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Triethylbenzylammonium chloride (TEBAC) is a quaternary ammonium salt widely used as a phase-transfer catalyst (PTC) in organic synthesis.

Description:

Triethylbenzylammonium chloride consists of a positively charged quaternary ammonium cation (bearing three ethyl groups and one benzyl group) paired with a chloride anion. It is typically a white to off-white crystalline solid or powder, readily soluble in water and many polar organic solvents.

TEBAC facilitates reactions between reagents located in immiscible phases (commonly aqueous and organic phases) by transferring ionic species—such as anions—into the organic phase where the reaction can proceed efficiently.

Key Features

Phase-Transfer Catalyst.

Enhances reactions between water-soluble inorganic salts and organic substrates.

Commonly used in alkylation, substitution, condensation, and oxidation reactions.

Chemical Properties.

Chemical name: Triethylbenzylammonium chloride

Molecular formula: C₁₃H₂₂NCl

Molecular weight: ~227.77 g/mol

Structure: Quaternary ammonium salt (permanently charged).

Solubility:

Soluble in water.

Soluble in polar organic solvents (e.g., alcohols, acetone).

Limited solubility in nonpolar solvents.

Thermal & Chemical Stability.

Stable under normal laboratory and industrial conditions.

Non-volatile.

Resistant to hydrolysis compared with tertiary amines.

Handling & Safety.

Hygroscopic; should be stored in a dry, tightly closed container.

Can cause skin and eye irritation.

Standard PPE (gloves, goggles) recommended during handling.