Trifluoroacetic anhydride

Trifluoroacetic anhydride
Skeletal formula
Ball-and-stick model
Names
IUPAC name
trifluoroacetic anhydride
Identifiers
407-25-0 YesY
Jmol interactive 3D Image
PubChem 9845
Properties
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)
Hazards
Safety data sheet Oxford MSDS
Harmful (Xn); Corrosive (C)
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. In particular, trifluoroacetic anhydride is the perfluorinated derivative of acetic anhydride. Like many acid anhydrides, it may be used to introduce the corresponding trifluoroacetyl group. The corresponding trifluoroacetyl chloride, is a gas, making it inconvenient to work with. Trifluoroacetic anhydride is the recommended desiccant for trifluoroacetic acid.[1]

Preparation

Trifluoroacetic anhydride may be prepared from trifluoroacetic acid by dehydrating with excess α-halogenated acid chlorides. For example, with dichloroacetyl chloride:[2]

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

References

  1. Chai, Christina Li Lin; Armarego, W. L. F. (2003). Purification of laboratory chemicals (Google Books excerpt). Oxford: Butterworth-Heinemann. p. 376. ISBN 0-7506-7571-3.
  2. US 4595541
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