559-40-0

Basic information

• Product Name: OCTAFLUOROCYCLOPENTENE
• Synonyms: 1,2,3,3,4,4,5,5-Octafluoro-1-cyclopentene;Cyclopentene, octafluoro-;Cyclopentene, perfluoro;octafluoro-cyclopenten;OCTAFLUOROCYCLOPENTENE;PERFLUOROCYCLOPENTENE;PFC C-1418;FC-C-1418
• CAS NO: 559-40-0
• Molecular Formula: C₅F₈
• Molecular Weight: 212.04
• EINECS: 209-203-0
• Product Categories: monomer
• Mol File: 559-40-0.mol
• Article Data: 21

Chemical Properties

• Melting Point: -70°C
• Boiling Point: 27 °C
• Flash Point: °C
• Appearance: /
• Density: 1.58
• Vapor Pressure: 484mmHg at 25°C
• Refractive Index: 1.3000 (estimate)
• Storage Temp.: Refrigerator
• Water Solubility: Insoluble in water
• CAS DataBase Reference: OCTAFLUOROCYCLOPENTENE(CAS DataBase Reference)
• NIST Chemistry Reference: OCTAFLUOROCYCLOPENTENE(559-40-0)
• EPA Substance Registry System: OCTAFLUOROCYCLOPENTENE(559-40-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37-36/37/38-48/20/21/22
• Safety Statements: 23-26-36/37/39
• RIDADR: 2810
• RTECS: GY6000000
• HazardClass: IRRITANT, GAS
• Hazardous Substances Data: 559-40-0(Hazardous Substances Data)

Usage

Chemical Properties

Clear colorless liquid

InChI:InChI=1/C5F8/c6-1-2(7)4(10,11)5(12,13)3(1,8)9

Synthetic route

octachlorocyclopentene (706-78-5) → octaperfluorocyclopentene (559-40-0)

Conditions	Yield
With hydrogen fluoride at 350 - 450℃; under 3750.38 Torr; Temperature; Reagent/catalyst;	93.8%
With potassium fluoride In sulfolane at 190℃; for 15h;	89%
With pyridine; sulfolane; hydrogen fluoride at 140 - 170℃; Temperature;	85%

1,2-dichlorooctafluorocyclopentane (376-75-0) → octaperfluorocyclopentene (559-40-0)

Conditions	Yield
In N,N-dimethyl acetamide at 170℃; for 6h; Autoclave;	75.5%
With ethanol; zinc
With zinc In N,N-dimethyl-formamide at 80℃; for 0.5h; Temperature; Solvent; Inert atmosphere;

1,2-dichloro-3,3,4,4,5,5-hexafluorocyclopentene (706-79-6) → octaperfluorocyclopentene (559-40-0)

Conditions	Yield
With 1-methyl-pyrrolidin-2-one; potassium fluoride	70%
(i) CoF3, (ii) Zn, iPrOH; Multistep reaction;
With potassium fluoride In N,N-dimethyl-formamide

Perfluorobicyclo<3.1.1>heptane (161116-96-7) → octaperfluorocyclopentene (559-40-0) + Perfluoro-1,6-heptadiene (4263-29-0) + cis-Perfluorobicyclo<3.2.0>heptane

Conditions	Yield
at 740℃; under 1 Torr;	A 8% B 32% C 10%
at 740℃; under 1 Torr; Title compound not separated from byproducts;	A 8 % Spectr. B 32 % Spectr. C 10 % Spectr.

Chlorodifluoromethane (75-45-6) → octaperfluorocyclopentene (559-40-0)

Conditions	Yield
at 700℃;

polytetrafluoroethylene (116-14-3) + 1,2,3,3-tetrafluorocyclopropene (19721-29-0) → octaperfluorocyclopentene (559-40-0)

octafluoro-1,3-pentadiene (3109-88-4) → octafluoro-1,4-pentadiene (3109-87-3) + octaperfluorocyclopentene (559-40-0)

Conditions	Yield
at 400℃; under 8360 Torr; for 72h;

decafluoro-1,2-epoxycyclohexane (5927-67-3) → octaperfluorocyclopentene (559-40-0) + perfluoro-2-cyclohexene-1-one (5672-50-4)

