Trifluoroacetic anhydride

Trifluoroacetic anhydride
Names
	Preferred IUPAC name Trifluoroacetic anhydride
	Other names 2,2,2-Trifluoroacetic anhydride
Identifiers
CAS Number	407-25-0 ;
3D model (JSmol)	Interactive image;
ChemSpider	21106178;
ECHA InfoCard	100.006.349
PubChem CID	9845;
	InChI InChI=1S/C4F6O3/c5-3(6,7)1(11)13-2(12)4(8,9)10 Key: QAEDZJGFFMLHHQ-UHFFFAOYSA-N ;
	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	1.511 g/mL
Melting point	−65 °C (−85 °F; 208 K)
Boiling point	40 °C (104 °F; 313 K)
Hazards
Safety data sheet	Oxford MSDS
EU classification (DSD) (outdated)	Harmful (Xn); Corrosive (C)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. 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

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

↑ 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.
↑ US 4595541

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[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