3345-29-7

Basic information

• Product Name: 2,2,3,3,8,8,9,9-Octafluorotricyclo[8.2.2.24,7]hexadeca-4,6,10,12,13,15-hexaene
• Synonyms: 1,1,2,2,9,9,10,10-Octafluoro[2.2]paracyclophane;2,2,3,3,8,8,9,9-Octafluorotricyclo[8.2.2.24,7]hexadeca-4,6,10,12,13,15-hexaene;Tricyclo[8.2.2.24,7]hexadeca-4,6,10,12,13,15-hexaene, 2,2,3,3,8,8,9,9-octafluoro-;2,2,3,3,8,8,9,9-Octa;Tricyclo[8.2.2.24,7]hexadeca-4,6,10,12,13,15-hexaene, 2,2,3,3,8,8,9,9-octafluoro Tricyclo[8.2.2.24,7]hexadeca-4,6,10,12,13,15-hexaene, octafluoro;parylene AF4(parylene HT);Parylene-AF4
• CAS NO: 3345-29-7
• Molecular Formula: C₁₆H₈F₈
• Molecular Weight: 352.223
• Mol File: 3345-29-7.mol
• Article Data: 12

Chemical Properties

• Melting Point: 240-250°C
• Boiling Point: 259.3 °C at 760 mmHg
• Flash Point: 96 °C
• Appearance: /
• Density: 1.47 g/cm³
• Vapor Pressure: 0.0211mmHg at 25°C
• Refractive Index: 1.489
• CAS DataBase Reference: 2,2,3,3,8,8,9,9-Octafluorotricyclo[8.2.2.24,7]hexadeca-4,6,10,12,13,15-hexaene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2,3,3,8,8,9,9-Octafluorotricyclo[8.2.2.24,7]hexadeca-4,6,10,12,13,15-hexaene(3345-29-7)
• EPA Substance Registry System: 2,2,3,3,8,8,9,9-Octafluorotricyclo[8.2.2.24,7]hexadeca-4,6,10,12,13,15-hexaene(3345-29-7)

Safety Data

• Hazardous Substances Data: 3345-29-7(Hazardous Substances Data)

Usage

Uses

Parylen AF4 is extremely useful in high temperature applications and those in which long-term UV stability is required.AerospaceMilitaryElectronicMedical Industrial Semiconductor (3D IC TSV electrical insulation , AMOLED De-bonding layer , Barrier layer )Bio-MEMS electrode protection film EWD (Electro Wetting Device) Liquid lens

General Description

Characteristics of Parylen AF4 coating:Specialties:Unmatched UV stabilityExcellent thermal stability at high service temperature (350)Unmatched oxidation stabilityCompletely conformal coatingSuperior crevice penetration, pin hole freeAnti-saline damageAnti-stick ionBarrier properties:Chemical insolubility and solvent resistantLow water absorptionHydrophobic propertiesLow gas permeability , no out-gassingPhysical & mechanical properties:TransparentLight-weight and ultra-thinLow CTELow coefficient of frictionGood dry lubricityAbrasion resistanceStabilization of components and structuresParticulate immobilizationElectrical properties:Electrical insulationHigh dielectric strengthHigh volume resistivity ,ohm-cmLow dissipation factorLow dielectric constantMitigation of tin whisker growthBiocompatibility and bio-stabilityUSP class VIMicroorganism resistance

InChI:InChI=1/C16H8F8/c17-13(18)9-1-2-10(4-3-9)14(19,20)16(23,24)12-7-5-11(6-8-12)15(13,21)22/h1-8H

Synthetic route

4-iodo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (257863-40-4) → 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (3345-29-7)

Conditions	Yield
With phenylmagnesium bromide; palladium dichloride In tetrahydrofuran for 1h; Inert atmosphere; Reflux;	98%

4-bromo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (257863-41-5) → 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (3345-29-7)

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; zinc In N,N-dimethyl-formamide at 25℃; for 8h;	96%

4-chloro-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (257863-42-6) → 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (3345-29-7) + 4,4'-bis(1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane)

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; zinc In N,N-dimethyl-formamide at 80℃; for 8h;	A 94% B 3%

2,2-difluoro-2-(fluorosulfonyl)acetate (680-15-9) + 4-iodo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (257863-40-4) → 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (3345-29-7) + 4-trifluoromethyl-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

