773-82-0

Usage

Uses

Used in Chemical Catalysts:
Pentafluorobenzonitrile is used as a catalyst in various organic reactions. Its fluorinated structure and nitrile group enable it to act as a Lewis acid, facilitating the formation of desired products and improving reaction efficiency.
Used in Material Science:
Pentafluorobenzonitrile is also useful in the liquid-phase exfoliation of graphite for solubilized graphene. Its interaction with graphite layers allows for the separation and dispersion of graphene sheets in a liquid medium, which is crucial for the development of graphene-based materials and applications in various industries, such as electronics, energy storage, and composite materials.

InChI:InChI=1/C7F5N/c8-3-2(1-13)4(9)6(11)7(12)5(3)10

Synthetic route

pentachlorobenzonitrile (20925-85-3) → Pentafluorobenzonitrile (773-82-0)

Conditions	Yield
With potassium fluoride at 320 - 340℃; under 7500.75 Torr; for 20h; Temperature; Concentration; Pressure; Autoclave; Inert atmosphere;	98.7%
With potassium fluoride; tetrabutyl ammonium fluoride In toluene at 220℃; Reagent/catalyst;	90.4%
With potassium fluoride In benzonitrile at 230℃; for 30h; Temperature; Concentration;
With potassium fluoride at 110 - 120℃; for 10h; Time; Inert atmosphere;	270 kg

C26H15AuF5N2P → Pentafluorobenzonitrile (773-82-0)

Conditions	Yield
In 1,4-dioxane at 100℃; for 30h; Kinetics; Inert atmosphere; Schlenk technique; Sealed tube;	95%

trimethylsilyl cyanide (7677-24-9) + C34H40AuF6NP(1+)*F6Sb(1-) → Pentafluorobenzonitrile (773-82-0) + F6Sb(1-)*C32H49AuN2PSi(1+)

Conditions	Yield
In dichloromethane-d2 at 50℃; for 12h; Glovebox;	A 92% B n/a

perfluorobenzaldehyde (653-37-2) → Pentafluorobenzonitrile (773-82-0) + 2,3,4,5,6-pentafluorobenzamide (652-31-3)

Conditions	Yield
With [Ru(η6-C6Me6)Cl2(tris(dimethylamino)phosphine)]; hydroxylamine hydrochloride; sodium hydrogencarbonate In water at 100℃; for 7h; Reagent/catalyst; Inert atmosphere; Sealed tube; Green chemistry;	A n/a B 90%

1,2,3,4,5-pentafluoro-6-(trichloromethyl)benzene (778-34-7) → Pentafluorobenzonitrile (773-82-0)

Conditions	Yield
With ammonia at 5℃; for 3h; Temperature; Autoclave;	86%

2,3,4,5,6-pentafluorobenzaldehyde oxime (27318-28-1) → Pentafluorobenzonitrile (773-82-0)

Conditions	Yield
With [PdCl2{κ2-(P,N)-2-Ph2PC6H4CH=NOH}] In acetonitrile at 100℃; for 24h; Catalytic behavior; Temperature; Inert atmosphere; Sealed tube;	82%

pentachlorobenzonitrile (20925-85-3) → Pentafluorobenzonitrile (773-82-0) + 2,4,6-trifluoro-3,5-dichlorobenzonitrile (31881-89-7)

Conditions	Yield
With potassium fluoride In benzonitrile at 320 - 340℃; for 12 - 18h; Product distribution / selectivity;	A 76.9% B 3%

O,N-bis-(trifluoroacetyl)-hydroxylamine (684-78-6) + perfluorobenzaldehyde (653-37-2) → Pentafluorobenzonitrile (773-82-0)

Conditions	Yield
With pyridine In benzene heating on water bath, 3 h; washing with 2.5 N NaOH, 5 N HCl and NaHSO3;	75%
With pyridine In benzene heating on water bath, 3 h; washing with 2.5 N NaOH, 5 N HCl and NaHSO3;	75%

potassium fluoride + pentachlorobenzonitrile (20925-85-3) → Pentafluorobenzonitrile (773-82-0) + 3-chloro-2,4,5,6-tetrafluorobenzonitrile (31881-88-6)

Conditions	Yield
heating to 350°C, 20 h in autoclave; distn.;	A 70% B 9%
heating to 350°C, 20 h in autoclave; distn.;	A 70% B 9%
heating to 480°C, 20 h in autoclave; distn.;	A 47% B 9%
heating to 480°C, 20 h in autoclave; distn.;	A 47% B 9%

bromopentafluorobenzene (344-04-7) + copper(l) cyanide → Pentafluorobenzonitrile (773-82-0)

