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Benzyltrimethylammonium hydroxide

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Benzyltrimethylammonium hydroxide
Skeletal formula of 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 Edit this at Wikidata
  • InChI=1S/C10H16N.H2O/c1-11(2,3)9-10-7-5-4-6-8-10;/h4-8H,9H2,1-3H3;1H2/q+1;/p-1 checkY
    Key: NDKBVBUGCNGSJJ-UHFFFAOYSA-M checkY
  • InChI=1/C10H16N.H2O/c1-11(2,3)9-10-7-5-4-6-8-10;/h4-8H,9H2,1-3H3;1H2/q+1;/p-1
    Key: NDKBVBUGCNGSJJ-REWHXWOFAN
  • C[N+](C)(C)Cc1ccccc1.[OH-]
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).
checkY verify (what is checkY☒N ?)

Benzyltrimethylammonium hydroxide, also known as Triton B or trimethylbenzylammonium hydroxide, is a quaternary ammonium salt that functions as an organic base. 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.

Sources

  • http://www.chemcas.com/AnalyticalDetail.asp?pidx=1&id=19594&cas=100-85-6&page=490
  • Chaturvedi, D., & Ray, S. (2006). Triton b catalyzed, efficient, one-pot synthesis of carbamate esters from alcoholic tosylates. Monatshefte fuer Chemie, 137. Retrieved from http://www.springerlink.com/content/m48703268m3qw323/fulltext.pdf doi:10.1007/s00706-005-0452-2