Conditions	Yield
With copper(I) bromide; palladium dichloride In N,N-dimethyl-formamide at 80℃; Reduction; trifluoromethylation;	A 3% B 84%

phenylmagnesium bromide (100-58-3) + 4-iodo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (257863-40-4) → 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (3345-29-7) + 4-phenyl-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

Conditions	Yield
With palladium dichloride In tetrahydrofuran Kumada Cross-Coupling; Inert atmosphere; Reflux;	A 8% B 83%

4-iodo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (257863-40-4) → 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (3345-29-7) + 4,4'-bis(1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane)

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper In N,N-dimethyl-formamide at 80℃; for 8h;	A 11% B 74%
Stage #1: 4-iodo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane With palladium dichloride In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Stage #2: With <2.2>paracyclophan-4-ylmagnesium bromide In tetrahydrofuran at 20℃; for 8h; Inert atmosphere;	A 60% B 30%

phenylmagnesium bromide + 4-iodo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (257863-40-4) → 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (3345-29-7) + 4-phenyl-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

Conditions	Yield
palladium dichloride In tetrahydrofuran for 16h; Phenylation; reduction; Heating;	A 9% B 72%

4-amino-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (257863-37-9) → 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (3345-29-7) + 4-bromo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (257863-41-5)

Conditions	Yield
Stage #1: 4-amino-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane With sulfuric acid; sodium nitrite In water; acetic acid at 0℃; for 2h; Diazotization; Stage #2: With hydrogen bromide; copper(I) bromide In water; acetic acid at 70℃; for 1h; Substitution; Sandmeyer reaction; reduction;	A 6% B 66%

methyllithium lithium bromide + 4-iodo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (257863-40-4) → 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (3345-29-7) + 4-methyl-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

Conditions	Yield
With palladium dichloride In tetrahydrofuran for 2h; Kumada Cross-Coupling; Inert atmosphere; Reflux;	A 66% B 31%
With palladium dichloride In tetrahydrofuran; diethyl ether at 0℃; for 5h; Kumada Cross-Coupling; Inert atmosphere;	A 17 %Spectr. B 81 %Spectr.

1,4-bis-(difluorochloromethyl)-benzene (2629-68-7) → 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (3345-29-7) + (Z)-2,3,8,8,9,9-Hexafluoro-tricyclo[8.2.2.24,7]hexadeca-1(13),2,4(16),5,7(15),10(14),11-heptaene

Conditions	Yield
With zinc In N,N-dimethyl acetamide at 100℃; for 4h; Substitution;	A 60.5% B 6%

4-amino-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (257863-37-9) → 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (3345-29-7) + 4-chloro-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (257863-42-6)

Conditions	Yield
Stage #1: 4-amino-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane With sulfuric acid; sodium nitrite In water; acetic acid at 0℃; for 2h; Diazotization; Stage #2: With hydrogenchloride; copper(l) chloride In water; acetic acid at 70℃; for 1h; Substitution; Sandmeyer reaction; reduction;	A 10% B 60%

α-trimethylsilyl-α,α,α',α'-pentafluoroxylene (149194-32-1) → 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (3345-29-7)

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 4-tert-Butylcatechol; cesium fluoride In methoxybenzene at 160℃; for 24h;	53%

phenylmagnesium bromide (100-58-3) + 4-bromo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (257863-41-5) → 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (3345-29-7) + 4-phenyl-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

Conditions	Yield
With palladium dichloride In tetrahydrofuran for 2h; Kumada Cross-Coupling; Inert atmosphere; Reflux;	A 50% B 19%

C16H7F8I + potassium tert-butylate (865-47-4) + benzene (71-43-2) → C20H16F8O + 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (3345-29-7) + C22H12F8 (498556-71-1)

Conditions	Yield
In dibutyl ether at 110℃; for 5h;	A 35% B 45.8% C 3.5%

1,4-bis-(difluorochloromethyl)-benzene (2629-68-7) → 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (3345-29-7)

Conditions	Yield
With potassium iodide; zinc In N,N-dimethyl acetamide at 120 - 142℃; for 6h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature;	45.7%
With lithium aluminium tetrahydride; titanium tetrachloride In tetrahydrofuran Heating;	22%

phenylmagnesium bromide (100-58-3) + 4-iodo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (257863-40-4) → 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (3345-29-7) + 4-phenyl-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane + 4,4'-bis(1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane)

