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% ^*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:

• General 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 octafluoro[2.2]paracyclophane (AF4), is a fluorinated cyclophane derivative synthesized via a novel, non-high-dilution method involving the reaction of Zn with p-bis(chlorodifluoromethyl)benzene in DMA. 2,2,3,3,8,8,9,9-Octafluorotricyclo[8.2.2.24,7]hexadeca-4,6,10,12,13,15-hexaene serves as a key intermediate in palladium-catalyzed cross-coupling reactions with Grignard reagents and has been utilized in the synthesis of diastereomeric diparacyclophane systems. Its scalable and cost-effective preparation makes it valuable for both research and industrial applications.

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