Conditions	Yield
In N,N-dimethyl-formamide refluxing;	65%
With iron(III) chloride In N,N-dimethyl-formamide heating at 147-158°C, 13 h; after then with FeCl3 at 100°C, 0.5 h;
With FeCl3 In N,N-dimethyl-formamide heating at 147-158°C, 13 h; after then with FeCl3 at 100°C, 0.5 h;

potassium fluoride + pentachlorobenzonitrile (20925-85-3) → Pentafluorobenzonitrile (773-82-0) + 3-chloro-2,4,5,6-tetrafluorobenzonitrile (31881-88-6) + 2,4,6-trifluoro-3,5-dichlorobenzonitrile (31881-89-7)

Conditions	Yield
heating to 300°C, 40 h in autoclave; distn.;	A 3% B 12% C 64%
heating to 300°C, 40 h in autoclave; distn.;	A 3% B 12% C 64%

2,3,4,5,6-pentafluorophenylmagnesium bromide (879-05-0) + phenyl cyanate (1122-85-6) → Pentafluorobenzonitrile (773-82-0)

Conditions	Yield
In diethyl ether at -15℃; for 2h;	45%

1-chloro-2,3,4,5,6-pentafluorobenzene (344-07-0) + copper(l) cyanide → Pentafluorobenzonitrile (773-82-0)

Conditions	Yield
In N,N-dimethyl-formamide heating at 150°C, 48 h;	5%

2,3,4,5,6-pentafluorobenzamide (652-31-3) → Pentafluorobenzonitrile (773-82-0)

Conditions	Yield
With phosphorus pentoxide at 200℃;
With phosphorus pentoxide at 200 - 250℃; for 1.25h;

undecafluorocyclohexanecarbonitrile (51579-56-7) → Pentafluorobenzonitrile (773-82-0) + perfluoro(methylcyclohexane) (355-02-2) + nonafluorocyclohex-1-enecarbonitrile (90408-45-0)

Conditions	Yield
With iron(III) oxide at 400 - 435℃;	A 0.04 g B 0.03 g C 0.68 g

benzonitrile (100-47-0) → Pentafluorobenzonitrile (773-82-0) + perfluorocyclohexane (355-68-0) + 2-fluorobenzonitrile (394-47-8) + undecafluorocyclohexanecarbonitrile (51579-56-7)

Conditions	Yield
With caesium tetrafluorocobaltate(III) at 300℃; for 1.5h; Product distribution; fluorination of benzonitriles over caesium tetrafluorocobaltate(III) at elevates temperatures;	A 0.28 g B 0.22 g C 0.03 g D 0.99 g
With caesium tetrafluorocobaltate(III) at 300℃; for 1.5h; Yields of byproduct given;	A 0.28 g B 0.22 g C 0.03 g D n/a
With caesium tetrafluorocobaltate(III) at 300℃; for 1.5h; Yield given. Yields of byproduct given;

bromopentafluorobenzene (344-04-7) + copper(I) cyanide (544-92-3) → Pentafluorobenzonitrile (773-82-0)

Conditions	Yield
at 147 - 158℃;

perfluorobenzaldehyde (653-37-2) → Pentafluorobenzonitrile (773-82-0)

Conditions	Yield
With O,N-bis-(trifluoroacetyl)-hydroxylamine

1,2,3,4,5-pentafluoro-6-iodobenzene (827-15-6) + copper(I) cyanide (544-92-3) → Pentafluorobenzonitrile (773-82-0)

Conditions	Yield
at 160℃;

C8H3F5NO(1-)*Na(1+) → Pentafluorobenzonitrile (773-82-0)

Conditions	Yield
In methanol at 50.1℃; Equilibrium constant;

1,2,3,4,5-pentafluoro-6-iodobenzene (827-15-6) + CuCN → Pentafluorobenzonitrile (773-82-0)

Conditions	Yield
With pyridine

di-tert-butyl peroxide (110-05-4) + O-dodecyl pentafluorobenzaldoxime → 1-dodecene (112-41-4) + Dodecanal (112-54-9) + Pentafluorobenzonitrile (773-82-0) + tert-butyl alcohol (75-65-0)

Conditions	Yield
In benzene Product distribution; Disproportionation; Photolysis;

di-tert-butyl peroxide (110-05-4) + O-[3-(cyclohex-2-enyloxy)propionyl] pentafluorobenzaldoxime → perfluorobenzaldehyde (653-37-2) + Pentafluorobenzonitrile (773-82-0) + tert-butyl alcohol (75-65-0)

