Benzyltrimethylammonium hydroxide

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| Verifiedfields = changed

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| verifiedrevid = 461284361

| ImageFile = Triton B.png

| ImageSize = 160px

| ImageAlt = Skeletal formula of benzyltrimethylammonium hydroxide

| ImageFile1 = Benzyltrimethylammonium-hydroxide-3D-balls.png

| ImageSize1 = 150

| ImageAlt1 = Ball-and-stick model of the benzyltrimethylammonium hydroxide ions

| IUPACName = Benzyl(trimethyl)azanium hydroxide

| OtherNames = Triton B, Trimethylbenzylammonium hydroxide, N,N,N-Trimethyl-1-phenylmethanaminium hydroxide

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|??}}

| CASNo = 100-85-6

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = 8P4488425W

| SMILES = C[N+](C)(C)Cc1ccccc1.[OH-]

| PubChem = 66854

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 60218

| 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

| InChIKey = NDKBVBUGCNGSJJ-REWHXWOFAN

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = NDKBVBUGCNGSJJ-UHFFFAOYSA-M

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|Section2={{Chembox Properties

| C=10 | H=17 | N=1 | O=1

| Appearance = Liquid, clear, slightly yellow

| Density = 0.95 g/mL

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| Solubility = Miscible in water }}

|Section3={{Chembox Hazards

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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.Mary Ellen Bos "Benzyltrimethylammonium Hydroxide" in Encyclopedia of Reagents for Organic Synthesis, 2001 John Wiley & Sons. {{doi|10.1002/047084289X.rb079}} 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.{{Ullmann|doi=10.1002/14356007.a19_293|chapter=Phase-Transfer Catalysis|year=2000|last1=Halpern|first1=Marc|isbn=3527306730}}

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.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}}

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.{{cite journal |doi=10.1002/cssc.201403022|title=Alkaline Stability of Quaternary Ammonium Cations for Alkaline Fuel Cell Membranes and Ionic Liquids|year=2015|last1=Marino|first1=M. G.|last2=Kreuer|first2=K. D.|journal=ChemSusChem|volume=8|issue=3|pages=513–523|pmid=25431246|bibcode=2015ChSCh...8..513M }}

References

See also

  • http://www.chemcas.com/AnalyticalDetail.asp?pidx=1&id=19594&cas=100-85-6&page=490

Category:Hydroxides

Category:Quaternary ammonium compounds

Category:Reagents for organic chemistry

Category:Benzyl compounds