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

Base Information

• Chemical Name: 2,2,3,3,8,8,9,9-Octafluorotricyclo[8.2.2.24,7]hexadeca-4,6,10,12,13,15-hexaene
• CAS No.: 3345-29-7
• Molecular Formula: C16H8F8
• Molecular Weight: 352.227
• Mol file: 3345-29-7.mol

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;

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

Chemical Property:

• Vapor Pressure: 0.0211mmHg at 25°C
• Melting Point: 240-250°C
• Refractive Index: 1.489
• Boiling Point: 259.3 °C at 760 mmHg
• Flash Point: 96 °C
• PSA: 0.00000
• Density: 1.47 g/cm³
• LogP: 5.76760

Purity/Quality:

99.0% ^*data from raw suppliers

1,1,2,2,9,9,10,10-Octafluoro[2.2]paracyclophane 99.0% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• 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

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

There total 32 articles about 2,2,3,3,8,8,9,9-Octafluorotricyclo[8.2.2.24,7]hexadeca-4,6,10,12,13,15-hexaene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

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)

Guidance literature:

With phenylmagnesium bromide; palladium dichloride; In tetrahydrofuran; for 1h; Inert atmosphere; Reflux;

DOI:10.1016/j.jfluchem.2015.02.016

Reference yield: 96.0%

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)

Guidance literature:

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

DOI:10.1021/jo0157775

Reference yield: 94.0%

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)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; zinc; In N,N-dimethyl-formamide; at 80 ℃; for 8h;

DOI:10.1021/jo0157775

upstream raw materials:

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

1,4-bis-(difluorochloromethyl)-benzene

α,α,α',α'-tetrafluoro-p-xylylene

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

Downstream raw materials:

α,α,α',α'-tetrafluoro-p-xylylene

Refernces

• 1、 Roche, Alex J.. "Palladium catalyzed cross- and homo-coupling reactions of 4-Halo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophanes with various organometallic reagents". . p. 1 - 5. Retrieved 2015.
• 2、 Roche,Duan,Dolbier Jr.,Abboud. "The first synthesis and characterization of both diastereomers of a di[2.2]paracyclophane: 4,4′-Bis(1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane)". . p. 7055 - 7058. Retrieved 2001.
• 3、 -. "Preparation method of parylene". . . Retrieved 2021/04/03.
• 4、 Dolbier Jr., William R.,Zhai, Yi-An,Wheelus, Will,Battiste, Merle A.,Ghiviriga, Ion,Bartberger, Michael D.. "Remarkable efficiency of the aryne chemistry of (dehydro)octafluoro[2.2] paracyclophane when using the cadogan method". . p. 550 - 558. Retrieved 2008/02/01.