602-94-8

Basic information

• Product Name: Pentafluorobenzoic acid
• Synonyms: 2,3,4,5,6-pentafluoropropane acid;2,3,4,5,6-Pentafluorobenzoic acid, 98.0%(GC&T;2,3,4,5,6-Pentafluorobenzoic acid 99%;entafluorobenzoic acid;pentafluoro-benzoicaci;RARECHEM AL BO 0017;PERFLUOROBENZOIC ACID;PENTAFLUOROBENZOIC ACID
• CAS NO: 602-94-8
• Molecular Formula: C₇HF₅O₂
• Molecular Weight: 212.07
• EINECS: 210-026-6
• Product Categories: organofluorine compounds;carboxylic acid | alkyl Fluorine;Isoquinolines ,Quinolines ,Quinaldines;Benzoic acid;Fluorobenzene;C7;Carbonyl Compounds;Carboxylic Acids
• Mol File: 602-94-8.mol
• Article Data: 32

Chemical Properties

• Melting Point: 100-102 °C(lit.)
• Boiling Point: 220 °C(lit.)
• Flash Point: 219-221°C
• Appearance: white/crystal
• Density: 1,944 g/cm3
• Vapor Pressure: 1.17E-05mmHg at 25°C
• Refractive Index: 1.513
• Storage Temp.: Store below +30°C.
• PKA: 1.75(at 25℃)
• BRN: 2054395
• CAS DataBase Reference: Pentafluorobenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Pentafluorobenzoic acid(602-94-8)
• EPA Substance Registry System: Pentafluorobenzoic acid(602-94-8)

Safety Data

• Hazard Codes: T,Xi
• Statements: 25-36/37/38
• Safety Statements: 26-45-36/37/39-24/25
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: DH6195000
• TSCA: T
• HazardClass: IRRITANT
• Hazardous Substances Data: 602-94-8(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powder

Safety Profile

Poison by intraperitoneal route. A flammable liquid. When heated to decomposition it emits toxic vapors of Fí.

Purification Methods

Dissolve the acid in Et2O, treat it with charcoal, filter, dry (CaSO4), filter again, evaporate and recrystallise the residue from pet ether (b 90-100o) after adding a little toluene, to give large colourless plates. UV (H2O) has max at 265nm ( 761) (H2O). The S-benzylisothiuronium salt has m 187o (from H2O). [McBee & Rapkin J Am Chem Soc 73 1366 1951, Nield et al. J Chem Soc 166 1959, Beilstein 9 IV 956.]

InChI:InChI=1/C8H8BFO4/c1-14-8(11)5-2-3-6(9(12)13)7(10)4-5/h2-4,12-13H,1H3

Synthetic route

perfluorobenzaldehyde (653-37-2) → Pentafluorobenzoic acid (602-94-8)

Conditions	Yield
With cobalt(II) 2,9,16,23-phthalocyanine tetrasulfonic acid In water; acetonitrile at 20℃; under 760.051 Torr; for 150h; UV-irradiation;	100%
With 9-oxyl-9-azabicyclo<3.3.1>nonan-3-one; oxygen; nitric acid; sodium nitrite In water; acetonitrile at 23℃; under 760.051 Torr; for 8h; Sealed tube;	85%
Multi-step reaction with 2 steps 1: pyridine / benzene 2: H2SO4 View Scheme

pentafluorobenzoyl peroxide (22236-19-7) + 1,4-dimethoxybezene (150-78-7) → Pentafluorobenzoic acid (602-94-8) + 2,3,4,5,6-Pentafluoro-benzoic acid 2,5-dimethoxy-phenyl ester (98040-87-0) + C22H8F10O6 (98040-88-1)

Conditions	Yield
In 1,1,2-Trichloro-1,2,2-trifluoroethane at 25℃; Product distribution; Rate constant; Mechanism; different starting concentration ratios;	A 98% B n/a C n/a
In 1,1,2-Trichloro-1,2,2-trifluoroethane at 25℃; Yield given. Yields of byproduct given;

