1,1,2,2,9,9,10,10-Octafluoro[2.2]paracyclophane supplier

Name
2,2,3,3,8,8,9,9-Octafluorotricyclo[8.2.2.24,7]hexadeca-4,6,10,12,13,15-hexaene
EINECS
CAS No. 3345-29-7
Article Data15
CAS DataBase
Density 1.47 g/cm³
Solubility
Melting Point 240-250°C
Formula C₁₆H₈F₈
Boiling Point 259.3 °C at 760 mmHg
Molecular Weight 352.227
Flash Point 96 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 1,1,2,2,9,9,10,10-Octafluoro-p-cyclophane;1,1,2,2,9,9,10,10-Octafluoro[2.2]paracyclophane;Parylene AF 4 dimer;a-Perfluorodi-p-xylene;2,2,3,3,8,8,9,9-Octafluorotricyclo[8.2.2.24,7]hexadeca-4,6,10,12,13,15-hexaene;
PSA 0.00000
LogP 5.76760

Synthetic route

: 257863-40-4
4-iodo-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

Conditions

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

: 257863-41-5
4-bromo-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

Conditions

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

: 257863-42-6
4-chloro-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

A: 3345-29-7
1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

B: 4,4'-bis(1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane)

Conditions

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%

: 680-15-9
2,2-difluoro-2-(fluorosulfonyl)acetate

: 257863-40-4
4-iodo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

A: 3345-29-7
1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

B: 4-trifluoromethyl-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

Conditions

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

...Expand

: 100-58-3
phenylmagnesium bromide

: 257863-40-4
4-iodo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

A: 3345-29-7
1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

B: 4-phenyl-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

Conditions

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

...Expand

: 257863-40-4
4-iodo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

A: 3345-29-7
1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

B: 4,4'-bis(1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane)

Conditions

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

: 257863-40-4
4-iodo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

A: 3345-29-7
1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

B: 4-phenyl-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

Conditions

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

...Expand

: 257863-37-9
4-amino-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

A: 3345-29-7
1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

B: 257863-41-5
4-bromo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

Conditions

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

: 257863-40-4
4-iodo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

A: 3345-29-7
1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

B: 4-methyl-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

Conditions

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.

...Expand

: 2629-68-7
1,4-bis-(difluorochloromethyl)-benzene

A: 3345-29-7
1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

B: (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

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

: 257863-37-9
4-amino-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

A: 3345-29-7
1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

B: 257863-42-6
4-chloro-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

Conditions

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%

: 149194-32-1
α-trimethylsilyl-α,α,α',α'-pentafluoroxylene

: 3345-29-7
1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

Conditions

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

: 100-58-3
phenylmagnesium bromide

: 257863-41-5
4-bromo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

A: 3345-29-7
1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

B: 4-phenyl-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

Conditions

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

...Expand

: C16H7F8I

: 865-47-4
potassium tert-butylate

: 71-43-2
benzene

: C20H16F8O

B: 3345-29-7
1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

C: 498556-71-1
C22H12F8

Conditions

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

...Expand

: 2629-68-7
1,4-bis-(difluorochloromethyl)-benzene

: 3345-29-7
1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

Conditions

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%

: 100-58-3
phenylmagnesium bromide

: 257863-40-4
4-iodo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

A: 3345-29-7
1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

B: 4-phenyl-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

C: 4,4'-bis(1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane)

Conditions

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%

...Expand

: 651-12-7
α,α'-dibromo-α,α,α',α'-tetrafluoro-p-xylene

: 3345-29-7
1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

Conditions

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

: 651-12-7
α,α'-dibromo-α,α,α',α'-tetrafluoro-p-xylene

A: 3345-29-7
1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

B: dodecafluoro[2,2]paracyclophane

Conditions

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%

: 2629-68-7
1,4-bis-(difluorochloromethyl)-benzene

: 651-12-7
α,α'-dibromo-α,α,α',α'-tetrafluoro-p-xylene

: 3345-29-7
1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

Conditions

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

: 2629-68-7
1,4-bis-(difluorochloromethyl)-benzene

A: 3345-29-7
1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

B: dodecafluoro[2,2]paracyclophane

Conditions

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

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

: 3345-29-7
1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

Conditions

Conditions	Yield
In toluene at 110℃; Yield given;

: 433-19-2
1,4-bis(trifluoromethyl)benzene

: 3345-29-7
1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

Conditions

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

: 257863-35-7
4-nitro-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

Conditions

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

: 257863-37-9
4-amino-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

Conditions

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

: 257863-36-8
4-hydroxylamino-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

