TRIAZENE TRIEPOXIDE

Triazene triepoxide is a multifunctional epoxy compound characterized by a nitrogen-containing heterocyclic core structure bearing three reactive epoxide (oxirane) groups.
Triazene triepoxide is also a crosslinking agent in polymer synthesis; additive in plastic, rubber, and adhesives; hardener in polyester powder coatings; in protective coatings of electronic devices; in top-coated and solder-resistant inks.
Triazene triepoxide is widely applied in protective coatings, structural adhesives, fiber-reinforced composites, electrical encapsulation systems, and high-durability flooring materials.

CAS Number: 2451-62-9
EC Number: 219-514-3
Molecular Formula: C12H15N3O6
Molecular Weight: 297.26

Synonyms: .alpha.-triglycidyl isocyanurate, UNII-456V4159SL, TEROXIRONE [INN], |A-Triglycidyl isocyanurate, alpha-1,3,5-Tris(2,3-epoxypropyl)-s-triazine-2,4,6-(1H,3H,5H)-trione, 1,3,5-Triazine-2,4,6-(1H,3H,5H)-trione, 1,3,5-tris(oxiranylmethyl)-, (alpha)-, orb1740442, s-Triazine-2,4,6(1H,3H,5H)-trione, 1,3,5-tris(2,3-epoxypropyl)-, alpha-, 1,3,5-Triazine-2,4,6(1H,3H,5H)-trione, 1,3,5-tris(oxiranylmethyl)-, (1(R*),3(R*),5(S*))-(+-)-, 5-[[(2S)-oxiran-2-yl]methyl]-1,3-bis[[(2R)-oxiran-2-yl]methyl]-1,3,5-triazinane-2,4,6-trione, TRIGLYCIDYL ISOCYANURATE, .ALPHA.-, CS-0082046, D06080, TRIGLYCIDYL ISOCYANURATE .ALPHA.-FORM [MI], 1,3,5-TRIAZINE-2,4,6(1H,3H,5H)-TRIONE, 1,3,5-TRIS(OXIRANYLMETHYL)-, (1(R*),3(R*),5(S*))-(+/-)-, 1,3,5-TRIAZINE-2,4,6(1H,3H,5H)-TRIONE, 1,3-BIS((2R)-2-OXIRANYLMETHYL)-5-((2S)-2-OXIRANYLMETHYL)-, REL-, 1,3-BIS((2R)-2-OXIRANYLMETHYL)-5-((2S)-2-OXIRANYLMETHYL)-1,3,5-TRIAZINE-2,4,6(1H,3H,5H)-TRIONE, 1,3-Bis{[(2R)-oxiran-2-yl]methyl}-5-{[(2S)-oxiran-2-yl]methyl}-1,3,5-triazinane-2,4,6-trione, Teroxirone, Henkel's compound, 59653-73-5, alpha-Triglycidyl isocyanurate, Teroxironum, Teroxirona, ALPHATGI, NSC-296934, alpha-TGI, alpha-TGT, GATGI, 456V4159SL, DTXSID301318560, RefChem:203362, DTXCID901748367, alpha-1,3,5-triglycidyl-s-triazinetrione, NSC296934, 24N3OU2YDR, Triglycidyl isocyanurate, (R,R,S)-, UNII-24N3OU2YDR, (RS,RS,SR)-1,3,5-Tris(2,3-epoxypropyl)-s-triazine-2,4,6(1H,3H,5H)-trione, Teroxirone (USAN), TEROXIRONE [USAN], BRN 0765833, 1,3,5-Triazine-2,4,6(1H,3H,5H)-trione, 1,3-bis((2R)-2-oxiranylmethyl)-5-((2S)-2-oxiranylmethyl)-, 1,3,5-Triazine-2,4,6(1H,3H,5H)-trione, 1,3-bis((2R)-oxiranylmethyl)-5-((2S)-oxiranylmethyl)-, 1,5-bis[[(2R)-oxiran-2-yl]methyl]-3-[[(2S)-oxiran-2-yl]methyl]-1,3,5-triazinane-2,4,6-trione, 240408-79-1, Teroxirone [USAN:INN], Teroxironum [INN-Latin], Teroxirona [INN-Spanish]

Triazene triepoxide is a high-functionality epoxy compound designed for use in advanced thermosetting resin systems requiring exceptional crosslink density and long-term structural stability.
Triazene triepoxide's molecular architecture consists of a nitrogen-rich heterocyclic core integrated with three reactive epoxide (oxirane) groups.
This trifunctional configuration enables the material to participate in highly efficient curing reactions, forming tightly interconnected three-dimensional polymer networks when combined with suitable hardeners such as amines, anhydrides, or carboxyl-functional polymers.

