771-61-9

Usage

Uses

Used in Pharmaceutical Industry:
Pentafluorophenol is used as a key component in the preparation of pentafluorophenyl esters for peptide synthesis. This application is crucial in the development of new drugs and therapies, as peptides play a significant role in various biological processes and can be engineered to target specific diseases.
Used in Chemical Industry:
In the chemical industry, Pentafluorophenol is utilized for the preparation of vulcanized polymers. These polymers are essential in the manufacturing of various products, such as tires, rubber goods, and other materials with enhanced mechanical properties.
Used in Peptide Coupling:
Pentafluorophenol is used as a coupling agent in the synthesis of peptides. This process is vital for the creation of complex peptide structures, which can be used in drug development and other applications.
Used in Heterocyclic Acid Derivatives:
Pentafluorophenol is also employed in the synthesis of heterocyclic acid derivatives, which are important building blocks for various pharmaceuticals and chemical compounds.
Used in Pentafluorophenyl Formate Preparation:
Pentafluorophenol is involved in the preparation of pentafluorophenyl formate, which acts as a formulating agent for amines and amino acids. This application is essential in the development of new chemical products and materials.
Used in Novel Reagent Synthesis:
Pentafluorophenol can be used for synthesizing novel reagents that achieve highly diastereoselective acetal cleavage. This process is crucial in the development of new chemical compounds and materials with specific properties and applications.

Reference

3. Ishihara, Kazuaki, N. Hanaki, and H. Yamamoto. "Highly diastereoselective acetal cleavages using novel reagents prepared from organoaluminum and pentafluorophenol" Cheminform 25.9(2010):no-no.

Synthesis Reference(s)

The Journal of Organic Chemistry, 54, p. 5502, 1989 DOI: 10.1021/jo00284a022

Safety Profile

scu-rat LD50:322 mg/kg IZSBAI 3,91,65

Purification Methods

It is a hygroscopic low melting solid not freely soluble in H2O. Purify it by distillation, preferably in a vacuum [Forbes et al. J Chem Soc 2019 1959, IR and pKa: Birchall & Haszeldine J Chem Soc 13 1959]. IRofafilmhas max 3600 (OH) and 1575 (fluoroaromatic breathing) cm-1 . The benzoyl derivative has m 74-75o, 3,4-dinitrobenzoyl derivative has m 107o, the tosylate has m 64-65o (from EtOH) and the K salt crystallises from Me2CO, m 242o(dec), with 1H2O-salt the m is 248o(dec) and the 2H2O-salt has m 245o(dec). [Beilstein 6 IV 782.]

InChI:InChI=1/C6HF5O.K/c7-1-2(8)4(10)6(12)5(11)3(1)9;/h12H;/q;+1/p-1

Synthetic route

(S)-2-[(2,3,4,5,6-pentafluorophenoxy)phenoxyphosphorylamino]propionic acid isopropyl ester (1256490-52-4) → L-alanin (56-41-7) + 2,3,4,5,6-pentafluorophenol (771-61-9) + phenol (108-95-2)

Conditions	Yield
With sodium hydroxide In methanol; water at 25 - 60℃; for 4h; Reagent/catalyst; Temperature; Solvent;	A 94.2% B 95.7% C 98.2%

dimethyl pentafluorophenylboronate (848609-02-9) → 2,3,4,5,6-pentafluorophenol (771-61-9)

Conditions	Yield
With dihydrogen peroxide In water; toluene at 10 - 20℃; for 14.08h;	97.4%

Hexafluorobenzene (392-56-3) → 2,3,4,5,6-pentafluorophenol (771-61-9)

Conditions	Yield
With water; potassium hydroxide at 160℃; under 4500.45 Torr; for 5h; Pressure; Reagent/catalyst; Temperature;	97%
With water; sodium hydroxide at 120 - 125℃; for 2h; Temperature; Reagent/catalyst; Autoclave;	95%
With N,N-didodecylamine; sodium hydroxide In water at 150℃; for 3h; Temperature; Autoclave;	93.2%

Pentafluorobenzene (363-72-4) → 2,3,4,5,6-pentafluorophenol (771-61-9)

Conditions	Yield
With tetraethoxy orthosilicate; dihydrogen peroxide; cetyltrimethylammonim bromide; copper(II) nitrate In acetonitrile at 65℃; for 3h; Solvent; Reagent/catalyst; Molecular sieve;	96%
Stage #1: Pentafluorobenzene In 1,4-dioxane for 3h; Reflux; Stage #2: With dihydrogen peroxide; cobalt(II) acetate In 1,4-dioxane Reagent/catalyst; Reflux;	94.9%
With sulfolane; potassium hydroxide In water at 120℃; under 6000.6 Torr; for 8h; Autoclave; Inert atmosphere;	87.3%
Multi-step reaction with 3 steps 1.1: aluminum (III) chloride; bromine / 18 h / 45 °C 2.1: magnesium / tetrahydrofuran / 5 h / 40 - 45 °C / Inert atmosphere; Large scale 2.2: 2 h / -5 °C / Inert atmosphere; Large scale 2.3: 0.5 h / Inert atmosphere; Large scale 3.1: dihydrogen peroxide / water; tetrahydrofuran / 3 h / 70 °C View Scheme

tris(pentafluorophenyl)borate (1109-15-5) → 2,3,4,5,6-pentafluorophenol (771-61-9)

