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

Description

2,2,3,3,8,8,9,9-Octafluorotricyclo[8.2.2.24,7]hexadeca-4,6,10,12,13,15-hexaene, also known as Parylen AF4, is a unique chemical compound with a complex molecular structure. It is characterized by its exceptional UV stability, thermal stability, and oxidation stability. Parylen AF4 is a completely conformal coating that offers superior crevice penetration and is pinhole-free. It also has anti-saline damage and anti-stick ion properties. 2,2,3,3,8,8,9,9-Octafluorotricyclo[8.2.2.24,7]hexadeca-4,6,10,12,13,15-hexaene is chemically insoluble and solvent resistant, with low water absorption and hydrophobic properties. It has low gas permeability and no out-gassing. Physically, it is transparent, light-weight, and ultra-thin, with a low coefficient of thermal expansion (CTEL) and a low coefficient of friction. It also has good dry lubricity, abrasion resistance, and can stabilize components and structures. Electrically, Parylen AF4 provides excellent insulation, high dielectric strength, high volume resistivity, low dissipation factor, and a low dielectric constant. It can mitigate tin whisker growth and is biocompatible and bio-stable, with USP class VI and microorganism resistance.

Uses

Used in Aerospace:
2,2,3,3,8,8,9,9-Octafluorotricyclo[8.2.2.24,7]hexadeca-4,6,10,12,13,15-hexaene is used as a protective coating for aerospace applications due to its unmatched UV stability, thermal stability, and oxidation stability. It can protect components from harsh environmental conditions and extend their lifespan.
Used in Military:
In the military industry, 2,2,3,3,8,8,9,9-Octafluorotricyclo[8.2.2.24,7]hexadeca-4,6,10,12,13,15-hexaene is used as a protective coating for various equipment and systems. Its properties make it suitable for protecting sensitive components from environmental factors and ensuring their reliable operation in harsh conditions.
Used in Electronics:
2,2,3,3,8,8,9,9-Octafluorotricyclo[8.2.2.24,7]hexadeca-4,6,10,12,13,15-hexaene is used as an insulating coating in the electronics industry. Its electrical properties, such as high dielectric strength, high volume resistivity, and low dielectric constant, make it an ideal choice for protecting electronic components and ensuring their proper functioning.
Used in Medical Industry:
In the medical industry, 2,2,3,3,8,8,9,9-Octafluorotricyclo[8.2.2.24,7]hexadeca-4,6,10,12,13,15-hexaene is used as a protective coating for medical devices. Its biocompatibility and bio-stability make it suitable for use in medical applications, where it can protect devices from contamination and ensure their safe and effective use.
Used in Industrial Semiconductor:
2,2,3,3,8,8,9,9-Octafluorotricyclo[8.2.2.24,7]hexadeca-4,6,10,12,13,15-hexaene is used as an insulating coating in the semiconductor industry. Its properties, such as low gas permeability, no out-gassing, and high dielectric strength, make it an ideal choice for protecting and insulating components in semiconductor devices.
Used in 3D IC TSV Electrical Insulation:
2,2,3,3,8,8,9,9-Octafluorotricyclo[8.2.2.24,7]hexadeca-4,6,10,12,13,15-hexaene is used as an electrical insulating coating in 3D integrated circuit (IC) through-silicon via (TSV) applications. Its excellent thermal stability and electrical properties make it suitable for protecting and insulating TSV structures in 3D ICs.
Used in AMOLED De-bonding Layer:
In the manufacturing of active-matrix organic light-emitting diode (AMOLED) displays, 2,2,3,3,8,8,9,9-Octafluorotricyclo[8.2.2.24,7]hexadeca-4,6,10,12,13,15-hexaene is used as a de-bonding layer. Its properties, such as low coefficient of friction and good dry lubricity, make it an ideal choice for facilitating the de-bond

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 
• 1073-67-2 4-vinylbenzyl chloride 
• 369-54-0 p-bis(difluoromethyl)benzene 
• 1592-31-0 1,4-bis(dibromomethyl)benzene 
• 106-42-3 para-xylene 
• 433-19-2 1,4-bis(trifluoromethyl)benzene 
• 865-47-4 potassium tert-butylate 
• 71-43-2 benzene 
• 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 
• 2250-30-8 α,α,α',α'-tetrafluoro-p-xylylene 
• 100-58-3 phenylmagnesium bromide 
• 257863-41-5 4-bromo-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 

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.