1,1,1-trifluoroacetone

1,1,1-Trifluoroacetone

Names
IUPAC name 1,1,1-Trifluoropropan-2-one
Other names Trifluoracetone, TFA
Identifiers
CAS Number	421-50-1
3D model (JSmol)	Interactive image
ChemSpider	21111803
ECHA InfoCard	100.006.370
EC Number	207-005-9
PubChem CID	9871
InChI InChI=1S/C3H3F3O/c1-2(7)3(4,5)6/h1H3 Key: FHUDAMLDXFJHJE-UHFFFAOYSA-N
SMILES CC(=O)C(F)(F)F
Properties
Chemical formula	C3H3F3O
Molar mass	112.05 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
GHS precautionary statements	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

Trifluoroacetone (1,1,1-trifluoroacetone) is an organofluorine derivative of acetone with the chemical formula C
3H
3F
3O. In contrast to fluoroacetone, the compound has three fluorine atoms. Under normal conditions, the compound is a colorless liquid with chloroform-like odour.

At room temperature, trifluoroacetone is a colorless liquid. In contrast to the less volatile fluoroacetone, the compound boils starting at 22 °C. Trifluoroacetone is highly flammable because of its low boiling point. The vapors of trifluoroacetone may form an explosive mixture with air if heated above the flash point, so there has to be sufficient ventilation of the area.

Trifluoroacetone can be used 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.

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 via a Strecker reaction followed by either nitrile hydrolysis or reduction.