Conditions	Yield
With dihydrogen peroxide at 20℃; for 14h;	95.8%
With dihydrogen peroxide at 20℃; for 3h;	92.6%

pentafluorophenylboronic acid isopropyl ester (267006-38-2) → 2,3,4,5,6-pentafluorophenol (771-61-9)

Conditions	Yield
With dihydrogen peroxide In water; 1,3,5-trimethyl-benzene at 10 - 20℃; for 16.8h;	95.7%

pentafluorophenylboronic acid (1582-24-7) → 2,3,4,5,6-pentafluorophenol (771-61-9)

Conditions	Yield
With dihydrogen peroxide In ethanol at 40℃; for 0.0466667h; Temperature; Time; Solvent; Inert atmosphere;	95.2%
With dihydrogen peroxide In tetrahydrofuran; water at 70℃; for 3h; Temperature;	94.1%
With dihydrogen peroxide In toluene at 20 - 50℃; for 24h; Temperature; Solvent; Reagent/catalyst;	85%
With dihydrogen peroxide at 20℃; Flow reactor;	85.8%
With dihydrogen peroxide at 10 - 15℃; for 6h; Temperature;	80%

2-(2,4-dinitrophenylthio)ethanol (18595-35-2) + pentafluorophenyl 5-methyl-2-oxo-1,3-dioxane-5-carboxylate (1252553-69-7) → 2,3,4,5,6-pentafluorophenol (771-61-9) + 2-(2,4-dinitrophenylthio)ethyl 5-methyl-2-oxo-1,3-dioxane-5-carboxylate (1252553-78-8)

Conditions	Yield
With cesium fluoride In tetrahydrofuran for 24h;	A n/a B 90%

bromopentafluorobenzene (344-04-7) → 2,3,4,5,6-pentafluorophenol (771-61-9)

Conditions	Yield
With copper(I) oxide; sodium carbonate; sodium hydroxide In water at 20 - 140℃; for 5h; Autoclave;	89%
With sulfolane; palladium on activated charcoal; potassium hydroxide In water at 150℃; under 7500.75 Torr; for 10h; Reagent/catalyst; Temperature; Pressure; Autoclave; Inert atmosphere;	84.7%
With potassium hydroxide In ammonia at -33℃; for 2h;	8.2 mmol

methanol (67-56-1) + 2,4,5,6-tetrafluoro-3-(pentafluorophenoxy)-6-phenyl-2,4-cyclohexadienone (152342-45-5) → 2,3,4,5,6-pentafluorophenol (771-61-9) + 2,4,5,6-tetrafluoro-3-methoxy-6-phenyl-2,4-cyclohexadienone

Conditions	Yield
at 60℃; for 4h;	A n/a B 86%

1-chloro-2,3,4,5,6-pentafluorobenzene (344-07-0) → 2,3,4,5,6-pentafluorophenol (771-61-9)

Conditions	Yield
With copper(I) oxide; sodium carbonate; sodium hydroxide In water at 20 - 140℃; for 5h; Autoclave;	85%

2,3,4,5,6-pentafluoroaniline (771-60-8) → 2,3,4,5,6-pentafluorophenol (771-61-9)

Conditions	Yield
Stage #1: 2,3,4,5,6-pentafluoroaniline With hydrogenchloride; tert.-butylnitrite In water at 0 - 5℃; for 1h; Stage #2: With copper(l) chloride In water; acetonitrile at 20 - 30℃; Reagent/catalyst; Solvent; Temperature;	85%

sodium ethanolate (141-52-6) + 2,3,4,5,6-Pentafluoro-benzenesulfonic acid pentafluorophenyl ester (140200-31-3) → 2,3,4,5,6-pentafluorophenol (771-61-9) + sodium p-ethoxytetrafluorobenzenesulphonate + Sodium; 2,4,6-triethoxy-3,5-difluoro-benzenesulfonate (135736-88-8)

Conditions	Yield
In ethanol at 80℃; for 10h; 1a:EtONa = 1:6;	A 81.5% B 50.1% C 61.9%

Pentafluoroanisole (389-40-2) → 2,3,4,5,6-pentafluorophenol (771-61-9)

Conditions	Yield
With aluminum (III) chloride In 1,2-dichloro-ethane at 50 - 60℃; for 4h;	80%
With hydrogen iodide
With aluminium trichloride at 120℃;
With N,N,N,N-tetraethylammonium tetrafluoroborate In acetonitrile

2,3,4,5,6-Pentafluoro-benzenesulfonic acid pentafluorophenyl ester (140200-31-3) → 2,3,4,5,6-pentafluorophenol (771-61-9) + C6F4O4S(2-)*2Na(1+) (135736-85-5)

