Benzyltributylammonium chloride
[CAS# 23616-79-7]

Identification

• Classification: Chemical reagent >> Organic reagent >> Amine salt (ammonium salt)
• Name: Benzyltributylammonium chloride
• Molecular Formula: C₁₉H₃₄N.Cl
• Molecular Weight: 311.94
• CAS Registry Number: 23616-79-7
• EC Number: 245-787-3
• SMILES: CCCC[N+](CCCC)(CCCC)CC1=CC=CC=C1.[Cl-]

Properties

• Melting point: 155-163 °C (Expl.)
• Water solubility: soluble

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H302-H314-H315-H318-H319
• Safety Statements: P260-P264-P264+P265-P270-P280-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P351+P338-P305+P354+P338-P316-P317-P321-P330-P332+P317-P337+P317-P362+P364-P363-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Skin corrosion	Skin Corr.	1B	H314
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Serious eye damage	Eye Dam.	1	H318
Skin corrosion	Skin Corr.	1C	H314
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332

• Transport Information: UN 3263

Discovery and Applications

Benzyltributylammonium chloride (C20H34ClN) is a quaternary ammonium salt composed of a benzyl group (C6H5CH2) and three butyl groups (C4H9) attached to a nitrogen atom, with chloride (Cl−) as the counter ion. It is typically synthesized through the reaction of benzyl chloride with tributylamine in a suitable solvent. The resulting compound is often used as a phase-transfer catalyst in organic synthesis.

Benzyltributylammonium chloride serves as a phase-transfer catalyst, facilitating the transfer of ionic species between immiscible solvents, particularly between aqueous and organic phases. This property is particularly useful in reactions that require the presence of ions in an organic phase, such as nucleophilic substitutions and reactions involving hydroxide, cyanide, or other nucleophiles.

In organic chemistry, it is commonly employed in various reactions, including the synthesis of ethers, esters, and other organic compounds. By enabling the reaction of inorganic salts with organic compounds in non-aqueous media, it significantly increases the efficiency of these processes.

Additionally, benzyltributylammonium chloride has been explored in the context of its use in organic reactions requiring controlled solubility and reactivity. It has found utility in the synthesis of specific functionalized compounds, where its ability to solvate ionic intermediates is beneficial. This versatility in catalysis makes it a valuable reagent in laboratory-scale organic synthesis, as well as in some industrial applications.

References

1987. Spectrophotometric determination of ruthenium after extraction of perruthenate with benzyltributylammonium chloride. Fresenius' Journal of Analytical Chemistry, 328(4-5).
DOI: 10.1007/BF00323663

1977. Extraction of steroid sulphates from plasma by use of quaternary ammonium salts. Fresenius' Zeitschrift für analytische Chemie, 287(2).
DOI: 10.1007/BF00487933

1976. Selective extraction and determination of testosterone sulphate from plasma. Fresenius' Zeitschrift für analytische Chemie, 281(2).
DOI: 10.1007/BF00488398