Conditions	Yield
at 500℃;	A 3.7 g B 2.2 g

perfluoro-1,3-cyclopentadiene (699-39-8) → octaperfluorocyclopentene (559-40-0)

Conditions	Yield
With antimony pentafluoride In liquid sulphur dioxide at -60℃; for 10h;

1-trifluoromethyl-2,3,3,4,4,5,5-heptafluoro-cyclopentene (780-87-0) → difluoro-methylene (2154-59-8) + octaperfluorocyclopentene (559-40-0)

Conditions	Yield
at 750℃; under 0.01 Torr; Product distribution; ΔI;

perfluoro-11-oxadispiro<4.0.4.1>undecane (98713-80-5) → octaperfluorocyclopentene (559-40-0) + perfluorocyclopentanone (376-66-9)

Conditions	Yield
With cesium fluoride at 200℃; for 16h; Title compound not separated from byproducts;	A 83 % Spectr. B 57 % Spectr.

Perfluoro-1,6-heptadiene (4263-29-0) → polytetrafluoroethylene (116-14-3) + octaperfluorocyclopentene (559-40-0) + Perfluorobicyclo<3.1.1>heptane (161116-96-7) + cis-Perfluorobicyclo<3.2.0>heptane

Conditions	Yield
at 750℃; Yields of byproduct given. Title compound not separated from byproducts;
at 750℃; under 1 Torr; Yields of byproduct given. Title compound not separated from byproducts;	A n/a B 90 % Spectr. C n/a D n/a

Perfluorobicyclo<3.2.0>heptane (85625-40-7) → octaperfluorocyclopentene (559-40-0)

Conditions	Yield
at 450℃; for 22h;	85 % Spectr.

2,3,4,5-Tetrachlor-1,1,2,3,4,5-hexafluorcyclopentan (1453-38-9) → octaperfluorocyclopentene (559-40-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 67 percent / Zn / various solvent(s) / 1 h / Heating 2: SbF5 / liquid sulphur dioxide / 10 h / -60 °C View Scheme

1,2,3,4-tetrachloro-5,5-difluoro-cyclopenta-1,3-diene (562-19-6) → octaperfluorocyclopentene (559-40-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 40 percent / F2 / various solvent(s) / 12 h / 0 °C 2: 67 percent / Zn / various solvent(s) / 1 h / Heating 3: SbF5 / liquid sulphur dioxide / 10 h / -60 °C View Scheme

hexachlorocyclopentadiene (77-47-4) + SbF5 → octaperfluorocyclopentene (559-40-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: 1.) HgF2 / 1.) 1 to 2 h, reflux; 2.) 500 to 600 deg C 2: 40 percent / F2 / various solvent(s) / 12 h / 0 °C 3: 67 percent / Zn / various solvent(s) / 1 h / Heating 4: SbF5 / liquid sulphur dioxide / 10 h / -60 °C View Scheme

4,5-dichloro-1,1,1,2,3,4,5,5-octafluoro-pent-2-ene → octaperfluorocyclopentene (559-40-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: Zn / propan-2-ol 2: 72 h / 400 °C / 8360 Torr View Scheme

1,2,4,5,6,6,7,7-octafluoro-3-oxatricyclo[3.2.0.02,4]heptane (911291-50-4) → octaperfluorocyclopentene (559-40-0)

Conditions	Yield
With antimony pentafluoride In various solvent(s) at 90℃; for 7h;

1,4,5,6,7,7-hexafluoro-2,3-diazabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid dimethyl ester (911225-21-3) → octaperfluorocyclopentene (559-40-0)

Conditions	Yield
With fluorine In trichlorofluoromethane

3,3-dichloro-1,1,1,2,2,4,4,5,5,5-decafluoropentane (146721-82-6) → 2-chloropentafluoropropene (2804-50-4) + 2‑chloro‑1,1,1,4,4,4‑hexafluoro‑2‑butene (400-44-2) + methane (34557-54-5) + trifluoromethan (75-46-7) + 1,1,1,4,4,5,5,5-octafluoropent-2-yne (378-22-3) + (E/Z)-2H-nonafluoro-2-pentene (73401-37-3) + octaperfluorocyclopentene (559-40-0) + perfluoro-2-pentene (72804-49-0) + 1,3,3,4,4,5,5-heptafluorocyclopentene (1892-03-1) + 3-chloroperfluoro-2-pentene