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;

pentafluorobenzoyl peroxide (22236-19-7) + 1,3-Dimethoxybenzene (151-10-0) → Pentafluorobenzoic acid (602-94-8) + 2,3,4,5,6-Pentafluoro-benzoic acid 2,4-dimethoxy-phenyl ester (98040-85-8) + C22H8F10O6 (98040-86-9)

Conditions	Yield
In 1,1,2-Trichloro-1,2,2-trifluoroethane at 50℃; Product distribution; Rate constant; Mechanism; different starting concentration ratios;	A 95% B n/a C n/a
In 1,1,2-Trichloro-1,2,2-trifluoroethane at 50℃; Yield given. Yields of byproduct given;

(2,3,4,5,6-pentafluorophenyl)methanol (440-60-8) → Pentafluorobenzoic acid (602-94-8)

Conditions	Yield
With diethylene glycol dimethyl ether at 70℃; for 0.5h; Sonication;	95%
With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium bromide In water; acetonitrile at 20℃; aq. buffer;	82%

pentafluorobenzoyl peroxide (22236-19-7) + 2-isopropyl-5-tert-butyl-1,4-dimethoxybenzene → Pentafluorobenzoic acid (602-94-8) + tert-butyl 2,3,4,5,6-pentafluorobenzoate (98040-93-8) + 4-isopropyl-2,5-dimethoxyphenyl pentafluorobenzoate

Conditions	Yield
In various solvent(s) at 20℃; Product distribution; Oxidation;	A 30% B 74% C 94%
In various solvent(s) at 20℃; Oxidation;	A 30% B 74% C 94%

tris(pentafluorophenyl)silane (20160-40-1) + methyllithium (917-54-4) → Pentafluorobenzoic acid (602-94-8)

Conditions	Yield
With carbon dioxide In diethyl ether; water react. of (C6F5)3SiH with CH3Li at -50°C, 1 h gives after treatment of the react. product with CO2 in H2O/H(1+) C6F5COOH;	90%
With CO2 In diethyl ether; water react. of (C6F5)3SiH with CH3Li at -50°C, 1 h gives after treatment of the react. product with CO2 in H2O/H(1+) C6F5COOH;	90%

N-((perfluorophenyl)methylene)aniline (2341-86-8) → Pentafluorobenzoic acid (602-94-8)

Conditions	Yield
With formic acid; dihydrogen peroxide for 5h;	89%

pentafluorobenzoylchloride (2251-50-5) → Pentafluorobenzoic acid (602-94-8)

Conditions	Yield
With sodium hydroxide at 20℃;	87%
Multi-step reaction with 3 steps 1: 85 percent / pyridine / diethyl ether / 1.5 h / Heating 2: 80 percent / H2 / 5 percent Pd/C / methanol / 760 Torr / Ambient temperature 3: 5 percent / potassium carbonate / H2O / 10 h / Heating View Scheme

bromopentafluorobenzene (344-04-7) + carbon dioxide (124-38-9) → Pentafluorobenzoic acid (602-94-8)

Conditions	Yield
Stage #1: bromopentafluorobenzene; carbon dioxide With tert.-butyl lithium In pentane at -70℃; Inert atmosphere; Stage #2: With sulfuric acid; water In pentane at 20℃; Inert atmosphere;	86%

N-pentafluorophenyl-pentafluorophenylaldimine (853-75-8) → pentafluoronitrobenzen (880-78-4) + Pentafluorobenzoic acid (602-94-8)

Conditions	Yield
With dihydrogen peroxide; trifluoroacetic anhydride In dichloromethane for 10h; Heating;	A 85% B 82%

pentafluorobenzoyl peroxide (22236-19-7) + 2-methyl-5-tert-butyl-1,4-dimethoxybenzene (92101-95-6) → Pentafluorobenzoic acid (602-94-8) + tert-butyl 2,3,4,5,6-pentafluorobenzoate (98040-93-8) + 4-methyl-2',5'-dimethoxyphenyl pentafluorobenzoate + 4-tert-butyl-2-dimethoxybenzyl pentafluorobenzoate

