N-Phenyltriflimide

Basic Information of N-Phenyltriflimide

CAS No.:	37595-74-7
EC No.:	609-445-0
Linear Formula:	PhN(SO₂CF₃)₂
Molecular Weight:	357.25
Appearance:	White to off-white crystalline solid.
Melting Point:	100-102 °C(lit.)
Boiling point:	305.3±52.0 °C(Predicted)
Density:	1.766±0.06 g/cm3(Predicted)
Solubility:	Soluble in many common organic solvents (e.g., dichloromethane, THF, toluene, acetonitrile).
Stability:	Relatively stable under anhydrous conditions.
Purity:	Available in high purity grades (e.g., 98% min) for sensitive synthetic applications.
Chemical Structure:

Our commitment to delivering high-purity N-Phenyltriflimide ensures a reliable and efficient component for your critical processes, offering consistent quality for diverse synthetic and industrial applications.

Primary Applications of N-Phenyltriflimide (PhNTf2)

N-Phenyltriflimide's unique properties as a non-nucleophilic triflating agent and mild Lewis acid make it an invaluable reagent with significant applications in various advanced chemical processes:

1. Triflating Agent / Derivatizing Agent:

   PhNTf2 is widely used for introducing the trifluoromethanesulfonyl (triflyl) group (CF₃SO₂–) into organic molecules. Its key applications include:

• Synthesis of Enol Triflates: Reacts with ketones and aldehydes (often in the presence of a non-nucleophilic base) to form enol triflates, which are highly reactive intermediates for cross-coupling reactions (e.g., Suzuki, Heck) and other C-C bond formations.

• Synthesis of Vinyl Triflates: Similarly used to prepare vinyl triflates from enones, useful in palladium-catalyzed couplings.

• Activation of Hydroxyl Groups: Converts alcohols into triflates, making them excellent leaving groups for substitution, elimination, and rearrangement reactions, often with high stereoselectivity.

2. Lewis Acid Catalyst:

   It can function as a mild Lewis acid catalyst in various organic reactions where stronger Lewis acids might lead to undesirable side reactions or decomposition. This includes certain types of condensations, additions, and rearrangements.

3. Non-Nucleophilic Base / Proton Scavenger:

   Although primarily a triflating agent, the imide anion formed after triflation is a very weak nucleophile. In some contexts, it can act as a non-nucleophilic base or proton scavenger, particularly when paired with a strong acid.

4. Pharmaceutical and Agrochemical Synthesis:

   PhNTf2 is a crucial reagent in the synthesis of complex active pharmaceutical ingredients (APIs) and agrochemicals, enabling precise and selective functionalization of molecules, which is vital for drug discovery and development.

5. Natural Product Synthesis:

   Its ability to facilitate stereoselective reactions and generate reactive intermediates makes it highly valuable in the total synthesis of intricate natural products.

Its role as a selective triflating reagent is discussed in triflation reagents in organic synthesis.

For a system-level understanding of how non-nucleophilic triflating agents fit within triflate chemistry, refer to the overview of triflic acid and triflate chemistry.

• Exceptional Purity & Consistent Quality: Our N-Phenyltriflimide is manufactured to stringent purity specifications, crucial for achieving optimal and reproducible results in sensitive organic syntheses and demanding industrial processes.

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