675-14-9

Usage

Uses

Used in Chemical Synthesis:
Cyanuric fluoride is used as a fluorinating agent for converting carboxylic acids into acyl fluorides, which are important intermediates in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds.
Used in Textile Industry:
In the textile industry, cyanuric fluoride serves as a precursor for fiber-reactive dyes, enabling the production of vibrant and colorfast textiles.
Used in Enzyme Research:
Cyanuric fluoride is a specific reagent for tyrosine residues in enzymes, making it a valuable tool in enzyme research and the study of protein structure and function.
Used in Analytical Chemistry:
It is involved in the preparation of cyanuric acid by hydrolysis, which can be used as a reagent in analytical chemistry for various applications, including the detection and quantification of metal ions.

Synthesis

HF offers the attraction of cheapness, although this may be offset by its handling difficulties and lack of reactivity due to H-bonding. However, it may be used to fluorinate very reactive substrates. Trichlorotriazine may be converted to trifluorotriazine.

Characteristics

Cyanuric fluoride is a key intermediate in the synthesis of fluorine homotriazine reactive dyes. Compared with the traditional chlorotriazine reactive dyestuff, fluorine homotriazine reactive dyestuff has the following five advantages: 1. Energy saving, low dyeing temperature (medium temperature type) 60℃, lower than KE type reactive dyestuff and comparable to M type reactive dyestuff. 2. Emission reduction, environmental protection, high fixation rate, 15-20 percentage points higher than the corresponding chlorotriazine reactive dyestuff fixation rate, can improve the utilization rate of dyestuff, but also reduce the environmental pollution in the printing and dyeing process. 3. Good stability of dyestuff. 4. High stability of peroxide resistance. 5. Not restricted by AOX regulations.

Preparation

In a dry three-necked flask equipped with stirrer, thermometer and reflux condenser, add 0.2mol (36.9g) of cyanuric chloride, 0.63mol (36.5g) of finely ground anhydrous potassium fluoride, 60mL of xylene and 2.0g of polyethylene glycol-600, heat and stir at 110℃, reflux for 16h and distill after a little cooling, collect the fraction at 72℃~75℃, and get liquid of cyanuric trioxide.

Reactivity Profile

Cyanuric fluoride is used as a mild fluorinating agent for organic chemicals, and it reacts with water in a manner similar to an acyl halide, forming hydrofluoric acid and cyanuric acid. Since it forms hydrofluoric acid, cyanuric fluoride is a source of soluble fluoride ions. Unlike other halide ions, fluoride is quite reactive, acting as a weak base and participating in some unique reactions. In particular, fluorides react strongly with compounds containing calcium, magnesium, or silicon ions, which means that solutions containing soluble fluorides are corrosive to both living tissue and glass. Hydrofluoric acid can cause severe chemical burns and is one of the few materials that can etch glass. It is also a toxic gas in its anhydrous form.

Health Hazard

Cyanuric fluoride is highly toxic by skin contact and inhalation.

Fire Hazard

When heated to decomposition, Cyanuric fluoride emits very toxic fumes of fluorides and nitrogen oxides. Avoid decomposing heat.

InChI:InChI=1/C3F3N3/c4-1-2(5)7-9-8-3(1)6

Synthetic route

1,3,5-trichloro-2,4,6-triazine (108-77-0) → trifluoro-[1,3,5]triazine (675-14-9)

Conditions	Yield
With sulfolane; sodium fluoride at 150℃; Reagent/catalyst; Large scale;	97%
With tetrabutyl ammonium fluoride In dimethyl sulfoxide at 60℃; for 6h; Temperature; Solvent;	95%
With 1-methyl-pyrrolidin-2-one; hydrogen fluoride; triethylamine at 20 - 25℃; for 0.5h;	90%

1,3,5-trichloro-2,4,6-triazine (108-77-0) + antimony(III) fluoride (7783-56-4) → trifluoro-[1,3,5]triazine (675-14-9)

Conditions	Yield
With antimony(III) chloride; chlorine 160-180°C, 10 mol SbF3, 1 mol SbCl3, 3 mol Cl2;	91%
With antimony(III) chloride; chlorine 160-180°C, 10 mol SbF3, 1 mol SbCl3, 3 mol Cl2;	91%
With chlorine at 100°C, exclusion of H2O; destillation;	71.4%

