551-62-2

Basic information

• Product Name: 1,2,3,4-Tetrafluorobenzene
• Synonyms: 2,3,4,5-Tetrafluorobenzene;benzene,1,2,3,4-tetrafluoro-;o-Tetrafluorobenzene;1,2,3,4-TETRAFLUOROBENZENE;1,2,3,4-Tetrafluorobenzene, 99+%;4-flurobenzoyl chloride;1,2,3,4-Tetrafluorobenzene 99%;1,2,3,4-Tetrafluorbenzol
• CAS NO: 551-62-2
• Molecular Formula: C₆H₂F₄
• Molecular Weight: 150.07
• EINECS: 208-997-6
• Product Categories: Aromatic Halides (substituted);Fluorobenzene;Aryl;C6;Halogenated Hydrocarbons;Pyridines
• Mol File: 551-62-2.mol
• Article Data: 27

Chemical Properties

• Melting Point: −42 °C(lit.)
• Boiling Point: 95 °C(lit.)
• Flash Point: 69 °F
• Appearance: colourless liquid
• Density: 1.4 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.408(lit.)
• Storage Temp.: Flammables area
• Stability: Stable. Highly flammable. Incompatible with strong oxidizing agents.
• BRN: 1910024
• CAS DataBase Reference: 1,2,3,4-Tetrafluorobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4-Tetrafluorobenzene(551-62-2)
• EPA Substance Registry System: 1,2,3,4-Tetrafluorobenzene(551-62-2)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26-36/37/39-33-7/9
• RIDADR: UN 1993 3/PG 2
• WGK Germany: 3
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 551-62-2(Hazardous Substances Data)

Usage

Chemical Properties

colourless liquid

InChI:InChI=1/C6H2F4/c7-3-1-2-4(8)6(10)5(3)9/h1-2H

Synthetic route

2,3,4,5-tetrafluorobenzoic acid (1201-31-6) → 1,2,3,4-tetrafluorobenzene (551-62-2)

Conditions	Yield
With ammonia; copper In water at 240℃; for 1.25h; Temperature; Reagent/catalyst;	94.4%
Multi-step reaction with 3 steps 1: acetonitrile / 2 h / 20 °C / Darkness 2: acetonitrile / Darkness 3: water / d7-N,N-dimethylformamide / 1 h / 100 °C / Inert atmosphere; Glovebox; Sealed tube; Darkness View Scheme

3,4,5,6-tetrafluorophthalic acid (652-03-9) → 1,2,3,4-tetrafluorobenzene (551-62-2)

Conditions	Yield
With ammonium hydroxide at 250℃; for 0.416667h; Temperature; Time; Autoclave; Green chemistry;	90.1%

Pentafluorobenzene (363-72-4) → 1,2,4,5-Tetrafluorobenzene (327-54-8) + 1,2,3,4-tetrafluorobenzene (551-62-2) + 1,2,3,5-tetrafluorobenzene (2367-82-0)

Conditions	Yield
With H2SiEt2; tetrabutylammonium triphenyldifluorosilicate In tetrahydrofuran; benzene-d6 at 60℃; for 40h; Inert atmosphere; Sealed tube;	A 90% B n/a C n/a
With radical anion of p,p'-di-tert-butylbiphenyl In tetrahydrofuran at 45℃; Irradiation;	A 71.6% B 16.4% C 30.6%
With radical anion of p,p'-di-tert-butylbiphenyl In tetrahydrofuran at -40℃; Product distribution; Rate constant; Mechanism; Irradiation; radical anion of naphthalene, different temperatures;	A 69% B 21% C 10%

3,4,5,6-tetrafluorophthalic acid (652-03-9) → 1,2,3,4-tetrafluorobenzene (551-62-2) + 2,3,4,5-tetrafluorobenzoic acid (1201-31-6)

Conditions	Yield
With ammonium hydroxide at 190℃; for 2h; Temperature; Time; Autoclave; Green chemistry;	A 10.5% B 86.1%
With ammonium hydroxide at 240℃; for 0.666667h; Temperature; Time; Autoclave; Green chemistry;	A 82% B 8.1%