Conditions	Yield
With sodium hydroxide In water at 100℃; for 10h;	A 79.3% B 100 mg
With hydrogenchloride; sodium hydroxide 1) H2O, 100 degC, 10 h; Yield given. Multistep reaction. Yields of byproduct given;

2,2-bis(hydroxymethyl)butanoic acid (10097-02-6) + bis(pentafluorophenyl)carbonate (59483-84-0) → 2,3,4,5,6-pentafluorophenol (771-61-9) + pentafluorophenyl 5-ethyl-2-oxo-1,3-dioxane-5-carboxylate (1252553-70-0)

Conditions	Yield
With cesium fluoride In tetrahydrofuran at 20℃; for 20h;	A n/a B 75%

sodium ethanolate (141-52-6) + 2,3,4,5,6-Pentafluoro-benzenesulfonic acid pentafluorophenyl ester (140200-31-3) → 2,3,4,5,6-pentafluorophenol (771-61-9) + pentafluorophenyl p-ethoxytetrafluorobenzenesulphonate + sodium p-ethoxytetrafluorobenzenesulphonate

Conditions	Yield
In ethanol at 80℃; for 10h; 1a:EtONa = 1:1;	A 72.8% B 19% C 20.1%

pentafluorophenyl 5-methyl-2-oxo-1,3-dioxane-5-carboxylate (1252553-69-7) + 1-bromo-3-propanol (627-18-9) → 2,3,4,5,6-pentafluorophenol (771-61-9) + 3-bromopropyl 5-methyl-2-oxo-1,3-dioxane-5-carboxylate (1252553-75-5)

Conditions	Yield
With cesium fluoride In tetrahydrofuran for 24h;	A n/a B 70%

pentafluorophenyl 5-methyl-2-oxo-1,3-dioxane-5-carboxylate (1252553-69-7) + benzyl alcohol (100-51-6) → 2-methyl-2-(benzyloxycarbonyl)-1,3-trimethylene carbonate (247142-68-3) + 2,3,4,5,6-pentafluorophenol (771-61-9)

Conditions	Yield
With cesium fluoride In tetrahydrofuran for 24h;	A 68% B n/a

pentafluorophenyl 5-methyl-2-oxo-1,3-dioxane-5-carboxylate (1252553-69-7) + allyl alcohol (107-18-6) → 2,3,4,5,6-pentafluorophenol (771-61-9) + 5-methyl-5-allyloxycarbonyl-1 ,3-dioxane-2-one (532424-75-2)

Conditions	Yield
With cesium fluoride In tetrahydrofuran for 24h;	A n/a B 65%

pentafluorophenyl 5-methyl-2-oxo-1,3-dioxane-5-carboxylate (1252553-69-7) + propargyl alcohol (107-19-7) → propargyl 5-methyl-2-oxo-1,3-dioxane-5-carboxylate (945841-51-0) + 2,3,4,5,6-pentafluorophenol (771-61-9)

Conditions	Yield
With cesium fluoride In tetrahydrofuran at 20℃; for 24h;	A 65% B n/a

2-(tetrahydropyran-2-yloxy)ethanol (2162-31-4) + pentafluorophenyl 5-methyl-2-oxo-1,3-dioxane-5-carboxylate (1252553-69-7) → 2,3,4,5,6-pentafluorophenol (771-61-9) + 2-(tetrahydro-2H-pyran-2-yloxy)ethyl 5-methyl-2-oxo-1,3-dioxane-5-carboxylate (1075204-22-6)

Conditions	Yield
With cesium fluoride In tetrahydrofuran for 24h;	A n/a B 65%

pentafluorophenyl 5-methyl-2-oxo-1,3-dioxane-5-carboxylate (1252553-69-7) + 2-(2-(Pyridin-2-yl)disulfanyl)ethanol (111625-28-6) → 2-(pyridin-2-yl-disulfanyl)ethyl 5-methyl-2-oxo-1,3-dioxane-5-carboxylate + 2,3,4,5,6-pentafluorophenol (771-61-9)

Conditions	Yield
With cesium fluoride In tetrahydrofuran for 24h;	A 65% B n/a

pentafluorophenyl 5-methyl-2-oxo-1,3-dioxane-5-carboxylate (1252553-69-7) + 2-(N-tert-butoxycarbonylamino)ethanol (26690-80-2) → 2-(tert-butoxycarbonylamino)ethyl 5-methyl-2-oxo-1,3-dioxane-5-carboxylate + 2,3,4,5,6-pentafluorophenol (771-61-9)

Conditions	Yield
With cesium fluoride In tetrahydrofuran for 24h;	A 65% B n/a

C48H64N4O8 + (2,3,4,5,6-pentafluorophenyl)pyridine-2-carboxylate (188837-53-8) → 2,3,4,5,6-pentafluorophenol (771-61-9) + 5,17-di-t-butyl-11,23-dinitro-26,28-dipicolinamidopropoxy-25,27-dipropoxycalix[4]arene

