Triethylmethylammonium hydroxide
[CAS# 109334-81-8]

Identification

• Classification: Surfactant >> Cationic surfactant >> Quaternary ammonium salt type
• Name: Triethylmethylammonium hydroxide
• Synonyms: triethyl(methyl)azanium hydroxide
• Molecular Formula: C₇H₁₉NO
• Molecular Weight: 133.23
• CAS Registry Number: 109334-81-8
• EC Number: 600-911-9
• SMILES: CC[N+](C)(CC)CC.[OH-]

Properties

• Boiling point: 102 °C (Expl.)
• Refraction index: 1.373 (Expl.)

Safety Data

• Hazard Symbols: GHS05 Danger
• Risk Statements: H314
• Safety Statements: P260-P264-P280-P301+P330+P331-P302+P361+P354-P304+P340-P305+P354+P338-P316-P321-P363-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1A	H314

Discovery and Applications

Triethylmethylammonium hydroxide is a chemical compound that consists of a quaternary ammonium salt, where a central nitrogen atom is bonded to three ethyl groups and one methyl group, with the hydroxide ion as the counterion. It is a colorless or pale yellow liquid, and it is commonly used as a strong base and a phase transfer catalyst in various chemical reactions. The compound plays a significant role in organic synthesis and in industrial applications.

Triethylmethylammonium hydroxide is typically synthesized by reacting triethylmethylammonium chloride with a strong base, such as sodium hydroxide or potassium hydroxide. The reaction displaces the chloride ion and forms the hydroxide salt. The compound is known to be a strong nucleophile due to the presence of the hydroxide ion, which makes it highly reactive in various chemical processes.

One of the primary applications of Triethylmethylammonium hydroxide is in organic synthesis, particularly in phase transfer catalysis. In this context, it serves to facilitate the transfer of reactants between different phases, often between aqueous and organic phases. It is widely used in reactions where the reactants are not readily soluble in the same phase, enabling the formation of products that would be difficult to synthesize otherwise. Phase transfer catalysis is crucial in many industrial processes, including the synthesis of pharmaceuticals, agrochemicals, and fine chemicals.

Triethylmethylammonium hydroxide is also utilized in the preparation of various quaternary ammonium compounds, which have applications in surfactant chemistry, as disinfectants, and in the formulation of some types of polymer materials. These quaternary ammonium salts are important in the cleaning industry, especially as disinfectants for industrial and household use, as they exhibit strong antimicrobial properties.

In addition to its use in organic synthesis and as a phase transfer catalyst, Triethylmethylammonium hydroxide finds applications in the field of analytical chemistry. It is used as a base in titration methods, particularly in the analysis of acidic compounds. The compound's strong basicity and ability to react efficiently with acidic substances make it useful in various analytical techniques, including the preparation of buffers and in acid-base neutralization reactions.

In conclusion, Triethylmethylammonium hydroxide is a valuable chemical compound with a broad range of applications in organic synthesis, phase transfer catalysis, the preparation of quaternary ammonium salts, and analytical chemistry. Its reactivity and ability to facilitate reactions between different phases make it an important tool in industrial and laboratory settings.

References

2010. Hydrocarbonation Using Nitroalkane Anions. Science of Synthesis, 47, 1046.
DOI: 10.1055/sos-SD-047-00418