Conditions	Yield
With hydrogen; Ni/Cu/Cr/CaF2 at 307 - 425℃; Product distribution / selectivity; Gas phase;

...Expand

1,4,4-trichloro-2,3,3,5,5-pentafluorocyclopentene → octaperfluorocyclopentene (559-40-0) + 1,4-dichloro-2,3,3,4,5,5-hexafluorocyclopentene

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium fluoride / N,N-dimethyl-formamide / 7 h / 130 °C 2: potassium fluoride / N,N-dimethyl-formamide / 6 h / 110 °C View Scheme
Multi-step reaction with 3 steps 1: potassium fluoride / N,N-dimethyl-formamide / 7 h / 130 °C 2: potassium fluoride / N,N-dimethyl-formamide / 7 h / 130 °C 3: potassium fluoride / N,N-dimethyl-formamide / 6 h / 110 °C View Scheme
Multi-step reaction with 3 steps 1: potassium fluoride / N,N-dimethyl-formamide / 7 h / 90 °C 2: potassium fluoride / N,N-dimethyl-formamide / 7 h / 130 °C 3: potassium fluoride / N,N-dimethyl-formamide / 6 h / 110 °C View Scheme

1,4,4-trichloro-2,3,3,5,5-pentafluorocyclopentene → octaperfluorocyclopentene (559-40-0) + 1,3-dichloro-2,3,4,4,5,5-hexafluorocyclopentene

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium fluoride / N,N-dimethyl-formamide / 7 h / 130 °C 2: potassium fluoride / N,N-dimethyl-formamide / 6 h / 110 °C View Scheme

1,4,4-trichloro-2,3,3,5,5-pentafluorocyclopentene → octaperfluorocyclopentene (559-40-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium fluoride / N,N-dimethyl-formamide / 7 h / 130 °C 2: potassium fluoride / N,N-dimethyl-formamide / 6 h / 110 °C 3: potassium fluoride / N,N-dimethyl-formamide / 6 h / 110 °C View Scheme
Multi-step reaction with 3 steps 1: potassium fluoride / N,N-dimethyl-formamide / 7 h / 130 °C 2: potassium fluoride / N,N-dimethyl-formamide / 6 h / 110 °C 3: potassium fluoride / N,N-dimethyl-formamide / 6 h / 110 °C View Scheme
Multi-step reaction with 3 steps 1: potassium fluoride / N,N-dimethyl-formamide / 7 h / 130 °C 2: potassium fluoride / N,N-dimethyl-formamide / 6 h / 80 °C 3: potassium fluoride / N,N-dimethyl-formamide / 6 h / 110 °C View Scheme

1,3,3-trichloro-2,4,4,5,5-pentafluorocyclopentene → octaperfluorocyclopentene (559-40-0) + 1,4-dichloro-2,3,3,4,5,5-hexafluorocyclopentene

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium fluoride / N,N-dimethyl-formamide / 7 h / 130 °C 2: potassium fluoride / N,N-dimethyl-formamide / 6 h / 110 °C View Scheme
Multi-step reaction with 3 steps 1: potassium fluoride / N,N-dimethyl-formamide / 7 h / 90 °C 2: potassium fluoride / N,N-dimethyl-formamide / 7 h / 130 °C 3: potassium fluoride / N,N-dimethyl-formamide / 6 h / 110 °C View Scheme

1,3,3-trichloro-2,4,4,5,5-pentafluorocyclopentene → octaperfluorocyclopentene (559-40-0) + 1,3-dichloro-2,3,4,4,5,5-hexafluorocyclopentene

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium fluoride / N,N-dimethyl-formamide / 7 h / 90 °C 2: potassium fluoride / N,N-dimethyl-formamide / 7 h / 130 °C 3: potassium fluoride / N,N-dimethyl-formamide / 6 h / 110 °C View Scheme