Conditions	Yield
With di-tert-butyl peroxide for 24h; Product distribution; Irradiation;

pentachlorobenzonitrile (20925-85-3) → benzoyl fluoride (455-32-3) + Pentafluorobenzonitrile (773-82-0)

Conditions	Yield
With potassium fluoride; potassium hydroxide In benzonitrile at 315℃; for 18h;

1,2,3,4,5-pentafluoro-6-iodobenzene (827-15-6) + copper(l) cyanide → Pentafluorobenzonitrile (773-82-0)

Conditions	Yield
With iron(III) chloride In N,N-dimethyl-formamide heating at 147-158°C, 13 h; after then with FeCl3 at 100°C, 0.5 h;
In pyridine heating at 150°C (becomes black), 5 min; distn.;
In pyridine heating at 150°C (becomes black), 5 min; distn.;
With FeCl3 In N,N-dimethyl-formamide heating at 147-158°C, 13 h; after then with FeCl3 at 100°C, 0.5 h;
In pyridine heating at 150°C (becomes black), 5 min; distn.;

carbon disulfide (75-15-0) + C34H43F5N4OTi → Pentafluorobenzonitrile (773-82-0) + Cp*Ti-{PhC(NiPr)2}{SC(S)N(OtBu)}

Conditions	Yield
In benzene-d6 at 20℃; for 360h; Inert atmosphere;

pentafluoro(difluoroiodo)benzene (24973-39-5) → Pentafluorobenzonitrile (773-82-0) + 1,2,3,4,5-pentafluoro-6-iodobenzene (827-15-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: dichloromethane / 1 h 2: dichloromethane / 0.37 h / 20 °C 3: dichloromethane / 94 °C / Sealed tube; Inert atmosphere View Scheme

C12F10I(1+)*F(1-) (121824-93-9) → Pentafluorobenzonitrile (773-82-0) + 1,2,3,4,5-pentafluoro-6-iodobenzene (827-15-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: dichloromethane / 0.37 h / 20 °C 2: dichloromethane / 94 °C / Sealed tube; Inert atmosphere View Scheme

C13F10IN → Pentafluorobenzonitrile (773-82-0) + 1,2,3,4,5-pentafluoro-6-iodobenzene (827-15-6)

Conditions	Yield
In dichloromethane at 94℃; Sealed tube; Inert atmosphere;

(pentamethylcyclopentadienyl)(dicarbonyl)iridium(I) (32660-96-1) + Pentafluorobenzonitrile (773-82-0) + water (7732-18-5) → Cp*Ir(CO)(COOH)(C6F4CN)

Conditions	Yield
at 20℃; Inert atmosphere; Schlenk technique; Molecular sieve; Irradiation;	100%
In water (Ar); Schlenk technique or Carius tube; F ligand and H2O were added to Ir complex in tube; degassed by freeze-pump-thaw; stirred at room temp.; filtered; solvent removed (vac.); hexane/CH2Cl2 added to supernatant; slowly evapd.; combined; elem. anal.;	99%

Pentafluorobenzonitrile (773-82-0) → 6-pentafluorophenyl-1,3,2,4,5-dioxadithiazine-2,2,4,4-tetroxide (499099-69-3)

Conditions	Yield
With sulfur trioxide at 20℃; for 24h;	99%

Pentafluorobenzonitrile (773-82-0) → 2,6-bis(pentafluorophenyl)-1,4,3,5-oxathiadiazine-4,4-dioxide (507221-58-1)

Conditions	Yield
With sulfur trioxide at 65℃; for 12h;	99%

Pentafluorobenzonitrile (773-82-0) + ethyl 2-cyanoacetate (105-56-6) → potassium 2-cyano-2-(4-cyano-2,3,5,6-tetrafluorophenyl)-1-ethoxyethen-1-olate

Conditions	Yield
With potassium carbonate In acetonitrile at 82℃; for 17h; Inert atmosphere; Industrial scale;	99%
With potassium carbonate In acetonitrile at 82℃; for 17h; Inert atmosphere; Industrial scale;	99%

Pentafluorobenzonitrile (773-82-0) + ethyl 2-cyanoacetate (105-56-6) → ethyl 2-cyano-2-(4-cyanoperfluorophenyl)acetate (64934-70-9)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 48h;	99%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 48h;	99%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 48h;	99%

Pentafluorobenzonitrile (773-82-0) + tert-butylamine (75-64-9) → 4-(tert-butylamino)tetrafluorobenzonitrile

