FAQ

2,4,6-Trifluoro-1,3,5-triazine, also known as cyanuric fluoride or trifluorotriazine, is a chemical compound with the molecular formula C₃F₃N₃ and a molecular weight of 135.05 g/mol.

• Physical State: Colorless liquid (though some sources note it may appear as a white solid depending on purity or handling).
• Melting Point: Not explicitly defined in all sources but typically handled as a liquid under standard conditions.
• Boiling Point: 73°C (varies slightly in literature, e.g., 69.5–70.5°C in some references).
• Density: Approximately 1.45 g/cm³ (density values may vary slightly across sources).
• Solubility: Reacts violently with water and alcohols, decomposing upon contact.

Synthesis and Reactivity

2,4,6-Trifluoro-1,3,5-triazine is synthesized by the fluorination of cyanuric chloride (2,4,6-trichloro-1,3,5-triazine) using hydrogen fluoride (HF) under controlled conditions. The reaction is highly exothermic and requires careful handling due to the compound’s reactivity:

1. Cyanuric chloride is dissolved in a suitable solvent (e.g., polyethylene container) and cooled to low temperatures (e.g., -78°C).
2. Dry hydrogen fluoride gas is introduced, leading to substitution of chloride groups with fluoride.
3. Excess HF is removed by heating and purging with nitrogen, followed by distillation to isolate the product.

The compound is notable for its electrophilic trifluoromethylating agent properties, making it useful in organic synthesis for introducing trifluoromethyl groups into aromatic or heterocyclic compounds. However, its instability in the presence of nucleophiles (e.g., water, alcohols) limits its direct use in aqueous reactions.

Applications

• Organic Synthesis: Acts as a reagent for introducing trifluoromethyl groups, though its use is often restricted to specialized applications due to reactivity concerns.
• Intermediate in Pharmaceuticals: Potentially used in the synthesis of fluorinated pharmaceuticals or agrochemicals, though specific examples are limited in open literature.

Safety and Handling

• Toxicity: Highly reactive and toxic; requires strict inert atmosphere handling (e.g., glove boxes, dry solvents) to avoid decomposition.
• Storage: Must be stored under anhydrous conditions, away from moisture and nucleophiles, to prevent violent decomposition.
• Hazards: Releases toxic fumes upon contact with water or alcohols; poses risks of fire and explosion if improperly handled.

CAS Number and Alternatives

• CAS Registry Number: 675-14-9
• Alternative Names:
  • 2,4,6-Trifluoro-s-triazine
  • Cyanuric fluoride
  • Trifluorotriazine