Benzyltrimethylammonium hydroxide
[CAS# 100-85-6]

Identification

• Classification: Chemical reagent >> Organic reagent >> Amine salt (ammonium salt)
• Name: Benzyltrimethylammonium hydroxide
• Molecular Formula: C₁₀H₁₆N^.OH
• Molecular Weight: 167.25
• CAS Registry Number: 100-85-6
• EC Number: 202-895-5
• SMILES: C[N+](C)(C)CC1=CC=CC=C1.[OH-]

Properties

• Density: 0.95
• Flash point: 15 ºC

Safety Data

• Hazard Symbols: GHS02;GHS05 Danger
• Hazard Statements: H224-H314-H318
• Precautionary Statements: P210-P233-P240-P241-P242-P243-P260-P264-P264+P265-P280-P301+P330+P331-P302+P361+P354-P303+P361+P353-P304+P340-P305+P354+P338-P316-P317-P321-P363-P370+P378-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Serious eye damage	Eye Dam.	1	H318
Skin corrosion	Skin Corr.	1A	H314
Skin corrosion	Skin Corr.	1B	H314
Flammable liquids	Flam. Liq.	1	H224
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	3	H311
Acute toxicity	Acute Tox.	3	H331
Acute toxicity	Acute Tox.	3	H301
Specific target organ toxicity - single exposure	STOT SE	1	H370
Flammable liquids	Flam. Liq.	2	H225
Skin corrosion	Skin Corr.	1C	H314
Specific target organ toxicity - repeated exposure	STOT RE	1	H372

Discovory and Applicatios

Benzyltrimethylammonium hydroxide is a quaternary ammonium compound with the chemical formula C7H11NO. It is composed of a benzyl group attached to a nitrogen atom that is further bonded to three methyl groups, with hydroxide as the counterion. This compound is often synthesized through the alkylation of trimethylamine with benzyl chloride.

Benzyltrimethylammonium hydroxide is primarily used as a phase transfer catalyst in organic synthesis. Phase transfer catalysts are substances that facilitate the transfer of a reactant between two immiscible phases, such as an aqueous and an organic phase. In this context, benzyltrimethylammonium hydroxide is particularly valuable in reactions involving ionized or polar compounds that are poorly soluble in organic solvents. The compound enables these reactions to proceed more efficiently by helping to transfer reactants into the appropriate phase for reaction.

Beyond its catalytic role, benzyltrimethylammonium hydroxide is also used in the synthesis of other quaternary ammonium salts. These salts are important in a wide range of industrial and chemical applications, including in the production of surfactants, detergents, and fabric softeners. Due to the ability of quaternary ammonium compounds like benzyltrimethylammonium hydroxide to interact with both organic and aqueous systems, they are widely utilized in various formulations for cleaning, disinfection, and emulsification.

The compound also plays a role in the development of ionic liquids, which are a class of salts that remain in liquid form at relatively low temperatures. Ionic liquids have garnered interest in various chemical and industrial processes due to their non-volatile nature, high thermal stability, and ability to dissolve a wide range of materials.

While benzyltrimethylammonium hydroxide has proven useful in chemical and industrial applications, it is also of interest in research related to its interactions with biological systems. Quaternary ammonium compounds like this one have been studied for their potential interactions with cell membranes, proteins, and other biological targets, as they are known to exhibit surfactant-like properties.

In summary, benzyltrimethylammonium hydroxide is an important compound in organic synthesis and industrial chemistry, particularly as a phase transfer catalyst. It is also involved in the production of other quaternary ammonium compounds and the development of ionic liquids, although its direct applications in pharmaceuticals or other biological uses remain limited.

References

2023. Assessing the impact of choline chloride and benzyltrimethylammonium chloride-based deep eutectic solvents on the structure and conformational dynamics of bovine serum albumin: a combined steady-state, time-resolved fluorescence and fluorescence correlation spectroscopic study. Physical Chemistry Chemical Physics, 25(29).
DOI: 10.1039/d3cp01380d

2023. Development of a radical polymerization algorithm for molecular dynamics simulations of antifreezing hydrogels with double-network structures. npj Computational Materials, 9(1).
DOI: 10.1038/s41524-023-01161-x

2001. Benzyltrimethylammonium hydroxide trihydrate containing hydroxide-water layers. Acta Crystallographica Section C, 57(3).
DOI: 10.1107/S0108270100019363