Benzyltrimethylammonium chloride
[CAS# 56-93-9]

Identification

• Classification: Chemical reagent >> Organic reagent >> Amine salt (ammonium salt)
• Name: Benzyltrimethylammonium chloride
• Synonyms: BTM; N,N,N-Trimethylbenzenemethanaminium chloride; TMBAC
• Molecular Formula: C₁₀H₁₆N.Cl
• Molecular Weight: 185.70
• CAS Registry Number: 56-93-9
• EC Number: 200-300-3
• SMILES: C[N+](C)(C)CC1=CC=CC=C1.[Cl-]

Properties

• Density: 0.99 g/mL (Expl.)
• Melting point: 230-235 °C (dec.) (Expl.)
• Refraction index: 1.444 (Expl.)Water solubility

Safety Data

• Hazard Symbols: GHS05;GHS07;GHS08;GHS09 Danger
• Risk Statements: H301+H311-H301-H311-H315-H319-H332-H341-H400-H412
• Safety Statements: P203-P261-P262-P264-P264+P265-P270-P271-P273-P280-P301+P316-P302+P352-P304+P340-P305+P351+P338-P316-P317-P318-P321-P330-P332+P317-P337+P317-P361+P364-P362+P364-P391-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	4	H332
Germ cell mutagenicity	Muta.	2	H341
Acute toxicity	Acute Tox.	3	H311
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Acute toxicity	Acute Tox.	4	H302
Skin corrosion	Skin Corr.	1B	H314
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Skin corrosion	Skin Corr.	1	H314
Serious eye damage	Eye Dam.	1	H318
Specific target organ toxicity - single exposure	STOT SE	3	H336

Discovery and Applications

Benzyltrimethylammonium chloride is a quaternary ammonium salt with the molecular formula C9H12ClN. It is formed by the reaction of benzyl chloride with trimethylamine. The compound is typically a white or colorless crystalline solid that is soluble in water and a variety of organic solvents. As a quaternary ammonium compound, it has a positively charged nitrogen atom surrounded by three methyl groups and a benzyl group, with chloride serving as the counterion.

Benzyltrimethylammonium chloride is widely utilized in the chemical industry, particularly as a phase transfer catalyst. In this role, it facilitates the transfer of ionic species between immiscible phases, such as water and organic solvents. The compound helps accelerate reactions involving ionic reactants in one phase with non-ionic reactants in another. This ability to promote the transfer of ions across different phases makes benzyltrimethylammonium chloride valuable in a variety of organic syntheses, especially in processes where traditional methods may not be effective or efficient.

One key application of benzyltrimethylammonium chloride is in the synthesis of organic compounds. It is commonly used in nucleophilic substitution reactions, where it can enhance the reactivity of nucleophiles and electrophiles in a non-aqueous environment. This feature makes it particularly useful in processes like alkylation, acylation, and the preparation of esters. In these reactions, the compound helps solvate the ionic intermediates, thereby improving reaction rates and yields.

In addition to its use in organic synthesis, benzyltrimethylammonium chloride also finds application in the preparation of ionic liquids. Ionic liquids are salts that are in a liquid state at relatively low temperatures, and they have gained attention in recent years for their unique properties, such as low volatility, high ionic conductivity, and good solvating ability. Benzyltrimethylammonium chloride can be used as a precursor or an additive in the formation of ionic liquids, which are employed in a wide range of processes, including electrochemical applications and green chemistry initiatives.

The compound is also involved in the production of surfactants. Due to the presence of both a hydrophilic ammonium group and a hydrophobic benzyl group, benzyltrimethylammonium chloride can act as a surfactant, helping to reduce surface tension and stabilize emulsions. This property is beneficial in various cleaning applications, including in the formulation of disinfectants, detergents, and fabric softeners.

Benzyltrimethylammonium chloride has also been explored for its potential in antimicrobial applications. Like other quaternary ammonium compounds, it is thought to possess some degree of antimicrobial activity. It is believed to work by disrupting the structure of microbial cell membranes, leading to cell death. However, while it has been studied for such applications, it is primarily recognized for its utility as a chemical reagent and catalyst in industrial processes.

In terms of safety, benzyltrimethylammonium chloride should be handled with care. As with other quaternary ammonium compounds, it may cause irritation to the skin, eyes, and respiratory system upon exposure. It is important to follow proper safety protocols, including wearing appropriate personal protective equipment such as gloves, goggles, and ensuring adequate ventilation when working with this substance.

In conclusion, benzyltrimethylammonium chloride is a versatile chemical compound widely used in organic synthesis, phase transfer catalysis, the preparation of ionic liquids, and as a surfactant. Its ability to facilitate the transfer of ionic species between immiscible phases makes it particularly valuable in a variety of chemical processes. Additionally, its potential antimicrobial properties add to its range of applications in industrial and cleaning products. However, as with all chemicals, it should be handled with appropriate safety precautions.

References

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

2024 Esterification of lignin-derived phenolic compound eugenol to eugenol benzoate using acidic deep eutectic solvent as a catalyst Chemical Papers
DOI: 10.1007/s11696-024-03762-2

2024 Rapid degradation of thermosetting ester epoxies and monomer recovery methods Colloid and Polymer Science
DOI: 10.1007/s00396-024-05287-2