1,3,3-trichloro-2,4,4,5,5-pentafluorocyclopentene → octaperfluorocyclopentene (559-40-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium fluoride / N,N-dimethyl-formamide / 7 h / 130 °C 2: potassium fluoride / N,N-dimethyl-formamide / 6 h / 110 °C 3: potassium fluoride / N,N-dimethyl-formamide / 6 h / 110 °C View Scheme
Multi-step reaction with 3 steps 1: potassium fluoride / N,N-dimethyl-formamide / 7 h / 130 °C 2: potassium fluoride / N,N-dimethyl-formamide / 6 h / 80 °C 3: potassium fluoride / N,N-dimethyl-formamide / 6 h / 110 °C View Scheme
Multi-step reaction with 4 steps 1: potassium fluoride / N,N-dimethyl-formamide / 7 h / 90 °C 2: potassium fluoride / N,N-dimethyl-formamide / 7 h / 130 °C 3: potassium fluoride / N,N-dimethyl-formamide / 6 h / 110 °C 4: potassium fluoride / N,N-dimethyl-formamide / 6 h / 110 °C View Scheme

1,2,3-Trichloro-3,4,4,5,5-pentafluorocyclopentene → octaperfluorocyclopentene (559-40-0) + 1,4-dichloro-2,3,3,4,5,5-hexafluorocyclopentene

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium fluoride / N,N-dimethyl-formamide / 7 h / 130 °C 2: potassium fluoride / N,N-dimethyl-formamide / 6 h / 110 °C View Scheme

1,2,3-Trichloro-3,4,4,5,5-pentafluorocyclopentene → octaperfluorocyclopentene (559-40-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium fluoride / N,N-dimethyl-formamide / 7 h / 130 °C 2: potassium fluoride / N,N-dimethyl-formamide / 6 h / 110 °C 3: potassium fluoride / N,N-dimethyl-formamide / 6 h / 110 °C View Scheme
Multi-step reaction with 3 steps 1: potassium fluoride / N,N-dimethyl-formamide / 7 h / 130 °C 2: potassium fluoride / N,N-dimethyl-formamide / 6 h / 80 °C 3: potassium fluoride / N,N-dimethyl-formamide / 6 h / 110 °C View Scheme

1,4-dichloro-2,3,3,4,5,5-hexafluorocyclopentene → octaperfluorocyclopentene (559-40-0) + 1,3-dichloro-2,3,4,4,5,5-hexafluorocyclopentene

Conditions	Yield
With potassium fluoride In N,N-dimethyl-formamide at 110℃; for 6h;	A 32.5 %Spectr. B 34.4 %Spectr.

octaperfluorocyclopentene (559-40-0) + 1-Phenyl-2-(trimethylsilyl)acetylene (2170-06-1) → 1,2-(bisphenylethynyl)-3,3,4,4,5,5-hexafluorocyclopentene

Conditions	Yield
With tetrabutylammonium triphenyldifluorosilicate In benzene-d6 at 20℃; for 2h; Reagent/catalyst;	100%

octaperfluorocyclopentene (559-40-0) → (Z)-3,3,4,4,5,5-hexafluorocyclopent-1-ene (1005-73-8)

Conditions	Yield
With sodium tetrahydroborate In diethylene glycol dimethyl ether for 0.5h; cooling;	99%
With lithium aluminium tetrahydride In diethyl ether

octaperfluorocyclopentene (559-40-0) + [(4-bromo-5-methylthiophen-2-yl)methoxy](tert-butyl)dimethylsilane (216864-69-6) → C29H42F6O2S2Si2

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane	99%

benzo[b]thiophen-2-yl triethylsilane + octaperfluorocyclopentene (559-40-0) → 2,2'-(perfluorocyclopent-1-ene-1,2-diyl)bis(benzo[b]thiophene)