Hexafluorobenzene (392-56-3) → 1,2,3,4-tetrafluorobenzene (551-62-2) + Pentafluorobenzene (363-72-4)

Conditions	Yield
With C32H46N2Ru; sodium carbonate; isopropyl alcohol at 70℃; for 2h; Inert atmosphere; Schlenk technique; Glovebox;	A 11% B 80%
Stage #1: Hexafluorobenzene With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; [(HC[(CMe)N(2,4,6-Me3C6H2)]2)Al(H)2] In benzene-d6; benzene at 100℃; for 8h; Inert atmosphere; Glovebox; Sealed tube; Stage #2: With methanol In benzene-d6; benzene at 100℃; for 2h; Catalytic behavior; Inert atmosphere; Glovebox; Sealed tube; regioselective reaction;	A 20.5% B 16%

Hexafluorobenzene (392-56-3) → 1,2,4,5-Tetrafluorobenzene (327-54-8) + 1,2,3,4-tetrafluorobenzene (551-62-2) + Pentafluorobenzene (363-72-4) + 1,2,4-trifluorobenzene (367-23-7)

Conditions	Yield
With (1,3-dimethylimidazolin-2-ylidene)*AlH3 In 5,5-dimethyl-1,3-cyclohexadiene at 135℃; for 25h;	A 74% B 3% C 18% D 4%

1,2,3,4,7,7-hexafluorobicyclo<2,2,1>hepta-2,5-diene (17065-31-5) → Octafluorocyclobutane (115-25-3) + 1,2,3,4-tetrafluorobenzene (551-62-2)

Conditions	Yield
at 450℃; for 0.5h;	A 56% B 73%

Hexafluorobenzene (392-56-3) → 1,3,5-trifluorobenzene (372-38-3) + 1,2,4,5-Tetrafluorobenzene (327-54-8) + 1,2,3,4-tetrafluorobenzene (551-62-2)

Conditions	Yield
With (1,3-diisopropylimidazolin-2-ylidene)*AlH3 In 5,5-dimethyl-1,3-cyclohexadiene at 135℃; for 60h;	A 21% B 71% C 8%

Hexafluorobenzene (392-56-3) → 1,2,4,5-Tetrafluorobenzene (327-54-8) + 1,2,3,4-tetrafluorobenzene (551-62-2) + 1,2,3,5-tetrafluorobenzene (2367-82-0) + Pentafluorobenzene (363-72-4)

Conditions	Yield
With H2SiEt2; tetrabutylammonium triphenyldifluorosilicate In tetrahydrofuran; benzene-d6 at 60℃; for 40h; Inert atmosphere; Sealed tube;	A 70% B 2% C 2% D 19%

Pentafluorobenzene (363-72-4) → 1,2,3-trifluorobenzene (1489-53-8) + 1,2,3,4-tetrafluorobenzene (551-62-2)

Conditions	Yield
Stage #1: Pentafluorobenzene With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; [(HC[(CMe)N(2,4,6-Me3C6H2)]2)Al(H)2] In benzene-d6; benzene at 100℃; for 3h; Inert atmosphere; Glovebox; Sealed tube; Stage #2: With methanol In benzene-d6; benzene at 100℃; for 2h; Catalytic behavior; Inert atmosphere; Glovebox; Sealed tube; regioselective reaction;	A 19.5% B 57%

1,2,3,4,5,6-hexafluoro-7,8-diazatricyclo<4.3.0.02,5>nona-3,7-diene (23657-35-4, 83860-55-3) → polytetrafluoroethylene (116-14-3) + 1,2,4,5-Tetrafluorobenzene (327-54-8) + 1,2,3,4-tetrafluorobenzene (551-62-2) + 1,2,3,5-tetrafluorobenzene (2367-82-0)

Conditions	Yield
1.) 60 deg C, vacuo; 2.) 0.15 mmHg, 450 deg C;	A 52% B 52% C 7% D 34%

Pentafluorobenzene (363-72-4) → 1,2,4,5-Tetrafluorobenzene (327-54-8) + 1,2,3,4-tetrafluorobenzene (551-62-2)

