Benzyltrimethylammonium hydroxide, also known as Triton B or trimethylbenzylammonium hydroxide, is a

quaternary ammonium salt In chemistry, quaternary ammonium cations, also known as quats, are positively charged polyatomic ions of the structure , R being an alkyl group or an aryl group. Unlike the ammonium ion () and the primary, secondary, or tertiary ammonium cation ...

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.

Uses

Together with the benzyltriethylammonium salt, benzyltrimethylammonium hydroxide is a popular

phase-transfer catalyst In chemistry, a phase-transfer catalyst or PTC is a catalyst that facilitates the transition of a reactant from one phase into another phase where reaction occurs. Phase-transfer catalysis is a special form of heterogeneous catalysis. Ionic r ...

. It is used in

aldol condensation An aldol condensation is a condensation reaction in organic chemistry in which two carbonyl moieties (of aldehydes or ketones) react to form a β-hydroxyaldehyde or β-hydroxyketone (an aldol reaction), and this is then followed by dehydration to ...

reactions and base-catalyzed

dehydration reaction In chemistry, a dehydration reaction is a chemical reaction that involves the loss of water from the reacting molecule or ion. Dehydration reactions are common processes, the reverse of a hydration reaction. Dehydration reactions in organic ch ...

s. 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