Trifluoroacetyl chloride

Structural formula
General
Surname	Trifluoroacetyl chloride
other names	Trifluoroacetic acid chloride; TFAC;
Molecular formula	C 2 ClF 3 O
Brief description	colorless gas with a pungent odor
External identifiers / databases
EC number	206-556-2
ECHA InfoCard	100.005.961
PubChem	61106
Wikidata	Q2453085
properties
Molar mass	132.47 g mol −1
Physical state	gaseous
density	1.3844 g cm −3
Melting point	−146 ° C
boiling point	−24.8 ° C
Vapor pressure	4.8 bar (20 ° C)
solubility	rapid hydrolysis in water
safety instructions
H and P phrases	H: 280-330-314-318-372-412
	P: 260-280-310-273
	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

Web links

[solvay-1] ta sheet TFAC at Solvay.

[GESTIS-2] ↑ ^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) .

[3] Michael Heck and Michael Fresenius; Anesthesiology revision course; ISBN 978-3-540-46575-1

[4] Trifluoroacetyl Chloride doi : 10.1002 / 047084289X.rt239

[5] Trifluoroacetyl Chloride (HaloCarbon) (PDF; 24 kB)

[6] Preparation of halides and salts of carboxylic acids