Conditions	Yield
With (1,3-diisopropylimidazolin-2-ylidene)*AlH3 In toluene at 105℃; for 84h; Solvent; Reagent/catalyst;	A 43% B 10%
With [Cp2*ZrH2]2 In Cyclohexane-d12 at 85℃; for 6h; Product distribution; Kinetics;

Hexafluorobenzene (392-56-3) → 1,3,5-trifluorobenzene (372-38-3) + 1,2,4,5-Tetrafluorobenzene (327-54-8) + 1,2,3,4-tetrafluorobenzene (551-62-2) + Pentafluorobenzene (363-72-4)

Conditions	Yield
With (1,3-diisopropylimidazolin-2-ylidene)*AlH3 In 5,5-dimethyl-1,3-cyclohexadiene at 135℃; for 12h; Solvent; Temperature; Reagent/catalyst;	A 5% B 13% C 3% D 37%

1-chloro-2,3,4,5-tetrafluorobenzene (769-37-9) → 1,2,3,4-tetrafluorobenzene (551-62-2)

Conditions	Yield
With hydrogen at 280℃; Leiten ueber Palladium/Kohle;

ethyl-cyclohexane (1678-91-7) + 1,2,3,4-tetrafluorobenzene cation (551-62-2) → 1,2,3,4-tetrafluorobenzene (551-62-2) + ethyl cyclohexane cation

Conditions	Yield
at 61.9℃; Equilibrium constant; Irradiation;

1,2-dibromo-3,4,5,6-tetrafluorobenzene (827-08-7) → 1-bromo-2,3,4,5-tetrafluorobenzene (1074-91-5) + 1,2,3,4-tetrafluorobenzene (551-62-2)

Conditions	Yield
With water; hexaethylphosphoric triamide In N,N-dimethyl-formamide at 20℃; for 84h; protodebromination;	A 50 % Spectr. B 50 % Spectr.

Hexafluorobenzene (392-56-3) + hydrogen + palladium/charcoal → 1,2,3-trifluorobenzene (1489-53-8) + ortho-difluorobenzene (367-11-3) + 1,2,3,4-tetrafluorobenzene (551-62-2) + Pentafluorobenzene (363-72-4)

Conditions	Yield
at 300℃;

Hexafluorobenzene (392-56-3) + hydrogen + platinum/charcoal → 1,2,3-trifluorobenzene (1489-53-8) + ortho-difluorobenzene (367-11-3) + 1,2,3,4-tetrafluorobenzene (551-62-2) + Pentafluorobenzene (363-72-4)

Conditions	Yield
at 300℃;

1-chloro-2,3,4,5-tetrafluorobenzene (769-37-9) + palladium/charcoal → 1,2,3,4-tetrafluorobenzene (551-62-2)

Conditions	Yield
at 280℃; Hydrogenation;

1-chloro-2,3,4,5-tetrafluoro-6-trifluoromethyl-benzene (715-30-0) → 1,2,3,4-tetrafluorobenzene (551-62-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: steam / 330 °C / Leiten ueber Aluminiumoxid 2: hydrogen / 280 °C / Leiten ueber Palladium/Kohle View Scheme

pentafluorophenyl hydrazine (828-73-9) → 1,2,4,5-Tetrafluorobenzene (327-54-8) + 1,2,3,4-tetrafluorobenzene (551-62-2) + Pentafluorobenzene (363-72-4)

Conditions	Yield
hydrolysis;
hydrolysis;

Co4(CO)10C6F4 → 1,2,3,4-tetrafluorobenzene (551-62-2)

Conditions	Yield
With hydrogenchloride diluted HCl;
With HCl diluted HCl;

water (7732-18-5) + 2,3,4,5-tetrafluorophenyl(dihydroxy)borane (179923-32-1) → 1,2,3,4-tetrafluorobenzene (551-62-2)

