Trimesic acid
[CAS# 554-95-0]

Identification

• Classification: Chemical reagent >> Organic reagent >> Aromatic acid
• Name: Trimesic acid
• Synonyms: Trimesinic acid; 1,3,5-Benzenetricarboxylic acid
• Molecular Formula: C₉H₆O₆
• Molecular Weight: 210.14
• CAS Registry Number: 554-95-0
• EC Number: 209-077-7
• SMILES: C1=C(C=C(C=C1C(=O)O)C(=O)O)C(=O)O

Properties

• Melting point: 374-376 °C
• Flash point: 328 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319
Specific target organ toxicity - single exposure	STOT SE	3	H336

Discovery and Applications

Trimesic acid, chemically known as 1,3,5-benzenetricarboxylic acid, is a compound with notable significance in the fields of organic chemistry and materials science. Discovered in the mid-19th century, trimesic acid has since found a variety of applications due to its unique chemical properties and structural attributes.

Trimesic acid is a derivative of benzene with three carboxyl groups (-COOH) attached to the 1, 3, and 5 positions of the aromatic ring. This arrangement of functional groups provides the compound with high reactivity and the ability to form stable complexes with metal ions. The molecule's ability to form three-dimensional structures through hydrogen bonding and metal coordination has made it an important component in the development of advanced materials.

One of the primary applications of trimesic acid is in the synthesis of metal-organic frameworks (MOFs). MOFs are a class of materials characterized by their porous structures, which are created by linking metal ions or clusters with organic ligands such as trimesic acid. The resulting frameworks are highly porous and can be used for a variety of applications, including gas storage, separation processes, and catalysis. Trimesic acid, as a bridging ligand, helps to create robust and versatile MOFs with tailored properties.

In addition to its role in MOFs, trimesic acid is also used in the production of polyesters. It is a key monomer in the synthesis of poly(ethylene terephthalate) (PET), a widely used thermoplastic polymer. PET is known for its strength, durability, and clarity, making it suitable for applications ranging from beverage bottles to fibers for clothing. The incorporation of trimesic acid into PET contributes to its thermal and mechanical properties, enhancing the performance of the final polymer.

Trimesic acid has also found use in the field of organic electronics. Its ability to form stable coordination complexes with metals and its planar structure make it an attractive candidate for use in organic semiconductors and photovoltaic devices. Research has shown that incorporating trimesic acid into organic electronic materials can improve their charge transport properties and overall device performance.

Despite its beneficial applications, the synthesis of trimesic acid requires careful handling due to its acidic nature. The compound is typically produced through the oxidation of mesitylene or by the catalytic oxidation of benzene derivatives. Safety protocols are essential to manage its reactivity and prevent exposure to its corrosive properties.

In summary, trimesic acid is a versatile compound with significant applications in materials science, polymer chemistry, and organic electronics. Its discovery has paved the way for the development of advanced materials and technologies, demonstrating its continued relevance and importance in scientific research and industrial applications.

References

1972. The thermodynamics of ionization of polycarboxylic acids. Journal of Solution Chemistry, 1(5).
DOI: 10.1007/bf00645609

2024. Interface potential-induced natural antioxidant mimic system for the treatment of Alzheimer’s disease. Communications Chemistry, 7(1).
DOI: 10.1038/s42004-024-01299-9

2024. Novel unlabeled electrochemical sensing platform based on highly electroactive Cu-MOF film for nanoplastic detection in water. Microchimica Acta, 191(12).
DOI: 10.1007/s00604-024-06841-z