Phenyltrimethylammonium chloride
[CAS# 138-24-9]

Identification

• Classification: Chemical reagent >> Organic reagent >> Amine salt (ammonium salt)
• Name: Phenyltrimethylammonium chloride
• Synonyms: N,N,N-Trimethylanilinium chloride; Trimethylphenylammonium chloride
• Molecular Formula: C₉H₁₄N.Cl
• Molecular Weight: 171.67
• CAS Registry Number: 138-24-9
• EC Number: 205-319-0
• SMILES: C[N+](C)(C)C1=CC=CC=C1.[Cl-]

Properties

• Melting point: 246-248 °C (dec.) (Expl.)
• Water solubility: soluble

Safety Data

• Hazard Symbols: GHS06 Danger
• Risk Statements: H301-H311
• Safety Statements: P262-P264-P270-P280-P301+P316-P302+P352-P316-P321-P330-P361+P364-P405-

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	3	H311
Skin irritation	Skin Irrit.	2	H315
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H332

• Transport Information: UN 2811

Discovery and Applications

Phenyltrimethylammonium chloride (C6H5N+(CH3)3Cl) is a quaternary ammonium salt that consists of a phenyl group attached to a trimethylammonium cation (C6H5N+(CH3)3) and a chloride anion (Cl−). It is synthesized by reacting trimethylamine with benzyl chloride or phenylmethyl chloride in an appropriate solvent.

Phenyltrimethylammonium chloride is commonly used as a phase transfer catalyst in organic synthesis. A phase transfer catalyst facilitates the transfer of reactants between two immiscible phases, often between water and an organic solvent. The compound’s quaternary ammonium structure allows it to solvate anionic species and transfer them into organic solvents, where they would otherwise be insoluble. This ability to assist in the movement of ions between phases is particularly useful in reactions involving anions, where it enhances the reactivity of certain nucleophiles in organic reactions.

Its primary application is in organic synthesis, particularly in nucleophilic substitution reactions, where it aids in the formation of various organic compounds. For instance, phenyltrimethylammonium chloride can be used to catalyze the alkylation of phenols, the preparation of alkyl and aryl derivatives, and various other transformations involving halides and other reactive anionic species. Additionally, it has been utilized in reactions where ionic species need to be transferred between aqueous and organic phases to facilitate efficient reactions.

The compound has also found use in research as a reagent for various synthetic applications due to its phase transfer capabilities. In some cases, it is employed to aid in the solubilization of water-soluble anions in nonpolar solvents or to promote the synthesis of other quaternary ammonium salts.

In summary, phenyltrimethylammonium chloride is an important chemical used in organic synthesis, primarily as a phase transfer catalyst. It plays a critical role in facilitating reactions that require the transfer of anionic species between immiscible phases, thereby enhancing the efficiency of various chemical transformations.

References

2024. Self-powered and charge-transport-layer-free photodetectors based on chloride treated perovskites for weak light detection. Science China Materials, 67(6).
DOI: 10.1007/s40843-023-2832-y

2024. Phase stabilization of cesium lead iodide perovskites for use in efficient optoelectronic devices. NPG Asia Materials, 16(1).
DOI: 10.1038/s41427-024-00540-0

2024. Weakly Polarized Organic Cation-Modified Hydrated Vanadium Oxides for High-Energy Efficiency Aqueous Zinc-Ion Batteries. Nano-Micro Letters, 16(1).
DOI: 10.1007/s40820-024-01339-y