Conditions	Yield
In various solvent(s) at 20℃; Product distribution; Oxidation;	A 85% B 19% C 24% D 75%
In various solvent(s) at 20℃; Oxidation;	A 85% B 19% C 24% D 78%

pentafluorobenzoyl peroxide (22236-19-7) + 2-cyclopropylmethyl-5-tert-butyl-1,4-dimethoxybenzene → Pentafluorobenzoic acid (602-94-8) + tert-butyl 2,3,4,5,6-pentafluorobenzoate (98040-93-8) + 2,3,4,5,6-pentafluoro-benzoic acid 4-cyclopropylmethyl-2,5-dimethoxy-phenyl ester + 2,3,4,5,6-pentafluoro-benzoic acid (4-tert-butyl-2,5-dimethoxy-phenyl)-cyclopropyl-methyl ester

Conditions	Yield
In various solvent(s) at 20℃; Product distribution; Oxidation;	A 85% B 15% C 17% D n/a

pentafluorobenzoyl peroxide (22236-19-7) + 2-cyclopropylmethyl-5-tert-butyl-1,4-dimethoxybenzene → Pentafluorobenzoic acid (602-94-8) + 2,3,4,5,6-pentafluoro-benzoic acid 4-cyclopropylmethyl-2,5-dimethoxy-phenyl ester + 4-(4'-tert-butyl-2',5'-dimethoxy)phenyl-3-butenyl pentafluorobenzoate + 2,3,4,5,6-pentafluoro-benzoic acid (4-tert-butyl-2,5-dimethoxy-phenyl)-cyclopropyl-methyl ester

Conditions	Yield
In various solvent(s) at 20℃; Oxidation;	A 85% B 17% C n/a D n/a

carbon dioxide (124-38-9) + bis-(pentafluoro phenyl) magnesium (17436-90-7) → Pentafluorobenzoic acid (602-94-8)

Conditions	Yield
In tetrahydrofuran reaction at 20°C, 3 hours;;	83%
In tetrahydrofuran reaction at 20°C, 3 hours;;	83%

bis(α-pentafluoroanilino-2,3,4,5,6-pentafluorobenzyl)peroxide (97580-75-1) + trifluoroacetic anhydride (407-25-0) → Pentafluorobenzoic acid (602-94-8) + α,α,α,2,3,4,5,6-octafluoroacetanilide (653-27-0)

Conditions	Yield
With dihydrogen peroxide In dichloromethane for 5h;	A 71% B 79%

perfluorotoluene (434-64-0) → Pentafluorobenzoic acid (602-94-8)

Conditions	Yield
With antimony pentafluoride; trifluoroacetic acid at 50℃; for 11h;	76%
With carbon monoxide; fluorosulfonylchloride; antimony pentafluoride at 80℃; under 15200 Torr; for 24h;	60%
With carbon monoxide; fluorosulfonylchloride; antimony pentafluoride at 80℃; under 15200 Torr; for 24h; Product distribution; -80 - -70deg C as temper. for 2 h.;	60%
With sulfuric acid
With water; antimony pentafluoride; silica gel 1.) 70 deg C, 5 h; Yield given. Multistep reaction;

pentafluorobenzoyl peroxide (22236-19-7) + 1-benzyl-4-tert-butyl-2,5-dimethoxybenzene → Pentafluorobenzoic acid (602-94-8) + tert-butyl 2,3,4,5,6-pentafluorobenzoate (98040-93-8) + 4-benzyl-2,5-dimethoxyphenyl pentafluorobenzoate + 1-(4'-tert-butyl-2',5'-dimethoxy)phenylbenzyl pentafluorobenzoate

Conditions	Yield
In various solvent(s) at 20℃; Product distribution; Oxidation;	A 75% B 24% C 31% D 69%
In various solvent(s) at 20℃; Oxidation;	A 75% B 24% C 31% D 69%

pentafluorobenzylidene 4-trifluoromethyl-2,3,5,6-tetrafluoroaniline → Pentafluorobenzoic acid (602-94-8) + 4-trifluoromethyl-2,3,5,6-tetrafluoroaniline (651-83-2)