Conditions	Yield
In chloroform at 20℃;	A n/a B 64%

ethanol (64-17-5) + pentafluorophenyl 5-methyl-2-oxo-1,3-dioxane-5-carboxylate (1252553-69-7) → 2-ethoxycarbonyl-2-methyltrimethylene carbonate (651718-45-5) + 2,3,4,5,6-pentafluorophenol (771-61-9)

Conditions	Yield
With cesium fluoride In tetrahydrofuran	A 56% B n/a

2-(2-methoxyethoxy)ethyl alcohol (111-77-3) + pentafluorophenyl 5-methyl-2-oxo-1,3-dioxane-5-carboxylate (1252553-69-7) → 2-(2-methoxyethoxy)ethyl 5-methyl-2-oxo-1,3-dioxane-5-carboxylate (1006903-36-1) + 2,3,4,5,6-pentafluorophenol (771-61-9)

Conditions	Yield
With cesium fluoride In tetrahydrofuran for 24h;	A 50% B n/a

dihydrogen peroxide (7722-84-1) + pentafluorophenyl lithium (1076-44-4) → 2,3,4,5,6-pentafluorophenol (771-61-9)

Conditions	Yield
With Trimethyl borate In tetrahydrofuran reaction in presence of (CH3O)3B at -70°C, 90 minutes;;	39%
With (CH3O)3B In tetrahydrofuran reaction in presence of (CH3O)3B at -70°C, 90 minutes;;	39%

4-nitro-phenol (100-02-7) + pentafluorophenyl acetate (19220-93-0) → 2,3,4,5,6-pentafluorophenol (771-61-9) + 4-nitrophenol acetate (830-03-5)

Conditions	Yield
In water; acetonitrile at 25℃; Rate constant; Mechanism; pH 7.00;

Hexafluorobenzene (392-56-3) → 2,3,4,5,6-pentafluorophenol (771-61-9) + 4-hydroxy-2,3,5,6-tetrafluoronitrobenzene (20994-04-1)

Conditions	Yield
With sodium nitrite In dimethyl sulfoxide at 160 - 170℃; for 5h; Yield given. Yields of byproduct given;

Pentafluoropyridine (700-16-3) + 2,3,4,5,6-pentafluorophenol (771-61-9) → 4-pentafluorophenoxy-2,3,5,6-tetrafluoropyridine (69585-26-8)

Conditions	Yield
With potassium fluoride; 18-crown-6 ether In acetonitrile at 80℃; for 1h; ratio of pentafluoropyridine and pentafluorophenol 1:0.1;	100%
With cesium fluoride In N,N-dimethyl-formamide at 80℃; for 1h; Product distribution; other reagents, time;	95%

2,6-bis-pentafluorophenoxy-3,4,5-trifluoropyridine (69620-40-2) + 2,3,4,5,6-pentafluorophenol (771-61-9) → 2,4,6-tris(2,3,4,5,6-pentafluorophenoxy)-3,5-difluoropyridine

Conditions	Yield
With potassium fluoride; 18-crown-6 ether In acetonitrile at 80℃; for 5h;	100%

2,3,4,5,6-pentafluorophenol (771-61-9)

Conditions	Yield
With dicyclohexyl-carbodiimide In ethyl acetate at 20℃; for 1h;	100%
With dicyclohexyl-carbodiimide In dichloromethane at 25℃;	92%
With dicyclohexyl-carbodiimide In 1,4-dioxane for 2h;	86.5%
With dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 1.75h;

2,3,4,5,6-pentafluorophenol (771-61-9) + N-(pentafluorophenyl)carbonimidoyl dichloride (64317-34-6) → C19F15NO2 (94055-40-0)

Conditions	Yield
With potassium carbonate In acetonitrile at 80℃; for 5h;	100%

2,3,4,5,6-pentafluorophenol (771-61-9) + Fmoc-Pro-OH (71989-31-6) → Fmoc-L-proline pentafluorophenyl ester (125281-38-1, 86060-90-4)

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane for 1h; Esterification;	100%
With dicyclohexyl-carbodiimide In ethyl acetate 0 deg C, 1 h; r.t., 1 h;	82%
With dicyclohexyl-carbodiimide In ethyl acetate at 0℃; for 2h; Yield given;

2,3,4,5,6-pentafluorophenol (771-61-9) + N-<1-(4-biphenylyl)-1-methylethoxycarbonyl>-2-(acetamidomethyl)-L-cysteine (74706-03-9) → N<1-(4-biphenylyl)-1-methylethoxycarbonyl>-S-(acetamidomethyl)-L-cysteine pentafluorophenyl ester (73363-56-1)

Conditions	Yield
With dicyclohexyl-carbodiimide In ethyl acetate at 0℃; for 1h;	100%

2,3,4,5,6-pentafluorophenol (771-61-9) + Boc-Lys(Z)-Lys(Z)-Gly-OH (112471-83-7) → Boc-Lys(Z)-Lys(Z)-Gly-OPFP (141914-54-7)