Conditions

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

: 106-42-3
para-xylene

3-methyl-phthalic acid-dichloride: 3-methyl-phthalic acid-dichloride

: 3345-29-7
1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

Conditions

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

: 1592-31-0
1,4-bis(dibromomethyl)benzene

: 3345-29-7
1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

Conditions

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

: 369-54-0
p-bis(difluoromethyl)benzene

: 3345-29-7
1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

Conditions

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

: 623-27-8
terephthalaldehyde,

: 3345-29-7
1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

Conditions

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

: 3345-29-7
1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

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

Conditions

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

: 3345-29-7
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

Conditions

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

: 3345-29-7
1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

A: 1173111-79-9
1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane-4,7-dione

B: 1173111-81-3
C16H6F8O3

Conditions

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

: 3345-29-7
1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

A: 257863-41-5
4-bromo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

B: 299975-30-7
p-dibromo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

Conditions

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

: 3345-29-7
1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

: 299975-30-7
p-dibromo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

Conditions

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

: 3345-29-7
1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

A: 257863-35-7
4-nitro-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

B: 300700-86-1, 300766-00-1
pseudo-o-dinitro-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

C: pseudo-m-dinitro-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

Conditions

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%

...Expand

: 3345-29-7
1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

A: 300700-86-1, 300766-00-1
pseudo-o-dinitro-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

B: pseudo-m-dinitro-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

Conditions

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%

: 75-77-4
chloro-trimethyl-silane

: 3345-29-7
1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

: 2,9,9,10,10-pentafluoro-1-trimethylsilyl[2.2]paracyclophan-1-ene

Conditions

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

: 3345-29-7
1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

: 1,1,2,2,9,9,10,10-octafluoro<2.2>paracyclophane radical anion

Conditions

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

1,1,2,2,9,9,10,10-Octafluoro[2.2]paracyclophane Specification

The systematic name of 1,1,2,2,9,9,10,10-Octafluoro[2.2]paracyclophane is 2,2,3,3,8,8,9,9-octafluorotricyclo[8.2.2.24,7]hexadeca-1(12),4,6,10,13,15-hexaene. With the CAS registry number 3345-29-7, it is also named as Tricyclo(8.2.2.24,7)hexadeca-4,6,10,12,13,15-hexaene, 2,2,3,3,8,8,9,9,-octafluoro-. In addition, its molecular formula is C₁₆H₈F₈ and molecular weight is 352.22.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 3.53; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.53; (4)ACD/LogD (pH 7.4): 3.53; (5)ACD/BCF (pH 5.5): 281.6; (6)ACD/BCF (pH 7.4): 281.6; (7)ACD/KOC (pH 5.5): 1972.65; (8)ACD/KOC (pH 7.4): 1972.65; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 0 Å²; (13)Index of Refraction: 1.489; (14)Molar Refractivity: 68.91 cm³; (15)Molar Volume: 238.3 cm³; (16)Polarizability: 27.31×10^-24cm³; (17)Surface Tension: 31.1 dyne/cm; (18)Density: 1.47 g/cm³; (19)Flash Point: 96 °C; (20)Enthalpy of Vaporization: 47.69 kJ/mol; (21)Boiling Point: 259.3 °C at 760 mmHg; (22)Vapour Pressure: 0.0211 mmHg at 25 °C.

Preparation of 1,1,2,2,9,9,10,10-Octafluoro[2.2]paracyclophane: this chemical can be prepared by Difluoro-fluorosulfonyl-acetic acid methyl ester and 2,2,3,3,8,8,9,9-Octafluoro-5-iodo-tricyclo[8.2.2.24,7]hexadeca-1(13),4(16),5,7(15),10(14),11-hexaene.

This reaction needs Copper(I) bromide, Palladium dichloride and Dimethylformamide at temperature of 80 °C. The yield is 84 %.

Uses of 1,1,2,2,9,9,10,10-Octafluoro[2.2]paracyclophane: it can be used to produce 3,6-Bis(difluoromethylene)cyclohexa-1,4-diene.

This reaction will occur at temperature of 450 - 600 °C. The yield is 100 %.

People can use the following data to convert to the molecule structure.
(1)SMILES: FC3(F)c1ccc(cc1)C(F)(F)C(F)(F)c2ccc(cc2)C3(F)F
(2)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
(3)InChIKey: KCKIWSAAWFKXMA-UHFFFAOYAB
(4)Std. InChI: InChI=1S/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
(5)Std. InChIKey: KCKIWSAAWFKXMA-UHFFFAOYSA-N

Product Name

2,2,3,3,8,8,9,9-Octafluorotricyclo[8.2.2.24,7]hexadeca-4,6,10,12,13,15-hexaene

Synthetic route

1,1,2,2,9,9,10,10-Octafluoro[2.2]paracyclophane Specification

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