771-61-9

Basic information

• Product Name: Pentafluorophenol
• Synonyms: Pentafluorophenol, 99+% 10GR;Pentafluorophenol, 99+% 5GR;pentafluorophenol cation;PENTAFLUOROPHENOL FOR SYNTHESIS;Pentafluorophenol ReagentPlus(R), >=99%;Pentafluorophenol SynonyMs 2,3,4,5,6-Pentafluorophenol;Pentafluorophe;Pentafluorophenol Vetec(TM) reagent grade, 98%
• CAS NO: 771-61-9
• Molecular Formula: C₆HF₅O
• Molecular Weight: 184.06
• EINECS: 212-235-8
• Product Categories: Aromatic Phenols;Fluorobenzene;Phenol&Thiophenol&Mercaptan;Biochemistry;Coupling Reactions (Peptide Synthesis);Peptide Synthesis;organofluorine compounds
• Mol File: 771-61-9.mol
• Article Data: 58

Chemical Properties

• Melting Point: 34-36 °C(lit.)
• Boiling Point: 143 °C(lit.)
• Flash Point: 162 °F
• Appearance: White to almost white/Low Melting Crystalline Solid
• Density: 1.757
• Vapor Pressure: 3.69mmHg at 25°C
• Refractive Index: 1.4270
• Storage Temp.: Store in dark!
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 5.50±0.33(Predicted)
• Water Solubility: soluble
• Stability: Stable. Incompatible with strong oxidizing agents, bases, acid chlorides, acid anhydrides.
• BRN: 1912584
• CAS DataBase Reference: Pentafluorophenol(CAS DataBase Reference)
• NIST Chemistry Reference: Pentafluorophenol(771-61-9)
• EPA Substance Registry System: Pentafluorophenol(771-61-9)

Safety Data

• Hazard Codes: Xi,T,C,Xn
• Statements: 36/37/38-34-20/21/22-63-43-23/24/25-45-67-40
• Safety Statements: 26-36-45-36/37/39-36/37-24/25-23-53
• RIDADR: 2811
• WGK Germany: 3
• RTECS: SM6680000
• F: 3
• TSCA: T
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 771-61-9(Hazardous Substances Data)

Usage

Description

Pentafluorophenol can be used for the preparation of penta-fluorophenyl esters for peptide synthesis. It is used in the preparation of pentafluorophenyl esters for peptide synthesis and vulcanized polymers. It is also used for peptide coupling and heterocyclic acid derivatives. It is involved in the preparation of pentafluorophenyl formate which acts as a formulating agent for amines and amino acids. It can be used for synthesizing novel reagents which can achieve highly diastereoselective acetal cleavage.

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.

Chemical Properties

White solid

Uses

Different sources of media describe the Uses of 771-61-9 differently. You can refer to the following data:
1. Used for the preparation of pentafluorophenyl esters for peptide synthesis
2. Pentafluorophenol is used in the preparation of pentafluorophenyl esters for peptide synthesis and vulcanized polymers. It is also used for peptide coupling and heterocyclic acid derivatives. It is involved in the preparation of pentafluorophenyl formate which acts as a formulating agent for amines and amino acids.
3. For the preparation of pentafluorophenyl esters for peptide synthesis.

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

• 19220-93-0 pentafluorophenyl acetate 
• 188837-53-8 (2,3,4,5,6-pentafluorophenyl)pyridine-2-carboxylate 
• 1256490-52-4 (S)-2-[(2,3,4,5,6-pentafluorophenoxy)phenoxyphosphorylamino]propionic acid isopropyl ester 
• 363-72-4 Pentafluorobenzene 
• 4767-03-7 2,2-bis(hydroxymethyl)propionic acid 
• 59483-84-0 bis(pentafluorophenyl)carbonate 
• 1582-24-7 pentafluorophenylboronic acid 
• 392-56-3 Hexafluorobenzene 
• 42289-22-5 4-chloro-2,3,4,5,6-pentafluorocyclohexa-2,5-dienone 
• 29897-30-1 2,3,4,5,6-pentafluoro-6-chloro-2,4-cyclohexadienone 
• 4615-85-4 potassium perfluorophenolate 
• 1386398-06-6 4,5,6,7,8-pentafluoro-6-pentafluorophenoxy-1-oxaspiro[2.5]octa-4,7-diene 
• 602-94-8 Pentafluorobenzoic acid 
• 118-91-2 ortho-chlorobenzoic acid 

Downstream Products

• 56318-65-1 Trihexyl-pentafluorophenyloxy-silane 
• 56318-66-2 Triheptyl-pentafluorophenyloxy-silane 
• 214832-32-3 Pentafluorophenyl (thiophen-3-yl)ethanoate 
• 111333-98-3 N-(CHO)-Lys(Z)-ε Ahx-OCH3 
• 111333-97-2 formic acid pentafluorophenyl ester 
• 78987-88-9 2,4,6-tris(2,3,4,5,6-pentafluorophenoxy)-3,5-difluoropyridine 
• 137601-08-2 pentafluorophenyl propynoate 
• 60129-85-3 Perfluorophenyl trifluoromethanesulfonate 
• 129274-47-1 bis(diethylamido)-pentafluorophenyl phosphite 
• 138194-58-8 pentafluorophenyl 4-maleimidobenzoate 
• 138194-57-7 3-(2,5-Dioxo-2,5-dihydro-pyrrol-1-yl)-benzoic acid pentafluorophenyl ester 
• 134915-86-9 (1-Benzyl-2-piperidin-1-yl-2-thioxo-ethyl)-carbamic acid benzyl ester 
• 389-40-2 Pentafluoroanisole 
• 14606-26-9 2,4,6-tris(pentafluorophenoxy)borazine 

Relevant articles and documents

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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.