Conditions	Yield
With dicyclohexyl-carbodiimide	100%
With dicyclohexyl-carbodiimide	100%

2,3,4,5,6-pentafluorophenol (771-61-9) + 5-tert-butoxycarbonylamino-2-phenyl-1,3-dioxane-5-carboxylic acid (154627-63-1) → pentafluorophenyl 5-tert-butoxycarbonylamino-2-phenyl-1,3-dioxane-5-carboxylate (154627-60-8)

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane at -20 - 20℃; for 16h;	100%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at -20 - 20℃; for 16h;	99%

2,3,4,5,6-pentafluorophenol (771-61-9) + Fmoc-D-DMTP-Pro-OH (141636-68-2) → Fmoc-D-DMPT-Pro-OPfp (141636-69-3)

Conditions	Yield
With dicyclohexyl-carbodiimide In ethyl acetate; N,N-dimethyl-formamide at 5 - 20℃; for 3h;	100%

2,3,4,5,6-pentafluorophenol (771-61-9) + Diphenylphosphinic chloride (1499-21-4) → pentafluorophenyl diphenyl-phosphinate (138687-69-1)

Conditions	Yield
With 1H-imidazole In dichloromethane for 1h; Ambient temperature;	100%
With 1H-imidazole In dichloromethane at 25℃; for 3h;	97%
With 1H-imidazole In dichloromethane Ambient temperature;	92%

2,3,4,5,6-pentafluorophenol (771-61-9) + 6-(1-t-butoxycarbonyl-2,3,4,5-tetrahydro-2-pyrrolyl)-5-hexenoic acid → 2-((Z)-5-Pentafluorophenyloxycarbonyl-pent-1-enyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Conditions	Yield
With dicyclohexyl-carbodiimide In ethyl acetate for 2.5h;	100%

2,3,4,5,6-pentafluorophenol (771-61-9) + 5-nitro-1-(phenylmethyl)-1H-imidazole-4-carboxylic acid (69195-96-6) → 1-Benzyl-5-nitro-1H-imidazole-4-carboxylic acid pentafluorophenyl ester (204527-99-1)

Conditions	Yield
With ethyl acetate; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 0 - 20℃; for 3h;	100%
With dicyclohexyl-carbodiimide In ethyl acetate; N,N-dimethyl-formamide 1) 0 deg C, 1 h; 2) rt, 1 h;	95%
With dicyclohexyl-carbodiimide In ethyl acetate; N,N-dimethyl-formamide 1.) 0 deg C, 3 h, 2.) room temperature, 1 h;	95%

2,3,4,5,6-pentafluorophenol (771-61-9) + 2-((S)-1-{[2-({(S)-2-[(2-{6-Benzyloxymethyl-2-[2-((S)-1-tert-butoxycarbonylamino-ethyl)-5-methyl-oxazol-4-yl]-pyridin-3-yl}-thiazole-4-carbonyl)-amino]-3-methyl-butyrylamino}-methyl)-5-methyl-oxazole-4-carbonyl]-amino}-ethyl)-thiazole-4-carboxylic acid (216481-09-3) → C51H50F5N9O10S2 (216481-10-6)

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane	100%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 16h; Esterification;	100%

2,3,4,5,6-pentafluorophenol (771-61-9) + Boc-β3-HTrp-β3-HPhe-β3-HThr(OBn)-β3-HLys(2-Cl-Z)-OH → Boc-β3-HTrp-β3-HPhe-β3-HThr(OBn)-β3-HLys(2-Cl-Z)-OC6F5

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide Esterification;	100%

propargyl chloroformate (35718-08-2) + 2,3,4,5,6-pentafluorophenol (771-61-9) → propargyl pentafluorophenyl carbonate (439912-32-0)

Conditions	Yield
With ethyl azide In diethyl ether at 0℃; for 7h;	100%
With triethylamine In dichloromethane at -10℃; for 4h;	98%

2,3,4,5,6-pentafluorophenol (771-61-9) + (2'-azido-biphenyl-2-yl)-acetic acid (683277-82-9) → (2'-azido-biphenyl-2-yl)-acetic acid pentafluorophenyl ester (683277-83-0)

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane at 20℃;	100%

6-(4-(tert-butoxycarbonyl)piperazin-1-yl)-5-chloronicotinic acid (683241-92-1) + 2,3,4,5,6-pentafluorophenol (771-61-9) → tert-butyl 4-(3-chloro-5-((perfluorophenoxy)carbonyl)pyridin-2-yl)piperazine-1-carboxylate (683241-96-5)

Conditions	Yield
With dicyclohexyl-carbodiimide In ethyl acetate at 20℃; for 16h;	100%
With dicyclohexyl-carbodiimide In ethyl acetate at 0 - 20℃; for 16h;

2,3,4,5,6-pentafluorophenol (771-61-9) + benzyl chloroformate (501-53-1) → benzyl (perfluorophenyl) carbonate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;	100%
With 4-methyl-morpholine; dmap In dichloromethane at 0℃; for 0.55h; Inert atmosphere;	89%
With pyridine In dichloromethane at 0 - 20℃;	89%