The presence of the nitrogen-containing backbone enhances thermal endurance and contributes to improved resistance against chemical attack, moisture ingress, and solvent exposure.
When incorporated into epoxy-based coatings or composite systems, Triazene triepoxide significantly increases hardness, abrasion resistance, and dimensional stability.
Triazene triepoxide's ability to raise glass transition temperature (Tg) makes it particularly valuable in applications exposed to elevated operating temperatures or cyclic thermal stress.

In industrial formulations, Triazene triepoxide is selected for its balanced reactivity, allowing controlled processing while still achieving high-performance final properties.
Triazene triepoxide is widely applied in protective coatings, structural adhesives, fiber-reinforced composites, electrical encapsulation systems, and high-durability flooring materials.
Triazene triepoxide supports the development of solvent-free or low-emission systems, making it compatible with modern environmental and regulatory requirements while maintaining superior mechanical and chemical performance.

Triazene triepoxide appears as a while crystalline solid, is a Triazene triepoxide with anticancer and antineoplastic activity.
Teroxine alkylates and cross-links DNA, thereby inhibiting DNA replication.

Triazene triepoxide is a novel triepoxide, synthesized as an alkylator and showing a broad spectrum of preclinical activity.
Triazene triepoxide is also a crosslinking agent in polymer synthesis; additive in plastic, rubber, and adhesives; hardener in polyester powder coatings; in protective coatings of electronic devices; in top-coated and solder-resistant inks.

Triazines are a class of nitrogen-containing heterocycles.
The parent molecules' molecular formula is C3H3N3.
They exist in three isomeric forms, 1,3,5-triazines being common.

Triazene triepoxide is a Triazene triepoxide with antiangiogenic and antineoplastic activities.
Triazene triepoxide inhibits the growth of non-small-cell-lung cancer cells via p53 activation.

Triazene triepoxide induces cell apoptosis.
Triazene triepoxide can be used for cancer research.

Triazene triepoxide is a multifunctional epoxy compound characterized by a nitrogen-containing heterocyclic core structure bearing three reactive epoxide (oxirane) groups.
The presence of three epoxy functionalities enables the formation of highly crosslinked thermosetting polymer networks when reacted with suitable curing agents such as amines, anhydrides, or carboxyl-functional resins.

The triazene-based backbone contributes to enhanced thermal stability, chemical resistance, and mechanical strength in cured systems.
Due to its trifunctional nature, Triazene triepoxide is commonly used as a crosslinking agent in powder coatings, protective coatings, adhesives, electrical encapsulation materials, and advanced composite systems.

Formulations containing Triazene triepoxide typically exhibit high hardness, excellent solvent resistance, improved abrasion resistance, and elevated glass transition temperature (Tg).
Triazene triepoxide is particularly suitable for applications requiring durable performance under thermal and chemical stress while maintaining structural integrity and long service life.

Uses of Triazene Triepoxide:
Triazene triepoxide is applied in a wide range of high-performance thermosetting systems where enhanced crosslink density and durability are required.
Triazene triepoxide is incorporated into protective and powder coating formulations to improve chemical resistance, corrosion protection, hardness, and long-term weather stability.

In structural adhesive systems, Triazene triepoxide contributes to strong bonding performance and elevated temperature resistance.
Triazene triepoxide is also used in fiber-reinforced composites and laminates to increase mechanical strength and dimensional stability under thermal and environmental stress.
Additionally, Triazene triepoxide is utilized in electrical encapsulation materials and industrial flooring systems where dielectric properties, abrasion resistance, and chemical durability are critical for extended service life.

Protective Coatings:
Triazene triepoxide is used in high-performance protective coating systems to improve chemical resistance, corrosion protection, and long-term durability on metal and industrial substrates.

Powder Coatings:
Triazene triepoxide is incorporated into thermosetting powder coating formulations to enhance crosslink density, hardness, weather resistance, and thermal stability.

Structural Adhesives:
Triazene triepoxide is applied in advanced adhesive systems requiring strong bonding strength, elevated temperature resistance, and mechanical reliability.

