Benzyltrimethylammonium hydroxide explained

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.[1] 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.[2]

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.[3]

References

  1. Mary Ellen Bos "Benzyltrimethylammonium Hydroxide" in Encyclopedia of Reagents for Organic Synthesis, 2001 John Wiley & Sons.
  2. Chaturvedi, D., & Ray, S. (2006). Triton b catalyzed, efficient, one-pot synthesis of carbamate esters from alcoholic tosylates. Monatshefte fuer Chemie, 137. Retrieved from https://doi.org/10.1007%2Fs00706-005-0452-2
  3. 10.1002/cssc.201403022. Alkaline Stability of Quaternary Ammonium Cations for Alkaline Fuel Cell Membranes and Ionic Liquids. 2015. Marino. M. G.. Kreuer. K. D.. ChemSusChem. 8. 3. 513–523. 25431246.

See also