2,3,4,5,6-pentafluorophenol (771-61-9) + Boc-Tyr(t-Bu)-OH (47375-34-8) → Boc-Tyr(tBu)-OPfp

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 1h;	100%

2,3,4,5,6-pentafluorophenol (771-61-9) + 4-t-butylphenylacetic acid (32857-63-9) → pentafluorophenyl 2-(4-tert-butylphenyl)acetate (681810-54-8)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 16h;	100%

3-methoxy-2-methylsulfanylmethyl-benzoic acid (755014-13-2) + 2,3,4,5,6-pentafluorophenol (771-61-9) → pentafluorophenyl 2-(methylthiomethyl)-3-methoxybenzoate

Conditions	Yield
With dicyclohexyl-carbodiimide In ethyl acetate for 1h;	100%

2,3,4,5,6-pentafluorophenol (771-61-9) + Boc-D-Pen-OH (119222-62-7) → (2,2-Dimethyl4-oxo-thietan-3-yl)-carbamic acid tert-butyl ester

Conditions	Yield
With 1,2-dichloro-ethane In dichloromethane	100%

1,4,7,10-tetraazacyclododecane-1,7-bis(t-butyloxycarbonyl-methyl)-4,10-bis[2-(R)-pentanedioic acid, 1-t-butyl ester] (914639-15-9) + 2,3,4,5,6-pentafluorophenol (771-61-9) → 1,4,7,10-tetraazacyclododecane-1,7-bis(t-butyloxycarbonyl-methyl)-4,10-bis[2-(R)-pentanedioic acid, 1-t-butyl-5-pentafluorophenyl ester] (914639-12-6)

Conditions	Yield
With PS-CDI for 2h; Polystyrene;	100%

(2S)-3-(4-benzyloxy-3'-{(2S)-2-[{(2S)-5-benzyloxycarbonylamino-2-tert-butoxycarbonylamino-pentanoyl}-(methyl)-amino]-3-methoxy-3-oxo-propyl}-4'-fluoro-biphenyl-3-yl)-2-benzyloxycarbonylamino-propionic acid (856223-02-4) + 2,3,4,5,6-pentafluorophenol (771-61-9) → pentafluorophenyl (2S)-3-(4-benzyloxy-3'-{(2S)-2-[{(2S)-5-benzyloxycarbonylamino-2-tert-butoxycarbonylamino-pentanoyl}-(methyl)-amino]-3-methoxy-3-oxo-propyl}-4'-fluoro-biphenyl-3-yl)-2-benzyloxycarbonylamino-propanoate (856223-15-9)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at -25 - 20℃;	100%

2,3,4,5,6-pentafluorophenol (771-61-9) + bis[tris(trimethylsilylmethyl)molybdenum](Mo-Mo) (34439-17-3) → Mo2(OC6F5)6 (124461-95-6)

Conditions	Yield
In benzene byproducts: SiMe4; under Ar atm.; soln. of C6F5OH added to complex, stirred for 48h; solvent removed (vac.), washed (hexane), dried;	100%

2,3,4,5,6-pentafluorophenol (771-61-9) + trimethylaluminum (75-24-1) → Al(OC6F5)3

Conditions	Yield
In hexane (inert atmosphere); -30°C slowly to room temp., stirring (2 h); evapn. to dryness, washing (hexane);	100%

{(π-C5H5)2Zr(CH3)}2O + 2,3,4,5,6-pentafluorophenol (771-61-9) → zirconocene bis(pentafluorophenoxide) (90491-53-5)

Conditions	Yield
In diethyl ether; toluene (inert atmosphere); stirring (4 h); evapn. to dryness, washing (hexane), recrystn. (toluene/hexane); elem. anal.;	100%

bis(cyclopentadienyl)dimethylzirconium(IV) (12636-72-5) + 2,3,4,5,6-pentafluorophenol (771-61-9) → zirconocene bis(pentafluorophenoxide) (90491-53-5)

Conditions	Yield
In diethyl ether; toluene (inert atmosphere); stirring (2 h); evapn. to dryness, washing (hexane), recrystn. (toluene/hexane); elem. anal.;	100%

2,3,4,5,6-pentafluorophenol (771-61-9) + acetic acid (64-19-7) → pentafluorophenyl acetate (19220-93-0)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere;	100%
With dicyclohexyl-carbodiimide In ethyl acetate at 20℃; for 12h;
With diisopropyl-carbodiimide In ethyl acetate at 20℃; for 12h;

(2S)-3-[4-(benzyloxy)-3'-(2-{[(2S)-5-{[(benzyloxy)carbonyl]amino}-2-(tert-butoxycarbonylamino)pentanoyl]amino}-4-methoxy-4-oxobutyl)biphenyl-3-yl]-2-{[(benzyloxy)carbonyl]amino}propanoic acid (919988-49-1) + 2,3,4,5,6-pentafluorophenol (771-61-9) → methyl 4-{4'-(benzyloxy)-3'-[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-oxo-3-(pentafluorophenoxy)propyl]biphenyl-3-yl}-3-({(2S)-5-{[(benzyloxy)carbonyl]amino}-2-[(tert-butoxycarbonyl)amino]pentanoyl}amino)butanoate (919988-50-4)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at -25 - 20℃;	100%