4-N,N-dichloroamino-2,3,5,6-tetrafluoropyridine (57310-43-7) → trifluoro-[1,3,5]triazine (675-14-9) + 4-chloro-2,3,5,6-tetrafluoropyridine (52026-98-9) + Pentafluoropyridine (700-16-3) + trichlorofluoromethane (75-69-4) + 2-chloro-3,3-difluoro-acrylonitrile (667-42-5) + tetrafluoropyrazine (13177-77-0)

Conditions	Yield
at 550℃; under 2 Torr; Mechanism; vacuum pyrolysis, other fluoropyridine compounds;	A n/a B 75% C n/a D n/a E n/a F n/a

1,2,3-trifluoro-4,5,6-triazine (112291-51-7) + perfluoro-4,6-di-isopropyl-1,2,3-triazine (112291-50-6) → trifluoro-[1,3,5]triazine (675-14-9) + perfluoro-2,4-di-isopropylpyridine (20017-47-4) + perfluoro-2,4,6,8-tetraisopropyl-1,5-diazatricyclo<4.2.0.02,5>octa-3,7-diene (129574-48-7)

Conditions	Yield
In 1,1,2-Trichloro-1,2,2-trifluoroethane for 24h; Irradiation;	A 0.01 g B 53% C 11%
In 1,1,2-Trichloro-1,2,2-trifluoroethane for 24h; Irradiation;	A 0.01 g B 4% C 11 g
In 1,1,2-Trichloro-1,2,2-trifluoroethane for 24h; Mechanism; Irradiation;	A 0.01 g B 0.17 g C 0.03 g

1,3,5-trichloro-2,4,6-triazine (108-77-0) → trifluoro-[1,3,5]triazine (675-14-9) + 2-chloro-4,6-difluoro-[1,3,5]triazine (696-85-5) + 2,4-dichloro-6-fluoro-[1,3,5]triazine (696-84-4)

Conditions	Yield
With potassium fluoride at 300℃; for 2h; Product distribution; C3Cl3N3/KF = 16 x 10 E-2, other temperatures, other times, other molar ratios;	A n/a B n/a C 48%
With cesium fluoride; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 80℃;

1,3,5-trichloro-2,4,6-triazine (108-77-0) + sulfur tetrafluoride (7783-60-0) → trifluoro-[1,3,5]triazine (675-14-9)

Conditions	Yield
in 1:6 molar ratio, at 250°C, in autoclave;	40%

nitrogen trifluoride (7783-54-2) + cyanogen chloride (506-77-4) → trifluoro-[1,3,5]triazine (675-14-9) + cis-hexafluoroazomethane (73513-59-4) + Perfluoro-2-azapropen (371-71-1)

Conditions	Yield
In not given at 500°C, in Ni-tube, in excess of NF3;	A 40% B 30% C 30%

trifluoro-1,2,4-triazine (75995-67-4) → trifluoro-[1,3,5]triazine (675-14-9) + Perfluoro-2-azapropen (371-71-1) + silicon tetrafluoride

Conditions	Yield
at 500℃; for 42h;	A 32% B 12% C n/a

1,3,5-trichloro-2,4,6-triazine (108-77-0) → trifluoro-[1,3,5]triazine (675-14-9) + 2-chloro-4,6-difluoro-[1,3,5]triazine (696-85-5)

Conditions	Yield
With antimonypentachloride; antimony(III) fluoride
With antimonypentachloride; antimony(III) fluoride melting, heating, 1 h distn.; fractionated distn.;
With SbF3; SbCl5 melting, heating, 1 h distn.; fractionated distn.;

1,3,5-trichloro-2,4,6-triazine (108-77-0) + antimony(III) fluoride (7783-56-4) + antimony(III) chloride (10025-91-9) + chlorine (7782-50-5) → trifluoro-[1,3,5]triazine (675-14-9)

1,3,5-trichloro-2,4,6-triazine (108-77-0) + SbCl2F3 → trifluoro-[1,3,5]triazine (675-14-9)

1,3,5-trichloro-2,4,6-triazine (108-77-0) + hydrogen fluoride (7664-39-3) → trifluoro-[1,3,5]triazine (675-14-9) + 2-chloro-4,6-difluoro-[1,3,5]triazine (696-85-5) + 2,4-dichloro-6-fluoro-[1,3,5]triazine (696-84-4)