Conditions	Yield
In methanol; water 33% H2O in MeOH, 20 °C, several h; monitored by (19)F NMR;
With potassium hydroxide In methanol; water 2 M KOH in MeOH was added to MeOH:H2O mixt., several h; monitored by (19)F NMR;

potassium perfluorophenyltrifluoroborate → 1,2,3-trifluorobenzene (1489-53-8) + ortho-difluorobenzene (367-11-3) + 1,2,3,4-tetrafluorobenzene (551-62-2) + 2,3,4,5-tetrafluorophenyltrifluoroborate anion

Conditions	Yield
With [2,2]bipyridinyl; nickel(II) chloride hexahydrate; lithium chloride; zinc In 1-methyl-pyrrolidin-2-one; water at 80℃; for 8h;

potassium perfluorophenyltrifluoroborate → 1,2,3,4-tetrafluorobenzene (551-62-2) + 2,3,4,5-tetrafluorophenyltrifluoroborate anion

Conditions	Yield
With [2,2]bipyridinyl; nickel(II) chloride hexahydrate; lithium chloride; zinc In 1-methyl-pyrrolidin-2-one; water at 80℃; for 8h;

Hexafluorobenzene (392-56-3) → 1,2,3-trifluorobenzene (1489-53-8) + para-difluorobenzene (540-36-3) + 1,2,4,5-Tetrafluorobenzene (327-54-8) + 1,2,3,4-tetrafluorobenzene (551-62-2) + Pentafluorobenzene (363-72-4) + 1,2,4-trifluorobenzene (367-23-7)

Conditions	Yield
With NiCl2*3Bpy; 1-n-butyl-3-methylimidazolim bromide; zinc In water at 70℃; for 7h;

Hexafluorobenzene (392-56-3) → 1,2,4,5-Tetrafluorobenzene (327-54-8) + 1,2,3,4-tetrafluorobenzene (551-62-2) + Pentafluorobenzene (363-72-4)

Conditions	Yield
With NiCl2*2Phen; 1-n-butyl-3-methylimidazolim bromide; zinc In water at 70℃; for 7h;
With titanocene difluoride; diphenylsilane In diethylene glycol dimethyl ether at 100℃; for 72h; Catalytic behavior; regioselective reaction;	A 39 %Spectr. B 17 %Spectr. C 37 %Spectr.

1-chloro-2,3,4,5,6-pentafluorobenzene (344-07-0) → 1,2,4,5-Tetrafluorobenzene (327-54-8) + 1,2,3,4-tetrafluorobenzene (551-62-2) + Pentafluorobenzene (363-72-4)

Conditions	Yield
With NiCl2*2Phen; 1-n-butyl-3-methylimidazolim bromide; zinc In water at 70℃; for 7h;

carbon disulfide (75-15-0) + 1,2,3,4-tetrafluorobenzene (551-62-2) + benzyl bromide (100-39-0) → benzyl 2,3,4,5-tetrafluorobenzodithioate

Conditions	Yield
Stage #1: 1,2,3,4-tetrafluorobenzene With sec.-butyllithium; copper(l) cyanide In hexane; cyclohexane at -78℃; for 3h; Schlenk technique; Inert atmosphere; Stage #2: carbon disulfide In hexane; cyclohexane at -50 - 20℃; for 1h; Schlenk technique; Inert atmosphere; Stage #3: benzyl bromide In hexane; cyclohexane at 20℃; for 4h; Schlenk technique; Inert atmosphere;	97%

1,2,3,4-tetrafluorobenzene (551-62-2) → tetrafluorobenzenesulfonyl chloride (591249-21-7)

Conditions	Yield
With chlorosulfonic acid at 150℃; for 3h;	95%
With n-butyllithium; sulfuryl dichloride In tetrahydrofuran; hexane at -80 - 0℃; for 12h; Inert atmosphere; Schlenk technique;	29%

NH-pyrazole (288-13-1) + 1,2,3,4-tetrafluorobenzene (551-62-2) → 1,2,3,4-tetrakis(pyrazol-1-yl)benzene (1172112-97-8)

Conditions	Yield
Stage #1: NH-pyrazole With sodium hydride In N,N-dimethyl-formamide; mineral oil for 0.5h; Stage #2: 1,2,3,4-tetrafluorobenzene In N,N-dimethyl-formamide; mineral oil at 50℃; for 10h;	94%

