Tetrabutylammonium hydrogen sulfate
[CAS# 32503-27-8]

Identification

• Classification: Surfactant >> Cationic surfactant >> Quaternary ammonium salt type
• Name: Tetrabutylammonium hydrogen sulfate
• Synonyms: TBAHS
• Molecular Formula: C₁₆H₃₅N.H₂SO₄
• Molecular Weight: 339.53
• CAS Registry Number: 32503-27-8
• EC Number: 251-068-5
• SMILES: CCCC[N+](CCCC)(CCCC)CCCC.OS(=O)(=O)[O-]

Properties

• Melting point: 168-172 °C
• Water solubility: Soluble

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H302-H314-H315-H318-H319-H335-H412
• Safety Statements: P260-P261-P264-P264+P265-P270-P271-P273-P280-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P351+P338-P305+P354+P338-P316-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P363-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Serious eye damage	Eye Dam.	1	H318
Skin corrosion	Skin Corr.	1B	H314
Skin corrosion	Skin Corr.	1	H314
Skin corrosion	Skin Corr.	1A	H314
Acute toxicity	Acute Tox.	4	H312
Eye irritation	Eye Irrit.	2A	H319
Acute toxicity	Acute Tox.	4	H332

Discovery and Applications

Tetrabutylammonium hydrogen sulfate is a quaternary ammonium salt that has gained prominence in various fields of chemistry due to its unique properties and versatile applications. The compound is known for its ability to act as a phase transfer catalyst, facilitating reactions between reactants in different phases, particularly in organic synthesis. Its discovery is linked to the need for efficient catalysts that can enhance reaction rates and selectivity, particularly in processes involving ionic compounds and organic substrates.

The synthesis of tetrabutylammonium hydrogen sulfate typically involves the neutralization of tetrabutylammonium hydroxide with sulfuric acid. This process not only yields the desired salt but also highlights its stability and solubility in polar organic solvents, making it an attractive candidate for numerous applications. The discovery of this compound emerged from ongoing research into improving catalytic processes and optimizing reaction conditions in synthetic organic chemistry.

One of the primary applications of tetrabutylammonium hydrogen sulfate is in the field of organic synthesis, where it serves as an effective phase transfer catalyst. By facilitating the migration of reactants between aqueous and organic phases, it significantly enhances the efficiency of various chemical reactions, including alkylation, acylation, and nucleophilic substitutions. The use of this compound in synthetic methodologies has allowed chemists to achieve higher yields and shorter reaction times, which are critical factors in both academic research and industrial applications.

Moreover, tetrabutylammonium hydrogen sulfate is utilized in the synthesis of a variety of compounds, including pharmaceuticals and agrochemicals. Its ability to promote reactions involving polar substrates makes it particularly valuable in the production of complex organic molecules. The compound's effectiveness in catalyzing reactions involving functional groups such as alcohols, amines, and carboxylic acids has been well-documented in the literature, further solidifying its role in modern synthetic chemistry.

In addition to its applications in organic synthesis, tetrabutylammonium hydrogen sulfate has found utility in analytical chemistry, particularly in the extraction and purification of various compounds. Its unique solubility properties allow for selective extraction processes that can enhance the analysis of target compounds in complex mixtures. This has made it a useful reagent in various analytical techniques, including chromatography.

The versatility and effectiveness of tetrabutylammonium hydrogen sulfate continue to inspire research aimed at discovering new synthetic methodologies and improving existing processes. Ongoing studies are focused on optimizing its use in diverse chemical reactions and exploring its potential in new applications, including catalysis and materials science. As researchers uncover more about this compound, it is likely to play an increasingly important role in the advancement of synthetic organic chemistry.

References

2024 Combined experimental and computational investigation of tetrabutylammonium bromide-carboxylic acid-based deep eutectic solvents. Journal of Molecular Graphics and Modelling, 108, 2.
DOI: 10.1016/j.jmgm.2024.108805


2024 Synthesis of Phosphine Chalcogenides Using Tetrabutylammonium Chalcogenocyanates. Chemical and Pharmaceutical Bulletin, 72, 8.
DOI: 10.1248/cpb.c24-00372

2024 Spectrophotometric determination for green hydrophobic deep eutectic solvent-based microextraction of Brilliant Blue FCF (E133) from beverages. Journal of chromatography. A,1763, 1.
DOI: 10.1016/j.chroma.2024.465374