Conditions	Yield
In chloroform at 20℃; for 1.5h;	99%

Pentafluorobenzonitrile (773-82-0) + dimethyl amine (124-40-3) → 4-(dimethylamino)-2,3,5,6-tetrafluorobenzonitrile (5291-87-2)

Conditions	Yield
In benzene	98%
In benzene	98%
In nitromethane
In nitromethane

Pentafluorobenzonitrile (773-82-0) + methylamine (74-89-5) → N-Methyl-p-cyanotetrafluoroaniline (28012-05-7)

Conditions	Yield
In water; isopropyl alcohol at 20℃; for 72h;	98%
In nitromethane

Pentafluorobenzonitrile (773-82-0) → 2,3,4,5,6-pentafluorobenzylamine (1548-77-2)

Conditions	Yield
With borane-THF In tetrahydrofuran for 10h; Heating;	98%

Pentafluorobenzonitrile (773-82-0) + methylamine (74-89-5) → C6F4CNNHCH3 + N-Methyl-p-cyanotetrafluoroaniline (28012-05-7)

Conditions	Yield
In nitromethane	A <1 B 98%
In nitromethane	A <1 B 98%
In benzene at 20°C, 5 min;	A 6% B 94%
In benzene at 20°C, 5 min;	A 6% B 94%

Pentafluorobenzonitrile (773-82-0) → 4-amino-2,3,5,6-tetrafluorobenzonitrile (17823-38-0)

Conditions	Yield
With ammonium hydroxide In acetonitrile at 20℃; for 10h; Cooling with ice;	98%
With ammonium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In ethyl acetate at -15 - -5℃; for 10h; Large scale;	98%
With ammonia In water; ethyl acetate at 20℃; for 6h;	93%

Pentafluorobenzonitrile (773-82-0) + (+)-usnic acid (17669-01-1, 56190-51-3, 15853-98-2) → 2,6-diacetyl-3,9-dihydroxy-7-(2',3',5',6'-tetrafluoro-4'-(cyano)-phenoxy)-8,9b-dimethyl-9bH-dibenzofuran-1-one

Conditions	Yield
Stage #1: (+)-usnic acid With potassium carbonate In N,N-dimethyl-formamide at 20 - 45℃; Stage #2: Pentafluorobenzonitrile	98%

1,5-dioxaspiro[5.5]undecane-2,4-dione (1658-27-1) + Pentafluorobenzonitrile (773-82-0) + N-ethyl-N,N-diisopropylamine (7087-68-5) → C16H11F4NO4*C8H19N

Conditions	Yield
In acetonitrile at 80℃; for 7h;	98%

Pentafluorobenzonitrile (773-82-0) → 2,3,5,6-tetrafluorobenzonitrile (5216-17-1) + 2,3,4,5-tetrafluorobenzonitrile (16582-93-7)

Conditions	Yield
With tetrabutylammonium triphenyldifluorosilicate; HSiPh3 In tetrahydrofuran; benzene-d6 at 20℃; for 8h; Inert atmosphere; Sealed tube;	A 97% B 3%
With 4,5-bis-(di-tert-butyl-phosphanyl)-9,9-dimethyl-9H-xanthene; [t-BuXantphosAu]+[Cl-Au-Cl]-; diphenylsilane; acetic acid In 1,2-dichloro-ethane at 80℃; for 24h; Inert atmosphere;
With Dimethylphenylsilane; o-phenylenebis(diphenylphosphine); potassium tert-butylate; copper(l) chloride In tetrahydrofuran for 12h; Inert atmosphere; Reflux; Overall yield = 100 %Spectr.; regioselective reaction;

Pentafluorobenzonitrile (773-82-0) → 4-azido-2,3,5,6-tetrafluorobenzonitrile (31469-89-3)

Conditions	Yield
With sodium azide; copper(II) acetate monohydrate In acetonitrile at 20℃; Schlenk technique;	97%
With sodium azide; N,N,N,N-tetraethylammonium tetrafluoroborate In water; N,N-dimethyl-formamide at 25℃; for 4h; Reagent/catalyst;	95%
With sodium azide In water; acetone at 70℃; for 0.25h; Reflux; Microwave irradiation;	90%
With sodium azide In water; acetone at 85℃; for 6h;	65%
With sodium azide In water; acetone at 85℃; for 6h;	65%

Pentafluorobenzonitrile (773-82-0) + 9H-carbazole (86-74-8) → 2,3,4,5,6-penta(9H-carbazol-9-yl)benzonitrile