1,2,3,4-tetrafluorobenzene (551-62-2) → 1,2,4-trifluorobenzene (367-23-7)

Conditions	Yield
With [(bis(diisopropylphosphino)ethane)Ni(H)]2; triethylphosphine In 1,4-dioxane at 120℃; for 72h;	94%
With C32H46N2Ru; sodium carbonate; isopropyl alcohol at 70℃; for 6h; Inert atmosphere; Schlenk technique; Glovebox;	63%
With (1,3-dimethylimidazolin-2-ylidene)*AlH3 In 5,5-dimethyl-1,3-cyclohexadiene at 135℃; for 25h;	19%

1,2,3,4-tetrafluorobenzene (551-62-2) + 2-naphthyl triflate (3857-83-8) → C16H8F4

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel (0); 18-crown-6 ether; 2-[bis((3,5-dimethyl-4-methoxyphenyl)phosphino)phenyl]ether; isopropylmagnesium chloride In tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane at 40℃; for 2h;	93%

1,2,3,4-tetrafluorobenzene (551-62-2) + 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → 1’,4’-difluoro-2’,3’-di-O-(1,2:5,6-di-O-isopropylidene-α-D-glucofuranoside)benzene

Conditions	Yield
With potassium hexamethylsilazane In N,N-dimethyl-formamide; toluene at 0 - 20℃; for 16h; Inert atmosphere; Schlenk technique; regioselective reaction;	92%

1,2,3,4-tetrafluorobenzene (551-62-2) → 5,6-diiodo-1,2,3,4-tetrafluorobenzene (2708-97-6)

Conditions	Yield
With formic acid; sulfuric acid; periodic acid at 70℃; for 4h; Schlenk technique;	91%
With iodine; fluorine In 1,1,2-Trichloro-1,2,2-trifluoroethane; sulfuric acid Ambient temperature;	76%
With sulfuric acid; iodine; fluorine In 1,1,2-Trichloro-1,2,2-trifluoroethane Ambient temperature;	76%

1,2,3,4-tetrafluorobenzene (551-62-2) → 1,2,3,4-tetrafluoro(5,6-d2)benzene

Conditions	Yield
With dimethylsulfoxide-d6; caesium carbonate at 90℃; for 4h; Inert atmosphere; Schlenk technique;	90%
With C(2)H3CN(2)H(1+) In gas at 57.9℃; Rate constant; experiment conditions: NBS pulsed ion cyclotron resonance;

1,2,3,4-tetrafluorobenzene (551-62-2) + 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → 1,2:5,6-di-O-isopropylidene-3-O-(2',3',6'-trifluoro)-benzene-α-D-glucofuranoside

Conditions	Yield
With potassium hexamethylsilazane In tetrahydrofuran; toluene at 0 - 20℃; for 16h; Inert atmosphere; Schlenk technique; regioselective reaction;	90%

1,2,3,4-tetrafluorobenzene (551-62-2) + isopropyl (4-methoxybenzyl) carbonate → 1,2,4-trifluoro-3-((4-methoxybenzyl)oxy)benzene

Conditions	Yield
Stage #1: isopropyl (4-methoxybenzyl) carbonate With potassium tert-butylate In toluene at 20℃; for 0.166667h; Sealed tube; Stage #2: 1,2,3,4-tetrafluorobenzene In toluene at 20℃; for 0.5h; Sealed tube;	85%

1,2,3,4-tetrafluorobenzene (551-62-2) + (1,3-dimethylimidazol-2-ylidene)borane (1211417-77-4) → (1,3-dimethyl-1H-imidazol-3-ium-2-yl)(2,3,6-trifluorophenyl)dihydroborate

Conditions	Yield
With [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; sodium acetate; ethyl 2-sulfanylacetate In tetrahydrofuran at 20℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube; Irradiation; regioselective reaction;	85%

(kappa.3-N,N',N''-hydrotris(3,5-dimethylpyrazolyl)borate)Rh(PMe3)(H)2 (249643-82-1) + 1,2,3,4-tetrafluorobenzene (551-62-2) → [Rh(tris(3,5-dimethylpyrazolyl)borate)H(2,3,4,5-C6F4H)(PMe3)] (1258937-64-2)