Conditions	Yield
With dihydrogen peroxide; acetic acid In dichloromethane at 20℃; for 5h;	A 58% B 70%

pentafluorobenzoyl peroxide (22236-19-7) + 2-ethyl-5-tert-butyl-1,4-dimethoxybenzene → Pentafluorobenzoic acid (602-94-8) + tert-butyl 2,3,4,5,6-pentafluorobenzoate (98040-93-8) + 4-ethyl-2,5-dimethoxyphenyl pentafluorobenzoate + 1-(4-tert-butyl-2,5-dimethoxy)phenylethyl pentafluorobenzoate

Conditions	Yield
In various solvent(s) at 20℃; Product distribution; Oxidation;	A 70% B 30% C 33% D 66%

pentafluorobenzoyl peroxide (22236-19-7) + 2-Methyl-1,4-benzoquinone (553-97-9) → Pentafluorobenzoic acid (602-94-8) + tert-butyl 2,3,4,5,6-pentafluorobenzoate (98040-93-8) + 4-ethyl-2,5-dimethoxyphenyl pentafluorobenzoate + 1-(4-tert-butyl-2,5-dimethoxy)phenylethyl pentafluorobenzoate

Conditions	Yield
In various solvent(s) at 20℃; Oxidation;	A 70% B 30% C 33% D 66%

carbon dioxide (124-38-9) + 2,3,4,5,6-pentafluorophenylmagnesium bromide (879-05-0) → Pentafluorobenzoic acid (602-94-8)

Conditions	Yield
In tetrahydrofuran 0.5 hours;;	67%
In tetrahydrofuran 0.5 hours;;	67%

carbon dioxide (124-38-9) + pentafluorophenylmagnesium chloride (879-06-1) → Pentafluorobenzoic acid (602-94-8)

Conditions	Yield
In tetrahydrofuran 12 hours;;	66%
In tetrahydrofuran 12 hours;;	66%
In tetrahydrofuran reaction in BrCH2CH2Br, then in THF at 20°C, 1.5 hours;;	41%
In tetrahydrofuran reaction in BrCH2CH2Br, then in THF at 20°C, 1.5 hours;;	41%
In tetrahydrofuran reaction in BrCH2CH2Br, then in THF at 20°C, 1.5 hours;;	41%

1-chloro-2,3,4,5,6-pentafluorobenzene (344-07-0) + carbon dioxide (124-38-9) → Pentafluorobenzoic acid (602-94-8)

Conditions	Yield
Stage #1: 1-chloro-2,3,4,5,6-pentafluorobenzene With magnesium In tetrahydrofuran at 47 - 65℃; for 1.5h; Stage #2: carbon dioxide In tetrahydrofuran at -10 - 20℃; for 0.416667h;	65%
Stage #1: 1-chloro-2,3,4,5,6-pentafluorobenzene With magnesium In tetrahydrofuran at 10℃; Stage #2: carbon dioxide In tetrahydrofuran at -10 - 20℃; under 1137.76 - 1965.21 Torr; for 0.25 - 0.533333h;	92 - 95 %Spectr.

N-pentafluorophenyl-pentafluorophenylaldimine (853-75-8) + trifluoroacetic anhydride (407-25-0) → Pentafluorobenzoic acid (602-94-8) + α,α,α,2,3,4,5,6-octafluoroacetanilide (653-27-0)

Conditions	Yield
With dihydrogen peroxide In dichloromethane for 10h;	A 59% B 57%

1,4-dimethoxy-2,5-dimethylbenzene (2674-32-0) + pentafluorobenzoyl peroxide (22236-19-7) → Pentafluorobenzoic acid (602-94-8) + 2,3,4,5,6-Pentafluoro-benzoic acid 2,5-dimethoxy-4-methyl-benzyl ester + C24H12F10O6

Conditions	Yield
In 1,1,2-Trichloro-1,2,2-trifluoroethane at 25℃; Product distribution; Rate constant; Mechanism;	A 53% B n/a C n/a
In 1,1,2-Trichloro-1,2,2-trifluoroethane at 25℃; Yield given. Yields of byproduct given;

