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.[1] Commercial samples often have a distinctive fish-like odour, presumably due to the presence of trimethylamine via hydrolysis.

Benzyltrimethylammonium hydroxide
Names
IUPAC name
Benzyl(trimethyl)azanium hydroxide
Other names
Triton B, Trimethylbenzylammonium hydroxide, N,N,N-Trimethyl-1-phenylmethanaminium hydroxide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.632
UNII
Properties
C10H17NO
Molar mass 167.252 g·mol−1
Appearance Liquid, clear, slightly yellow
Density 0.95 g/mL
Miscible in water
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Uses

Together with benzyltriethylammonium salt, benzyltrimethylammonium hydroxide is a popular phase-transfer catalyst.[2]

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.[3]

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References
  1. Mary Ellen Bos "Benzyltrimethylammonium Hydroxide" in Encyclopedia of Reagents for Organic Synthesis, 2001 John Wiley & Sons. doi:10.1002/047084289X.rb079
  2. Marc Halpern "Phase-Transfer Catalysis" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a19_293
  3. 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 doi:10.1007/s00706-005-0452-2

See also
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