Trifluoroacetic anhydride/Pharmaceutical Grade | 99.9% Purity | CAS 407-25-0

Trifluoroacetic anhydride
Properties
Melting point
-65 °C (lit.)
Boiling point
39.5-40 °C (lit.)
Density
1.511 g/mL at 20 °C (lit.)
Vapor Pressure
6.28 psi (20 °C)
Refractive Index
n20/D 1.3 (lit.)
Flash Point
-26 °C
Storage Condition
2-8°C
Solubility
Miscible with benzene, dichloromethane, diethyl ether, DMF, THF and acetonitrile.
Form
Liquid
pKa
0.43 (20 ℃)
Specific Gravity
1.487
Color
Clear
Water Solubility
Hydrolyzes upon contact with water
Sensitivity
Moisture Sensitive
BRN
746197
Stability
Stable under recommended storage conditions; moisture-sensitive. Incompatible with water and strong oxidants.
InChI
1S/C4F6O3/c5-3(6,7)1(11)13-2(12)4(8,9)10
InChIKey
QAEDZJGFFMLHHQ-UHFFFAOYSA-N
SMILES
FC(F)(F)C(=O)OC(=O)C(F)(F)F
LogP
0.79 at 25℃
CAS Database Reference
407-25-0
NIST Chemical Information
Acetic acid, trifluoro-, anhydride (407-25-0)
EPA Chemical Information
Acetic acid, trifluoro-, anhydride (407-25-0)
Applications and Synthetic Methods
Brief Introduction
Trifluoroacetic anhydride (TFAA) is a powerful dehydrating agent with versatile chemical reactivity. It serves as solvent, catalyst, dehydration condensing agent and protective reagent in synthesis of various polymers and fine chemicals. It is widely applied in dyes, photosensitive materials, liquid crystal materials, aerospace materials, agrochemicals, pharmaceuticals and polymer materials. It can accelerate polymerization and improve product yield. As a derivatization reagent, it is used in GC and HPLC detection of toxic metabolites and toxins in meat, fruits and vegetables, presenting promising development prospect.
Common Laboratory Reagent
Trifluoroacetic anhydride is a frequently used laboratory reagent. Containing two strong electron-withdrawing trifluoromethyl groups in its molecular structure, it is a highly reactive strong organic acid anhydride with extensive applications in organic synthesis. It can react with carboxylic acids to form mixed anhydrides (activated esters), enhancing the electrophilicity of carboxylic carbonyl groups. Owing to its hygroscopicity, it can act as dehydrating agent in many reactions. Mixture of trifluoroacetic anhydride and sodium iodide works as reducing agent; mixture of trifluoroacetic anhydride and DMSO can be used as oxidant. It also covers many other applications in synthetic chemistry.
Typical Chemical Reactions
Reaction with Carboxylic Acids
Trifluoroacetic anhydride reacts with carboxylic acids to form activated anhydrides and greatly increase carboxylic acid electrophilicity. For example, activated anhydride generated from trifluoroacetic acid and benzoic acid undergoes Friedel-Crafts acylation with anisole, achieving yield up to 98%.
Dehydration Reaction
In presence of weak bases, trifluoroacetic anhydride acts as dehydrating agent to convert amides, oximes, hydroxyketones or hydroxycarboxylates into corresponding nitriles, unsaturated ketones or carboxylates. It can also convert vicinal diols and vicinal hydroxy acid derivatives into vicinal diketones. Common weak bases include triethylamine, pyridine and 2,6-lutidine.
Notes
This reagent is moisture-sensitive and undergoes hydrolysis to produce trifluoroacetic acid when contacting water. Purification treatment is suggested before use to remove trifluoroacetic acid generated from partial hydrolysis. Operations should be carried out in well-ventilated environment.
Chemical Properties
Clear, colorless volatile liquid; m.p.-63.5℃, b.p.39.15℃, relative density 1.4980; hydrolyzable upon contact with water.
Applications
Intermediate for Chlorfenapyr
Used as analytical reagent, solvent, catalyst, dehydration condensing agent, protective reagent for trifluoroacetylation of hydroxyl and amino groups
Agrochemical intermediate
Applied in esterification within organic synthesis; also used as solvent, analytical reagent, catalyst and dehydration condensing agent
Raw material for fluorine fine chemicals, pharmaceuticals and agrochemicals
Nitration accelerator for organic synthesis
Derivatization reagent for biologically active compounds in gas chromatography analysis
Protecting reagent for primary amines and secondary amines; derivatives feature better volatility
Applied in oxidation of aldehydes to acids, esters and amines
Synthetic Route
Prepared via reaction between trifluoroacetic acid and dichloroacetic anhydride.
Reaction Equation: CF₃COOH+(Cl₂CHCO)₂O→(CF₃CO)₂O+Cl₂CHCOOH
Hazard Category
Corrosive substance
Irritation Data
Skin (Rabbit): 0.75 mg/24h, severe irritation; Eye (Rabbit): 5 mg/24h, severe irritation
Combustion Hazard
Vapors are lachrymatory; hazardous fluoride-containing fumes may generate during combustion.
Storage & Transportation
Store in dry, cool and well-ventilated warehouse; separate from foaming agents, alkalis and cyanides.
Fire Extinguishing Media
Dry sand, dry mineral powder