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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).
|
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.
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]
![]() | |
![]() | |
Names | |
---|---|
IUPAC name
Benzyl(trimethyl)azanium hydroxide
| |
Other names
Triton B, Trimethylbenzylammonium hydroxide, N,N,N-Trimethyl-1-phenylmethanaminium hydroxide
| |
Identifiers | |
3D model (
JSmol)
|
|
ChemSpider | |
ECHA InfoCard | 100.002.632 |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
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).
|
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.
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]