Conditions	Yield
Stage #1: 4-iodo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane With palladium dichloride In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Stage #2: phenylmagnesium bromide In tetrahydrofuran at 20℃; for 11h; Inert atmosphere;	A 15% B 38% C 44%

α,α'-dibromo-α,α,α',α'-tetrafluoro-p-xylene (651-12-7) → 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (3345-29-7)

Conditions	Yield
With trimethylsilyltributyltin; cesium fluoride In tetrahydrofuran; dimethyl sulfoxide at 78℃; for 28h;	40%
With trimethylsilyltributyltin; cesium fluoride In tetrahydrofuran; dimethyl sulfoxide at 75 - 80℃; Substitution;	40%
With calcium chloride; zinc In N,N-dimethyl acetamide at 120 - 136℃; for 3h; Catalytic behavior; Reagent/catalyst;	32.8%
With water; copper at 650℃;
Multi-step reaction with 2 steps 1: Cu / 640 °C 2: toluene / 110 °C View Scheme

α,α'-dibromo-α,α,α',α'-tetrafluoro-p-xylene (651-12-7) → 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (3345-29-7) + dodecafluoro[2,2]paracyclophane

Conditions	Yield
With lithium aluminium tetrahydride; titanium tetrachloride In tetrahydrofuran Heating;	A 31.8% B 2.1%
With lithium aluminium tetrahydride; titanium tetrachloride In tetrahydrofuran Mechanism; Heating;	A 31.8% B 2.1%
With lead(II) bromide; aluminium In N,N-dimethyl-formamide at 0 - 20℃; for 30h; Product distribution; Further Variations:; Reagents; Solvents; Temperatures;	A 22% B 19%

1,4-bis-(difluorochloromethyl)-benzene (2629-68-7) + α,α'-dibromo-α,α,α',α'-tetrafluoro-p-xylene (651-12-7) → 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (3345-29-7)

Conditions	Yield
With calcium chloride; zinc In N,N-dimethyl acetamide at 120 - 140℃; for 4h; Catalytic behavior; Reagent/catalyst;	31.4%

1,4-bis-(difluorochloromethyl)-benzene (2629-68-7) → 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (3345-29-7) + dodecafluoro[2,2]paracyclophane

Conditions	Yield
With aluminium In N,N-dimethyl-formamide at 0 - 20℃; for 50h;	A 22% B 20%

α,α,α',α'-tetrafluoro-p-xylylene (2250-30-8) → 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (3345-29-7)

Conditions	Yield
In toluene at 110℃; Yield given;

1,4-bis(trifluoromethyl)benzene (433-19-2) → 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (3345-29-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 48 percent / Mg / dimethylformamide / 0.5 h / 20 °C 2: 53 percent / CsF; Pd2(dba)3*CHCl3; 4-tert-butylcatechol / methoxybenzene / 24 h / 160 °C View Scheme
Multi-step reaction with 2 steps 1: 58 percent Spectr. / Mg / dimethylformamide / 1 h / 20 °C 2: 53 percent / CsF; Pd2(dba)3*CHCl3; 4-tert-butylcatechol / methoxybenzene / 24 h / 160 °C View Scheme

4-nitro-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (257863-35-7) → 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (3345-29-7)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 82 percent / iron; hydrochloric acid / ethanol; H2O / 4 h / Heating 2.1: H2SO4; NaNO2 / acetic acid; H2O / 2 h / 0 °C 2.2: 6 percent / copper(I) bromide; hydrobromic acid / H2O; acetic acid / 1 h / 70 °C View Scheme
Multi-step reaction with 2 steps 1.1: 82 percent / iron; hydrochloric acid / ethanol; H2O / 4 h / Heating 2.1: H2SO4; NaNO2 / acetic acid; H2O / 2 h / 0 °C 2.2: 10 percent / copper(I) chloride; hydrochloric acid / H2O; acetic acid / 1 h / 70 °C View Scheme
Multi-step reaction with 3 steps 1.1: 82 percent / iron; hydrochloric acid / ethanol; H2O / 4 h / Heating 2.1: H2SO4; NaNO2 / acetic acid; H2O / 2 h / 0 °C 2.2: 78 percent / potassium iodide / H2O; acetic acid / 1 h / 70 °C 3.1: 9 percent / palladium dichloride / tetrahydrofuran / 16 h / Heating View Scheme