Conditions	Yield
auch unter Zusatz von Sb2O3 oder SbCl5;
With SbCl5

1,3,5-trichloro-2,4,6-triazine (108-77-0) + KF*HF → trifluoro-[1,3,5]triazine (675-14-9) + 2-chloro-4,6-difluoro-[1,3,5]triazine (696-85-5) + 2,4-dichloro-6-fluoro-[1,3,5]triazine (696-84-4)

Conditions	Yield
auch unter Zusatz von Sb2O3 oder SbCl5;
auch unter Zusatz von Sb2O3 oder SbCl5;

1,3,5-trichloro-2,4,6-triazine (108-77-0) + KF → trifluoro-[1,3,5]triazine (675-14-9) + 2-chloro-4,6-difluoro-[1,3,5]triazine (696-85-5) + 2,4-dichloro-6-fluoro-[1,3,5]triazine (696-84-4)

Conditions	Yield
auch unter Zusatz von Sb2O3 oder SbCl5;
auch unter Zusatz von Sb2O3 oder SbCl5;

1,3,5-trichloro-2,4,6-triazine (108-77-0) + KSO2F → trifluoro-[1,3,5]triazine (675-14-9) + 2-chloro-4,6-difluoro-[1,3,5]triazine (696-85-5) + 2,4-dichloro-6-fluoro-[1,3,5]triazine (696-84-4)

Conditions	Yield
auch unter Zusatz von Sb2O3 oder SbCl5;
auch unter Zusatz von Sb2O3 oder SbCl5;

Trifluoromethylsulfenyl chloride (421-17-0) + 1,3,5-Trichlor-2,2,4,4,6,6-hexafluor-1,3,5-triazinan (832-34-8) → trifluoro-[1,3,5]triazine (675-14-9) + Bis(trifluoromethyl)disulfid (372-64-5) + trifluoromethanesulfinyl fluoride (812-12-4)

Conditions	Yield
byproducts: Cl2; at 20°C (1 h);
byproducts: Cl2; at 20°C (1 h);

cis-hexafluoroazomethane (73513-59-4) → trifluoro-[1,3,5]triazine (675-14-9) + carbon tetrafluoride (75-73-0) + N,N-Bis(trifluoromethyl)amine (371-77-7) + Perfluoro-2-azapropen (371-71-1) + tetrakis(trifluoromethyl)hydrazine (383-96-0)

Conditions	Yield
heating in autoclave at 483°C; further product;
heating in autoclave at 483°C; further product;

cyanogen fluoride (1495-50-7) → trifluoro-[1,3,5]triazine (675-14-9)

Conditions	Yield
at ambient temp. quick polimn.;
room temp., polymerisation;
at ambient temp. quick polimn.;

2,2,2-trifluoro-1-oxoethanesulphenylchloride (21690-85-7) + 1,3,5-Trichlor-2,2,4,4,6,6-hexafluor-1,3,5-triazinan (832-34-8) → trifluoro-[1,3,5]triazine (675-14-9) + 2,2,2-trifluoro-1-oxoethanesulfenyl fluoride (57160-00-6)

Conditions	Yield
byproducts: Cl2;
byproducts: Cl2;

1,3,5-trichloro-2,4,6-triazine (108-77-0) → trifluoro-[1,3,5]triazine (675-14-9) + 2-chloro-4,6-difluoro-[1,3,5]triazine (696-85-5) + 2,4-dichloro-6-fluoro-[1,3,5]triazine (696-84-4) + Hexafluormethandiamin (4394-93-8) + cycloperfluoro dimethylenediamine (4394-92-7)

Conditions	Yield
With fluorine 125°C, under N2;

1,3,5-trichloro-2,4,6-triazine (108-77-0) + hydrogen fluoride (7664-39-3) → trifluoro-[1,3,5]triazine (675-14-9)

1,3,5-trichloro-2,4,6-triazine (108-77-0) + fluorine (7782-41-4) → trifluoro-[1,3,5]triazine (675-14-9)

Conditions	Yield
other products, in N2, at 125°C;

2-chloro-4,6-difluoro-[1,3,5]triazine (696-85-5) + 2,4-dichloro-6-fluoro-[1,3,5]triazine (696-84-4) + 1,3,5-trichloro-2,4,6-triazine (108-77-0) → trifluoro-[1,3,5]triazine (675-14-9)

Conditions	Yield
With Sb2O3; KHF2 In benzene
With KF
With KHF2

cyanuric bromide (14921-00-7) → trifluoro-[1,3,5]triazine (675-14-9)

