Tosyl azide

Description

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

Applications

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.

Safety

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

Chemical Properties

Colorless to slight yellow liquid

Uses

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.

Uses

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.

Uses

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

Synthesis Reference(s)

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