4-amino-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (257863-37-9) → 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (3345-29-7)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: H2SO4; NaNO2 / acetic acid; H2O / 2 h / 0 °C 1.2: 78 percent / potassium iodide / H2O; acetic acid / 1 h / 70 °C 2.1: 9 percent / palladium dichloride / tetrahydrofuran / 16 h / Heating View Scheme

4-hydroxylamino-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (257863-36-8) → 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (3345-29-7)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 77 percent / iron; hydrochloric acid / ethanol; H2O / 4 h / Heating 2.1: H2SO4; NaNO2 / acetic acid; H2O / 2 h / 0 °C 2.2: 6 percent / copper(I) bromide; hydrobromic acid / H2O; acetic acid / 1 h / 70 °C View Scheme
Multi-step reaction with 2 steps 1.1: 77 percent / iron; hydrochloric acid / ethanol; H2O / 4 h / Heating 2.1: H2SO4; NaNO2 / acetic acid; H2O / 2 h / 0 °C 2.2: 10 percent / copper(I) chloride; hydrochloric acid / H2O; acetic acid / 1 h / 70 °C View Scheme
Multi-step reaction with 3 steps 1.1: 77 percent / iron; hydrochloric acid / ethanol; H2O / 4 h / Heating 2.1: H2SO4; NaNO2 / acetic acid; H2O / 2 h / 0 °C 2.2: 78 percent / potassium iodide / H2O; acetic acid / 1 h / 70 °C 3.1: 9 percent / palladium dichloride / tetrahydrofuran / 16 h / Heating View Scheme

para-xylene (106-42-3) + 3-methyl-phthalic acid-dichloride → 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (3345-29-7)

Conditions	Yield
Multi-step reaction with 5 steps 1: 80 percent / Br2 / 5 h / 130 - 160 °C 2: 85 percent / SbF3 / 120 °C / 40 Torr 3: 55 percent / N-bromosuccinimide / CCl4 / Heating; Irradiation 4: Cu / 640 °C 5: toluene / 110 °C View Scheme

1,4-bis(dibromomethyl)benzene (1592-31-0) → 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (3345-29-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: 85 percent / SbF3 / 120 °C / 40 Torr 2: 55 percent / N-bromosuccinimide / CCl4 / Heating; Irradiation 3: Cu / 640 °C 4: toluene / 110 °C View Scheme

p-bis(difluoromethyl)benzene (369-54-0) → 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (3345-29-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 55 percent / N-bromosuccinimide / CCl4 / Heating; Irradiation 2: Cu / 640 °C 3: toluene / 110 °C View Scheme
Multi-step reaction with 2 steps 1: 78 percent / N-bromosuccinimide / CCl4 / Heating; Irradiation 2: 31.8 percent / TiCl4, LiAlH4 / tetrahydrofuran / Heating View Scheme
Multi-step reaction with 2 steps 1: NBS / CCl4 / Irradiation 2: Cu, H2O / 650 °C View Scheme

terephthalaldehyde, (623-27-8) → 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (3345-29-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 88 percent / SF4 / 150 °C 2: 78 percent / N-bromosuccinimide / CCl4 / Heating; Irradiation 3: 31.8 percent / TiCl4, LiAlH4 / tetrahydrofuran / Heating View Scheme

1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (3345-29-7) → α,α,α',α'-tetrafluoro-p-xylylene (2250-30-8)

Conditions	Yield
at 450 - 600℃; under 0 Torr; Decomposition; flash vacuum pyrolysis;	100%

1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (3345-29-7) → 4-nitro-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (257863-35-7)

Conditions	Yield
With nitric acid	90%
With nitronium tetrafluoborate In sulfolane at 25℃; for 16h; Nitration;	86%

1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (3345-29-7) → 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane-4,7-dione (1173111-79-9) + C16H6F8O3 (1173111-81-3)

Conditions	Yield
With sulfuric acid; iodic acid In trifluoroacetic acid at 20℃; Reflux;	A 56% B 20%