Conditions	Yield
With ZnF2
With KF; Sb2O3

dichloromethylene-trifluoromethylmercaptoamine (33278-60-3) + silver fluoride → trifluoro-[1,3,5]triazine (675-14-9) + CF3SNCF2 + bis(trifluoromethylmercapto)-trifluoromethylamine (34764-16-4)

Conditions	Yield
byproducts: AgCl; 130°C; 21 h;; detected by IR and Mass spectr.;
byproducts: AgCl; 130°C; 21 h;; detected by IR and Mass spectr.;

manganese(III) fluoride (7783-53-1) + cyanogen chloride (506-77-4) → trifluoro-[1,3,5]triazine (675-14-9) + carbon tetrafluoride (75-73-0) + chlorotrifluoromethane (75-72-9) + pentafluoro chloro azomethane (660-80-0)

Conditions	Yield
byproducts: Cl2; at 160-190°C;

nitrogen trifluoride (7783-54-2) + cyanogen chloride (506-77-4) → trifluoro-[1,3,5]triazine (675-14-9) + carbon tetrafluoride (75-73-0) + cis-hexafluoroazomethane (73513-59-4) + trichlorofluoromethane (75-69-4) + Perfluoro-2-azapropen (371-71-1)

Conditions	Yield
With chlorine In not given at 450-500°C, in Ni-tube, in excess of NF3;

nitrogen trifluoride (7783-54-2) + cyanogen chloride (506-77-4) → trifluoro-[1,3,5]triazine (675-14-9)

Conditions	Yield
In not given ClCN/NF3 = 1:1;

trifluoro-[1,3,5]triazine (675-14-9) + tris(dimethylamino)sulfonium trimethylsilyldifluoride (150746-76-2) → C6H18N3S(1+)*C3F4N3(1-)

Conditions	Yield
In acetonitrile at -196 - -40℃; for 0.75h;	100%

trifluoro-[1,3,5]triazine (675-14-9) + (2R)-2-({formyl[(phenylmethyl)oxy]amino}methyl)hexanoic acid (301685-23-4) → (2R)-2-({formyl[(phenylmethyl)oxy]amino}methyl)hexanoyl fluoride (1398752-25-4)

Conditions	Yield
With pyridine	100%

trifluoro-[1,3,5]triazine (675-14-9) + 6-chloro-2-(ethylamino)pyridine-3-carboxylic acid (1092523-21-1) → 6-chloro-2-(ethylamino)pyridine-3-carbonyl fluoride (1092523-22-2)

Conditions	Yield
In dichloromethane at 20℃; for 3h;	99%

trifluoro-[1,3,5]triazine (675-14-9) + Propargylamine (2450-71-7) → 4,6-difluoro-2-(prop-2-yn-1-yl-amino)-1,3,5-triazine

Conditions	Yield
In N,N-dimethyl-formamide Inert atmosphere;	98%

trifluoro-[1,3,5]triazine (675-14-9) + trifluoroethylamine (753-90-2) → 2-fluoro-4,6-bis<(2,2,2-trifluoroethyl)amino>-1,3,5-triazine (144535-16-0)

Conditions	Yield
	97%

trifluoro-[1,3,5]triazine (675-14-9) + 2,2,2-trifluoroethylamine → 2-fluoro-4,6-bis<(2,2,2-trifluoroethyl)amino>-1,3,5-triazine (144535-16-0)

Conditions	Yield
	97%

trifluoro-[1,3,5]triazine (675-14-9) + 5-(t-butoxycarbonyl)-2-[N-(butoxycarbonyl)-N-(2-phenylethyl)aminomethyl]phenylpropionic acid → 5-(t-butoxycarbonyl)-2-[N-(butoxycarbonyl)-N-(2-phenylethyl)aminomethyl]phenylpropionyl fluoride

Conditions	Yield
With pyridine In dichloromethane	96%

trifluoro-[1,3,5]triazine (675-14-9) + 3-phenyl-4-(trifluoromethyl)isoxazole-5-carboxylic acid (1236188-80-9) → 3-phenyl-4-(trifluoromethyl)isoxazole-5-carbonyl fluoride (1236188-83-2)

Conditions	Yield
With pyridine In dichloromethane at 20℃;	96%

trifluoro-[1,3,5]triazine (675-14-9) + water (7732-18-5) → cyanuric acid (108-80-5)

