Tosyl azide

At room temperature, 13.8 g of p-toluenesulfonyl chloride (73 mmol), 50 mL of water, and 5.7 g of sodium azide (87 mmol) were added sequentially to a 500 mL flask. The mixture was stirred for 2 hours, and the reaction was monitored by TLC until complete. The mixture was then extracted three times with 50 mL of dichloromethane. The organic phases were combined, dried over anhydrous sodium sulfate, and concentrated to obtain 12.7 g of Tosyl azide product, with a yield of 88%.

Tosyl azide is a reagent used in organic synthesis. It is prepared by the reaction of tosyl chloride with sodium azide in aqueous acetone.

Tosyl azide is utilized for the introduction of diazo and azide functional groups. Moreover, it is used as a nitrene and a substrate for [3+2] cycloaddition reactions.

Tosyl azide is a very volatile chemical that should be carefully stored and handled.

Colorless to slight yellow liquid

p-Toluenesulfonyl azide solution can be employed as a reagent along with alkyne, and amine in the three-component coupling reaction for the synthesis of N-sulfonylamidines in presence of copper catalyst.
It can also be used in the synthesis of N-sulfonyl-1,2,3-triazoles by azide-alkyne cycloaddition reaction in the presence of copper catalyst.

Used for the introduction of azide and diazo functional groups. It is also used as a nitrene source and as a substrate for [3+2] cycloaddition reactions.

4-Methylbenzenesulfonyl Azide can be used to target Bcl-2 family proteins to potentially treat cancer.

Synthetic Communications, 17, p. 1015, 1987 DOI: 10.1080/00397918708063962
Tetrahedron Letters, 28, p. 5091, 1987 DOI: 10.1016/S0040-4039(00)95598-9