1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (3345-29-7) → 4-bromo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (257863-41-5) + p-dibromo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (299975-30-7)

Conditions	Yield
With N-Bromosuccinimide; sulfuric acid In trifluoroacetic acid at 20 - 80℃; for 28h; Bromination;	A n/a B 55%

1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (3345-29-7) → p-dibromo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (299975-30-7)

Conditions	Yield
With N-Bromosuccinimide; sulfuric acid In trifluoroacetic acid at 20 - 80℃; for 28h;	55%

1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (3345-29-7) → 4-nitro-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (257863-35-7) + pseudo-o-dinitro-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (300700-86-1, 300766-00-1) + pseudo-m-dinitro-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

Conditions	Yield
With nitronium tetrafluoborate In sulfolane at 80℃; Nitration;	A 36% B 16% C 16%
With nitronium tetrafluoborate	A 36% B n/a C 16%

1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (3345-29-7) → pseudo-o-dinitro-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (300700-86-1, 300766-00-1) + pseudo-m-dinitro-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

Conditions	Yield
With nitronium tetrafluoborate In sulfolane at 80℃; for 16h; Nitration;	A 27% B n/a
With nitronium tetrafluoborate In sulfolane at 20 - 80℃;	A n/a B 27%

chloro-trimethyl-silane (75-77-4) + 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (3345-29-7) → 2,9,9,10,10-pentafluoro-1-trimethylsilyl[2.2]paracyclophan-1-ene

Conditions	Yield
With magnesium In N,N-dimethyl-formamide at 0 - 20℃; for 0.5h; Inert atmosphere;	23%

1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (3345-29-7) → 1,1,2,2,9,9,10,10-octafluoro<2.2>paracyclophane radical anion

Conditions	Yield
With tetrabutylammonium perchlorate In 1,2-dimethoxyethane at -85.1℃; Product distribution; study of the radical anion formation by continous electrolysis;

Upstream product

• 651-12-7 α,α'-dibromo-α,α,α',α'-tetrafluoro-p-xylene 
• 2629-68-7 1,4-bis-(difluorochloromethyl)-benzene 
• 257863-37-9 4-amino-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane 
• 257863-42-6 4-chloro-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane 
• 257863-40-4 4-iodo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane 
• 865-47-4 potassium tert-butylate 
• 71-43-2 benzene 
• 1073-67-2 4-vinylbenzyl chloride 
• 623-27-8 terephthalaldehyde, 
• 1592-31-0 1,4-bis(dibromomethyl)benzene 
• 106-42-3 para-xylene 
• 257863-36-8 4-hydroxylamino-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane 
• 257863-35-7 4-nitro-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane 
• 433-19-2 1,4-bis(trifluoromethyl)benzene 

Downstream Products

• 2250-30-8 α,α,α',α'-tetrafluoro-p-xylylene 

Relevant articles and documents

A novel, non-high-dilution method for preparation of 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

(Formula presented) A novel synthesis of octafluoro[2.2]paracyclophane (AF4), one that remarkably does not require the use of high dilution methodology, is presented. Using this unprecedented methodology, AF4 is produced in 60% yield in a reaction of Zn with 0.35 M p-bis(chlorodifluoromethyl)-benzene in DMA at 100°C. The process comprises a convenient, inexpensive, and highly scaleable preparation of AF4 for both research and commercial purposes.

A new ans Practical Synthesis of Octafluoroparacyclophane

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A convenient preparation of octafluoro[2,2]paracyclophane and dodecafluoro[2,2]paracyclophane

A new and convenient synthesis of octafluoro[2,2]paracyclophane and dodeca-fluoro[2,2]paracyclophane is reported. It is accomplished by treatment of 1,4-bis(halodifluoromethyl)benzene with PbBr2/Al in DMF at room temperature via the cyclocoupling of the reactive intermediate α,α,α′α′-tetrafluoro-p-xylylene.

CATALYTIC OR PHOTOCATALYTIC PREPARATION METHOD OF PARYLENE AF4

The present invention disclosed a preparation method of parylene AF4, which provides a reactant and a reducing agent with the use of catalyst or exposure to UV light with photo-initiator, to shorten the reaction time as a result of minimized the byproduct(s) formation, and obtain high purity (>99.0%) of parylene AF4 product under high concentrated reaction mixture.