Upstream product

• 392-56-3 Hexafluorobenzene 
• 389-40-2 Pentafluoroanisole 
• 100-02-7 4-nitro-phenol 
• 19220-93-0 pentafluorophenyl acetate 
• 50903-47-4 perfluorophenyl 2-((tert-butoxycarbonyl)amino)acetate 
• 16679-94-0 N-[(phenylmethoxy)carbonyl]-L-tyrosine 
• 17540-47-5 4-nitro-2,3,4,5,6-pentafluorocyclohexa-2,5-dien-1-one 
• 83701-40-0 Hexane-1,6-dioic acid bis(pentafluorophenyl) ester 
• 124650-87-9 (1S,5R,7S)-1,5,7-Trimethyl-2,4-dioxo-3-aza-bicyclo[3.3.1]nonane-7-carboxylic acid 6-pentafluorophenyloxycarbonyl-naphthalen-2-yl ester 
• 21950-36-7 5'-amino-5'-deoxy-2',3'-O-isopropylideneadenosine 
• 52189-72-7 1,2,3,4,5-pentafluorophenyl propargyl ether 
• 91-66-7 N,N-diethylaniline 
• 107-10-8 propylamine 
• 1548-84-1 pentafluorophenyl benzoate 

Downstream Products

• 1548-84-1 pentafluorophenyl benzoate 
• 63331-00-0 1-Pentafluorphenyloxy-silatran 
• 56318-57-1 Triethyl-pentafluorophenyloxy-silane 
• 50903-47-4 perfluorophenyl 2-((tert-butoxycarbonyl)amino)acetate 
• 50903-49-6 2-tert-Butoxycarbonylamino-3-methyl-butyric acid pentafluorophenyl ester 
• 3856-58-4 difluoromethoxypentafluorobenzene 
• 16536-48-4 bis(pentafluorophenyl) oxalate 
• 19220-93-0 pentafluorophenyl acetate 
• 56318-60-6 Dibutyl-methyl-pentafluorophenyloxy-silane 
• 56318-61-7 Tributyl-pentafluorophenyloxy-silane 
• 35523-39-8 heptafluorobenzyl bromide 
• 53106-74-4 perfluorobenzyl phenyl ether 
• 53106-75-5 1-(2-Bromo-1,1,2,2-tetrafluoro-ethoxy)-2,3,4,5,6-pentafluoro-benzene 
• 56318-64-0 Pentafluorophenyloxy-tripentyl-silane 

Relevant academic research and scientific papers

Tetra-cmpo-derivatives of calix[4]arenes fixed in the 1,3-alternate conformation

Calix[4]arene derivatives fixed in the 1,3-alternate conformation and substituted at one side by four carbamoylmethyl-phosphine oxide (CMPO) residues were synthesised. Two CMPO groups are directly attached to the wide rim, while the second pair is bound to the narrow rim via a tri- or tetramethylene spacer. Similar compounds, in which two CMPO groups at the wide rim are combined with two picolinamide groups or two ionisable carboxylic groups at the narrow rim, were also prepared. Some of these calixarene derivatives were studied as extractants for lanthanides (La3+,Eu3+,Yb3+) and thorium (Th4+) from acidic solution into methylene chloride. For selected samples, stability constants in methanol were determined by spectrophotometric titrations. Three compounds (1b′, 13, 17) in the 1,3-alternate conformation and one intermediate in the cone conformation (18) were confirmed by a crystal structure.

Reactions of polyfluorinated 3-substituted 2,4-cyclohexadienones with alkynes

Reactions of 2,3,4,5,6-pentafluoro-6-chloro-2,4-cyclohexadienone with anthranylic acid, 2,6-dichloro- and 2,6-dimethylaniline, diethylamine, sodium azide, and also the reaction of 6-phenyl-3-pentafluorophenoxy-2,4,5,6-tetrafluoro-2,4-cyclohexadienone with methanol afford 3-substituted 2,4,5,6-tetrafluoro-2,4-cyclohexadienones. The 3-methoxy-2,4,5,6-tetrafluoro-6-chloro-2,4-cyclohexadienone and 3-methoxy-6-phenyl-2,4,5,6-tetrafluoro-2,4-cyclohexadienone form cycloadducts with 1-hexyne and propargyl alcohol that under treatment with propyl alcohol in the presence of potassium carbonate undergo ring cleavage to furnish propyl arylfluorochloroacetates and diarylacetates. The reaction between 3-azido-2,4,5,6-tetrafluoro-6-chloro-2,4-cyclohexadienone and phenylacetylene gives rise to 4-oxo-2-phenyl-3,5,6,7-tetrafluoro-5-chlorobicyclo[4.1.0] hept-2-ene-7-carbonitrile.

