Cyanuric fluoride

Structural formula
General
Surname	Cyanuric fluoride
other names	2,4,6-trifluoro-s-triazine; 2,4,6-trifluoro-1,3,5-triazine; TFT;
Molecular formula	C 3 F 3 N 3
Brief description	colorless to yellowish liquid with a pungent odor
External identifiers / databases
EC number	211-620-8
ECHA InfoCard	100.010.565
PubChem	12664
Wikidata	Q5197491
properties
Molar mass	135.05 g mol −1
Physical state	liquid
density	1.574 g cm −3
Melting point	−38 ° C
boiling point	74 ° C
solubility	decomposes in water
safety instructions
H and P phrases	H: 310-330-314
	P: 280-301 + 330 + 331-303 + 361 + 353-304 + 340-305 + 351 + 338-310-320-361-405-501
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Cyanuric fluoride or 2,4,6-trifluoro-1,3,5-triazine ( IUPAC ) is a chemical compound from the group of triazines and belongs to the halogenated heteroaromatic compounds .

Extraction and presentation

Cyanuric fluoride can be prepared by reacting cyanuric chloride with hydrogen fluoride at 40 ° C or with sodium fluoride in an aprotic polar solvent such as. B. sulfolane or acetonitrile can be obtained.

{\ displaystyle \ mathrm {(ClCN) _ {3} +3 \ HF \ longrightarrow (FCN) _ {3} +3 \ HCl}}

{\ displaystyle \ mathrm {(ClCN) _ {3} +3 \ NaF \ longrightarrow (FCN) _ {3} +3 \ NaCl}}

When producing in sulfolane as solvent, the reaction is preferably carried out in the temperature range from 120 to 220.degree. Under these conditions, the product formed is distilled off directly from the reaction mixture.

properties

Cyanuric fluoride is a very toxic, colorless to yellowish liquid with a pungent odor. The compound reacts violently with water to form cyanuric acid and dilute hydrofluoric acid . Cyanuric fluoride is more reactive than cyanuric chloride.

use

On an industrial scale, cyanuric fluoride is used as an intermediate in the production of reactive dyes . In the aqueous medium at low temperatures (<5 ° C) and under pH control, two fluorine substituents are exchanged for an amino group-containing chromophore and an aromatic or aliphatic amine .

The product can be used for the mild and direct conversion of carboxylic acids to carboxylic acid fluorides :

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on 2,4,6-trifluoro-1,3,5-triazine in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .
^ CW Tullock, DD Coffman: Synthesis of Fluorides by Metathesis with Sodium Fluoride. In: The Journal of Organic Chemistry. 25, 1960, pp. 2016-2019, doi: 10.1021 / jo01081a050 .
↑ Patent EP0035704 , Bayer AG , issued January 26, 1983.
↑ George A. Olah, Masatomo Nojima, Istvan Kerekes: Synthetic Methods and Reactions; IV. Fluorination of Carboxylic Acids with Cyanuric Fluoride . In: Synthesis . tape 1973 , no. 08 , 1973, p. 487 , doi : 10.1055 / s-1973-22238 .

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on 2,4,6-trifluoro-1,3,5-triazine in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .

[2] CW Tullock, DD Coffman: Synthesis of Fluorides by Metathesis with Sodium Fluoride. In: The Journal of Organic Chemistry. 25, 1960, pp. 2016-2019, doi: 10.1021 / jo01081a050 .

[3] Patent EP0035704 , Bayer AG , issued January 26, 1983.

[4] George A. Olah, Masatomo Nojima, Istvan Kerekes: Synthetic Methods and Reactions; IV. Fluorination of Carboxylic Acids with Cyanuric Fluoride . In: Synthesis . tape 1973 , no. 08 , 1973, p. 487 , doi : 10.1055 / s-1973-22238 .