1,4-di-tert-butyl-2,5-dimethoxybenzene (7323-63-9) + pentafluorobenzoyl peroxide (22236-19-7) → Pentafluorobenzoic acid (602-94-8) + tert-butyl 2,3,4,5,6-pentafluorobenzoate (98040-93-8) + 2,3,4,5,6-Pentafluoro-benzoic acid 4-tert-butyl-2,5-dimethoxy-phenyl ester (98040-90-5) + 2,3,4,5,6-Pentafluoro-benzoic acid 2,5-di-tert-butyl-3,6-dimethoxy-phenyl ester + C22H8F10O6 (98040-88-1)

Conditions	Yield
In 1,1,2-Trichloro-1,2,2-trifluoroethane at 25℃; Product distribution; Rate constant; Mechanism;	A 53% B 40% C n/a D n/a E n/a

1,2,3,4,5-pentafluoro-6-(perfluoroallyl)benzene (67899-41-6, 83976-95-8) → Pentafluorobenzoic acid (602-94-8) + heptafluorobenzeneacetic acid (91407-89-5)

Conditions	Yield
With (iron phthalocyanine)(μ-nitrido)(iron octapropylporphyrazine); dihydrogen peroxide In [D3]acetonitrile at 60℃; for 6h; Reagent/catalyst;	A 6% B 37%

F-benzohydroxamic acid (80684-62-4) → 2,3,4,5,6-pentafluoroaniline (771-60-8) + Pentafluorobenzoic acid (602-94-8) + 1,2-(F-benz)isoxazol-3(2H)-one (80684-66-8)

Conditions	Yield
With potassium carbonate In water for 10h; Heating;	A 11% B 5% C 15%

2,4-difluoro-benzoic acid (1583-58-0) → Pentafluorobenzoic acid (602-94-8)

Conditions	Yield
With fluorine In sulfuric acid Ambient temperature;	5%

Pentafluorobenzoic acid (602-94-8) → pentafluorobenzoylchloride (2251-50-5)

Conditions	Yield
With thionyl chloride for 2h; Reflux;	100%
With thionyl chloride for 3h; Reflux;	99%
With phosphorus pentachloride	78%

ethanol (64-17-5) + Pentafluorobenzoic acid (602-94-8) → ethyl pentafluorobenzoate (4522-93-4)

Conditions	Yield
With hydrogenchloride	100%
With thionyl chloride at 0℃; for 12h; Reflux;	88%
With thionyl chloride for 1h; Heating;

(1R,2R)-(-)-N,N'-bis(3,5-di-tert-butylsalicydene)-1,2-cyclohexanediaminocobalt(II) (176763-62-5) + Pentafluorobenzoic acid (602-94-8) → [((R,R)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-diaminocyclohexane)Co(pentafluorobenzoate)]

Conditions	Yield
In toluene at 22℃; for 12h;	100%
In toluene (N2); std. Schlenk technique; toluene was added to mixt. of Co complex and acid; stirred in air at 22°C for 12 h; evapd.; pentane added; filtered; dried (vac.);

Pentafluorobenzoic acid (602-94-8) → Cyclohexanecarboxylic acid (98-89-5)

Conditions	Yield
With water In aq. phosphate buffer at 25℃; for 15h; pH=2.7 - 3.2; Electrochemical reaction;	100%

Pentafluorobenzoic acid (602-94-8) + tetramethyl ammoniumhydroxide (75-59-2) → C7F5O2(1-)*C4H12N(1+)

Conditions	Yield
With water In ethanol at 0 - 20℃; for 0.0833333h;	100%

Pentafluorobenzoic acid (602-94-8) → Pentafluorobenzene (363-72-4)

Conditions	Yield
With triethylamine In toluene at 100 - 110℃; for 24h; Solvent; Temperature;	99%
With ammonia; copper In water at 180℃; for 0.25h; Temperature; Reagent/catalyst;	94.6%
In N,N-dimethyl-formamide at 160℃; for 2h;	94.4%

Pentafluorobenzoic acid (602-94-8) + benzyl alcohol (100-51-6) → benzyl 2,3,4,5,6-pentafluorobenzoate (104856-46-4)

Conditions	Yield
With [Cl(C6F13C2H4)2SnOSn(C2H4C6F13)2Cl]2 In various solvent(s) at 150℃; for 10h;	99%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 3h;	78%