Composite Materials:
Triazene triepoxide is used in fiber-reinforced composites and laminates to increase dimensional stability, stiffness, and resistance to environmental degradation.

Electrical Encapsulation:
Triazene triepoxide is utilized in electrical potting and encapsulation compounds to provide dielectric strength, heat resistance, and long-term insulation performance.

Industrial Flooring Systems:
Triazene triepoxide is incorporated into epoxy flooring and mortar systems to improve abrasion resistance, load-bearing capacity, and chemical durability.

Melamine:
A well known triazine is melamine (2,4,6-triamino-1,3,5-triazine).
With three amino substituents, melamine is a precursor to commercial resins.

Guanamines are closely related to melamine, except with one amino substituent replaced by an organic group.
This difference is exploited in the use of guanamines to modify the crosslinking density in melamine resins.
Some commercially important guanamines are benzoguanamine and acetoguanamine.

Cyanuric chloride:
Another important triazine is cyanuric chloride (2,4,6-trichloro-1,3,5-triazine).
Chlorine-substituted triazines are components of reactive dyes.

These compounds react through a chlorine group with hydroxyl groups present in cellulose fibres in nucleophilic substitution, the other triazine positions contain chromophores.
Triazine compounds are often used as the basis for various herbicides, e.g. atrazine.

Pharmacology:
Triazines are an uncommon but known moiety in pharmaceuticals.
Lamotrigine is an antiepileptic drug containing a 1,2,4-triazine, while azacitidine is a chemotherapy drug containing a 1,3,5-triazine.

Other:
Triazines also have wide use in the oil and gas and petroleum processing industries as a non-regenerating sulfide removal agent: they are applied to fluid streams to remove hydrogen sulfide gas and mercaptan species, which can decrease the quality of the processed hydrocarbon and be harmful to pipeline and facility infrastructure if not removed.[citation needed]

Pharmacokinetics of Triazene Triepoxide:
The pharmacokinetic profile of Triazene triepoxide is not well established in humans due to its primary industrial use as a reactive epoxy compound rather than a pharmaceutical substance.
However, based on the general behavior of multifunctional epoxides, limited systemic absorption is expected under normal industrial exposure conditions.

Absorption:
Dermal absorption may occur to a limited extent due to the small molecular size of epoxy groups, particularly if skin integrity is compromised.
Inhalation exposure to dust or aerosols may allow respiratory tract absorption.
Oral absorption data are generally unavailable because ingestion is not an intended route of exposure.

Distribution:
Once absorbed, reactive epoxide groups may bind to proteins and cellular macromolecules due to their electrophilic nature.
Distribution is expected to be limited because such compounds tend to react locally rather than circulate extensively in unchanged form.

Metabolism:
Epoxide-containing compounds are typically metabolized through enzymatic pathways such as epoxide hydrolase–mediated conversion to diols or conjugation with glutathione via glutathione S-transferases.
These reactions reduce reactivity and facilitate detoxification.

Elimination:
Metabolites formed through hydrolysis or conjugation are generally excreted via renal pathways.
Due to rapid reactivity and metabolic transformation, bioaccumulation is not expected.

Because Triazene triepoxide is a reactive industrial chemical rather than a therapeutic agent, toxicokinetic data are generally limited and should be evaluated through safety data sheets and regulatory toxicology assessments rather than clinical pharmacokinetic models.

Structure of Triazene Triepoxide:
Triazene triepoxide possesses a multifunctional molecular structure consisting of a nitrogen-containing heterocyclic core linked to three reactive epoxide (oxirane) groups.
The central framework typically contains a triazene or triazine-type ring system, which provides rigidity and thermal stability to the molecule.
This heterocyclic backbone is responsible for enhanced chemical resistance and structural integrity in cured systems.

Each of the three epoxy groups is attached to the core structure through glycidyl-type linkages.
These oxirane rings are highly reactive toward nucleophilic curing agents such as amines, anhydrides, and hydroxyl-containing polymers.
The presence of three epoxy functionalities makes Triazene triepoxide trifunctional, enabling the formation of highly crosslinked three-dimensional polymer networks during curing.

The combination of a rigid nitrogen-rich core and multiple reactive epoxy groups results in elevated crosslink density, improved mechanical strength, high glass transition temperature (Tg), and excellent resistance to solvents, chemicals, and thermal degradation in the final thermoset material.

