Benzyltrimethylammonium hydroxide: Difference between revisions
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==Uses== |
==Uses== |
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Together with benzyltriethylammonium salt, benzyltrimethylammonium hydroxide is a popular [[phase-transfer catalyst]].<ref name=Ullmann> |
Together with benzyltriethylammonium salt, benzyltrimethylammonium hydroxide is a popular [[phase-transfer catalyst]].<ref name=Ullmann>{{Ullmann|doi=10.1002/14356007.a19_293|chapter=Phase-Transfer Catalysis|year=2000|last1=Halpern|first1=Marc|isbn=3527306730}}</ref> |
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It is used in [[aldol condensation]] reactions and base-catalyzed [[dehydration reaction]]s. It is also used as a base in Ando's Z-selective variant of [[Horner–Wadsworth–Emmons_reaction | Horner-Wadsworth-Emmons Olefination]] reactions.<ref>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}}</ref> |
It is used in [[aldol condensation]] reactions and base-catalyzed [[dehydration reaction]]s. It is also used as a base in Ando's Z-selective variant of [[Horner–Wadsworth–Emmons_reaction | Horner-Wadsworth-Emmons Olefination]] reactions.<ref>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}}</ref> |
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Relative to |
Relative to tetramethylammonium hydroxide, benzyltriethylammonium hydroxide is more labile. In 6M NaOH at 160 °C their halflives are 61.9 and 4 h, respectively.<ref>{{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}}</ref> |
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== References == |
== References == |
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Revision as of 15:56, 5 March 2021
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| Names | |
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| IUPAC name
Benzyl(trimethyl)azanium hydroxide
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| Other names
Triton B, Trimethylbenzylammonium hydroxide, N,N,N-Trimethyl-1-phenylmethanaminium hydroxide
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.002.632 |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| 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).
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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.[1] Commercial samples often have a distinctive fish-like odour, presumably due to the presence of trimethylamine via hydrolysis.
Uses
Together with 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 halflives are 61.9 and 4 h, respectively.[4]
References
- ^ Mary Ellen Bos "Benzyltrimethylammonium Hydroxide" in Encyclopedia of Reagents for Organic Synthesis, 2001 John Wiley & Sons. doi:10.1002/047084289X.rb079
- ^ Halpern, Marc (2000). "Phase-Transfer Catalysis". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_293. ISBN 3527306730.
- ^ 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
- ^ 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. doi:10.1002/cssc.201403022. PMID 25431246.