Benzyltrimethylammonium hydroxide

Benzyltrimethylammonium hydroxide
IUPAC name Benzyl(trimethyl)azanium hydroxide
Other names Triton B, Trimethylbenzylammonium hydroxide, N,N,N-Trimethyl-1-phenylmethanaminium hydroxide
Identifiers
CAS number	100-85-6 Y
PubChem	66854
ChemSpider	60218 Y
Jmol-3D images	{{#if:C[N+](C)(C)Cc1ccccc1.[OH-]|Image 1
SMILES C[N+](C)(C)Cc1ccccc1.[OH-]
InChI 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 Y Key: NDKBVBUGCNGSJJ-UHFFFAOYSA-M Y 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
Properties
Molecular formula	C10H17NO
Molar mass	167.25 g mol−1
Appearance	Liquid, clear, slightly yellow
Density	0.95 g/mL
Solubility in water	Miscible in water
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

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