Benzyltrimethylammonium hydroxide

Benzyltrimethylammonium hydroxide, also known as Triton B or trimethylbenzylammonium hydroxide, is a quaternary ammonium salt that functions as an organic base. It is usually handled as a solution in water or methanol. The compound is colourless, although the solutions often appear yellowish. Commercial samples often have a distinctive fish-like odour, presumably due to the presence of trimethylamine via hydrolysis. Benzyltrimethylammonium hydroxide, also known as Triton B or trimethylbenzylammonium hydroxide, is a quaternary ammonium salt that functions as an organic base. It is usually handled as a solution in water or methanol. The compound is colourless, although the solutions often appear yellowish. Commercial samples often have a distinctive fish-like odour, presumably due to the presence of trimethylamine via hydrolysis. Together with benzyltriethylammonium salt, benzyltrimethylammonium hydroxide is a popular phase-transfer catalyst. It is used in aldol condensation reactions and base-catalyzed dehydration reactions. It is also used as a base in Ando's Z-selective variant of Horner-Wadsworth-Emmons Olefination reactions.