Conditions	Yield
Stage #1: 9H-carbazole With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.5h; Inert atmosphere; Stage #2: Pentafluorobenzonitrile In tetrahydrofuran; mineral oil at 20℃; for 12h; Inert atmosphere;	97%
Stage #1: 9H-carbazole With sodium hydride In tetrahydrofuran at 20℃; for 0.5h; Schlenk technique; Inert atmosphere; Stage #2: Pentafluorobenzonitrile In tetrahydrofuran at 20℃; for 24h; Schlenk technique; Inert atmosphere;	95%
With potassium tert-butylate In dichloromethane; N,N-dimethyl-formamide for 6h; Inert atmosphere;	90%
With potassium carbonate In dimethyl sulfoxide at 20 - 150℃; for 24h; Inert atmosphere;	61%

3-tert-butyltitanacyclobutane (75687-68-2) + Pentafluorobenzonitrile (773-82-0) → (C5H5)2Ti(C3H2N2)(C6F5)2

Conditions	Yield
In benzene (Ar); Ti compd. in benzene was stirred with C6F5CN (1:2,0 mol) at 50°C for 5,5 h; removal of solvent yielded the product;	96%

piperidine (110-89-4) + carbon disulfide (75-15-0) + Pentafluorobenzonitrile (773-82-0) → 4-cyano-2,3,5,6-tetrafluorophenyl piperidine-1-carbodithioate

Conditions	Yield
Stage #1: piperidine; carbon disulfide With potassium phosphate In dimethyl sulfoxide at 20℃; for 2h; Schlenk technique; Green chemistry; Stage #2: Pentafluorobenzonitrile In dimethyl sulfoxide at 20℃; for 2h; Schlenk technique; Green chemistry; regioselective reaction;	96%

carbon disulfide (75-15-0) + Pentafluorobenzonitrile (773-82-0) + Benzyl-isopropyl-amin (102-97-6) → 4-cyano-2,3,5,6-tetrafluorophenyl-N-benzyl-N-isopropylcarbamodithioate

Conditions	Yield
Stage #1: carbon disulfide; Benzyl-isopropyl-amin With potassium phosphate In dimethyl sulfoxide at 20℃; for 2h; Schlenk technique; Green chemistry; Stage #2: Pentafluorobenzonitrile In dimethyl sulfoxide at 20℃; for 2h; Schlenk technique; Green chemistry; regioselective reaction;	96%

triisopropyl phosphite (116-17-6) + Pentafluorobenzonitrile (773-82-0) → (Amino-pentafluorophenyl-methyl)-phosphonic acid diisopropyl ester

Conditions	Yield
With nickel(II) chloride hexahydrate In toluene at 100℃; for 16h; Schlenk technique; Glovebox;	96%

Pentafluorobenzonitrile (773-82-0) + 1-phenyl-2-(tetrahydropyrimidin-2(1H)-ylidene)ethan-1-one (82100-30-9) → 10-benzoyl-7-cyano-6,8,9-trifluoro-1,2,3,4-tetrahydropyrimido[1,2-a]indole

Conditions	Yield
Stage #1: Pentafluorobenzonitrile; 1-phenyl-2-(tetrahydropyrimidin-2(1H)-ylidene)ethan-1-one With sodium carbonate In 1,4-dioxane at 85℃; for 4h; Stage #2: With caesium carbonate In 1,4-dioxane for 2.5h; Reflux;	96%

Pentafluorobenzonitrile (773-82-0) → Pentafluorobenzoic acid (602-94-8)

Conditions	Yield
With sulfuric acid In water at 155℃; for 2h; Temperature;	95.3%
With sulfuric acid In water at 145 - 165℃; for 15h;
With sulfuric acid hydrolysis at 180°C, with 75 % H2SO4;

Pentafluorobenzonitrile (773-82-0) → 2,3,4,5,6-pentafluorobenzamide (652-31-3)

Conditions	Yield
With [OsCl2(η6-p-cymene)(PMe2OH)]; water at 80℃; for 1.5h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; Sealed tube;	95%
With fac-[(CO)3Mn(iPr2P(CH2)2PiPr2)(triflato)]; water In tetrahydrofuran at 100℃; for 18h; Glovebox; Inert atmosphere; Schlenk technique;	94%
With N-ethyl-N-hydroxy-ethanamine; water; copper diacetate In ethanol at 35℃; for 3h;	92%

dimethylbis(η5-pentamethylcyclopentadienyl)thorium (67506-90-5) + Pentafluorobenzonitrile (773-82-0) → (C5(CH3)5)2Th(NC(CH3)C6F5)2 (937037-26-8)

