Benzyltributylammonium bromide
[CAS# 25316-59-0]

Identification

• Classification: Chemical reagent >> Organic reagent >> Amine salt (ammonium salt)
• Name: Benzyltributylammonium bromide
• Molecular Formula: C₁₉H₃₄N.Br
• Molecular Weight: 356.39
• CAS Registry Number: 25316-59-0
• EC Number: 246-819-9
• SMILES: CCCC[N+](CCCC)(CCCC)CC1=CC=CC=C1.[Br-]

Properties

• Melting point: 169-171 °C (Expl.)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319
• Safety Statements: P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312

Discovery and Applications

Benzyltributylammonium bromide (C20H34BrN) is a quaternary ammonium salt formed by the combination of benzyl chloride and tributylamine in the presence of a bromide source. It is commonly used as a phase-transfer catalyst in organic synthesis. This chemical is composed of a benzyl group (C6H5CH2), three butyl groups (C4H9), and a bromide anion (Br−) associated with a nitrogen atom.

As a phase-transfer catalyst, benzyltributylammonium bromide facilitates the transfer of anionic species between two immiscible solvents, usually water and an organic solvent. This process is particularly useful in reactions where an ionic compound is involved in a non-aqueous medium. It can accelerate reactions such as nucleophilic substitutions, alkylation reactions, and esterification by transferring the ionic species into the organic phase where the reaction occurs.

Benzyltributylammonium bromide is often employed in reactions that involve nucleophilic attack on electrophilic centers, enhancing the rate of the reaction and improving overall yields. It is especially useful in reactions that require the solubilization of ions in non-polar organic solvents.

Due to its ability to assist in various organic transformations, it is applied in both laboratory-scale and industrial-scale synthetic processes. The chemical's role in improving the efficiency of reactions, particularly those involving organic anions, makes it a valuable reagent in synthetic chemistry, particularly in the preparation of a variety of organic compounds.

References

1988. Improvement of the extraction spectrophotometric determination of total carbonate using uranyl quinolin-8-olate and benzyltributylammonium bromide. Microchimica Acta, 95(1-6).
DOI: 10.1007/BF01244062

2021. Preparation of new hydrophobic deep eutectic solvents and their application in dispersive liquid-liquid microextraction of Sudan dyes from food samples. Analytical and Bioanalytical Chemistry, 413(15).
DOI: 10.1007/s00216-021-03337-0

2019. Determination of sulfonated azo dyes in chili powders by MALDI-TOF MS. Analytical and Bioanalytical Chemistry, 411(20).
DOI: 10.1007/s00216-019-01965-1