773-82-0

Basic information

• Product Name: Pentafluorobenzonitrile
• Synonyms: Cyanopentafluorobenzene;pentafluoro-benzonitril;Pentafluorocyanobenzene;PERFLUOROBENZONITRILE;PENTAFLUOROBENZONITRILE;2,3,4,5,6-PENTAFLUORO BENZONITRILE;LABOTEST-BB LT00159675;Pentefluorobenzonitrile
• CAS NO: 773-82-0
• Molecular Formula: C₇F₅N
• Molecular Weight: 193.07
• EINECS: 212-259-9
• Product Categories: Nitrile;C6 to C7;Cyanides/Nitriles;Nitrogen Compounds;Pyridines
• Mol File: 773-82-0.mol
• Article Data: 21

Chemical Properties

• Melting Point: 2.4 °C
• Boiling Point: 162-164 °C(lit.)
• Flash Point: 85 °F
• Appearance: white crystal
• Density: 1.532 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.21mmHg at 25°C
• Refractive Index: n20/D 1.442(lit.)
• Storage Temp.: Store below +30°C.
• BRN: 1913453
• CAS DataBase Reference: Pentafluorobenzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: Pentafluorobenzonitrile(773-82-0)
• EPA Substance Registry System: Pentafluorobenzonitrile(773-82-0)

Safety Data

• Hazard Codes: Xi,F,T
• Statements: 10
• Safety Statements: 16
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• TSCA: T
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 773-82-0(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR COLOURLESS TO VERY SLIGHTLY YELLOW LIQUID

Uses

Pentafluorobenzonitrile is useful as a catalyst in organic reactions, and as well is useful in liquid-?phase exfoliation of graphite for solubilized graphene.

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

• 51579-56-7 undecafluorocyclohexanecarbonitrile 
• 100-47-0 benzonitrile 
• 827-15-6 1,2,3,4,5-pentafluoro-6-iodobenzene 
• 20925-85-3 pentachlorobenzonitrile 
• 7789-23-3 potassium fluoride 
• 31881-88-6 3-chloro-2,4,5,6-tetrafluorobenzonitrile 
• 31881-89-7 3,5-dichloro-2,4,6-trifluorobenzonitrile 
• 1582-24-7 pentafluorophenylboronic acid 
• 778-34-7 1,2,3,4,5-pentafluoro-6-(trichloromethyl)benzene 
• 27318-28-1 2,3,4,5,6-pentafluorobenzaldehyde oxime 
• 121824-93-9 C₁₂F₁₀I⁽¹⁺⁾*F^(1-) 
• 24973-39-5 pentafluoro(difluoroiodo)benzene 
• 75-15-0 carbon disulfide 
• 653-37-2 perfluorobenzaldehyde 

Downstream Products

• 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 
• 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 
• 65748-21-2 (4-Cyano-2,3,5,6-tetrafluoro-phenyl)-phosphonic acid diethyl ester 
• 132120-07-1 1,1,3,3-tetrakis(dimethylamino)-4-(4-cyano-2,3,5,6-tetrafluorophenyl)-1-fluoro-1λ⁵,3λ⁵-diphosphabuta-1,3-diene 
• 79042-45-8 dimethyl 4-cyanotetrafluorophenylphosphonate 
• 79042-43-6 diethyl 4-cyanotetrafluorophenylthiophosphonate 
• 79042-42-5 diethyl 4-(trifluoromethyl)tetrafluorophenylthiophosphonate 
• 1835-49-0 tetrafluoroterephthalonitrile 
• 107608-44-6 2,3,5,6-Tetrafluoro-4-(hydroxy-pentafluorophenylmethyl-amino)-benzonitrile 
• 51579-56-7 undecafluorocyclohexanecarbonitrile 

Relevant articles and documents

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.

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.