Conditions	Yield
In tetrahydrofuran hydrolysis at 0°C;	94%
In water hydrolysis at 0°C;	>99

trifluoro-[1,3,5]triazine (675-14-9) + Propargylamine (2450-71-7) → N2,N4,N6-tri(prop-2-yn-1-yl)-1,3,5-triazine-2,4,6-triamine (144535-20-6)

Conditions	Yield
In toluene for 20h; Heating;	93%
In toluene Reflux;	83%

trifluoro-[1,3,5]triazine (675-14-9) + trifluoroethylamine (753-90-2) → 2,4,6-tris<(2,2,2-trifluoroethyl)amino>-1,3,5-triazine (144535-17-1)

Conditions	Yield
With cesium fluoride In N,N-dimethyl-formamide at 40℃; for 72h;	91%
With cesium fluoride In N,N-dimethyl-formamide

trifluoro-[1,3,5]triazine (675-14-9) + N-tert-butoxycarbonyl-3-(2-naphthyl)-L-alanine (56583-58-5, 76985-10-9, 58438-04-3) → ((S)-1-Fluorocarbonyl-2-naphthalen-2-yl-ethyl)-carbamic acid tert-butyl ester

Conditions	Yield
With pyridine In dichloromethane at -15℃; for 1h;	91%

trifluoro-[1,3,5]triazine (675-14-9) + 2-[N-(tert-butoxycarbonyl)-N-(2,2,2-trifluoroethyl)aminomethyl]-4-methoxydihydrocinnamic acid (205677-08-3) + (R)-4-(phenylmethyl)-2-oxazolidinone (40217-17-2, 90719-32-7, 120574-96-1, 102029-44-7) → (R)-4-benzyl-2-oxazolidinonyl 2-[N-(tert-butoxycarbonyl)-N-(2,2,2-trifluoroethyl)aminomethyl]-4-methoxydihydrocinnamide

Conditions	Yield
With pyridine; n-butyllithium; ammonium chloride In tetrahydrofuran; dichloromethane	91%

trifluoro-[1,3,5]triazine (675-14-9) + ferrocenylamidoundecanoic acid (1111735-43-3) → ferrocenylamidoundecanoic acid fluoride (1111735-46-6)

Conditions	Yield
With pyridine In dichloromethane (Ar, Schlenk technique); addn. of cyanuric fluoride to suspn. of ferrocene deriv. and pyridine in dry CH2Cl2, stirring for 2 h; addn. of ice cold water, filtration, separating organic layer, washing with cold water, drying over MgSO4, filtration, evapn., elem. anal.;	91%

polytetrafluoroethylene (116-14-3) + trifluoro-[1,3,5]triazine (675-14-9) → tris(perfluoroethyl)-s-triazine (858-46-8)

Conditions	Yield
at 140℃; Large scale;	91%

trifluoro-[1,3,5]triazine (675-14-9) + 2-[N-(tert-butoxycarbonyl)-N-(4-trifluoromethylbenzyl)aminomethyl]-4-methoxydihydrocinnamic acid (205676-97-7) + (R)-4-(phenylmethyl)-2-oxazolidinone (40217-17-2, 90719-32-7, 120574-96-1, 102029-44-7) → (R)-4-Benzyl-2-oxazolidinonyl 2-[N-(tert-butoxycarbonyl)-N-(4-trifluoromethylbenzyl) aminomethyl]-4-methoxydihydrocinnamide

Conditions	Yield
With pyridine; n-butyllithium; ammonium chloride In tetrahydrofuran; dichloromethane	90%
With pyridine; n-butyllithium; ammonium chloride In tetrahydrofuran; dichloromethane	90%

trifluoro-[1,3,5]triazine (675-14-9) + K{Mn(CO)5} (15693-51-3) → 2-(pentacarbonylmanganese)-4,6-difluoro-1,3,5-triazene

Conditions	Yield
In not given -18°C; sublimed in vacuo (50°C/0.01 Torr), recrystd. from dry hexane;	90%

trifluoro-[1,3,5]triazine (675-14-9) + perfluoropropylene (116-15-4) → perfluoro-2,4,6-triisopropyl-s-triazine (10271-37-1)