Self anion radical induced breaking carbon–oxygen bond in bay area of perylene diimide, and nucleophilic substitution with SRN1 mechanism

Perylene diimide and its various derivatives tend to form their anion radicals after obtaining one electron, which will alter their chemical properties. Herein, we reported firstly synthesis of the unsymmetrically substituted perylene diimide in bay area

Method for continuously preparing pentafluorophenol by micro-reactor

The invention relates to a method for continuously preparing pentafluorophenol by a microreactor, which belongs to the field of chemical production processes. The method comprises the following steps:simultaneously pumping hexafluorobenzene and an inorganic alkali aqueous solution into a micro-channel reactor by using a metering pump respectively, and mixing for a hydrolysis reaction; keeping thetemperature of the reactor at 130-170 DEG C, controlling and maintaining the pressure of a pipeline at 0.5-1.0 Mpa by an outlet quantitative pressure control valve, connecting an outlet with a heat exchanger, obtaining an aqueous solution of pentafluorophenolate from the outlet of the heat exchanger, adding hydrochloric acid steam, distilling to obtain an oil layer, and rectifying and dehydratingthe oil layer to obtain pentafluorophenol. The method is simple in process, low in cost, free of amplification effect and capable of achieving continuous production.

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.

Method for industrially producing pentafluorophenol

The invention discloses a method for industrially producing pentafluorophenol. According to the invention, pentafluorobenzene is used as a raw material and the method comprises the following steps: grabbing benzene ring hydrogen in an organic solvent by using a solid super-strong alkali reagent, adding hydrogen peroxide for a reaction to obtain a desired product pentafluorophenol. The method has the advantages of simple process, realization of the separation yield reaching 94% or above (based on pentafluorobenzene), realization of the product content being greater than 99.2%, great reduction of the synthesis cost, and suitableness for industrial large-scale production. According to the method, solid super alkali is adopted to replace conventional inorganic alkali, corrosion of a conventional inorganic alkali solution to equipment is avoided, the requirement for equipment materials is lowered, products are easy to separate, operation is easy and convenient, and industrial production isfacilitated.

Preparation method of pentafluorophenol

The invention relates to a preparation method of pentafluorophenol, and belongs to the field of chemical production technologiesprocesses. The preparation method of the pentafluorophenol is carried out according to the following technologies processes that hexafluorobenzene, strong base and water are put in a sealed container, to be prepared intothus a mixed solution is prepared, heat preservationis conducted at the temperature of 100-150 DEG C for reaction, and thus a system solution is obtained; the system solution is neutralized until the pH value is not higher than 6, then a coarse product is extracted, rectification is conducted, and the pentafluorophenol is obtained. According to the preparation method, the cost is low, organic matter and heavy metal are not adopted except for substrate, pollution is small, side reactions is are lessfewer, the reaction steps are simple, and operation is easy.

Additive-free cobalt-catalysed hydrogenation of carbonates to methanol and alcohols

Reduction of various organic carbonates to methanol and alcohols can be achieved in the presence of a molecularly-defined homogeneous cobalt catalyst. Specifically, the use of Co(BF4)2 in combination with either commercial or tailor-made tridentate phosphine ligands allows for additive-free hydrogenations of carbonates. Optimal results are obtained at relatively mild conditions (120 °C, 50 bar hydrogen pressure) in the presence of xylyl-Triphos L4.

A five-fluoro phenol preparation method

The invention relates to a preparation method for pentafluorophenol. By taking hexafluorobenzene as an initial raw material, pentafluorophenol is prepared through etherification reaction and cracking reaction or by taking hexafluorobenzene as the initial raw material, pentafluorophenol is prepared by virtue of a one-step method. The preparation method provided by the invention does not need high temperature and pressurization, is less in energy consumption, and does not use expensive hydroiodic acid, so that the cost of the raw materials is low. Moreover, wastewater generated by etherification reaction is less, so that the preparation method is environmental-friendly; Cracking is carried out in a solvent, the material stirring effect is good, the reaction temperature is easy to control, and industrialization is easy to implement.

Pentafluorophenol preparation mehtod

The invention provides a pentafluorophenol preparation method. The pentafluorophenol preparation method is characterized by comprising the following preparation steps: adding 500-1000 parts of water, 50-100 parts of sodium hydroxide, 3-10 parts of a hydrolysis catalyst, 100 parts of hexafluorobenzene and 0.1-1 part of dodecyl secondary amine into a high pressure kettle according to parts by weight, sealing the high pressure kettle, raising the temperature to 110-150 DEG C, reacting for 3-8 hours, cooling to the room temperature, filtering, acidizing, extracting with methyl tert-butyl ether, combining an organic phase, distilling to recycle a solvent, and obtaining a crude product of 2,3,4,5,6-pentafluorophenol, adsorbing the crude product of pentafluorophenol in a crude product tank through five rectifying columns, and obtaining a purified product of pentafluorophenol.