Conditions	Yield
In toluene dropwise addn. of soln. of nitrile in toluene to a stirred soln. of (C5Me5)2ThMe2 in toluene under inert atmosphere, stirring at room temp. for 14 h; removal of volatiles in vac., dissolution in pentane, hot filtration through Celite, isolation of product from filtrate, drying under reduced pressure;	95%

Pentafluorobenzonitrile (773-82-0) + p-cyanophenyl n-dodecanoate (90149-61-4) → n-Dodecanoyl fluoride (2266-69-5) + C14H4F4N2O

Conditions	Yield
With hydridotetakis(triphenylphosphine)rhodium(I); cis-1,2-bis-(diphenylphosphino)ethene In chlorobenzene for 2h; Inert atmosphere; Reflux;	A 95% B n/a

Pentafluorobenzonitrile (773-82-0) + 1-(4-bromophenyl)-2-(tetrahydropyrimidin-2(1H)-ylidene)ethan-1-one (112030-64-5) → 10-(4-bromobenzoyl)-7-cyano-6,8,9-trifluoro-1,2,3,4-tetrahydropyrimido[1,2-a]indole

Conditions	Yield
Stage #1: Pentafluorobenzonitrile; 1-(4-bromophenyl)-2-(tetrahydropyrimidin-2(1H)-ylidene)ethan-1-one With caesium carbonate In 1,4-dioxane at 85℃; for 3h; Stage #2: With caesium carbonate In 1,4-dioxane for 2.5h; Reflux;	95%

Pentafluorobenzonitrile (773-82-0) → {C6F5CNSNS}(1+)*AsF6(1-)={C6F5CNSNS}{AsF6}

Conditions	Yield
With dithionitronium hexafluoroarsenate for 3h; Ambient temperature;	94%

Pentafluorobenzonitrile (773-82-0) + disodiumtetrafluorohydroquinone (7640-65-5) → 1,4-bis(4'-cyano-2,3,5,6-tetrafluorophenoxytetrafluoro)benzene (15053-71-1)

Conditions	Yield
In acetone at 20°C, 12 d;	94%
In acetone at 20°C, 12 d;	94%

Upstream product

• 652-31-3 2,3,4,5,6-pentafluorobenzamide 
• 51579-56-7 undecafluorocyclohexanecarbonitrile 
• 100-47-0 benzonitrile 
• 879-05-0 2,3,4,5,6-pentafluorophenylmagnesium bromide 
• 1122-85-6 phenyl cyanate 
• 344-04-7 bromopentafluorobenzene 
• 544-92-3 copper(I) cyanide 
• 653-37-2 perfluorobenzaldehyde 
• 827-15-6 1,2,3,4,5-pentafluoro-6-iodobenzene 
• 110-05-4 di-tert-butyl peroxide 
• 20925-85-3 pentachlorobenzonitrile 
• 344-07-0 1-chloro-2,3,4,5,6-pentafluorobenzene 
• 684-78-6 O,N-bis-(trifluoroacetyl)-hydroxylamine 
• 7789-23-3 potassium fluoride 

Downstream Products

• 20017-54-3 perfluoro(4-isopropylphenyl) cyanide 
• 56973-54-7 perfluoro(2-isopropylphenyl) cyanide 
• 56973-55-8 perfluoro(2,4-diisopropylphenyl) cyanide 
• 56973-56-9 perfluoro(2,5-diisopropylphenyl) cyanide 
• 56973-53-6 perfluoro(2,4,6-triisopropylphenyl) cyanide 
• 56973-52-5 perfluoro(2,4,5-triisopropylphenyl) cyanide 
• 31743-12-1 C₁₆H₆B₂Cl₄F₁₀N₂S₂ 
• 5291-87-2 4-(dimethylamino)-2,3,5,6-tetrafluorobenzonitrile 
• 14560-19-1 1,3,5-Tris-<2,3,4,5,6-pentafluor-benzyl>-borazin 
• 55330-51-3 (E)-3-Amino-3-pentafluorophenyl-acrylonitrile 
• 90619-68-4 2-(F-phenyl)-4,4,6-trimethyl-5,6-dihydro-4H-oxazine 
• 137445-17-1 tetrafluoro-4-(2,2,2-trifluoroethyl)benzonitrile 
• 137445-16-0 perfluoro-4-(2H-hexafluoroisopropyl)benzonitrile 
• 137445-18-2 perfluoro-4-<4H-decafluoro(4-methylpent-2-en-2-yl)>benzonitrile 

