfonation of toluene. This reaction typically involves treating toluene with chlorosulfonic acid. The product is usually purified by recrystallization. Due to its reactivity, tosylikloridi should be handled with care, as it can irritate the skin and eyes and reacts exothermically with water, producing corrosive hydrogen chloride gas. It is typically stored in a cool, dry place away from moisture. Its utility in facilitating various chemical transformations makes it a valuable tool for organic chemists.