CAS No.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 Suppliers

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Basic Information

Molecular Structure:
CAS No.:	3345-29-7
Name:	2,2,3,3,8,8,9,9-Octafluorotricyclo[8.2.2.24,7]hexadeca-4,6,10,12,13,15-hexaene
Article Data:	15

Formula:	C₁₆H₈F₈
Molecular Weight:	352.227
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;
Density:	1.47 g/cm³
Melting Point:	240-250°C
Boiling Point:	259.3 °C at 760 mmHg
Flash Point:	96 °C
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%

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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