Triallyl 1,3,5-Benzenetricarboxylate: Properties & Lab Use

Triallyl 1,3,5-Benzenetricarboxylate is a trifunctional allyl ester monomer derived from benzene-1,3,5-tricarboxylic acid (trimesic acid) that serves as an efficient crosslinking agent and reactive comonomer in polymer and materials science research.

Chemical Name

Triallyl 1,3,5-benzenetricarboxylate (Triallyl trimesate)

SKU

T162568

Functional Groups

Three allyl ester groups arranged symmetrically on a benzene ring core

Primary Application

Crosslinking agent and trifunctional comonomer in radical polymerization and UV-curable resin systems

Functionality

Trifunctional (f = 3); enables formation of three-dimensional polymer networks

Molecular Symmetry

C3 symmetry; all three ester arms are equivalent, promoting uniform network formation

What Is Triallyl 1,3,5-Benzenetricarboxylate?

Triallyl 1,3,5-benzenetricarboxylate, also known as triallyl trimesate, is an organic ester formed by the esterification of benzene-1,3,5-tricarboxylic acid (trimesic acid) with allyl alcohol. The molecule features a rigid, symmetrical aromatic core bearing three allyl ester (–COOCH₂CH=CH₂) pendant groups at the 1-, 3-, and 5-positions of the benzene ring.

The three terminal carbon–carbon double bonds (vinyl groups within each allyl arm) are polymerizable under radical, thermal, or photochemical initiation conditions. This trifunctionality makes the compound capable of participating in crosslinking reactions that produce three-dimensional polymer networks with enhanced mechanical and thermal properties compared to linear analogues.

Aladdin Scientific supplies this compound as SKU T162568 for research and development applications.

Key Physical and Chemical Properties

Triallyl 1,3,5-benzenetricarboxylate possesses several noteworthy physicochemical characteristics relevant to laboratory handling and formulation:

• Molecular Formula: C₁₈H₁₈O₆
• Molecular Weight: 330.33 g/mol
• Appearance: Typically a colorless to pale yellow liquid or low-melting solid at room temperature (exact physical state should be confirmed on the Certificate of Analysis for lot T162568).
• Solubility: Soluble in common organic solvents such as dichloromethane, ethyl acetate, acetone, and THF; limited solubility in water due to its hydrophobic aromatic ester structure.
• Reactivity: The allyl double bonds are susceptible to radical addition polymerization and can undergo thiol–ene click reactions. The ester linkages are hydrolytically sensitive under strongly acidic or basic conditions.
• Stability: Should be stored in a cool, dark environment, ideally under inert atmosphere with an inhibitor present to prevent premature polymerization.

Note: Specific numerical values for melting point, boiling point, refractive index, and density are not provided in the current source material and should be verified against the product Certificate of Analysis or established chemical databases before use in formulations.

Applications in Research and Industry

The trifunctional allyl ester architecture of Triallyl 1,3,5-benzenetricarboxylate makes it broadly useful across several research domains:

1. Polymer Crosslinking: As a trifunctional monomer, it introduces chemical crosslinks into polymer matrices during radical polymerization, increasing gel content, reducing swelling, and improving thermal stability of the resulting network.
2. UV-Curable Coatings and Resins: The allyl groups participate in photoinitiated radical curing, making this compound a candidate crosslinker in UV-curable coating formulations alongside acrylate or methacrylate monomers.
3. Thiol–Ene Click Chemistry: The electron-neutral allyl double bonds are excellent substrates for photoinitiated thiol–ene reactions, enabling rapid, oxygen-tolerant network formation under mild conditions.
4. Porous Organic Polymers and MOF Precursors: The rigid C3-symmetric trimesate core is structurally analogous to building blocks used in reticular chemistry; allyl-functionalized variants can serve as precursors for functional porous materials.
5. Model Network Studies: The well-defined trifunctionality and symmetry make this monomer useful for preparing model crosslinked networks whose topology can be theoretically analyzed.

Researchers should optimize initiator type, concentration, and curing conditions based on the specific application and co-monomer system employed.

