Benzyltriethylammonium chloride
[CAS# 56-37-1]

Identification

• Classification: Surfactant >> Cationic surfactant >> Quaternary ammonium salt type
• Name: Benzyltriethylammonium chloride
• Synonyms: N,N,N'-Triethylbenzenemethanaminium chloride; BTEAC
• Molecular Formula: C₁₃H₂₂ClN
• Molecular Weight: 227.78
• CAS Registry Number: 56-37-1
• EC Number: 200-270-1
• SMILES: CC[N+](CC)(CC)CC1=CC=CC=C1.[Cl-]

Properties

• Melting point: 190-192 °C (decomp.) (Expl.)
• Bpoiling point: 445 °C (Expl.)
• Water solubility: 700 g/L (20 °C)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H317-H319-H335-H412
• Safety Statements: P261-P264-P264+P265-P270-P271-P272-P273-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P333+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Skin sensitization	Skin Sens.	1B	H317
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin sensitization	Skin Sens.	1	H317
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332
Flammable solids	Flam. Sol.	2	H228
Flammable liquids	Flam. Liq.	2	H225
Eye irritation	Eye Irrit.	2A	H319
Specific target organ toxicity - single exposure	STOT SE	3	H371
Skin corrosion	Skin Corr.	1B	H314
Serious eye damage	Eye Dam.	1	H318
Specific target organ toxicity - single exposure	STOT SE	3	H336

Discovery and Applications

Benzyltriethylammonium chloride is a quaternary ammonium salt composed of a benzyl group and three ethyl groups attached to a nitrogen atom, with chloride as the counterion. It is synthesized by reacting benzyl chloride with triethylamine. This compound is typically encountered as a white crystalline solid, highly soluble in water and organic solvents such as ethanol and acetone.

The primary use of benzyltriethylammonium chloride lies in its role as a phase transfer catalyst. As a quaternary ammonium salt, it exhibits amphiphilic properties, which enable it to facilitate the transfer of ions between immiscible phases, such as aqueous and organic solvents. In this capacity, it is commonly employed to accelerate reactions where ionic species in one phase need to react with non-ionic reactants in another phase. One of its key applications is in organic synthesis, where it is used to promote nucleophilic substitutions, particularly in reactions involving halides and other electrophiles.

Benzyltriethylammonium chloride is also used in the synthesis of various organic compounds, including alkylation reactions and other processes requiring the activation of reagents that are less reactive under normal conditions. It is valuable in the preparation of more complex molecules in the pharmaceutical and chemical industries.

In addition to its role as a phase transfer catalyst, benzyltriethylammonium chloride is also explored in research contexts involving its interactions with biological systems. Quaternary ammonium compounds like benzyltriethylammonium chloride are known to exhibit antibacterial and antifungal properties, and as such, they have been studied for their potential applications in antimicrobial formulations. They can disrupt microbial cell membranes by interacting with phospholipid bilayers, thereby affecting cellular function.

Benzyltriethylammonium chloride is also used in electrochemical applications. In some cases, it has been explored as a component in ionic liquids, where its properties are useful for facilitating various types of electrochemical reactions. Its high solubility in both polar and non-polar solvents makes it suitable for use in applications that require the manipulation of ionic species in heterogeneous environments.

While it is considered relatively stable, safety precautions should be taken when handling benzyltriethylammonium chloride, as it may cause irritation to the skin, eyes, or respiratory system. Appropriate protective measures, such as wearing gloves, goggles, and working in a well-ventilated area, are recommended when working with this substance.

In summary, benzyltriethylammonium chloride is a versatile chemical compound widely used in organic synthesis, particularly as a phase transfer catalyst. Its ability to promote the transfer of ions across immiscible solvents enhances the efficiency of various reactions, making it a valuable reagent in both research and industrial settings. Its antimicrobial properties and potential applications in electrochemical systems further broaden its scope of use in the chemical sciences.

References

2024 Supramolecular deep eutectic solvents in extraction processes: a review Environmental Chemistry Letters
DOI: 10.1007/s10311-024-01795-3

2024 High biomass content in epoxy vitrimers: a study on bio-based and reprocessable thermosets Macromolecular Research
DOI: 10.1007/s13233-024-00333-y

2024 Helicobacter pylori and acne vulgaris: is there a relationship? Archives of Dermatological Research
DOI: 10.1007/s00403-024-03300-w