Conditions	Yield
With tetrabutylammonium triphenyldifluorosilicate In tetrahydrofuran; tetrahydrofuran-d8 at 60℃; for 6h;	99%

octaperfluorocyclopentene (559-40-0) + 2-(5-(trimethylsilyl)thiophen-2-yl)pyridine (51459-67-7) → 2,2'-((perfluorocyclopent-1-ene-1,2-diyl)bis(thiophene-5,2-diyl))dipyridine

Conditions	Yield
With tetrabutylammonium triphenyldifluorosilicate In tetrahydrofuran; tetrahydrofuran-d8 at 60℃; for 6h;	99%

octaperfluorocyclopentene (559-40-0) → 1,3,3,4,4,5,5-heptafluorocyclopentene (1892-03-1)

Conditions	Yield
With water; zinc In N,N-dimethyl acetamide at 80℃; for 6h; Sealed tube;	99%

3,4-dimercaptotoluene (496-74-2) + octaperfluorocyclopentene (559-40-0) → 1,1,2,2,3,3-hexafluoro-6-methyl-2,3-dihydro-1H-benzocyclopenta-p-dithiine (110890-06-7)

Conditions	Yield
With potassium carbonate In acetonitrile for 24h; Ambient temperature;	98%

4-bromo-phenol (106-41-2) + octaperfluorocyclopentene (559-40-0) → 1-bromo-4-[2-(4-bromophenoxy)-3,3,4,4,5,5-hexafluorocyclopenten-1-yl]oxy-benzene

Conditions	Yield
Stage #1: 4-bromo-phenol; octaperfluorocyclopentene With triethylamine In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: With caesium carbonate In N,N-dimethyl-formamide at 20℃; chemoselective reaction;	98%

octaperfluorocyclopentene (559-40-0) + 2-amino-benzenethiol (137-07-5) → 1,1,2,2,3-Pentafluoro-1,2-dihydro-benzo[b]cyclopenta[e][1,4]thiazine (110890-13-6)

Conditions	Yield
With potassium carbonate In acetonitrile for 24h; Ambient temperature;	97%

octaperfluorocyclopentene (559-40-0) + 3-bromo-2-methoxy-4-methyl-5-phenylthiophene (811830-43-0) → 1-(2-methoxy-4-methyl-5-phenylthiophen-3-yl)-2,3,3,4,4,5,5-heptafluorocyclopentene (811830-45-2)

Conditions	Yield
Stage #1: 3-bromo-2-methoxy-4-methyl-5-phenylthiophene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: octaperfluorocyclopentene In tetrahydrofuran; hexane at -78 - 20℃;	97%

octaperfluorocyclopentene (559-40-0) + 2-benzofuranyl lithium (2786-03-0) → 1,2-bis(2-benzo[b]furyl)-3,3,4,4,5,5-hexafluorocyclopentene

Conditions	Yield
In tetrahydrofuran; diethyl ether at -78℃;	97%

octanol (111-87-5) + octaperfluorocyclopentene (559-40-0) → 1,3,3,4,4,5,5-heptafluoro-2-octoxy-cyclopentene

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 0.5h; chemoselective reaction;	97%

octaperfluorocyclopentene (559-40-0) + Bromine(I) trifluoromethanesulfonate (70142-16-4) → 2-bromooctafluorocyclopentyl trifluoromethanesulfonate (73323-48-5)

Conditions	Yield
at -111 - 22℃; for 24h;	96%
-111 to 22°C, 24 h;	96%

octaperfluorocyclopentene (559-40-0) + 3-(trimethylsilylethynyl)thiophene (130995-13-0) → 1,2-bis(2-(3-thienyl)ethynyl)-3,3,4,4,5,5-hexafluorocyclopentene

Conditions	Yield
With tetrabutyl ammonium fluoride In benzene-d6 at 20℃; for 0.5h;	96%

3-bromo-2-methylbenzo[b]thiophene (10243-15-9) + octaperfluorocyclopentene (559-40-0) → 3-(2-fluoro-3,3,4,4,5,5-hexafluorocyclopent-1-en-1-yl)-2-methylbenzo[b]thiophene (152431-65-7)