Conditions	Yield
at 140℃; Reagent/catalyst; Temperature; Large scale;	89%

trifluoro-[1,3,5]triazine (675-14-9) + 4-[1-(tert-butoxycarbonyl)-4-piperidyl]-2-{2-[1-(tert-butoxycarbonyl)-4-piperidyl]ethyl}butanoic acid + glycine ethyl ester hydrochloride (5680-79-5) → 2-[(4-[1-(tert-butoxycarbonyl)-4-piperidyl]-2-{2-[1-(tert-butoxycarbonyl)-4-piperidyl]ethyl}butanoyl)amino]acetic acid (255880-67-2)

Conditions	Yield
With pyridine; hydrogenchloride; lithium hydroxide monohydrate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; dichloromethane; water	88%

trifluoro-[1,3,5]triazine (675-14-9) + Propargylamine (2450-71-7) → 2-fluoro-4,6-bis(propargylamino)-1,3,5-triazine

Conditions	Yield
In N,N-dimethyl-formamide	87%
In N,N-dimethyl-formamide

trifluoro-[1,3,5]triazine (675-14-9) + 1,3-dimethanol benzene (626-18-6) → C14H8F4N6O2 (1228184-79-9)

Conditions	Yield
With triethylamine In diethyl ether at 20℃; for 2.5h;	87%

trifluoro-[1,3,5]triazine (675-14-9) + boron trifluoride diethyl etherate (109-63-7) + 2,3-Dihydro-1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene (151515-23-0) → 2-(4,6-difluoro-1,3,5-triazin-2-yl)-1,3-diisopropyl-4,5-dimethylimidazolium tetrafluoroborate (1210257-36-5)

Conditions	Yield
In diethyl ether (Ar); imidazolylidene deriv. added to Et2O soln. of cyanuric trifluorideat -70°C; stirred for 12 h at room temp.; BF3*OEt2 added dropwis e; stirred for 4 h at room temp.; ppt. isolated; washed with Et2O; vac. dried; recrystd. from MeCN/Et2O; elem. anal.;	86%

trifluoro-[1,3,5]triazine (675-14-9) + 4-[2-[N-(tert-butoxycarbonyl)-N-(2-phenylethyl)amino]methyl-4-methoxyphenyl]propionic acid + (R)-4-(phenylmethyl)-2-oxazolidinone (40217-17-2, 90719-32-7, 120574-96-1, 102029-44-7) → (R)-1,1-Dimethylethyl[[5-methoxy-2-[3-oxo-3-[2-oxo-4-(phenylmethyl)-3-oxazolidinyl]propyl]phenyl]methyl](2-phenylethyl)carbamate

Conditions	Yield
With pyridine; n-butyllithium In tetrahydrofuran; dichloromethane	85%

trifluoro-[1,3,5]triazine (675-14-9) + cis-Octadecenoic acid (112-80-1) → oleoyl fluoride (1480-60-0)

Conditions	Yield
With pyridine In acetonitrile	85%

trifluoro-[1,3,5]triazine (675-14-9) + 2,3-Dihydro-1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene (151515-23-0) → 2-(4,6-difluoro-1,3,5-triazin-2-yl)-1,3-diisopropyl-4,5-dimethylimidazolium tetrafluoroborate (1210257-36-5)

Conditions	Yield
Stage #1: trifluoro-[1,3,5]triazine; 2,3-Dihydro-1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene In diethyl ether at -70 - 20℃; Inert atmosphere; Stage #2: With boron trifluoride diethyl etherate at 20℃; Inert atmosphere;	85%

trifluoro-[1,3,5]triazine (675-14-9) + (Sp)-2-formylferrocene-1-carboxylic acid (433301-35-0) → (Sp)-2-formylferrocenoyl fluoride (1296752-87-8)

Conditions

Yield

With pyridine In dichloromethane pyridine (1.650 ml) and cyanuric fluoride (3.605 ml) added to CH2Cl2 soln. of Fc(CHO)CO2H (10 mmol) at 0°C under Ar, after few min cooling bath removed, mixt. stirred at room temp. for 90 min; crushed ice added, suspn. filtered, organic phase sepd., washed with cold H2O, dried over Na2SO4, filtered, solidified for few min, crystals collected, dried in vac. exicator over P2O5 overnight at room temp.; elem. anal.;

85%

trifluoro-[1,3,5]triazine (675-14-9) + ruthenocene carboxylic acid → fluorocarbonyl ruthenocene (1279129-18-8) + [Ru(η5-C5H5)(η5-C5H4CO)]2O (1279129-20-2)

