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  Y
3D model (JSmol)	Interactive image
ChemSpider	60218  Y
ECHA InfoCard	100.002.632
PubChem CID	66854
UNII	8P4488425W  N
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 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
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). N  verify  (what is  YN ?) 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 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. ^[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]

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. ^[4]

References

1. Mary Ellen Bos "Benzyltrimethylammonium Hydroxide" in Encyclopedia of Reagents for Organic Synthesis, 2001 John Wiley & Sons. doi : 10.1002/047084289X.rb079
2. Halpern, Marc (2000). "Phase-Transfer Catalysis". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_293. ISBN   3527306730.
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
4. Marino, M. G.; Kreuer, K. D. (2015). "Alkaline Stability of Quaternary Ammonium Cations for Alkaline Fuel Cell Membranes and Ionic Liquids". ChemSusChem. 8 (3): 513–523. Bibcode:2015ChSCh...8..513M. doi:10.1002/cssc.201403022. PMID   25431246.