Methyl tributyl ammonium chloride
[CAS# 56375-79-2]

Identification

• Classification: Chemical reagent >> Organic reagent >> Amine salt (ammonium salt)
• Name: Methyl tributyl ammonium chloride
• Synonyms: Methyltributylammonium chloride; Tributylmethylammonium chloride; N,N-Dibutyl-N-methyl-1-butanaminium chloride; Aliquat 175
• Molecular Formula: C₁₃H₃₀ClN
• Molecular Weight: 235.84
• CAS Registry Number: 56375-79-2
• EC Number: 260-135-8
• SMILES: CCCC[N+](C)(CCCC)CCCC.[Cl-]

Properties

• Melting point: 95-99 ºC
• Water solubility: soluble

Safety Data

• Hazard Symbols: GHS07;GHS09 Warning
• Hazard Statements: H302-H315-H319-H335-H400-H410-H411-H413
• Precautionary Statements: P261-P264-P264+P265-P270-P271-P273-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H312
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - single exposure	STOT SE	3	H335
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413

Discovory and Applicatios

Methyl tributylammonium chloride is a quaternary ammonium compound that consists of a methyl group and three butyl groups attached to a nitrogen atom, with chloride serving as the counterion. This compound is commonly synthesized by reacting methyl chloride with tributylamine. Methyl tributylammonium chloride is typically a white solid that is soluble in water and organic solvents like ethanol and acetone.

One of the primary applications of methyl tributylammonium chloride is as a phase transfer catalyst. In this role, it facilitates the transfer of ionic species between immiscible phases, such as water and organic solvents. By bridging the gap between the two phases, it allows reactions that involve ionic reactants in one phase to take place with non-ionic reactants in another phase. This property makes it valuable in various organic syntheses, particularly in reactions where traditional methods may be inefficient or impractical.

Methyl tributylammonium chloride is often used in nucleophilic substitution reactions, where it can enhance the reactivity of certain reagents. It is also employed in alkylation and acylation reactions, as well as in the synthesis of other organic compounds. Its ability to improve the efficiency of these reactions has made it useful in the chemical and pharmaceutical industries, particularly in processes where the conversion of less reactive substrates is required.

In addition to its role in organic synthesis, methyl tributylammonium chloride has also been studied for its use in electrochemical applications. Its solubility in both polar and non-polar solvents allows it to be used in various systems, including those that require the manipulation of ionic species in heterogeneous environments. Furthermore, its role in the preparation of ionic liquids has also been explored, where it serves to enhance the properties of the resulting mixtures in electrochemical processes.

Another potential application of methyl tributylammonium chloride is in the field of antimicrobial treatments. As with other quaternary ammonium compounds, it is believed to exhibit antimicrobial activity. It is thought to interact with microbial cell membranes, disrupting their structure and causing cell death. However, further research is needed to fully understand its potential in this area.

In terms of safety, methyl tributylammonium chloride should be handled with care, as it may cause irritation to the skin, eyes, and respiratory system. Standard safety protocols, such as wearing gloves, goggles, and ensuring adequate ventilation, should be followed when working with this substance.

In conclusion, methyl tributylammonium chloride is an important chemical compound used primarily as a phase transfer catalyst in organic synthesis. Its ability to promote the transfer of ionic species between immiscible phases makes it valuable in various chemical processes. Its applications extend beyond organic synthesis into areas such as electrochemistry and potentially antimicrobial treatments, showcasing its versatility in the chemical industry.

References

2024 Synthesis and Study of the Physicochemical Properties of Composite Solid Electrolytes (C4H9)3CH3NBF4�Cnanodiamonds Russian Journal of Electrochemistry
DOI: 10.1134/s1023193524010105

2024 Effects of a New Synthetic Ionic Liquid on Caking Properties of Coals with Three Different Ranks Coke and Chemistry
DOI: 10.3103/s1068364x2460012x

2023 Green Chemistry Approaches to Cellulose Dissolution and Regeneration Regenerated Cellulose and Composites
DOI: 10.1007/978-981-99-1655-9_2