Pentafluorobenzoic acid (602-94-8) + zinc(II) acetate dihydrate (5970-45-6) → zinc pentafluorobenzoate (15967-65-4)

Conditions	Yield
at 150℃; for 1.5h;	99%

Pentafluorobenzoic acid (602-94-8) → pentafluorophenyl potassium carboxylate (58521-27-0)

Conditions	Yield
With potassium tert-butylate In ethanol at 20℃; for 1.5h;	99%
With potassium tert-butylate In ethanol at 20℃; for 1h; Inert atmosphere;	99%
With potassium tert-butylate In ethanol at 20℃; for 3h; Inert atmosphere;
With potassium tert-butylate In ethanol for 3h; Inert atmosphere;
With potassium tert-butylate In ethanol at 20℃; for 1.5h;

Pentafluorobenzoic acid (602-94-8) + ethyl α-diazo-α-(4-bromophenyl)acetate (758692-47-6) → C17H10BrF5O4

Conditions	Yield
With air In dichloromethane at 20℃; Irradiation;	99%

tert.-butylhydroperoxide (75-91-2) + tris(3-fluorophenyl)antimony + Pentafluorobenzoic acid (602-94-8) → μ2-oxobis[pentafluorobenzoatetri(3-fluorophenyl)-antimony]

Conditions	Yield
In diethyl ether at 20℃; for 24h;	99%

Pentafluorobenzoic acid (602-94-8) + pentaphenylantimony (2170-05-0) → tetraphenylantimony pentafluorobenzoate (360572-77-6)

Conditions	Yield
In toluene heating at 90 °C for 1 h; solvent was removed, dry residue was recrystd. from a toluene-heptane (1:1) mixt.;	98%

Pentafluorobenzoic acid (602-94-8) + tri(p-tolyl)antimony (5395-43-7) → (CH3C6H4)3Sb(OCOC6F5)2 (460752-05-0)

Conditions	Yield
With dihydrogen peroxide In diethyl ether; water byproducts: H2O; react. of antimony compd. and acid with aq. H2O2 at room temp. in ether; elem. anal.;	98%

pentaphenylantimony (2170-05-0) + Pentafluorobenzoic acid (602-94-8) → tetraphenylantimony pentafluorobenzoate (360572-77-6)

Conditions	Yield
In toluene heating a mixt. of antimony compd. and acid in toluene at 90°C for 1 h; evapn., crystn. (toluene/heptane 1:1); elem. anal.;	98%

Pentafluorobenzoic acid (602-94-8) + tri(p-tolyl)antimony (5395-43-7) → tri-p-tolylantimony bis(pentafluorobenzoate)

Conditions	Yield
With H2O2 In diethyl ether (C6F5)COOH and 30% aq. H2O2 added to soln. of (p-tolyl)3Sb in ether; kept at 20°C for 12 h; crystals filtered off; dried; elem. anal.;	98%

Pentafluorobenzoic acid (602-94-8) + 4-cyanophenylboronic acid (126747-14-6) → 2’,3’,4’,5’,6’-pentafluoro-[1,1’-biphenyl]-4-carbonitrile

Conditions	Yield
With palladium(II) trifluoroacetate; silver carbonate In dimethyl sulfoxide at 120℃; for 2h; Suzuki coupling;	98%

Pentafluorobenzoic acid (602-94-8) + phenylacetylene (536-74-3) → 1-phenylvinyl 2,3,4,5,6-pentafluorobenzoate

Conditions	Yield
With C58H34F18O6P2Ru; silver trifluoromethanesulfonate In toluene at 70℃; for 1h; Inert atmosphere; Schlenk technique; regioselective reaction;	98%

Pentafluorobenzoic acid (602-94-8) + 4-methoxyphenylacetylen (768-60-5) → 1-(4-methoxyphenyl)vinyl 2,3,4,5,6-pentafluorobenzoate

Conditions	Yield
With C58H34F18O6P2Ru; silver trifluoromethanesulfonate In toluene at 25℃; for 4h; Inert atmosphere; Schlenk technique; regioselective reaction;	98%

Pentafluorobenzoic acid (602-94-8) + acetic anhydride (108-24-7) → 2,3,4,5,6-pentafluorobenzoic anhydride (15989-99-8)

