Imidazole-1-sulfonyl azide is an organic azide

Azide

Azide is the anion with the formula N3−. It is the conjugate base of hydrazoic acid. N3− is a linear anion that is isoelectronic with CO2 and N2O. Per valence bond theory, azide can be described by several resonance structures, an important one being N−=N+=N−...

 compound that can be used as an alternative to trifluoromethanesulfonyl azide

Trifluoromethanesulfonyl azide

Trifluoromethanesulfonyl azide or triflyl azide is an organic azide used as a reagent in organic synthesis.-Preparation:Trifluoromethanesulfonyl azide is not commercially available. It is prepared before use by reacting trifluoromethanesulfonic anhydride with sodium azide, traditionally in...

. It is a colorless liquid; it may also be used as a better-handled hydrochloride

Hydrochloride

In chemistry, hydrochlorides are salts resulting, or regarded as resulting, from the reaction of hydrochloric acid with an organic base . This is also known as muriate, derived from hydrochloric acid's other name: muriatic acid....

 salt.

Preparation

This compound is not readily available commercially. It may be prepared by reacting sulfuryl chloride

Sulfuryl chloride

Sulfuryl chloride is an inorganic compound with the formula SO2Cl2. At room temperature, it is a colorless liquid with a pungent odor. Sulfuryl chloride is not found in nature, as can be inferred from its rapid hydrolysis....

 with sodium azide

Sodium azide

Sodium azide is the inorganic compound with the formula NaN3. This colourless azide salt is the gas-forming component in many car airbag systems. It is used for the preparation of other azide compounds. It is an ionic substance and is highly soluble in water. It is extremely...

 in acetonitrile

Acetonitrile

Acetonitrile is the chemical compound with formula . This colourless liquid is the simplest organic nitrile. It is produced mainly as a byproduct of acrylonitrile manufacture...

, followed by the addition of excess imidazole

Imidazole

Imidazole is an organic compound with the formula C3H4N2. This aromatic heterocyclic is a diazole and is classified as an alkaloid. Imidazole refers to the parent compound, whereas imidazoles are a class of heterocycles with similar ring structure, but varying substituents...

. The hydrochloride salt may be obtained by precipitating with an ethanol solution of HCl.

Reactions

Like trifluoromethanesulfonyl azide

Trifluoromethanesulfonyl azide

Trifluoromethanesulfonyl azide or triflyl azide is an organic azide used as a reagent in organic synthesis.-Preparation:Trifluoromethanesulfonyl azide is not commercially available. It is prepared before use by reacting trifluoromethanesulfonic anhydride with sodium azide, traditionally in...

, this compound generally converts primary amines or ammonium salts to azides. This reaction is effectively the reverse of the Staudinger reaction

Staudinger reaction

The Staudinger reaction or Staudinger reduction is a chemical reaction in which the combination of an azide with a phosphine or phosphite produces an iminophosphorane intermediate. Combined with the hydrolysis of the aza-ylide to produce a phosphine oxide and an amine, this reaction is a mild...

. Similarly, it is able to transfer the diazo

Diazo

Diazo refers to a type of organic compound called diazo compound that has two linked nitrogen atoms as a terminal functional group. The general formula is R2C=N2. The simplest example of a diazo compound is diazomethane...

group (=N₂) when catalyzed by copper(II), nickel(II), zinc(II), and cobalt(II) salts.

Safety

As with all organic azides, this compound is potentially explosive. Impact tests, vigorous grinding, and prolonged heating at 80 °C of the hydrochloride salt did not result in any explosive reaction, though heating above 150 °C resulted in violent decomposition.