Conditions	Yield
With pyridine In dichloromethane under N2 or Ar; suspn. of Ru complex and pyridine in CH2Cl2 cooled to 0°C; N3C3F3 added; stirred at 0°C for 2 h; poured into ice-cold H2O; filtered; org. layer collected; concd. in vac.; purified by column chromy. (silica gel, ethyl acetate-hexane 1:5); elem. anal.;	A 82% B 2%

trifluoro-[1,3,5]triazine (675-14-9) + sulfanilamide (63-74-1) → 4-(4',6'-difluoro-1',3',5'-triazin-2'-ylamino)benzenesulfonamide

Conditions	Yield
Stage #1: trifluoro-[1,3,5]triazine; sulfanilamide In acetone at 0℃; for 0.5h; Stage #2: With sodium hydroxide In water; acetone at 20℃; for 1.33333h;	82%

Upstream product

• 108-77-0 1,3,5-trichloro-2,4,6-triazine 
• 75995-67-4 trifluoro-1,2,4-triazine 
• 421-17-0 Trifluoromethylsulfenyl chloride 
• 832-34-8 1,3,5-Trichlor-2,2,4,4,6,6-hexafluor-1,3,5-triazinan 
• 21690-85-7 2,2,2-trifluoro-1-oxoethanesulphenylchloride 
• 7664-39-3 hydrogen fluoride 
• 7783-56-4 antimony(III) fluoride 
• 7783-60-0 sulfur tetrafluoride 
• 7782-41-4 fluorine 
• 696-85-5 2-chloro-4,6-difluoro-[1,3,5]triazine 
• 696-84-4 2,4-dichloro-6-fluoro-[1,3,5]triazine 
• 14921-00-7 cyanuric bromide 
• 7783-53-1 manganese(III) fluoride 
• 506-77-4 cyanogen chloride 

Downstream Products

• 1598-99-8 2,4-Bis(diethylamino)-6-fluor-s-triazin 
• 1973-05-3 triphenyl melamine 
• 1054629-98-9 2-Fluoro-4,6-bis-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-[1,3,5]triazine 
• 823-95-0 2,4-Diamino-6-fluor-1.3.5-triazin 
• 108-80-5 isocyanuric acid 
• 877-89-4 2,4,6-trimethoxy-1,3,5-triazine 
• 343880-10-4 N-[2-Hydroxy-1-(4-{2-[4-(methoxymethyl)phenyl]ethoxyl}benzyl)ethyl]-2-methylpropanamide 
• 133010-02-3 1,1-dimethylethyl S-N-(1-fluorocarbonyl-2-methylpropyl)carbamate 
• 75-73-0 carbon tetrafluoride 
• 335-01-3 difluoramino trifluoromethane 
• 7783-54-2 nitrogen trifluoride 
• 1426-42-2 N-Trifluormethyl-perfluor-(methandiamin) 
• 666-95-5 Perfluor-(1,4-diazapent-2-en) 

Relevant academic research and scientific papers

Synthesis of (±) wine lactone and its analogues by a diels-alder approach

A novel route to (±)-wine lactone (1) by a cis-selective kinetically controlled intramolecular Diels-Alder (IMDA) cycloaddition of the linear triene 2 is reported. The triene precursor was synthesised by TBAF-catalysed coupling of an acyl fluoride with an silyl enol ether. Four butadienyl but-3-enoates were prepared and cyclised under mild conditions to give a series of wine lactone analogues. The diastereoselectivity of the IMDA cycloadditions was determined by NMR spectroscopy and GC-MS, whereby the formation of the natural cis-configured wine lactone (1) was established. The diastereomeric IMDA transition states were optimised by using density functional theory at the B3LYP/6-31+G(d) level, and the Boltzmann populations of the electronic energies were found to correlate well with the experimentally observed diastereoselectivity.

PROCESS AND DEVICE FOR PREPARING ENVIRONMENTALLY-FRIENDLY INSULATING GAS PERFLUOROALKYLNITRILE

Provided are a process and a device for preparing environmentally-friendly insulating gas perfluoroalkylnitrile. The device comprises a first tank reactor, a second tank reactor, and a fixed bed reactor. A condensing and collecting device is provided at the top of the first tank reactor, a collecting and guiding channel at the bottom of the condensing and collecting device is connected to an inlet of a storage tank, and an outlet of the storage tank is connected to an inlet of the second tank reactor. The second tank reactor is connected to a perfluoroolefin tank. An outlet of the second tank reactor is connected to a storage gasification tank. The storage gasification tank is connected to a carrier gas tank, and an outlet of the storage gasification tank is connected to an inlet of the fixed bed reactor. The present invention starts from cyanuric chloride and perfluoropropylene, and uses two tank reactors and a fixed bed reactor to realize production with high atom economy. The preparation method has simple reaction conditions, high atom economy, low cost, and is continuous and enables scale production.

