Trifluoroacetone

Trifluoroacetone (1,1,1-trifluoroacetone) is an organofluorine compound with the chemical formula CF3C(O)CH3.[1] The compound is a colorless liquid with chloroform-like odour.[2]

1,1,1-Trifluoroacetone
Names
IUPAC name
1,1,1-Trifluoropropan-2-one
Other names
Trifluoracetone, TFA
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.006.370
EC Number
  • 207-005-9
Properties
C3H3F3O
Molar mass 112.051 g·mol−1
Appearance Colorless liquid
Density 1.252 g/mL
Melting point −78 °C (−108 °F; 195 K)
Boiling point 21–24 °C (70–75 °F; 294–297 K)
Hazards
GHS pictograms
GHS Signal word Danger
GHS hazard statements
 H224, H315, H319, H335
P210, P261, P303, P351, P338
Flash point −30 °C (−22 °F; 243 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Preparation, reactions, uses

Trifluoroacetone is produced by decarboxylation of trifluoroacetoacetic acid:

CF3C(O)CH2CO2H → CF3C(O)CH3 + CO2

The acetoacetic acid in turn is obtained via condensation of acetate and trifluoroacetate esters.[2]

Trifluoroacetone has been examined as oxidizing agent in Oppenauer oxidation, in which case hydroxyl groups of secondary alcohols can be oxidized in the presence of hydroxy groups of primary alcohols.[3]

Trifluoracetone is also used in a synthesis of 2-trifluoromethyl-7-azaindoles starting with 2,6-dihalopyridines. The derived chiral imine is used to prepare enantiopure α-trifluoromethyl alanines and diamines by a Strecker reaction followed by either nitrile hydrolysis or reduction.[4]

See also

References
  1. "1,1,1-Trifluoracetone 95%". dk.vwr.com. Retrieved 6 June 2017.
  2. Günter Siegemund, Werner Schwertfeger, Andrew Feiring, Bruce Smart, Fred Behr, Herward Vogel, Blaine McKusick (2002). "Fluorine Compounds, Organic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a11_349. ISBN 978-3527306732.CS1 maint: uses authors parameter (link)
  3. Mello, Rossella; Martínez-Ferrer, Jaime; Asensio, Gregorio; González-Núñez, María Elena (2007). "Oppenauer Oxidation of Secondary Alcohols with 1,1,1-Trifluoroacetone as Hydride Acceptor". J. Org. Chem. 24 (72): 9376–9378. doi:10.1021/jo7016422. PMID 17975928.
  4. "Concise synthesis of enantiopure alpha-trifluoromethyl alanines, diamines, and amino alcohols by the Strecker-type reaction". sigmaaldrich.com. Retrieved 6 June 2017.
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