Relevant academic research and scientific papers

Preparation method of fluorine-containing aryl compound

The invention relates to the field of organic synthesis, and especially relates to a preparation method of a fluorine-containing aryl compound. The invention provides a preparation method of a compound as shown in a formula 1. The preparation method comprises the following steps: fluorination reaction: reacting a compound as shown in a formula 2 with alkali metal fluoride in the presence of a phase transfer catalyst to prepare the compound as shown in the formula 1. According to the preparation method of the fluorine-containing aryl compound provided by the invention, a reaction system does not contain a solvent, the boiling point of the phase transfer catalyst is relatively high, solvent interference is avoided during rectification or short steaming after the reaction is finished, the distillation yield is high, and the product purity is good.

Synthesis and Characterization of Bidentate (P^N)Gold(III) Fluoride Complexes: Reactivity Platforms for Reductive Elimination Studies

A new family of cationic, bidentate (P^N)gold(III) fluoride complexes has been prepared and a detailed characterization of the gold-fluoride bond has been carried out. Our results correlate with the observed reactivity of the fluoro ligand, which undergoes facile exchange with both cyano and acetylene nucleophiles. The resulting (P^N)arylgold(III)C(sp) complexes have enabled the first study of reductive elimination on (P^N)gold(III) systems, which demonstrated that C(sp2)?C(sp) bond formation occurs at higher rates than those reported for analogous phosphine-based monodentate systems.

Method for preparing polyfluorobenzonitrile through catalytic fluorination of polychlorobenzonitrile

The invention discloses a method for preparing polyfluorobenzonitrile through catalytic fluorination of polychlorobenzonitrile, and belongs to the field of preparation of fine chemical industry intermediates. The preparation method comprises the following steps: carrying out a heating activation reaction on a fluoride salt, an organic solvent and electron-withdrawing substituted phenylborate; andadding polychlorobenzonitrile, heating to 80-120 DEG C, rectifying while reacting, then supplementing polychlorobenzonitrile and potassium fluoride, and rectifying while reacting to obtain polyfluorobenzonitrile. According to the invention, the reaction system is high in catalytic activity, the technical problems of low conversion rate/medium selectivity and the like of the single nitrile compounds with low activity during fluoridation reactions are solved, the mode simultaneously performing reacting and product distilling in the reaction process promotes the continuous forward proceeding of the reaction so as to improve the reaction yield, and the method is suitable for industrial production.

Mechanistic Insights into C(sp2)?C(sp)N Reductive Elimination from Gold(III) Cyanide Complexes

A new family of phosphine-ligated dicyanoarylgold(III) complexes has been prepared and their reactivity towards reductive elimination has been studied in detail. Both, a highly positive entropy of activation and a primary 12/13C KIE suggest a late concerted transition state while Hammett analysis and DFT calculations indicate that the process is asynchronous. As a result, a distinct mechanism involving an asynchronous concerted reductive elimination for the overall C(sp2)?C(sp)N bond forming reaction is characterized herein, for the first time, complementing previous studies reported for C(sp3)?C(sp3), C(sp2)?C(sp2), and C(sp3)?C(sp2) bond formation processes taking place on gold(III) species.

Method for preparing 2,3,4,5,6-pentafluorophenol

The invention discloses a method for preparing 2,3,4,5,6-pentafluorophenol. The method comprises the following step of in water, performing an oxidation reaction on 2,3,4,5,6-pentafluoro phenylboronic acid as shown in the formula (VI) and hydrogen peroxide, thereby obtaining 2,3,4,5,6-pentafluorophenol as shown in the formula (VII). According to the method, an oxidation reaction is implemented in the water, so that the method is low in cost, and environmental-friendly; and besides, the method is high in reaction yield and purity and relatively applicable to industrial production.

Preparation method of pentafluorobenzonitrile

The invention discloses a preparation method of pentafluorobenzonitrile. The method comprises the following steps: (1) introducing oxygen gas and ammonia gas into a mixed system of 2,6-dichloro-3-fluoroacetophenone, copper salt, a phase transfer catalyst and a solvent A to perform reaction to obtain 2,6-dichloro-3-fluorobenzonitrile; (2) perchlorinating the 2,6-dichloro-3-fluorobenzonitrile under the action of a catalyst to obtain 2,3,4,6-tetrachloro-5- fluorobenzonitrile; (3) adding the 2,3,4,6-tetrachloro-5-fluorobenzonitrile, KF and the phase transfer catalyst into a solvent B, and performing fluoridation to obtain the pentafluorobenzonitrile. The 2,6-dichloro-3-fluoroacetophenone used in the preparation method is a by-product in producing 2,4-dichloro-5-fluoroacetophenone, and the total yield of a single cycle can reach 83%; the raw materials are cheap and easy to obtain, the cost is reduced, and the environment is protected; and the synthetic process is simple, the operation is convenient, the yield is relatively high, the purity is good, and the pentafluorobenzonitrile is suitable for industrial production.