Safe Handling, Storage, and Disposal

Appropriate precautions should be observed when working with Triallyl 1,3,5-benzenetricarboxylate in the laboratory:

• Personal Protective Equipment (PPE): Wear appropriate chemical-resistant gloves, safety goggles, and a laboratory coat. Work in a well-ventilated area or fume hood to minimize inhalation of vapors or aerosols.
• Storage: Store in a tightly sealed container in a cool, dry, well-ventilated location away from heat sources, oxidizers, and direct sunlight. An inhibitor is recommended to prevent autopolymerization during storage. Specific storage temperature recommendations should be confirmed from the product SDS.
• Fire Hazard: Allyl esters are generally combustible. Keep away from open flames and high-temperature surfaces. Have appropriate fire-extinguishing media (CO₂ or dry powder) accessible.
• Disposal: Dispose of waste material in accordance with local, regional, and national regulations governing organic chemical waste. Do not pour into drains or waterways.
• First Aid: In case of skin or eye contact, flush thoroughly with water for at least 15 minutes and seek medical attention. In case of ingestion or significant inhalation, consult the product Safety Data Sheet (SDS) and seek medical advice promptly.

Always consult the product-specific Safety Data Sheet (SDS) for T162568 before use. Hazard classifications and GHS pictograms should be verified from the official SDS document.

Ordering and Quality Information

Triallyl 1,3,5-benzenetricarboxylate is available from Aladdin Scientific under SKU T162568. When ordering or evaluating the product, consider the following:

• Purity and Grade: Confirm the purity grade and analytical specification (e.g., GC purity, NMR identity) from the product page or Certificate of Analysis (CoA) for your specific lot number. The source material does not specify a particular purity grade; contact Aladdin Scientific technical support for details.
• Lot-Specific CoA: Request a Certificate of Analysis for your lot to verify purity, water content, inhibitor level, and other quality parameters critical for reproducible research.
• Packaging: Available pack sizes should be confirmed on the Aladdin Scientific product page for T162568. Select the quantity appropriate for your experimental scale to minimize degradation from repeated opening.
• Custom Synthesis: For quantities or specifications not listed, contact Aladdin Scientific's custom synthesis team.
• Technical Support: For application-specific guidance, reagent compatibility questions, or safety information, Aladdin Scientific's technical support team is available to assist.

Frequently asked questions

What is Triallyl 1,3,5-Benzenetricarboxylate used for in polymer research?

Triallyl 1,3,5-benzenetricarboxylate is primarily used as a trifunctional crosslinking monomer in radical polymerization systems. Its three allyl ester groups enable the formation of three-dimensional polymer networks, improving mechanical strength, thermal stability, and solvent resistance. It is also applicable in UV-curable resins and thiol–ene click chemistry formulations.

How should Triallyl 1,3,5-Benzenetricarboxylate (T162568) be stored to prevent premature polymerization?

The compound should be stored in a tightly sealed container in a cool, dark, and dry location, away from heat, light, and oxidizing agents. The presence of a polymerization inhibitor in the formulation is strongly recommended. Always reseal the container promptly after use and verify storage conditions on the product Safety Data Sheet and Certificate of Analysis.

Is Triallyl 1,3,5-Benzenetricarboxylate compatible with acrylate-based UV-curing systems?

Allyl esters can be incorporated into acrylate-based UV-curing formulations; however, allyl groups polymerize more slowly than acrylates under radical conditions and may act as retarders at high concentrations due to allylic chain transfer. Researchers should evaluate compatibility, reactivity ratio, and optimal loading levels experimentally for each specific formulation before committing to large-scale use.

What is the molecular weight of Triallyl 1,3,5-Benzenetricarboxylate?

The molecular formula of Triallyl 1,3,5-benzenetricarboxylate is C18H18O6, corresponding to a molecular weight of approximately 330.33 g/mol. Always verify this value against the Certificate of Analysis provided with your specific lot (T162568).

Can Triallyl 1,3,5-Benzenetricarboxylate be used in thiol–ene click reactions?

Yes, the allyl double bonds in Triallyl 1,3,5-benzenetricarboxylate are well-suited for thiol–ene click chemistry. Allyl esters react efficiently with multifunctional thiols under photoinitiator-mediated radical conditions, enabling rapid, oxygen-tolerant network formation at ambient temperature. This makes the compound attractive for step-growth network synthesis and surface functionalization studies.

References

1. Hoyle, C. E.; Bowman, C. N. Thiol–Ene Click Chemistry. Angew. Chem. Int. Ed. 2010, 49, 1540–1573. doi:10.1002/anie.200903924
2. Decker, C. Kinetic Study and New Applications of UV Radiation Curing. Macromol. Rapid Commun. 2002, 23, 1067–1093. doi:10.1002/marc.200290002
3. Odian, G. Principles of Polymerization, 4th ed.; Wiley-Interscience: New York, 2004.

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.