Conditions	Yield
Stage #1: 3-bromo-2-methylbenzo[b]thiophene With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #2: octaperfluorocyclopentene In tetrahydrofuran at -78 - 20℃; for 1h;	94.9%
Stage #1: 3-bromo-2-methylbenzo[b]thiophene With n-butyllithium In diethyl ether at -78℃; for 1h; Stage #2: octaperfluorocyclopentene In diethyl ether at -78℃; for 17h;	92%
Stage #1: 3-bromo-2-methylbenzo[b]thiophene With n-butyllithium In tetrahydrofuran at -78.16℃; for 0.5h; Inert atmosphere; Stage #2: octaperfluorocyclopentene In tetrahydrofuran for 1h;	75%

3-bromo-2,5-dimethylthiophene (31819-37-1) + octaperfluorocyclopentene (559-40-0) → 2,5-dimethyl-3-(perfluorocyclopent-1-enyl)thiophene (676258-32-5)

Conditions	Yield
Stage #1: 3-bromo-2,5-dimethylthiophene With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #2: octaperfluorocyclopentene In tetrahydrofuran at -78℃; for 2h; Inert atmosphere;	94.9%
With n-butyllithium
Stage #1: 3-bromo-2,5-dimethylthiophene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Schlenk technique; Stage #2: octaperfluorocyclopentene In tetrahydrofuran; hexane at -78 - 20℃; for 17h; Inert atmosphere; Schlenk technique;

octaperfluorocyclopentene (559-40-0) + 1,3-bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene (173035-11-5) → C25H24F8N2

Conditions	Yield
In hexane; toluene at 20℃; for 1h;	94%

octaperfluorocyclopentene (559-40-0) + 1,3-bis(2,4,6-trimethylphenyl)4,5-dimethyl-1,3-dihydro-2H-imidazol-2-ylidene (848085-28-9) → C12H12F7N2(1+)*F5Si(1-)

Conditions	Yield
In toluene at 20℃; for 1h;	94%

4-allylguaiacol (97-53-0) + octaperfluorocyclopentene (559-40-0) → 4-allyl-1-[2-(4-allyl-2-methoxy-phenoxy)-3,3,4,4,5,5-hexafluoro-cyclopenten-1-yl]oxy-2-methoxybenzene

Conditions	Yield
Stage #1: 4-allylguaiacol; octaperfluorocyclopentene With triethylamine In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: With caesium carbonate In N,N-dimethyl-formamide at 20℃; chemoselective reaction;	94%
With triethylamine In N,N-dimethyl-formamide at 20 - 50℃; Inert atmosphere;	93.6%

glycerol methacrylate acrylate (433937-38-3) + octaperfluorocyclopentene (559-40-0) → [3-acryloyloxy-2-(2,3,3,4,4,5,5-heptafluorocyclopentenyloxy)]-propyl 2-methyl-acrylate (184474-71-3)

Conditions	Yield
With hydrogenchloride; triethylamine In dichloromethane; water; acetonitrile	93%

octaperfluorocyclopentene (559-40-0) + 1,2,4,5-tetrafluoro-3-(trifluoromethyl)benzene (651-80-9) → 1,2-bisperfluorotolyl-3,3,4,4,5,5-hexafluorocyclopentene

Conditions	Yield
Stage #1: 1,2,4,5-tetrafluoro-3-(trifluoromethyl)benzene With n-butyllithium In diethyl ether at -78℃; for 2h; Inert atmosphere; Stage #2: octaperfluorocyclopentene In diethyl ether at -78℃; for 3.67h; Inert atmosphere;	93%

octaperfluorocyclopentene (559-40-0) + ([1,1'-biphenyl]-4-ylethynyl)trimethylsilane (75867-42-4) → 1,2-bis((1,1'-biphenyl)-4-ylethynyl)-3,3,4,4,5,5-hexafluorocyclopentene

Conditions	Yield
With tetrabutylammonium triphenyldifluorosilicate In tetrahydrofuran; benzene-d6 at 20℃; for 4h;	93%

octaperfluorocyclopentene (559-40-0) + tris(1-methylethyl)(phenylethynyl)silane (4131-50-4) → 1,2-(bisphenylethynyl)-3,3,4,4,5,5-hexafluorocyclopentene

