Ethyl trifluoroacetoacetate
Structural formula | ||||||||||||||||
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General | ||||||||||||||||
Surname | Ethyl trifluoroacetoacetate | |||||||||||||||
other names |
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Molecular formula | C 6 H 7 F 3 O 3 | |||||||||||||||
Brief description |
colorless liquid with an ester-like odor |
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properties | ||||||||||||||||
Molar mass | 184.11 g mol −1 | |||||||||||||||
Physical state |
liquid |
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density |
1.259 g cm −3 (25 ° C) |
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Melting point |
−39 ° C |
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boiling point |
129-130 ° C |
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Vapor pressure |
8 hPa (20 ° C) |
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solubility |
sparingly soluble in water (10 g l −1 at 20 ° C) |
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Refractive index |
1.375 (20 ° C) |
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safety instructions | ||||||||||||||||
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Toxicological data | ||||||||||||||||
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C |
Ethyl trifluoroacetoacetate is a chemical compound that belongs to the ethyl esters of acetoacetic acid .
Extraction and presentation
Ethyl trifluoroacetoacetate (like other 4,4,4-trihaloacetoacetates) can be prepared by adding the corresponding substituted acid chloride to ethenone in the presence of strong Lewis acids (such as boron trifluoride ) , whereby the acetoacetyl chloride is formed, which is then combined with an alcohol is converted to ethyl trifluoroacetoacetate.
It can also be obtained by Claisen condensation between ethyl trifluoroacetate and ethyl acetate .
use
Ethyl trifluoroacetoacetate is used as an intermediate in the production of heterocyclic chemical compounds (for example dithiopyr and mefloquine ). It is also used to produce trifluoromethyl ketones through the Caroll reaction . It forms complexes with some rare earth compounds.
Individual evidence
- ↑ a b c d e f g data sheet ethyl 4,4,4-trifluoroacetoacetate (PDF) from Merck , accessed on June 12, 2014.
- ↑ a b c d e data sheet Ethyl 4,4,4-trifluoroacetoacetate, 99% from Sigma-Aldrich , accessed on June 11, 2014 ( PDF ).
- ↑ a b Wiley-VCH (Ed.): Ullmann's Fine Chemicals . John Wiley & Sons, 2013, ISBN 978-3-527-68357-4 , pp. 805 ( limited preview in Google Book search).
- ^ A b c Jean-Pierre Bégué, Daniele Bonnet-Delpon: Bioorganic and Medicinal Chemistry of Fluorine - Jean-Pierre Bégué, Daniele Bonnet-Delpon . John Wiley & Sons, 2008, ISBN 0-470-28187-1 , pp. 56 ( limited preview in Google Book search).
- ^ Gschneider: Handbook on the Physics and Chemistry of Rare Earths . Elsevier, 2009, p. 221 ( limited preview in Google Book search).