Conditions	Yield
at 128℃; for 0.0833333h; Inert atmosphere;	98%

dmap (1122-58-3) + trimethylsilyl trifluoromethanesulfonate (27607-77-8) + Pentafluorobenzoic acid (602-94-8) → 1,2,3,4,5-pentakis(4-dimethylamino-1-pyridino)benzol-pentakis(trifluormethansulfonat)

Conditions	Yield
In chlorobenzene for 24h; Heating;	97%

Pentafluorobenzoic acid (602-94-8) + triphenylantimony (603-36-1) → triphenylantimony bis(pentafluorobenzoate) (360572-79-8)

Conditions	Yield
With dihydrogen peroxide In diethyl ether; water byproducts: H2O; addn. of acid and aq. H2O2 to a soln. of antimony compd. in ether, keeping for 12 h at 20°C; filtration, drying; elem. anal.;	97%
With H2O2 In diethyl ether (C6F5)COOH and 30% aq. H2O2 added to soln. of Ph3Sb in ether; kept at 20°C for 12 h; crystals filtered off; dried; elem. anal.;	97%

Pentafluorobenzoic acid (602-94-8) + tri-p-fluorophenylstibine (33756-42-2) → bis(pentafluorobenzoato)[tris(4-fluorophenyl)antimony]

Conditions	Yield
With tert.-butylhydroperoxide In diethyl ether; water at 20℃; for 24h;	97%
With tert.-butylhydroperoxide In diethyl ether at 24℃; for 18h;	94%

Pentafluorobenzoic acid (602-94-8) + C105H138N6O12 + cobalt(II) acetate (71-48-7, 917-69-1, 5931-89-5, 55881-15-7, 68931-68-0, 68931-69-1, 93029-27-7) → C126H132Co3F15N6O18

Conditions	Yield
Stage #1: C105H138N6O12; cobalt(II) acetate In toluene at 20℃; for 5h; Schlenk technique; Inert atmosphere; Stage #2: Pentafluorobenzoic acid In dichloromethane at 20℃; for 5h;	97%

methanol (67-56-1) + Pentafluorobenzoic acid (602-94-8) → methyl pentafluorobenzoate (36629-42-2)

Conditions	Yield
With sulfuric acid In tetrachloromethane Heating;	96%
With thionyl chloride at 20 - 50℃; for 21h; Reflux; Large scale;	91%
With sulfuric acid Reflux;	75%

AuOH(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene) + Pentafluorobenzoic acid (602-94-8) → (1,3-bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene)(pentafluorophenyl)gold

Conditions	Yield
In toluene byproducts: H2O, CO2; N2 or air, 1:1 mixt. refluxed at 110°C for 6 h; dried (vac.);	96%

Pentafluorobenzoic acid (602-94-8) + C72H94N4O8 + cobalt(II) acetate (71-48-7, 917-69-1, 5931-89-5, 55881-15-7, 68931-68-0, 68931-69-1, 93029-27-7) → C86H90Co2F10N4O12

Conditions	Yield
Stage #1: C72H94N4O8; cobalt(II) acetate In toluene at 20℃; for 5h; Schlenk technique; Inert atmosphere; Stage #2: Pentafluorobenzoic acid In dichloromethane at 20℃; for 5h;	96%

Upstream product

• 653-34-9 2,3,4,5,6-pentafluorostyrene 
• 7323-63-9 1,4-di-tert-butyl-2,5-dimethoxybenzene 
• 22236-19-7 pentafluorobenzoyl peroxide 
• 853-75-8 N-pentafluorophenyl-pentafluorophenylaldimine 
• 97580-75-1 bis(α-pentafluoroanilino-2,3,4,5,6-pentafluorobenzyl)peroxide 
• 407-25-0 trifluoroacetic anhydride 
• 1583-58-0 2,4-difluoro-benzoic acid 
• 75-15-0 carbon disulfide 
• 363-72-4 Pentafluorobenzene 
• 59514-37-3 perfluorobenzocyclobutenedione 
• 434-64-0 perfluorotoluene 
• 124-38-9 carbon dioxide 
• 17318-00-2 (pentafluoro phenyl) magnesiumbromide 
• 879-05-0 2,3,4,5,6-pentafluorophenylmagnesium bromide 

