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 Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical and the simplest aliphatic alcohol, with the formula C H3 O H (a methyl group linked to a hydroxyl group, often abbreviated as MeOH). It is a ...

. 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.

Uses

Together with the 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. Relative to tetramethylammonium hydroxide, benzyltriethylammonium hydroxide is more labile. In 6M NaOH at 160 °C their half-lives are 61.9 and 4 h, respectively.{{cite journal , doi=10.1002/cssc.201403022, title=Alkaline Stability of Quaternary Ammonium Cations for Alkaline Fuel Cell Membranes and Ionic Liquids, year=2015, last1=Marino, first1=M. G., last2=Kreuer, first2=K. D., journal=ChemSusChem, volume=8, issue=3, pages=513–523, pmid=25431246

Uses

References

See also