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Trifluoroacetic Anhydride (TFAA) | Trifluoroacetic acid anhydride
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Description
Trifluoroacetic Anhydride (TFAA)
Other Names: TFAA, Trifluoroacetic acid anhydride
CAS Number: 407-25-0
Sum Formula: C₄F₆O₃
Molar Mass: 210.03 g/mol
Appearance: Colorless to pale yellow liquid with a sharp, pungent odor
Trifluoroacetic anhydride is a highly reactive fluorinated acid anhydride used extensively in organic synthesis as an acylating, dehydrating, and activating agent. It is particularly valued for introducing trifluoroacetyl groups, promoting selective transformations, and serving as a reagent in peptide synthesis and protection strategies. TFAA is moisture-sensitive and reacts vigorously with water.
Chemical and Physical Properties
Density: 1.489 g/cm³ (20°C)
Melting Point: -80°C
Boiling Point: 39–40°C
Vapor Pressure: ~160 mmHg (20°C)
Solubility: Reacts with water; miscible with many organic solvents
Odor: Sharp, penetrating
Reactivity: Strong electrophile; reacts violently with nucleophiles and bases
Stability: Moisture-sensitive; store under inert gas
Applications
Acylation and trifluoroacetylation in organic synthesis
Dehydrating agent in condensation reactions
Activation of carboxylic acids in peptide synthesis
Used in fluorinated compound preparation and derivatization for analytical chemistry
Safety
Signal Word: Danger
H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
H318 (21.9%): Causes serious eye damage [Danger Serious eye damage/eye irritation]
H332 (93%): Harmful if inhaled [Warning Acute toxicity, inhalation]
H361d (18.4%): Suspected of damaging the unborn child [Warning Reproductive toxicity]
H412 (51.8%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]
First Aid Measures
Eye Contact: Rinse cautiously with plenty of water for at least 15 minutes. Seek immediate medical attention
Skin Contact: Remove contaminated clothing and rinse with water/shower for at least 15 minutes. Seek medical help immediately
Inhalation: Move to fresh air. If breathing is difficult, seek urgent medical assistance
Ingestion: Do not induce vomiting. Rinse mouth and get medical attention immediately
Handling and Storage
Store in a tightly sealed container under inert atmosphere
Keep in a cool, well-ventilated place away from moisture and incompatible substances (water, alcohols, amines)
Use only in fume hoods with proper PPE due to corrosive vapors
Prevent contact with skin, eyes, and clothing