Downstream Products

• 362-49-2 4-nitro-benzoic acid-(2,3,4,5,6-pentafluoro-benzyl ester) 
• 14353-89-0 pentafluorophenyliodine bis(pentafluorobenzoate) 
• 27375-80-0 4-Aethoxytetrafluorbenzoesaeure 
• 76071-01-7 2,3,5,6-Tetrafluoro-4-pentyloxy-benzoic acid 
• 97206-29-6 4-(dodecyloxy)-2,3,5,6-tetrafluorobenzoic acid 
• 53772-47-7 1-(Diphenyl-phosphinoylmethyl)-2,3,4,5,6-pentafluoro-benzene 
• 76071-00-6 4-Butoxy-2,3,5,6-tetrafluorobenzoic acid 
• 76070-96-7 4-hexyloxy-2,3,5,6-tetrafluorobenzoic acid 
• 97206-26-3 2,3,5,6-Tetrafluoro-4-nonyloxy-benzoic acid 
• 4522-93-4 ethyl pentafluorobenzoate 
• 1478-07-5 2,3,4,5,6-pentafluorobenzoyl fluoride 
• 1201-31-6 2,3,4,5-tetrafluorobenzoic acid 
• 121602-93-5 3,4,5-trifluorobenzoic acid 
• 652-18-6 2,3,5,6-tetrafluorobenzoic acid 

Relevant articles and documents

On reactions of carbon disulphide induced by 'naked' fluoride part 1: Reactions with fluoroaromatics

On reaction with carbon disulphide and tetramethylammonium fluoride in dimethylformamide, pentafluorobenzonitrile undergoes nucleophilic substitution reactions, resulting eventually in trifluoromethylthio substituted polyfluorobenzonitrile. 2,4-Dinitrofluorobenzene and pentafluorobenzene undergo similar substitutions, however, the product mixtures are much more complex.

Mechanochemical Grignard Reactions with Gaseous CO2 and Sodium Methyl Carbonate**

A one-pot, three-step protocol for the preparation of Grignard reagents from organobromides in a ball mill and their subsequent reactions with gaseous carbon dioxide (CO2) or sodium methyl carbonate providing aryl and alkyl carboxylic acids in up to 82 % yield is reported. Noteworthy are the short reaction times and the significantly reduced solvent amounts [2.0 equiv. for liquid assisted grinding (LAG) conditions]. Unexpectedly, aryl bromides with methoxy substituents lead to symmetric ketones as major products.

Preparation method of pentafluorophenol

The invention relates to the field of organic synthesis, in particular to a preparation method of pentafluorophenol. The preparation method of pentafluorophenol comprises the steps as follows: 1) pentafluorobenzonitrile and bromoacetic ester are subjected to a coupling reaction in the presence of zinc powder, hydrolysis and decarboxylation are performed under the acid condition, and pentafluoroacetophenone is prepared; 2) pentafluoroacetophenone is subjected to a Baeyer-Villiger reaction in the presence of an oxidizing agent, and pentafluorophenol is prepared after hydrolysis. The preparationmethod of pentafluorophenol comprises simple and short operation steps and is low in production cost, high in industrial operability and suitable for large-scale industrial production.

Efficient aerobic photooxygenation of aldehydes to carboxylic acids using cobalt(II) phthalocyanine sulfonate as a photosensitizer in organic-water biphasic media

The aerobic oxidation of a variety of aromatic aldehydes to the corresponding carboxylic acids by molecular oxygen in the presence of 4-carboxyl tetraphenylporphyrin (H2TCPP), methylene blue (MB), cobalt(II) phthalocyanine sulfonate (CoPcS) and FeTCPPCl as water-soluble photosensitizers in organic-water biphasic media at room temperature under either visible light or sunlight is described. The products were obtained with 25–100% conversion and 100% selectivity. This method has a wide range of applicabilities, has a straightforward workup procedure, is chemoselective and proceeds under mild reaction conditions. The resulting products were obtained in good yields in reasonable times.