Production of Triazene Triepoxide:
Triazene triepoxide is produced through a controlled epoxidation or glycidylation process involving a nitrogen-containing heterocyclic precursor and epichlorohydrin.
In the initial stage, the hydroxyl- or amine-functional triazene/triazine-based compound reacts with excess epichlorohydrin to form chlorohydrin intermediates.
This reaction is typically carried out under controlled temperature and agitation to ensure complete functional substitution and uniform incorporation of reactive sites.

In the subsequent step, an alkaline agent such as sodium hydroxide is added to promote dehydrochlorination, converting the chlorohydrin groups into reactive epoxy (oxirane) rings.
This step generates the trifunctional epoxy structure characteristic of Triazene triepoxide.

After completion of the reaction, the mixture is neutralized and washed to remove inorganic salts and residual alkali.
Purification processes such as filtration and vacuum stripping are applied to eliminate unreacted epichlorohydrin and volatile impurities.
The final product is obtained as a solid or semi-solid epoxy compound with controlled epoxy equivalent weight and consistent functionality, suitable for high-performance thermosetting applications.

Synthesis of Triazene Triepoxide:
The esterification reaction was performed in a 100 mL screw-capped glass bottle using containing 6 mL of reaction mixture composed by stoichiometric molar ratio of reactants (ethanol and valeric acid) in heptane medium.
The reaction mixture was maintained under continuous agitation in an orbital shaker.

The conversion percentage was determined by measuring the concentration of residual valeric acid after a given reaction time.
Aliquots (0.1 mL) were periodically withdrawn from the reaction mixture, added to an ethanol/acetone 1:1 (v/v) mixture (10 mL) and titrated with NaOH solution (20 mM) using phenolphthalein as indicator. 

The more common 1,3,5-isomers are prepared by trimerization of nitrile and cyanide compounds, although more specialized methods are known.

The 1,2,3- and 1,2,4-triazines are more specialized methods.
The former family of triazines can be synthesized by thermal rearrangement of 2-azidocyclopropenes.

Also mainly of specialized interest, the 1,2,4-isomer is prepared from condensation of 1,2-dicarbonyl compounds with amidrazones.
A classical synthesis is also the Bamberger triazine synthesis.

Reactions of Triazene Triepoxide:
Although triazines are aromatic compounds, their resonance energy is much lower than in benzene.
Electrophilic aromatic substitution is difficult but nucleophilic aromatic substitution easier than typical chlorinated benzenes.

2,4,6-Trichloro-1,3,5-triazine is easily hydrolyzed to cyanuric acid by heating with water.
2,4,6-Tris(phenoxy)-1,3,5-triazine results when the trichloride is treated with phenol.

With amines, one or more chloride is displaced.
The remaining chlorides are reactive, and this theme is the basis of the large field of reactive dyes.

Cyanuric chloride assists in the amidation of carboxylic acids.

The 1,2,4-triazines can react with electron-rich dienophiles in an inverse electron demand Diels-Alder reaction.
This forms a bicyclic intermediate which normally then extrudes a molecule of nitrogen gas to form an aromatic ring again.

In this way the 1,2,4-triazines can be reacted with alkynes to form pyridine rings.
An alternative to using an alkyne is to use norbornadiene which can be thought of as a masked alkyne.

1,2,3-triazines undergo Zincke-like nucleophilic substitution with secondary amines to give β-amino aldehydes.

In 2007, a method for synthesizing highly porous triazine-based polymers was discovered, and found to be useful (in conjunction with palladium) for the selective reduction of phenols.

Ligands:
A series of 1,2,4-triazine derivatives known as bis-triazinyl bipyridines (BTPs) have been considered as possible extractants for use in the advanced nuclear reprocessing.
BTPs are molecules containing a pyridine ring bonded to two 1,2,4-triazin-3-yl groups.

Triazine-based ligands have been used to bind three dinuclear arene ruthenium (or osmium) compounds to form metallaprisms.

Stability and Reactivity of Triazene Triepoxide:

Chemical stability:
Triazene triepoxide is stable under recommended storage conditions when kept in tightly closed containers and protected from moisture.

Reactivity:
Triazene triepoxide reacts exothermically with curing agents such as amines.
Anhydrides.
Phenolic hardeners through epoxy ring-opening polymerization.

