Product Name

  • 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 Molecular Structure of 3345-29-7 (2,2,3,3,8,8,9,9-Octafluorotricyclo[8.2.2.24,7]hexadeca-4,6,10,12,13,15-hexaene)
  • 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

4-iodo-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

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
ConditionsYield
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

4-bromo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

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
ConditionsYield
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

4-chloro-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

A

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

B

4,4'-bis(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
ConditionsYield
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

2,2-difluoro-2-(fluorosulfonyl)acetate

4-iodo-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

A

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

B

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

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

Conditions
ConditionsYield
With copper(I) bromide; palladium dichloride In N,N-dimethyl-formamide at 80℃; Reduction; trifluoromethylation;A 3%
B 84%
phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

4-iodo-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

A

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

B

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

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

Conditions
ConditionsYield
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

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

A

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

B

4,4'-bis(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
ConditionsYield
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

phenylmagnesium bromide

4-iodo-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

A

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

B

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

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

Conditions
ConditionsYield
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

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

A

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

B

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

4-bromo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

Conditions
ConditionsYield
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

methyllithium lithium bromide

4-iodo-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

A

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

B

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

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

Conditions
ConditionsYield
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

1,4-bis-(difluorochloromethyl)-benzene

A

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

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

(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
ConditionsYield
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

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

A

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

B

4-chloro-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

Conditions
ConditionsYield
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

α-trimethylsilyl-α,α,α',α'-pentafluoroxylene

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
ConditionsYield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 4-tert-Butylcatechol; cesium fluoride In methoxybenzene at 160℃; for 24h;53%
phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

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

4-bromo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

A

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

B

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

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

Conditions
ConditionsYield
With palladium dichloride In tetrahydrofuran for 2h; Kumada Cross-Coupling; Inert atmosphere; Reflux;A 50%
B 19%
C16H7F8I

C16H7F8I

potassium tert-butylate
865-47-4

potassium tert-butylate

benzene
71-43-2

benzene

C20H16F8O

C20H16F8O

B

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

C

C22H12F8
498556-71-1

C22H12F8

Conditions
ConditionsYield
In dibutyl ether at 110℃; for 5h;A 35%
B 45.8%
C 3.5%
1,4-bis-(difluorochloromethyl)-benzene
2629-68-7

1,4-bis-(difluorochloromethyl)-benzene

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
ConditionsYield
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

phenylmagnesium bromide

4-iodo-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

A

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

B

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

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)

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

Conditions
ConditionsYield
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

α,α'-dibromo-α,α,α',α'-tetrafluoro-p-xylene

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
ConditionsYield
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

α,α'-dibromo-α,α,α',α'-tetrafluoro-p-xylene

A

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

B

dodecafluoro[2,2]paracyclophane

dodecafluoro[2,2]paracyclophane

Conditions
ConditionsYield
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

1,4-bis-(difluorochloromethyl)-benzene

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

α,α'-dibromo-α,α,α',α'-tetrafluoro-p-xylene

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
ConditionsYield
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

1,4-bis-(difluorochloromethyl)-benzene

A

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

B

dodecafluoro[2,2]paracyclophane

dodecafluoro[2,2]paracyclophane

Conditions
ConditionsYield
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

α,α,α',α'-tetrafluoro-p-xylylene

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
ConditionsYield
In toluene at 110℃; Yield given;
1,4-bis(trifluoromethyl)benzene
433-19-2

1,4-bis(trifluoromethyl)benzene

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
ConditionsYield
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

4-nitro-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

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
ConditionsYield
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

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

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
ConditionsYield
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

4-hydroxylamino-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

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
ConditionsYield
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

para-xylene

3-methyl-phthalic acid-dichloride

3-methyl-phthalic acid-dichloride

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
ConditionsYield
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

1,4-bis(dibromomethyl)benzene

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
ConditionsYield
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

p-bis(difluoromethyl)benzene

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
ConditionsYield
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

terephthalaldehyde,

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
ConditionsYield
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

1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

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

α,α,α',α'-tetrafluoro-p-xylylene

Conditions
ConditionsYield
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

1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

4-nitro-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
ConditionsYield
With nitric acid90%
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

A

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

1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane-4,7-dione

B

C16H6F8O3
1173111-81-3

C16H6F8O3

Conditions
ConditionsYield
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

1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

A

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

4-bromo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

B

p-dibromo-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
ConditionsYield
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

1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

p-dibromo-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
ConditionsYield
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

1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

A

4-nitro-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

B

pseudo-o-dinitro-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane
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

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

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

A

pseudo-o-dinitro-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane
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

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

Conditions
ConditionsYield
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

chloro-trimethyl-silane

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

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

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

Conditions
ConditionsYield
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

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

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

Conditions
ConditionsYield
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

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