Trifluoroacetic anhydride

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Trifluoroacetic anhydride
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
Trifluoroacetic anhydride
Other names
2,2,2-Trifluoroacetic anhydride
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.006.349
Properties
C4F6O3
Molar mass 210.03 g·mol−1
Density 1.511 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).
No verify (what is YesYNo ?)
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 acyl chloride, trifluoroacetyl chloride, is a gas, making it inconvenient to work with. Trifluoroacetic anhydride is the recommended desiccant for trifluoroacetic acid.[1]

Preparation[edit]

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[edit]

  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