Conditions	Yield
With tetrabutyl ammonium fluoride In benzene-d6 at 20℃; for 1h;	93%

octaperfluorocyclopentene (559-40-0) + 2-(α-bromobenzylidene)adamantane (461054-94-4) → 1-(1-adamantylidene-1-phenylmethyl)-2,3,3,4,4,5,5-heptafluorocyclopentene (461054-95-5)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 15h;	92%

octaperfluorocyclopentene (559-40-0) + 2,4-dimethyl-5-phenyl-3-bromothiophene (362513-28-8) → 2-(2,3,3,4,4,5,5-heptefluorocyclopent-1-en-1-yl)-2,4-dimethyl-5-phenylthiophene (362513-29-9)

Conditions	Yield
Stage #1: 2,4-dimethyl-5-phenyl-3-bromothiophene With n-butyllithium In tetrahydrofuran; hexane at -78℃; Inert atmosphere; Stage #2: octaperfluorocyclopentene In tetrahydrofuran; hexane at -78℃; Inert atmosphere;	92%
Stage #1: 2,4-dimethyl-5-phenyl-3-bromothiophene With n-butyllithium In tetrahydrofuran; hexane at -78℃; Stage #2: octaperfluorocyclopentene In tetrahydrofuran; hexane at -78℃; Further stages.;	78%
With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 3h;	75%
Stage #1: 2,4-dimethyl-5-phenyl-3-bromothiophene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: octaperfluorocyclopentene In tetrahydrofuran; hexane at -78℃; for 1.5h; Inert atmosphere;	70%
Stage #1: 2,4-dimethyl-5-phenyl-3-bromothiophene With n-butyllithium In tetrahydrofuran; hexane at -78℃; Inert atmosphere; Stage #2: octaperfluorocyclopentene In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere;	37%

octaperfluorocyclopentene (559-40-0) + C52H41NOS4 → C57H41F4NO3S4

Conditions	Yield
With acetic acid In water; 1,2-dichloro-ethane at 0 - 130℃; for 0.166667h; Inert atmosphere; Sealed tube; Microwave irradiation;	92%

octaperfluorocyclopentene (559-40-0) + 4-ethoxyphenylacetylene (79887-14-2) → 1,2-bis[2-[4-(ethoxyphenyl)ethyn]-1-yl]-3,3,4,4,5,5-hexafluorocyclopentene

Conditions	Yield
Stage #1: 4-ethoxyphenylacetylene With n-butyllithium In tetrahydrofuran at 0℃; for 2h; Stage #2: octaperfluorocyclopentene In tetrahydrofuran at -78 - 20℃; for 2h;	92%

4-bromo-phenol (106-41-2) + octaperfluorocyclopentene (559-40-0) → 1-bromo-4-(2,3,3,4,4,5,5-heptafluorocyclopenten-1-yl)oxy-benzene

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 0.5h; chemoselective reaction;	92%

Upstream product

• 75-45-6 Chlorodifluoromethane 
• 116-14-3 polytetrafluoroethylene 
• 19721-29-0 1,2,3,3-tetrafluorocyclopropene 
• 3109-88-4 octafluoro-1,3-pentadiene 
• 85625-40-7 Perfluorobicyclo<3.2.0>heptane 
• 706-78-5 octachlorocyclopentene 
• 911291-50-4 1,2,4,5,6,6,7,7-octafluoro-3-oxatricyclo[3.2.0.0^2,4]heptane 
• 911225-21-3 1,4,5,6,7,7-hexafluoro-2,3-diazabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid dimethyl ester 
• 146721-82-6 3,3-dichloro-1,1,1,2,2,4,4,5,5,5-decafluoropentane 
• 542-92-7 cyclopenta-1,3-diene 
• 376-77-2 decafluorocyclopentane 
• 14916-75-7 1,2-dichlorocyclopentane 
• 142-29-0 cyclopentene 
• 706-79-6 1,2-dichloro-3,3,4,4,5,5-hexafluorocyclopentene 

