Ethyl trifluoroacetate

Ethyl trifluoroacetate
Identifiers
CAS Number	383-63-1 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:192463;
ChEMBL	ChEMBL3185188;
ChemSpider	9411;
ECHA InfoCard	100.006.229
EC Number	206-851-6;
PubChem CID	9794;
UNII	A6TZK6X11X;
CompTox Dashboard (EPA)	DTXSID8041959 ;
	InChI InChI=1S/C4H5F3O2/c1-2-9-3(8)4(5,6)7/h2H2,1H3 Key: STSCVKRWJPWALQ-UHFFFAOYSA-N;
	SMILES CCOC(=O)C(F)(F)F;
Properties
Chemical formula	C4H5F3O2
Molar mass	142.077 g·mol−1
Density	1.1952 g/cm3 (16.7 °C)
Boiling point	61 °C (142 °F; 334 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Ethyl trifluoroacetate is a chemical compound from the trifluoroacetate group.

Production

Ethyl trifluoroacetate can be obtained by reacting 2,4,6-tris-(trifluoromethyl)-1,3,5-triazine with ethanol in the presence of hydrochloric acid. The former, in turn, can be prepared by a two-step reaction starting from trichloroacetonitrile by reaction with hydrogen chloride and fluorination of the intermediate with antimony trifluoride.^[1]

The compound can also be obtained by reacting trifluoroacetic acid or sodium trifluoroacetate^[2] with ethanol.^[3]

Properties

Ethyl trifluoroacetate is a colorless and odorless liquid that is sparingly soluble in water but miscible with chloroform and methanol. The compound exists in the gas phase in two more conformal^{[clarification needed]} forms.^[4]

Use

Ethyl trifluoroacetate is used as an intermediate in organic synthesis to prepare organic fluorine compounds such as 3-ethyl-1-methylimidazolium trifluoroacetate (EMITA). It is also used in the synthesis of various pharmaceutically active molecules and agricultural products, and is also useful for the preparation of trifluoroacetylated compounds. The trifluoroacetyl group is widely used as an amine protecting group in organic synthesis because it can be easily removed under mild conditions.^[5]

References

^ T. R. Norton (1950). "A New Synthesis of Ethyl Trifluoroacetate". Journal of the American Chemical Society. 72 (8): 3527–3528. doi:10.1021/ja01164a056. ISSN 0002-7863.
^ Murray, R. L.; Babcock, J. H. (1946). The Preparation of Sodium Trifluoroacetate and Ethyl Trifluoroacetate. Atomic Energy Commission.
^ Google Patents: US4879407A - Process for the preparation of ethyl trifluoroacetate - Google Patents, retrieved 7 August 2022
^ "Experimental and theoretical structure and vibrational analysis of ethyl trifluoroacetate, CF₃CO₂CH₂CH₃: Structure and vibrational analysis of CF₃CO₂CH₂CH₃". Journal of Raman Spectroscopy. 41 (10): 1357–1368. 2010. doi:10.1002/jrs.2550.
^ Xu, Daqiang; Prasad, Kapa; Repic, Oljan; Blacklock, Thomas J. (1995). "Ethyl trifluoroacetate: a powerful reagent for differentiating amino groups". Tetrahedron Letters (in German). 36 (41): 7357–7360. doi:10.1016/0040-4039(95)01655-4. ISSN 0040-4039.

[1] T. R. Norton (1950). "A New Synthesis of Ethyl Trifluoroacetate". Journal of the American Chemical Society. 72 (8): 3527–3528. doi:10.1021/ja01164a056. ISSN 0002-7863.

[R._L._Murray,_J._H._Babcock-2] Murray, R. L.; Babcock, J. H. (1946). The Preparation of Sodium Trifluoroacetate and Ethyl Trifluoroacetate. Atomic Energy Commission.

[google.com-3] Google Patents: US4879407A - Process for the preparation of ethyl trifluoroacetate - Google Patents, retrieved 7 August 2022

[4] "Experimental and theoretical structure and vibrational analysis of ethyl trifluoroacetate, CF₃CO₂CH₂CH₃: Structure and vibrational analysis of CF₃CO₂CH₂CH₃". Journal of Raman Spectroscopy. 41 (10): 1357–1368. 2010. doi:10.1002/jrs.2550.

[5] Xu, Daqiang; Prasad, Kapa; Repic, Oljan; Blacklock, Thomas J. (1995). "Ethyl trifluoroacetate: a powerful reagent for differentiating amino groups". Tetrahedron Letters (in German). 36 (41): 7357–7360. doi:10.1016/0040-4039(95)01655-4. ISSN 0040-4039.

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