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Benzyltributylammonium bromide
[CAS# 25316-59-0]

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Complete supplier list of Benzyltributylammonium bromide
Identification
Classification Chemical reagent >> Organic reagent >> Amine salt (ammonium salt)
Name Benzyltributylammonium bromide
Molecular Structure CAS # 25316-59-0, 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 ºC (Expl.)
Safety Data
Hazard Symbols symbol   GHS07 Warning    Details
Hazard Statements H315-H319    Details
Precautionary Statements P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313    Details
Hazard Classification
up    Details
HazardClassCategory CodeHazard Statement
Eye irritationEye Irrit.2H319
Skin irritationSkin Irrit.2H315
Specific target organ toxicity - single exposureSTOT SE3H335
Acute toxicityAcute Tox.4H302
Acute toxicityAcute Tox.4H332
Acute toxicityAcute Tox.4H312
SDS Available
up Discovory and Applicatios
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
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