Downstream Products

• 1759-60-0 1,3,3,4,4,5,5-heptafluoro-2-methoxy-cyclopentene 
• 10575-68-5 1-phenyl-2,3,3,4,4,5,5-heptafluorocyclopentene 
• 10575-69-6 1,2-diphenyl-3,3,4,4,5,5-hexafluorocyclopentene 
• 4045-66-3 2,4,4,5,5-Pentafluor-1-methylamino-3-methylimino-cyclopent-1-en 
• 66463-33-0 1-benzoxyperfluorocyclopentene 
• 137814-07-4 1,2-bis(2-methyl-1-benzothiophen-3-yl)-3,3,4,4,5,5-hexafluorocyclopent-1-ene 
• 7481-14-3 (cis/trans-2H-Octafluorcyclopentyl)methanol 
• 49851-76-5 perfluoprobicyclopentylidene 
• 26114-19-2 Eicosafluoro-1-cyclohexylcyclohexen 
• 74693-93-9 perfluorocyclohexylcyclopentene 
• 74835-68-0 (3,3,4,4,5,5-hexafluoro-2-phenoxy-cyclopenten-1-yl)oxybenzene 
• 141062-95-5 1,2-bis(2-phenyl-4-(trifluoromethyl)thiazol-5-yl)hexafluoro-1-cyclopentene 
• 156686-76-9 1,2-Bis-<5'-(4''-methoxyphenyl)-2'-methylthien-3'-yl>perfluorocyclopentene 
• 2154-59-8 difluoro-methylene 

Relevant articles and documents

Preparation method of octafluorocyclopentene

The invention relates to a preparation method of octafluorocyclopentene, and belongs to the technical field of chemical engineering. The method comprises the following steps: (1) dissolving 1, 2-dichlorocyclopentane in carbon tetrachloride, cooling to 0-20 DEG C, introducing diluted fluorine gas, stirring, heating to 30-50 DEG C, carrying out fluorination and fluorination reaction for 1-2 hours to obtain a product, and separating and purifying to obtain 1, 2-dichlorooctafluorocyclopentane; and (2) dissolving a reductive dechlorination reagent in a dry polar solvent, stirring, protecting by protective gas, heating to 50-80 DEG C, dropwise adding the 1, 2dichlorooctafluorocyclopentane by adopting a constant-pressure dropping funnel, continuously reacting for 0.5-1.5 hours when no foam is generated, and collecting the generated gas by using a cold trap. The method is simple to operate; high-temperature and high-pressure conditions are not set, and reaction conditions are mild; and less three wastes are generated, the environmental pressure is low, and the method belongs to a green synthesis process.

Continuous chemical industry preparation method of octafluorocyclopentene

The invention relates to the field of fine chemical industry, in particular to a continuous chemical industry preparation method of octafluorocyclopentene. The continuous chemical industry preparationmethod comprises the steps of gas phase chlorination reaction, intermediate product purification, gas phase fluorination reaction and the like. The final product octafluorocyclopentene is obtained from easily obtained raw material cyclopentene by using a gas phase method, compared with an existing liquid phase fluorination-method technology for preparing octafluorocyclopentene, the preparation method of the octafluorocyclopentene has the advantages of cheap reaction raw materials, simplicity in reaction, no applicability to solvent, no organic waste liquid generation, short reaction time, high product yield, capability of continuous production and great prospect of industrial production.

Industrial production method for perfluorocyclopentene

The invention discloses an industrial production method for perfluorocyclopentene, and belongs to the field of fine chemical intermediate synthesis. Cyclopentene, chlorine and pyridine hydrofluoride which are used as raw materials undergo high-temperature chlorination in a solvent sulfolane to obtain octachlorocyclopentene, and the octachlorocyclopentene and pyridine hydrofluoride undergo high-temperature fluorination substitution to obtain the perfluorocyclopentene. Residues obtained after the separation of the product undergo reduced pressure distillation to obtain the solvent sulfolane which can be reused. The method allows the product yield to reach 45-55%, the product content to be more than 99%, the water content to be less than 0.1% and the chloride ion content to be less than 0.1%. The method has the advantages of no pollution in the production process, green production process, high yield, simple steps, facilitation of the reduction of the production cost, high product purity, and facilitation of later application.