Trifluoroacetic anhydride

Trifluoroacetic anhydride

Skeletal formula
Ball-and-stick model
Names
IUPAC name trifluoroacetic anhydride
Identifiers
CAS Number	407-25-0 Y
Jmol 3D model	Interactive image
PubChem	9845
SMILES C(=O)(C(F)(F)F)OC(=O)C(F)(F)F
Properties
Chemical formula	C4F6O3
Molar mass	210.03 g·mol−1
Density	1.487 g/mL
Melting point	−65 °C (−85 °F; 208 K)
Boiling point	40 °C (104 °F; 313 K)
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Trifluoroacetic anhydride (TFAA) is the acid anhydride of trifluoroacetic acid. It is the perfluorinated derivative of acetic anhydride. Like many acid anhydrides, it may be used to introduce the corresponding trifluoroacetyl group. The corresponding chlorine compound, trifluoroacetyl chloride, is a gas, making it inconvenient to work with. Trifluoroacetic anhydride is the recommended desiccant for trifluoroacetic acid.

Preparation

Trifluoroacetic anhydride may be prepared from trifluoroacetic acid by dehydrating with excess α-halogenated acid chlorides. For example, with dichloroacetyl chloride:

2 CF₃COOH + Cl₂CHCOCl → (CF₃CO)₂O + Cl₂CHCOOH + HCl