Conditions	Yield
In neat (no solvent) Irradiation (UV/VIS); (N2, Schlenk) NMR tube containing complex was charged with fluorobenzenein the glove box, irradiated for 2 h (water-filtered 200-W Hg-Xe lamp, 270-370 nm band pass filter); flash chromy. (silica gel, 5:1 hexane-THF as eluent), the solvent was removed, washed with ice-cold hexane; elem. anal.;	83%

1,2,3,4-tetrafluorobenzene (551-62-2) + phenylacetonitrile (140-29-4) → 2-phenyl-2-(2,3,6-trifluorophenyl)acetonitrile

Conditions	Yield
With lithium tert-butoxide In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere; regioselective reaction;	83%

1,2,3,4-tetrafluorobenzene (551-62-2) → 3,4,5,6-tetrafluoro-1,2-benzenedithiol (25523-43-7)

Conditions	Yield
Stage #1: 1,2,3,4-tetrafluorobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1.25h; Stage #2: With sulfur In tetrahydrofuran; hexane at -78℃; for 2h;	82%
Multi-step reaction with 2 steps 1: 48 percent / 1.) butyl lithium; 2.) sulfur / hexane; tetrahydrofuran / -60 °C / 1.) 1 h 2: 40 percent / 1.) butyl lithium (2 equiv.); 2.) sulfur / hexane; tetrahydrofuran / -60 °C View Scheme
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran / 1.25 h / -78 °C / Inert atmosphere 1.2: 1 h / -78 °C 2.1: n-butyllithium / tetrahydrofuran / 1.25 h / -78 °C / Inert atmosphere 2.2: 1 h / -78 °C View Scheme
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere; Schlenk technique 1.2: 1 h / -78 °C / Inert atmosphere; Schlenk technique 2.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere; Schlenk technique 2.2: 1 h / -78 °C / Inert atmosphere; Schlenk technique View Scheme

1,2,3,4-tetrafluorobenzene (551-62-2) + (iPr3P)2Ni(η2-C14H10) (1256485-63-8) → trans-(iPr3P)2NiF(2,3,6-C6F3H2) + trans-(iPr3P)2NiF(2,3,4-C6F3H2)

Conditions	Yield
In toluene at 20℃; for 36h; Inert atmosphere;	A 81% B n/a

isopropyl chloride (75-29-6) + 1,2,3,4-tetrafluorobenzene (551-62-2) → 1-isopropyl-2,3,4,5-tetrafluorobenzene

Conditions	Yield
aluminum (III) chloride at 20℃; for 1h;	80.3%

[(tris(3,5-dimethylpyrazolyl)borate)RhH2(PPhMe2)] + 1,2,3,4-tetrafluorobenzene (551-62-2) → [(tris(3,5-dimethylpyrazolyl)borate)RhH(κ2-C6H4-2-PMe2)] (1258937-61-9) + [Rh(tris(3,5-dimethylpyrazolyl)borate)H(2,3,4,5-C6F4H)(PMe2Ph)] (1258937-73-3)

Conditions	Yield
In neat (no solvent) Irradiation (UV/VIS); (N2, Schlenk) a soln. of complex in fluorobenzene in NMR tube was irradiated for 5 h, heated at 120°C for 1 h; flash chromy. (silica gel, 5:1 hexane-THF), washed with a min amount of ice-cold hexane; elem. anal.;	A n/a B 79%

1,2,3,4-tetrafluorobenzene (551-62-2) + [2,6-diisopropylbenzene-β-diketiminate]Nb(NtBu)(η6-C6H6) → C39H52F4N3Nb

Conditions	Yield
With trimethoxybenzene In benzene-d6 at 60℃; for 6h;	79%

1,2,3,4-tetrafluorobenzene (551-62-2) + K2[B(CN)3] → C9H2BF3N3(1-)*K(1+)

Conditions	Yield
With lithium chloride In tetrahydrofuran at 20℃; for 1h; regioselective reaction;	77%

