Tetrabutylammonium cyanide

Uses

Tetrabutylammonium cyanide (TBACN) can be used as a source of cyanide ion for colorimetric studies.
It can be employed as a reactant in the preparation of:

• Tetrabutylammonium fluoride (TBAF), which can be used to remove silyl ether protecting groups.
• Rhenium-based single-chain magnets, (DMF)₄MReCl₄(CN)₂ (M = Mn, Fe, Co, Ni).
• Phosphorescent blue light-emitting anionic iridium complexes.

Uses

Tetrabutylammonium cyanide is commonly used as a catalyst for the synthesis of organic compounds such as multisubstituted dihydrofurans and pyrrolo[2,1-a]isoquinolines.

Synthesis

In a flask of 2 L capacity equipped with a stirring device and a dropping funnel, 200 ml of dichloromethane, 67.6 g (200 mmol) of tetrabutylammonium sulfoxide were added and stirred, to which 4 M of was added. NaOH aqueous solution 50 ml and stirred. Pre-addition was made dropwise through a dropping funnel to this dichloromethane solution of dissolved After 10 g (204 mmol) of sodium cyanide in 20 ml of water, the solution was stirred at room temperature (25C) for 30 minutes. The resulting suspension was filtered and the filtrate was concentrated to give 58.7 g of crude tetrabutylamine cyanide in oil form.