Trifluoroacetyl chloride
Structural formula | ||||||||||||||||
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General | ||||||||||||||||
Surname | Trifluoroacetyl chloride | |||||||||||||||
other names |
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Molecular formula | C 2 ClF 3 O | |||||||||||||||
Brief description |
colorless gas with a pungent odor |
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External identifiers / databases | ||||||||||||||||
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properties | ||||||||||||||||
Molar mass | 132.47 g mol −1 | |||||||||||||||
Physical state |
gaseous |
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density |
1.3844 g cm −3 |
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Melting point |
−146 ° C |
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boiling point |
−24.8 ° C |
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Vapor pressure |
4.8 bar (20 ° C) |
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solubility |
rapid hydrolysis in water |
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safety instructions | ||||||||||||||||
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As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . |
Trifluoroacetyl chloride is a chemical compound from the group of carboxylic acid halides , more precisely a chlorine derivative of trifluoroacetic acid .
Occurrence
In addition to trifluoroacetic acid, trifluoroacetyl chloride occurs as a metabolite of anesthetics such as halothane .
Extraction and presentation
Trifluoroacetyl chloride can be made from trifluoroacetic anhydride and lithium chloride or trifluoroacetic acid and phosphorus pentachloride .
properties
Trifluoroacetyl chloride is a colorless gas with a pungent odor. Its aqueous solution reacts strongly acidic. It is easily hydrolyzed, smokes in the air and is easily soluble in organic solvents. Trifluoroacetyl chloride has a critical temperature of 109 ° C., a critical pressure of 36 bar and a critical density of 0.56 g / cm 3 . The chlorine atom in trifluoroacetyl chloride can easily be replaced by other anions such as fluorine ( trifluoroacetyl fluoride ), bromine ( trifluoroacetyl bromide ), iodine ( trifluoroacetyl iodide ), nitrile , isocyanate , isothiocyan and others.
use
Trifluoroacetyl chloride is a typical intermediate in the organic synthesis of pesticides ( cyhalothrin , fluxofenim ) and pharmaceuticals. Due to the electron-withdrawing effect of the CF 3 group, the reactivity of the carbonyl group towards nucleophilic reagents is increased compared to the non-fluorinated analogue acetyl chloride and the basicity of the carbonyl oxygen is reduced. It is also used as a polymerization initiator for tetrafluoroethylene .
Individual evidence
- ↑ a b c data sheet TFAC at Solvay.
- ↑ a b c d e f g h Entry on trifluoroacetyl chloride in the GESTIS substance database of the IFA , accessed on July 23, 2016(JavaScript required) .
- ↑ Michael Heck and Michael Fresenius; Anesthesiology revision course; ISBN 978-3-540-46575-1
- ↑ Trifluoroacetyl Chloride doi : 10.1002 / 047084289X.rt239
- ↑ Trifluoroacetyl Chloride (HaloCarbon) (PDF; 24 kB)
- ↑ Preparation of halides and salts of carboxylic acids