Benzyltriethylammonium hydroxide
[CAS# 1836-42-6]

Identification

• Classification: Chemical reagent >> Organic reagent >> Amine salt (ammonium salt)
• Name: Benzyltriethylammonium hydroxide
• Molecular Formula: C₁₃H₂₂N.OH
• Molecular Weight: 209.33
• CAS Registry Number: 1836-42-6
• EC Number: 217-402-9
• SMILES: CC[N+](CC)(CC)CC1=CC=CC=C1.[OH-]

Properties

• Refraction index: 1.423 (Expl.)

Safety Data

• Hazard Symbols: GHS05 Danger
• Risk Statements: H314
• Safety Statements: P260-P280-P301+P330+P331+P310-P303+P361+P353+P310+P363-P304+P340+P310-P305+P351+P338+P310

Discovery and Applications

Benzyltriethylammonium hydroxide (C6H5CH2C2H5)3NHOH is a quaternary ammonium hydroxide, typically prepared by reacting benzyltriethylammonium chloride with a strong base like sodium hydroxide. It consists of a benzyl group attached to a nitrogen atom that is also bonded to three ethyl groups, with a hydroxide anion balancing the charge.

This compound is primarily used as a phase-transfer catalyst in various organic reactions. Phase-transfer catalysts are used to facilitate the transfer of reactants between two immiscible phases, such as an organic phase and an aqueous phase. By acting as a mediator, benzyltriethylammonium hydroxide increases the reactivity of certain reactions that otherwise would be slow or difficult to occur due to the poor solubility of reactants in different phases.

Benzyltriethylammonium hydroxide is particularly useful in nucleophilic substitution reactions where anionic nucleophiles, like halides or hydroxide ions, need to be transferred into an organic phase. In these reactions, the hydroxide anion helps facilitate the formation of desired products by increasing the rate of nucleophilic attack.

It is also used in the synthesis of various organic compounds, including alkylated amines and other nitrogen-containing compounds. Its ability to mediate reactions involving anionic species makes it valuable in a range of chemical processes, especially those that involve the synthesis of complex organic molecules. Additionally, its use as a catalyst in reactions like esterification and alkylation has been well-documented in the literature.

In conclusion, benzyltriethylammonium hydroxide is an important chemical compound in organic synthesis, primarily employed as a phase-transfer catalyst. Its ability to facilitate reactions between immiscible phases and to increase the reactivity of nucleophilic species makes it a versatile and valuable reagent in various chemical processes.

References

2022. Preparation of ceria by combined sol-gel and hydrothermal method: insights from the effects of different bases on the particle size distribution. Chemical Papers, 76(8).
DOI: 10.1007/s11696-022-02217-w

1977. Reaction of carbonyl compounds in the presence of phase transfer catalysts 10. Formation of benzyltriethylammonium hydroxide from chloride under conditions of interfacial catalysis, and their solubilities in mixtures of acetone and benzene. Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science, 26(6).
DOI: 10.1007/BF00963678