Conditions to avoid:
Excessive heat.
Open flames.

Moisture contamination.
Dust generation.
Uncontrolled mixing with reactive hardeners.

Incompatible materials:
Strong oxidizing agents.
Strong acids.

Strong bases.
Reactive nucleophiles under uncontrolled conditions.

Hazardous decomposition products:
Thermal decomposition or combustion may generate carbon oxides (CO, CO₂).
Nitrogen oxides (NOx).
Irritating organic vapors.

Handling and Storage of Triazene Triepoxide:

Handling:
Avoid inhalation of dust or vapors.
Avoid contact with skin and eyes.

Use appropriate ventilation.
Prevent dust accumulation.
Follow good industrial hygiene practices.

Storage:
Store in a cool, dry, well-ventilated area away from heat sources and direct sunlight.

Storage conditions:
Keep containers tightly sealed to prevent moisture ingress and contamination.

Shelf life:
Stable when stored properly in original unopened packaging under recommended conditions.

First Aid Measures of Triazene Triepoxide:

Inhalation:
Move the affected person to fresh air and keep at rest.
Seek medical attention if symptoms such as coughing or irritation persist.

Skin contact:
Remove contaminated clothing.
Wash affected skin thoroughly with soap and water.

Eye contact:
Rinse cautiously with water for at least 15 minutes.
Remove contact lenses if present and easy to do.
Seek medical attention if irritation continues.

Ingestion:
Rinse mouth with water.
Do not induce vomiting.
Seek medical advice if discomfort or symptoms occur.

Firefighting Measures of Triazene Triepoxide:

Suitable extinguishing media:
Dry chemical powder.
Carbon dioxide (CO₂).
Foam.
Water spray.

Specific hazards:
Combustion may release toxic fumes including carbon oxides.
Nitrogen oxides.

Protective equipment:
Firefighters should wear self-contained breathing apparatus (SCBA).
Full protective clothing.

Accidental Release Measures of Triazene Triepoxide:

Personal precautions:
Avoid dust formation.
Ensure adequate ventilation.
Wear appropriate personal protective equipment.

Environmental precautions:
Prevent material from entering drains, watercourses, or soil.

Methods for cleanup:
Carefully sweep or collect spilled material to minimize dust dispersion.
Place in suitable containers for disposal in accordance with local regulations.

Exposure Controls / Personal Protective Equipment of Triazene Triepoxide:

Engineering controls:
Provide local exhaust ventilation to control airborne dust concentrations.

Respiratory protection:
Use an approved respirator if airborne concentrations exceed recommended exposure limits.

Hand protection:
Wear chemical-resistant gloves such as nitrile or neoprene.

Eye protection:
Wear safety goggles or a face shield.

Skin protection:
Wear protective clothing to prevent prolonged or repeated skin contact.

Identifiers of Triazene Triepoxide:
CAS Number: 2451-62-9
EC Number: 219-514-3
Purity: 98.0
Molecular Formula: C12H15N3O6
Molecular Weight: 297.26
Mass Spectrometry: Reference Materials
Alternative Names: TGIC

Properties of Triazene Triepoxide:
Density: 1.6±0.1 g/cm3
Boiling Point: 501.1±15.0 °C at 760 mmHg
Melting Point: 95-98°C
Molecular Formula: C12H15N3O6
Molecular Weight: 297.264
Flash Point: 256.9±20.4 °C
Exact Mass: 297.096100
PSA: 103.59000
LogP: -2.77
Vapour Pressure: 0.0±1.3 mmHg at 25°C
Index of Refraction: 1.635
InChIKey: OUPZKGBUJRBPGC-UHFFFAOYSA-N
SMILES: O=c1n(CC2CO2)c(=O)n(CC2CO2)c(=O)n1CC1CO1
Water Solubility: <0.1 g/100 mL at 20 ºC

Molecular Weight: 297.26 g/mol
XLogP3-AA: -1.5
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 6
Rotatable Bond Count: 6
Exact Mass: 297.09608521 Da
Monoisotopic Mass: 297.09608521 Da
Topological Polar Surface Area: 98.5 Ų
Heavy Atom Count: 21
Complexity: 416
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 3
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Physical state: Solid
Appearance: White to off-white crystalline powder
Odor: Mild or nearly odorless
Functional groups: Three epoxide (oxirane) groups