Selective one-pot synthesis of aminopolyhalobenzonitriles from polyhalobenzotrichlorides in anhydrous ammonia

Polyhalogenated benzotrichlorides (pentafluoro-, chlorotetrafluoro-, chlorotrifluoro-, and tetrafluorobenzotrichlorides) undergo one-pot ammonolysis?+?aminodefluorination by the action of anhydrous ammonia to form mono- and diamino derivatives of polyhalobenzonitriles. For the substrates comprising halogen at the para-position, the ammonolysis of the CCl3 group and the first aminodefluorination occur simultaneously in the temperature range from ?33 to 5?°C. The temperature of introducing the second NH2 group is higher by 60–100?°C, whereby conditions were found for the selective synthesis of mono- and diaminopolyhalobenzonitriles. The use of anhydrous ammonia as a reagent and a solvent minimizes side reactions and simplifies an isolation of the high purity products.

Fluorobenzonitrile compound preparation method

The present invention provides a fluorobenzonitrile compound preparation method, fluorobenzonitrile compounds are as shown in the general formula (I), an objective product can be prepared from a general-formula-(II)-shown chlorobenzonitrile compound as a raw material by reacting with an anhydrous fluoride in the presence of an inert gas under high temperature high pressure reaction conditions and flashing a reaction product, wherein the objective product itself is used as a solvent. Due to use of the objective product itself as the solvent, a main component of the fluorine exchange reaction product only comprises the objective product, due to use of an inert gas pressurization method to improve the fluorine exchange reaction and product separation conditions, the product is separated and purified in the flashing manner, the reaction residual heat is rationally used, and the whole process is simple and feasible. The method is readily available in raw materials, simple in process, energy-saving, consumption-reducing, and more suitable for industrial scale production.

Pentafluorobenzonitrile production method

The present invention discloses a pentafluorobenzonitrile production method which belongs to the field of fine chemical production, pentafluorobenzonitrile is prepared from the raw materials of pentachlorophenylformonitrile, anhydrous potassium fluoride, benzonitrile and polyethylene glycol in the ratio of 1.0-1.1: 5.0-5.2: 23-25: 0.2-0.3 by fluorination process, and key points of the production method are as follows: 1, selection of the raw material ratio; 2, selection of appropriate temperature, to be more specific, the temperature is as low as possible under possible conditions, and when a better effect cannot be achieved by reduction of the temperature, the reaction temperature is improved to obtain a higher yield; and 3, selection of reaction time, to be more specific, by the selection of the reaction time, the reaction is more full to obtain a highest yield; the pentafluorobenzonitrile produced according to the formula and the method has the advantages of simple production process, low production cost, and no pollution, the pentafluorobenzonitrile yield can reach 78%, the content can reach 95%, and the product is an important medicine and pesticide intermediate.

Palladium(II) complexes with a phosphino-oxime ligand: Synthesis, structure and applications to the catalytic rearrangement and dehydration of aldoximes

The treatment of [PdCl2(COD)] (COD = 1,5-cyclooctadiene) with 1 and 2 equivalents of 2-(diphenylphosphino)benzaldehyde oxime in dichloromethane at room temperature led to the selective formation of [PdCl2{κ2-(P,N)-2-Ph2PC6H4CHNOH}] (1) and [Pd{κ2-(P,N)-2-Ph2PC6H4CHNOH}2][Cl]2 (2), respectively, which represent the first examples of Pd(II) complexes containing a phosphino-oxime ligand. These compounds, whose structures were fully confirmed by X-ray diffraction methods, were active in the catalytic rearrangement of aldoximes. In particular, using 5 mol% complex 1, a large variety of aldoximes could be cleanly converted into the corresponding primary amides at 100 °C, employing water as solvent and without the assistance of any cocatalyst. Palladium nanoparticles are the active species in the rearrangement process. In addition, when the same reactions were performed employing acetonitrile as solvent, selective dehydration of the aldoximes to form the respective nitriles was observed. For comparative purposes, the catalytic behaviour of an oxime-derived palladacyclic complex has also been briefly evaluated.