Tetrabutylammonium azide

In a dry reaction flask, a solution of NaN3 (1.00 g, 15.4 mmol) in water (2.3 mL) was added to tetrabutylammonium hydroxide (40% aqueous solution, 2.00 g, 7.69 mmol). The resulting reaction mixture was stirred at room temperature for several hours. After the reaction was complete, dichloromethane (12 mL) was slowly added to the reaction mixture, the organic layer was separated, and the aqueous layer was extracted with dichloromethane (3 × 4 mL). All organic layers were combined and dried on anhydrous magnesium sulfate. The reaction mixture was filtered to remove the drying agent, and the resulting filtrate was concentrated under vacuum to remove the organic solvent. The residue obtained was the target product molecule, tetrabutylammonium azide.

Tetrabutylammonium azide can be used as a reagent for the synthesis of:

• Heteroarylannulated bicyclic morpholines
• Cyanimide-based inhibitors of cathepsin C
• Trimethylene carbonate
• Aerobic oxidative transformation of primary azides to nitriles
• Substitution reactions at tetracoordinate boron

It is also used as a catalyst for cyclic carbonate formation.

reaction type: click chemistry