1-Bromo-4-(Tridecafluorohexyl)benzene

Base Information

• Chemical Name: 1-Bromo-4-(Tridecafluorohexyl)benzene
• CAS No.: 149068-56-4
• Molecular Formula: C12H4 Br F13
• Molecular Weight: 475.047
• Hs Code.: 2903998090
• DSSTox Substance ID: DTXSID70438417
• Nikkaji Number: J595.119D
• Wikidata: Q82254160
• Mol file: 149068-56-4.mol

Synonyms:149068-56-4;1-Bromo-4-(Tridecafluorohexyl)benzene;1-Bromo-4-(perfluorohexyl)benzene;4-(PERFLUOROHEXYL) BROMOBENZENE;1-bromo-4-(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl)benzene;Benzene, 1-bromo-4-(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl)-;4-(Perfluorohexyl)bromobenzene;SCHEMBL7138748;DTXSID70438417;GKOWYWPSKDBJAF-UHFFFAOYSA-N;MFCD03788327;AS-80393;CS-0161709;D81568

Chemical Property of 1-Bromo-4-(Tridecafluorohexyl)benzene

Chemical Property:

• Boiling Point: 89-92 °C(Press: 7.5 Torr)
• PSA: 0.00000
• Density: 1.718±0.06 g/cm3(Predicted)
• LogP: 6.64440
• Storage Temp.: 2-8°C
• XLogP3: 6.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 5
• Exact Mass: 473.92888
• Heavy Atom Count: 26
• Complexity: 502

Purity/Quality:

99%min ^*data from raw suppliers

4-(PERFLUOROHEXYL) BROMOBENZENE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)Br

Technology Process of 1-Bromo-4-(Tridecafluorohexyl)benzene

There total 5 articles about 1-Bromo-4-(Tridecafluorohexyl)benzene 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: 89.0%

n-perfluorohexyl iodide (355-43-1) + 1,4-bromoiodobenzene (589-87-7) → 4-(tridecafluoro-n-hexyl)bromobenzene (149068-56-4)

Guidance literature:

With [2,2]bipyridinyl; copper; In dimethyl sulfoxide; at 70 ℃; for 72h;

DOI:10.1039/a704872f

Reference yield:

bromobenzene (108-86-1,52753-63-6) + 1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexane-1-sulfonyl chloride (55591-23-6) → o-bromo(tridecafluorohexyl)benzene (157829-76-0) + m-bromo(tridecafluorohexyl)benzene (157829-77-1) + 4-(tridecafluoro-n-hexyl)bromobenzene (149068-56-4)

Guidance literature:

With dichlorotris(triphenylphosphine)ruthenium(II); In pentane; at 120 ℃; for 24h; Yield given. Yields of byproduct given;

Reference yield:

n-perfluorohexyl iodide (355-43-1) → 4-(tridecafluoro-n-hexyl)bromobenzene (149068-56-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / Cu / dimethylsulfoxide / 2 h / 120 °C

2: 1.) NaNO₂, HBr, 2.) CuBr

With hydrogen bromide; copper; copper(I) bromide; sodium nitrite; In dimethyl sulfoxide;

DOI:10.1002/anie.199726231

upstream raw materials:

bromobenzene

1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexane-1-sulfonyl chloride

4-(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl)phenylamine

n-perfluorohexyl iodide

Downstream raw materials:

(4-perfluorohexylphenyl)diphenylphosphine

bis(4-tridecafluoro-n-hexylphenyl)chlorophosphine

2-(4-perfluorohexylphenyl)-2-methyl-1,3-dioxolane

diethyl 4-tridecafluorohexylphenyl-phosphonate

Refernces

• 1、 Bhattacharyya, Pravat,Croxtall, Ben,Fawcett, Joanne,Fawcett, John,Gudmunsen, David,Hope, Eric G.,Kemmitt, Ray D.W.,Paige, Danny R.,Russell, David R.,Stuart, Alison M.,Wood, Dan R.W.. "Phosphorus(III) ligands in fluorous biphase catalysis". . p. 247 - 255. Retrieved 2007/10/03.
• 2、 Bhattacharyya, Pravat,Gudmunsen, David,Hope, Eric G.,Kemmitt, Ray D. W.,Paige, Danny R.,Stuart, Alison M.. "Phosphorus(III) ligands with fluorous ponytails". . p. 3609 - 3612. Retrieved 2007/10/03.