N,N,N-Trimethyloctadecan-1-aminium iodide
[CAS# 4292-25-5]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Amine
• Name: N,N,N-Trimethyloctadecan-1-aminium iodide
• Synonyms: N,N,N-Trimethyl-1-octadecanaminium iodide
• Molecular Formula: C₂₁H₄₆IN
• Molecular Weight: 439.50
• CAS Registry Number: 4292-25-5
• EC Number: 855-036-7
• SMILES: CCCCCCCCCCCCCCCCCC[N+](C)(C)C.[I-]

Safety Data

• Hazard Statements: H302-H311-H314-H318-H372-H400-H410
• Precautionary Statements: P260-P262-P264-P264+P265-P270-P273-P280-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P354+P338-P316-P317-P319-P321-P330-P361+P364-P363-P391-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	3	H311
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Skin corrosion	Skin Corr.	1C	H314
Acute toxicity	Acute Tox.	4	H302
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Specific target organ toxicity - repeated exposure	STOT RE	1	H372

Discovory and Applicatios

N,N,N-Trimethyloctadecan-1-aminium iodide, also known as trimethyl octadecylammonium iodide, is a quaternary ammonium compound with a long alkyl chain. It consists of an octadecyl group (18 carbon atoms) attached to a nitrogen atom, which is also bonded to three methyl groups and an iodide ion. This compound is typically synthesized by reacting octadecan-1-amine with methyl iodide in the presence of a base, resulting in the formation of the quaternary ammonium iodide salt.

The discovery of N,N,N-Trimethyloctadecan-1-aminium iodide can be traced to the broader field of quaternary ammonium salts, which are well-known for their surfactant properties. Quaternary ammonium compounds, including N,N,N-Trimethyloctadecan-1-aminium iodide, have been studied for their unique chemical and physical properties, such as their ability to act as surfactants, emulsifiers, and antimicrobial agents. The development of these compounds dates back to the early 20th century, with increasing interest in their applications in both industrial and medical fields.

N,N,N-Trimethyloctadecan-1-aminium iodide is primarily used in various applications due to its surfactant properties. It is commonly employed in the formulation of personal care products, such as shampoos, conditioners, and skin cleansers. Its ability to act as a cationic surfactant makes it effective in modifying the surface properties of hair and skin, imparting conditioning effects and providing antistatic properties. In hair care formulations, for example, it is used to improve the texture and manageability of hair by reducing static buildup and providing smoothness.

Another significant application of N,N,N-Trimethyloctadecan-1-aminium iodide is in the field of chemical manufacturing, where it serves as a phase transfer catalyst. Phase transfer catalysis is a technique that facilitates the transfer of reactants between immiscible phases, often between an aqueous and an organic phase. This is important in a variety of chemical reactions, particularly those that involve the exchange of ions or the synthesis of complex organic molecules. The use of quaternary ammonium salts like N,N,N-Trimethyloctadecan-1-aminium iodide enables efficient catalysis in reactions that would otherwise be slow or inefficient due to the immiscibility of the phases involved.

In addition to its role as a surfactant and catalyst, N,N,N-Trimethyloctadecan-1-aminium iodide has been studied for its antimicrobial properties. Many quaternary ammonium compounds, including this one, exhibit activity against a wide range of bacteria, fungi, and viruses. This antimicrobial effect makes N,N,N-Trimethyloctadecan-1-aminium iodide useful in applications such as disinfectants, antiseptics, and sanitizing agents. The compound's ability to interact with the cell membranes of microorganisms, disrupting their structure and function, contributes to its effectiveness as a biocide.

Furthermore, N,N,N-Trimethyloctadecan-1-aminium iodide has found use in the preparation of materials for controlled release and drug delivery systems. Its ability to form complexes with various substances, including drugs and other bioactive agents, makes it valuable in pharmaceutical formulations. The compound's structure allows for the encapsulation of active ingredients, ensuring their slow and controlled release over time, which is particularly beneficial in the treatment of chronic conditions or for enhancing the bioavailability of drugs.

In summary, N,N,N-Trimethyloctadecan-1-aminium iodide is a quaternary ammonium compound with diverse applications in the personal care, chemical, pharmaceutical, and antimicrobial industries. Its surfactant properties make it useful in hair and skin care formulations, while its role as a phase transfer catalyst facilitates various chemical reactions. The compound's antimicrobial activity further expands its utility in disinfectants and antiseptics. As research continues, N,N,N-Trimethyloctadecan-1-aminium iodide may find additional applications, further demonstrating its versatility in both industrial and health-related fields.

References

1995. Organic Compounds, C18 to C22. Enthalpies of Fusion and Transition of Organic Compounds.
DOI: 10.1007/10469434_11

1971. Amines and salts of quaternary ammonium bases. Chemistry of Pesticides.
DOI: 10.1007/978-1-4684-6251-7_8