NH-pyrazole (288-13-1) + 1,2,3,4-tetrafluorobenzene (551-62-2) → 1,4-difluoro-2,3-bis(pyrazol-1-yl)benzene (1172112-94-5)

Conditions	Yield
Stage #1: NH-pyrazole With sodium hydride In N,N-dimethyl-formamide; mineral oil for 0.5h; Stage #2: 1,2,3,4-tetrafluorobenzene In N,N-dimethyl-formamide; mineral oil at 20℃; for 10h;	76%

para-bromotoluene (106-38-7) + 1,2,3,4-tetrafluorobenzene (551-62-2) → 1,2-di-(p-tolyl)-3,4,5,6-tetrafluorobenzene + 2,3,4,5-tetrafluoro-4’-methyl-1,1’-biphenyl (3263-58-9)

Conditions	Yield
With palladium diacetate; caesium carbonate; tricyclohexylphosphine In toluene at 120℃; for 12h; Sealed tube;	A 13% B 75%
With di-tert-butyl(methyl)phosphonium tetrafluoroborate salt; potassium carbonate; palladium diacetate In N,N-dimethyl acetamide at 120℃;	A 10% B 68%
With C27H32N6Pd(2+)*2CF3O3S(1-); potassium carbonate In N,N-dimethyl acetamide at 120℃; for 24h; Schlenk technique; Inert atmosphere;	A 4 mg B 8 mg

1,2,3,4-tetrafluorobenzene (551-62-2) + 2,3-dihydroimidazo[1,2-c]quinazolin-9-ol → 9-(2,3,6-trifluorophenoxy)-2,3-dihydroimidazo[1,2-c]quinazoline

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 18h;	75%

1,2,3,4-tetrafluorobenzene (551-62-2) + di(p-tolyl) disulfide (103-19-5) → 2,3,6-trifluoro-1-(p-tolylthio)benzene (1055876-51-1) + 3,6-difluoro-1,2-bis(p-tolylthio)benzene (1055876-49-7)

Conditions	Yield
With hydridotetakis(triphenylphosphine)rhodium(I); o-phenylenebis(diphenylphosphine); triphenylphosphine In chlorobenzene for 6h; Reflux;	A 24% B 74%

6-bromo-2-methoxypyridine (40473-07-2) + 1,2,3,4-tetrafluorobenzene (551-62-2) → 2-methoxy-6-(2,3,4,5-tetrafluorophenyl)pyridine

Conditions	Yield
With PdCl(1,4-bis(diphenylphosphino)butane)(C3H5); potassium pivalate In N,N-dimethyl acetamide at 150℃; for 16h; Inert atmosphere; Green chemistry; regioselective reaction;	74%

Upstream product

• 363-72-4 Pentafluorobenzene 
• 827-08-7 1,2-dibromo-3,4,5,6-tetrafluorobenzene 
• 392-56-3 Hexafluorobenzene 
• 769-37-9 1-chloro-2,3,4,5-tetrafluorobenzene 
• 715-30-0 1-chloro-2,3,4,5-tetrafluoro-6-trifluoromethyl-benzene 
• 828-73-9 pentafluorophenyl hydrazine 
• 7732-18-5 water 
• 179923-32-1 2,3,4,5-tetrafluorophenyl(dihydroxy)borane 
• 652-03-9 3,4,5,6-tetrafluorophthalic acid 
• 827-15-6 1,2,3,4,5-pentafluoro-6-iodobenzene 
• 344-04-7 bromopentafluorobenzene 
• 1201-31-6 2,3,4,5-tetrafluorobenzoic acid 
• 941584-43-6 [(HC[(CMe)N(2,4,6-Me₃C₆H₂)]₂)Al(H)₂] 
• 67-56-1 methanol 