Cyanuric fluoride preparation method

The invention discloses a cyanuric fluoride preparation method. According to the method, 1, 3, 5-trichlorine s-triazine and tetrabutylammonium fluoride are subjected to fluorination to obtain cyanuricfluoride and tetrabutylammonium chloride. Catalysts are omitted, reaction selectivity is high, yield can reach up to 95%, usage of hydrogen fluoride serving as a high-risk fluorine reagent or a largequantity of metal fluoride and addition of expensive catalysts are avoided, and the method has the advantages of simplicity in operation, mild reaction conditions, low cost and the like, and is suitable for industrial production.

Ionic liquids as media for nucleophilic flurination

The use of Room Temperature Ionic Liquids (RTILs) for a variety of halogen exchange (Halex) fluorination processes using alkali metal fluorides is assessed. Whilst fluorination of a range of halogenated substrates is possible in good yield, the utility of RTILs as reusable, inert media for such reactions is limited by the gradual decomposition of the RTIL in the presence of highly basic fluoride ion.

Improved syntheses of cyanuric fluoride and carboxylic acid fluorides

Cyanuric fluoride (2) is one of the most popular fluorinating agents in organic chemistry. The title compound could be prepared in a 50 to 100 g scale by means of a chlorine fluorine exchange, the process was characterized by a simple preparation procedure, cheap reactants and a low time exposure. Carboxylic acids were converted into the corresponding acid fluorides 4a-g using cyanuric fluoride. A non-aqueous work-up led to high yields on synthesizing a range of functionalized acid fluorides. Wiley-VCH Verlag GmbH, 2000.

Synthesis and use of amino acid fluorides as peptide coupling reagents

The present invention is directed to the process of preparing a peptide comprising reacting a first amino acid or peptide with an amino acid fluoride of the formula: STR1 or the acid fluoride salts thereof wherein BLK is an N-amino protecting group AA is an amino acid residue and X is H or a protecting group useful, and the first amino and peptide have a free amino group and a blocked carboxy end.

Synthesis and use of amino acid fluorides as peptide coupling reagents

A compound of the formula STR1 or the acid fluoride salts thereof wherein BLK is an N-amino protecting group or hydrogenAA is an amino acid residue andX is H or a protecting group useful as a coupling agent in peptide synthesis.

Process for the preparation of 2,4,6-trifluoro-1,3,5-triazine

A process for the preparation of 2,4,6-trifluoro-1,3,5-triazine (cyanuric fluoride) in high purity and high yield at relatively low temperatures by reacting 2,4,6-trichloro-1,3,5-triazine (cyanuric fluoride [sic]) or mixed chlorinated/fluorinated 1,3,5-triazines with at least the equivalent amount of sodium fluoride, potassium fluoride or cesium fluoride or any desired mixture of these alkali metal fluorides in a dipolar aprotic solvent at temperatures from about 30° C. to about 110° C. and isolating the 2,4,6-trifluoro-1,3,5-triazine formed by distillation.

Photochemistry of Halogenocarbon Compounds. Part 5. Photolysis of Fluorinated 1,2,3-Triazine Derivatives

Photolysis experiments are described on perfluoro-1,2,3-triazine (9) and its corresponding perfluoroisopropyl derivatives.A polymer was obtained from (9) but a dimer of perfluoro-2,4-di-isopropylazete (16) is obtained, from (15) quantitatively.The endo structure of the dimer is revealed by formation of a stable carbanion on addition of CsF.Trapping of the azete (16) with furan gave interconvertible 1:1 cycloaddition products.Products consistent with co-dimerisation of azetes are described.

Water-soluble dyestuffs containing fibre-reactive groups of the vinylsulfone series and the fluoro-s-triazinyl-amino series

Water-soluble fibre-reactive dyestuffs containing one or two fibre-reactive groups of the vinylsulfone series and one or two fibre-reactive groups of the fluoro-s-triazinyl-amino series. These dyestuffs can be applied on fibre materials containing hydroxy and/or carbonamide groups by known application and fixation techniques for fibre-reactive dyes to yield deep and fast dyeings on these materials.