Benzyltrimethylammonium hydroxide

Benzyltrimethylammonium hydroxide
Names
	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 ;
3D model (JSmol)	Interactive image;
ChemSpider	60218 ;
ECHA InfoCard	100.002.632
PubChem CID	66854;
CompTox Dashboard (EPA)	DTXSID3044332 ;
	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 Key: NDKBVBUGCNGSJJ-UHFFFAOYSA-M ; 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;
	SMILES C[N+](C)(C)Cc1ccccc1.[OH-];
Properties
Chemical formula	C10H17NO
Molar mass	167.252 g·mol−1
Appearance	Liquid, clear, slightly yellow
Density	0.95 g/mL
Solubility in water	Miscible in water
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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. Commercial samples often have a distinctive fish-like odour, presumably due to the presence of trimethylamine via hydrolysis.

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