Fluoral

Fluoral
Names
	IUPAC name Trifluoroethanal
	Other names Trifluoroacetaldehyde
Identifiers
CAS Number	75-90-1 ; hydrate: 421-53-4;
3D model (JSmol)	Interactive image; hydrate: Interactive image;
ChemSpider	59007;
EC Number	200-914-1; hydrate: 207-006-4;
PubChem CID	65564; hydrate: 67901;
UNII	hydrate: DWG4394PJH;
CompTox Dashboard (EPA)	hydrate: DTXSID4059964;
	InChI 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;
	SMILES C(=O)C(F)(F)F; hydrate: OC(O)C(F)(F)F;
Properties
Chemical formula	CF; 3CHO
Molar mass	98.024 g·mol−1
Appearance	gas, hydrate is colourless crystals
Melting point	66 °C (hydrate)
Boiling point	–18 °C 104 °C (hydrate)
Solubility in water	forms hydrate
Related compounds
Related compounds	Chloral; Bromal; Iodal;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Trifluoroacetaldehyde, trifluoroethanal, or fluoral,^[2] is a fluorinated derivative of acetaldehyde with the formula CF
3CHO. 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 CF
3CH(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, CF
3CH(OCH
2CH
3)(OH)) due to the aldehyde's high reactivity, including the tendency to polymerise.^[5]

Synthesis and reactions

Upon storage, fluoral polymerises into a waxy, white solid that is soluble in diethyl ether and acetone but not water and chlorocarbons. Heating of this polymer gives monomeric fluoral.^[6] Fluoral can be prepared from trifluoroacetic acid with lithium aluminium hydride in diethyl ether:^[4] or with concentrated sulfuric acid.^{[clarification needed]}

Cathodic reduction of bromotrifluoromethane in dimethylformamide with aluminium as anode gives high yields of fluoral. In this reaction, DMF acts both as the solvent and the formylation agent.^[7] Vapour-phase oxidation of trifluoroethanol also gives fluoral.^[5]

Photolysis of fluoral gives fluoroform, hexafluoroethane and carbon monoxide, along with some hydrogen.^[8]

References

↑ ^1.0 ^1.1 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
↑ ^2.0 ^2.1 ^2.2 Trifluoroacetaldehyde, Peter Lin (2003), DOI:10.1002/047084289X.RN00213
↑ 2. Aldehydes, Fluorocarbon and Related Chemistry: Volume 2 (2007) Royal Society of Chemistry.
↑ ^4.0 ^4.1 Kitazume, T., Yamazaki, T. (2019). Experimental Methods in Organic Fluorine Chemistry
↑ ^5.0 ^5.1 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
↑ Oxidative Nitration of 1,1,1-Trifluoropropane. Trifluoroacetaldehyde, Harold Shechter and Franklin Conrad, in J. Am. Chem. Soc. 1950, 72, 8, 3371–3373
↑ Advances in Electron Transfer Chemistry. (1999)
↑ The photolysis of trifluoroacetaldehyde R. E. Dodd and J. Watson Smith, J. Chem. Soc., 1957, 1465-1473 https://doi.org/10.1039/JR9570001465

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[woods-1] 1.0 ^1.1 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

[lin-2] 2.0 ^2.1 ^2.2 Trifluoroacetaldehyde, Peter Lin (2003), DOI:10.1002/047084289X.RN00213

[aldehydes-3] 2. Aldehydes, Fluorocarbon and Related Chemistry: Volume 2 (2007) Royal Society of Chemistry.

[kitazume-4] 4.0 ^4.1 Kitazume, T., Yamazaki, T. (2019). Experimental Methods in Organic Fluorine Chemistry

[amino-5] 5.0 ^5.1 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

[shechter-6] Oxidative Nitration of 1,1,1-Trifluoropropane. Trifluoroacetaldehyde, Harold Shechter and Franklin Conrad, in J. Am. Chem. Soc. 1950, 72, 8, 3371–3373

[7] Advances in Electron Transfer Chemistry. (1999)

[8] The photolysis of trifluoroacetaldehyde R. E. Dodd and J. Watson Smith, J. Chem. Soc., 1957, 1465-1473 https://doi.org/10.1039/JR9570001465

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Fluoral

Topic: Chemistry

Synthesis and reactions

See also

References