Tetrabutylammonium hydroxide
[CAS# 2052-49-5]

Identification

• Classification: Chemical reagent >> Organic reagent >> Amine salt (ammonium salt)
• Name: Tetrabutylammonium hydroxide
• Molecular Formula: C₁₆H₃₆N.OH
• Molecular Weight: 259.47
• CAS Registry Number: 2052-49-5
• EC Number: 218-147-6
• SMILES: CCCC[N+](CCCC)(CCCC)CCCC.[OH-]

Properties

• Density: 0.97 g/mL (Expl.)
• Refraction index: 1.405 (Expl/)
• Flash point: 11 °C (Expl.)

Safety Data

• Hazard Symbols: GHS02;GHS05;GHS07 Danger
• Risk Statements: H226-H302-H314-H318
• Safety Statements: P210-P233-P240-P241-P242-P243-P260-P264-P264+P265-P270-P280-P301+P317-P301+P330+P331-P302+P361+P354-P303+P361+P353-P304+P340-P305+P354+P338-P316-P317-P321-P330-P363-P370+P378-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	4	H302
Flammable liquids	Flam. Liq.	3	H226
Skin corrosion	Skin Corr.	1A	H314
Skin sensitization	Skin Sens.	1	H317
Substances or mixtures corrosive to metals	Met. Corr.	1	H290
Specific target organ toxicity - single exposure	STOT SE	3	H336
Eye irritation	Eye Irrit.	2	H319
Flammable liquids	Flam. Liq.	2	H225
Acute toxicity	Acute Tox.	4	H312
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Skin irritation	Skin Irrit.	2	H315
Germ cell mutagenicity	Muta.	2	H341

• Transport Information: UN 1719; UN 2924

Discovery and Applications

Tetrabutylammonium hydroxide (C16H35NO) is a quaternary ammonium salt composed of a tetrabutylammonium cation (C4H9)4N+ and a hydroxide anion (OH−). It is typically synthesized by the reaction of tetrabutylammonium chloride with an aqueous solution of sodium hydroxide. This compound is usually encountered as an aqueous solution, since tetrabutylammonium hydroxide itself is highly soluble in water.

Tetrabutylammonium hydroxide is primarily used in organic synthesis, particularly as a phase-transfer catalyst. In phase-transfer catalysis, it facilitates the movement of hydroxide ions across an interface between immiscible solvents, such as water and organic solvents. This property significantly enhances the rate of reactions where a hydroxide ion is required but the hydroxide is present in a less reactive or less accessible phase. This is especially useful in reactions such as the deprotonation of weak acids or the conversion of certain functional groups.

Additionally, tetrabutylammonium hydroxide is employed in various reactions involving nucleophilic substitution, where it aids in the activation of certain reagents. It is used in the preparation of specific organic compounds, including alkylation and acylation products. Its strong basicity and solubility properties make it an essential reagent in synthetic chemistry, particularly for reactions requiring a source of hydroxide in non-aqueous systems.

In electrochemistry, tetrabutylammonium hydroxide has found applications in preparing ionic liquids, which are used in a variety of electrochemical processes. It can also be utilized in the synthesis of functional materials that require specific solubility or ionic conductivity.

Overall, tetrabutylammonium hydroxide is a versatile chemical with significant applications in organic synthesis, particularly as a phase-transfer catalyst, and in the preparation of ionic liquids and functional materials. Its ability to facilitate the transfer of hydroxide ions in organic reactions has made it a valuable tool in chemical research and industrial applications.

References

2024. Exploration of photoluminescence properties and photocatalytic efficiencies of organic contaminants using Ni-doped PbMoO4 nanoparticles. Emergent Materials.
DOI: 10.1007/s42247-024-00917-5

2024. A Cost-Effective, Eco-Friendly and Functional Wastewater Pre-Treatment Procedure Development for the Degradation of β-Lactam Antibiotic Residues Discharged from Cephalosporin Drug Manufacturing Plant. Water, Air, & Soil Pollution, 235(12).
DOI: 10.1007/s11270-024-07606-3

2010. Conjugated polymer nanoparticles for biomedical in vivo imaging. Chemical Communications, 46(10).
DOI: 10.1039/b923309a