Fluoral

Fluoral
Names
IUPAC name
Trifluoroethanal
Other names
Trifluoroacetaldehyde
Identifiers
3D model (JSmol)
ChemSpider
EC Number
  • 200-914-1
  • hydrate: 207-006-4
UNII
  • InChI=1S/C2HF3O/c3-2(4,5)1-6/h1H
    Key: JVTSHOJDBRTPHD-UHFFFAOYSA-N
  • hydrate: InChI=1S/C2H3F3O2/c3-2(4,5)1(6)7/h1,6-7H
    Key: VGJWVEYTYIBXIA-UHFFFAOYSA-N
  • C(=O)C(F)(F)F
  • hydrate: OC(O)C(F)(F)F
Properties
CF3CHO
Molar mass 98.024 g·mol−1
Appearance gas, hydrate is colourless crystals
Melting point 66 °C (hydrate)[1]
Boiling point –18 °C[2]

104 °C (hydrate)[1]

forms hydrate
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Trifluoroacetaldehyde, trifluoroethanal, or fluoral,[2] is a fluorinated derivative of acetaldehyde with the formula CF3CHO. It is a gas at room temperature. Fluoral is used to introduce trifluoromethyl groups into organic compounds.[2][3] It is highly electrophilic and fluoral forms a hydrate CF3CH(OH)2 upon contact with water like other halogenated acetaldehydes.[4] It is commonly used in form of ethyl hemiacetal (1-ethoxy-2,2,2-trifluoroethanol, CF3CH(OCH2CH3)(OH)) due to the aldehyde's high reactivity, including the tendency to polymerise.[5]

  1. ^ a b The Radiolysis of Some Organic Halogen Compounds in Aqueous Solutions, R. J. Woods and J. W. T Spinks (1960), Canadian Journal of Chemistry vol.38
  2. ^ a b c Trifluoroacetaldehyde, Peter Lin (2003), DOI:10.1002/047084289X.RN00213
  3. ^ 2. Aldehydes, Fluorocarbon and Related Chemistry: Volume 2 (2007) Royal Society of Chemistry.
  4. ^ Kitazume, T., Yamazaki, T. (2019). Experimental Methods in Organic Fluorine Chemistry
  5. ^ Trifluoroacetaldehyde: A useful industrial bulk material for the synthesis of trifluoromethylated amino compounds, Hideyuki Mimura, Kosuke Kawada, Tetsuya Yamashita, Takeshi Sakamoto, Yasuo Kikugawa. Journal of Fluorine Chemistry Volume 131, Issue 4, April 2010, Pages 477-486