2-Trifluoromethyl-4-(heptafluoroisopropyl)aniline
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Product Description
2-Trifluoromethyl-4-(heptafluoroisopropyl)aniline is a heavily fluorinated aromatic amine in which an aniline core is armored at C-2 with a trifluoromethyl group and at C-4 with a heptafluoroisopropyl chain, a substitution pattern that endows the molecule with exceptional lipophilicity, chemical inertness and metabolic stability. Primarily manufactured on multi-mole scale by electrophilic coupling of 2-(trifluoromethyl)aniline with 2-bromoheptafluoropropane (75 % yield, 60 °C, Na₂SO₃/CH₃CN) or, under greener conditions, by visible-light photoredox alkylation of the same aniline with fluorinated iodides, the ≥98.5 % pure product serves as the key advanced intermediate for the synthesis of new meta-diamide insecticides such as modoflaner, whose activity against lepidopteran pests far exceeds that of older chemistries. Beyond agrochemistry, the free amino group readily undergoes diazotization, acylation or cross-coupling, making the compound a versatile building block for fluorinated pharmaceuticals and specialty polymers.
Other Information
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Significance: This compound exemplifies how strategic introduction of multiple fluorine atoms and "super-CF₃" groups can dramatically alter a molecule's physicochemical properties (e.g., stability, lipophilicity), making it a highly effective intermediate for creating bioactive molecules with improved performance, particularly in agrochemicals.
Synthesis and Production
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Chemical Formula: C₁₀H₅F₁₀N
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CAS Number: 1207314-85-9
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Key Intermediate: Primarily synthesized as a key intermediate for the production of advanced insecticides, most notably Broflanilide.
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Common Synthetic Routes:
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Electrophilic Substitution (Industrial Scale): A commonly employed method using *2-trifluoromethylaniline* and *2-bromoheptafluoropropane* as starting materials. The reaction is typically conducted in a solvent like acetonitrile, with sodium sulfite/sodium bisulfite, at around 60°C for approximately 16 hours. This process can be scaled up, with yields around 75%.
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Visible Light Photocatalysis (Greener Method): A more recent, milder method involves reacting *2-trifluoromethylaniline* with specific fluoroalkyl iodides. The reaction is catalyzed by potassium carbonate and trimethyl phosphite under low-power visible or UV light irradiation at room temperature for about 24 hours. This method is suitable for smaller-scale laboratory synthesis.
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Uses and Applications
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Primary Application: Serves as a crucial building block (key intermediate) for synthesizing novel pesticides.
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Insecticide Synthesis: Specifically for the production of Broflanilide, a next-generation insecticide with a unique mode of action (targeting GABA receptors), effective against pests resistant to older insecticides like fipronil. It is also a precursor for other insecticides like modoflaner.
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Potential Applications:
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Pharmaceutical Intermediate: The aniline group (–NH₂) allows for various reactions (diazotization, coupling, acylation), making it a potential building block for fluorinated drug molecules. The multiple trifluoromethyl groups can enhance lipophilicity, metabolic stability, and bioavailability.
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Material Science: Could be used as a monomer or modifier for synthesizing specialty fluorinated polymers or functional materials, such as high-weather-resistance coatings or specialty dyes.
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Chemical and Physical Properties
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Molecular Weight: 329.14 g/mol (PubChem computed).
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Appearance: Typically described as a colorless to pale yellow liquid with a characteristic aromatic odor.
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Structural Features: The molecule consists of a benzene ring with an amine group (–NH₂), a trifluoromethyl group (–CF₃) at the 2-position, and a bulky perfluorinated isopropyl-like side chain (–C(F)(CF₃)₂) at the 4-position. This results in 10 fluorine atoms within the structure.
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Computed Physicochemical Properties (from PubChem):
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XLogP3: 4.4 (indicating high lipophilicity).
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Hydrogen Bond Donor Count: 1 (the amine –NH₂ group).
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Hydrogen Bond Acceptor Count: 11.
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Rotatable Bond Count: 1.
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Topological Polar Surface Area (TPSA): 26 Ų.
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Heavy Atom Count: 21.
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Complexity: 354 (indicating a highly complex molecular structure).
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Chemical Classification: Classified under PFAS (Per- and Polyfluoroalkyl Substances) in regulatory lists such as the NORMAN Suspect List Exchange and identified in REACH regulations (EC No. 1272/2008).
Safety and Handling
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Hazard Classification: According to aggregated data from the ECHA C&L Inventory, this chemical has been reported as not meeting GHS (Globally Harmonized System) hazard criteria by available reports. No specific hazard statements (e.g., acute toxicity, flammability) are classified based on the provided data.
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Toxicity & Handling (General Guidance for Similar Compounds): Despite the lack of formal GHS classification, as a fluorinated aromatic amine, standard prudent laboratory practices are recommended:
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Personal Protective Equipment (PPE): Use chemical-resistant gloves, safety goggles, and lab coats.
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Engineering Controls: Handle in a well-ventilated area, preferably within a fume hood.
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Toxicity Potential: May cause irritation to skin, eyes, and the respiratory tract.
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Storage: Store in a sealed container, protected from light, in a cool, dry place.
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Regulatory Status:
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REACH: The substance is actively registered under the EU's REACH regulation (Registration Dossier available).
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Other Regulations: Likely subject to oversight under other global chemical management frameworks (e.g., TSCA in the U.S., China's new chemical substance regulation), primarily for industrial and R&D use.
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