Downstream Products

• 2708-97-6 5,6-diiodo-1,2,3,4-tetrafluorobenzene 
• 1074-91-5 1-bromo-2,3,4,5-tetrafluorobenzene 
• 827-08-7 1,2-dibromo-3,4,5,6-tetrafluorobenzene 
• 5580-79-0 2,3,4,5-tetrafluoro-1-nitrobenzene 
• 2070-75-9 2,3,4,5-tetrafluorobenzenesulfonic acid 
• 5121-89-1 1-iodo 2,3,4,5-tetrafluoro benzene 
• 76980-95-5 1,2,3,4,6,7,8,9,10-Nonafluoro-5-methyl-fluoranthene 
• 76980-90-0 1,2,3,4,5,7-Hexafluoro-6-methyl-8-(2,3,4,5-tetrafluoro-phenyl)-naphthalene 
• 76980-94-4 1,2,3,4,6,7,8,9,10-Nonafluoro-fluoranthene 
• 76980-89-7 1,2,3,4,6,8-Hexafluoro-5-(2,3,4,5-tetrafluoro-phenyl)-naphthalene 
• 4920-34-7 2,3,6-trifluoroanisole 
• 96631-22-0 2,3-Diethoxy-1,4-difluoro-benzene 
• 3467-86-5 2,3,4,5-Tetrafluorobenzenethiol 
• 72323-99-0 1,2,3,4-Tetrafluorbenzoldisulfonsaeure 

Relevant articles and documents

NHC·Alane Adducts as Hydride Sources in the Hydrodefluorination of Fluoroaromatics and Fluoroolefins

We present herein the utilization of NHC-stabilized alane adducts of the type (NHC)·AlH3 [NHC = Me2Im (1), Me2ImMe (2), iPr2Im (3), iPr2ImMe (4), Dipp2Im (5)] and (NHC)·AliBu2H [NHC = iPr2Im (6), Dipp2Im (7)] as novel hydride transfer reagents in the hydrodefluorination (HDF) of different fluoroaromatics and hexafluoropropene. Depending on the alane adduct used, HDF of pentafluoropyridine to 2,3,5,6-tetrafluoropyridine in yields of 15–99 % was observed. The adducts 1, 2, and 5 achieved a quantitative conversion into 2,3,5,6-tetrafluoropyridine at room temperature immediately after mixing the reactants. Studies on the HDF of fluorobenzenes with the (NHC)·AlH3 adducts 1, 3, and 5 and (Dipp2Im)·AliBu2H (7) showed the decisive influence of the reaction temperature on the H/F exchange and that 135 °C in xylene afforded the best product distribution. Although the HDF of hexafluorobenzene yielded 1,2,4,5-tetrafluorobenzene in moderate yields with traces of 1,2,3,4-tetrafluorobenzene and 1,2,4-trifluorobenzene, pentafluorobenzene was converted quantitatively into 1,2,4,5-tetrafluorobenzene, with (Dipp2Im)·AliBu2H (7) showing the highest activity and reaching complete conversion after 12 h at 135 °C in xylene. The HDF of hexafluoropropene with (Me2Im)·AlH3 (1) occurred even at low temperatures and preferably at the CF2 group with the formation of 1,2,3,3,3-pentafluoropropene (with 0.4 equiv. of 1) or 2,3,3,3-tetra-fluoropropene (with 0.9 equiv. of 1) as the main product.

Transition-Metal-Free Catalytic Hydrodefluorination of Polyfluoroarenes by Concerted Nucleophilic Aromatic Substitution with a Hydrosilicate

A transition-metal-free catalytic hydrodefluorination (HDF) reaction of polyfluoroarenes is described. The reaction involves direct hydride transfer from a hydrosilicate as the key intermediate, which is generated from a hydrosilane and a fluoride salt. The eliminated fluoride regenerates the hydrosilicate to complete the catalytic cycle. Dispersion-corrected DFT calculations indicated that the HDF reaction proceeds through a concerted nucleophilic aromatic substitution (CSNAr) process.

A decarboxylation multi-monofluoro-benzene multifluoro-benzoic acid by the method of preparation (by machine translation)

This invention relates to a kind of the ammonia in the high-temperature liquid aqueous medium, in the copper-containing solid acid catalyst, reaction [...] multifluoro-benzoic acid by the method of preparation multi-monofluoro-benzene. The method disclosed by the present invention do not need to use organic solvent, cheap catalyst, has fast reaction speed, reaction time is short, the advantage of high product yield. (by machine translation)