5576-19-2

Usage

Uses

Used in Flame Retardant Applications:
1,1'-Biphenyl, 2,2'-dibromo-3,3',4,4',5,5',6,6'-octafluorois used as a flame retardant in various industrial applications, such as in the production of polymers and plastics. Its high thermal stability and resistance to degradation make it an effective additive for improving the fire resistance of materials.
Used in Polymer and Plastics Industry:
1,1'-Biphenyl, 2,2'-dibromo-3,3',4,4',5,5',6,6'-octafluorois used as a flame retardant in the polymer and plastics industry to enhance the fire resistance of these materials.
However, due to its halogenated nature, 1,1'-Biphenyl, 2,2'-dibromo-3,3',4,4',5,5',6,6'-octafluorois also considered to be a persistent organic pollutant and is subject to strict regulations and restrictions in its usage and disposal to minimize its environmental impact.

Upstream product

• 344-04-7 bromopentafluorobenzene 
• 827-08-7 1,2-dibromo-3,4,5,6-tetrafluorobenzene 
• 5121-90-4 2,2',3,3',4,4',5,5'-octafluorobiphenyl 
• 62983-79-3 octafluorobiphenylenemercury 

Downstream Products

• 324766-65-6 perfluorophenyl-9-bora-perfluorofluorene 
• 10380-43-5 diphenyl-(octafluoro biphenyl-(2,2')) germane 
• 1091603-70-1 9,10-bis(4-methoxyphenyl)-1,2,3,4,5,6,7,8-octafluorophenanthrene 
• 1091603-69-8 1,2,3,4,5,6,7,8-octafluoro-9,10-diphenylphenanthrene 
• 7136-57-4 octafluorodibenzothiophene 
• 36284-12-5 9-phenyloctafluorophosphafluorene 
• 1095101-37-3 2,2'-dibromo-4,4'-bis(phenylethynyl)-3,3',5,5',6,6'-hexafluorobiphenyl 

Relevant academic research and scientific papers

2,7-substituted hexafluoroheterofluorenes as potential building blocks for electron transporting materials

A series of 2,7-substituted hexafluoro-9-heterofluorenes was synthesized via nucleophilic aromatic substitution (SNArN) reactions of phenyllithium, thienyllithium, and lithium phenylacetylide with various octafluoroheterofluorenes and 2,2'-dibromooctafluorobiphenyl. These compounds are of interest as possible building blocks for materials with useful electron transport properties, since they possess relatively low LUMO energy levels. The HOMO-LUMO energy gaps, as determined by UV-vis spectroscopy, range between 3.0 and 3.9 eV, while photoluminescence emission spectra reveal λ ems values in the range of 365 to 420 nm (corresponding to ultraviolet to violet/blue emission). Dilute solution state quantum yields vary significantly with the nature of the heteroatom and the 2,7-substituents, and approach unity for a number of the di(phenylethynyl) derivatives. The experimentally determined LUMO energy levels (- 2.7 to - 3.3 eV as determined by differential pulse voltammetry) suggest that these compounds may be good candidates for electron transport applications. Single-crystal X-ray analyses of a number of compounds revealed cofacial packing in all cases, with intermolecular distances as short as 3.4 A.

Compounds having an ionic structure used as constituent of an olefin polymerization catalyst

Novel chemical compounds have an ionic structure and in combination with an organometallic transition metal compound form a catalyst system which is advantageously used for the polymerization of olefins.

SOME REACTIONS OF PHENYLENE- AND POLYPHENYLENE-MERCURIALS

Cleavage reactions of six phenylene- and polyphenylene-mercury heterocycles with the mercuric halides and mercuric acetate in suitable refluxing solvents readily produce 1,2-C6X4(HgX)2; 2,2'-C6H4C6H4(HgX)2 and 2,2''-C6H4C6H4C6H4(HgX)2 (X = Cl, Br, I or CH3CO2).Addition of silver acetate to 2,2'-C6H4C6H4(HgBr)2 gives 2,2'-C6H4C6H4(HgO2CCH3)2 which reacts with concentrated hydrochloric acid to form 2,2'-C6H4C6H4(HgCl)2.Treatment with sodium iodide, or in some cases simply the application of heat under vacuum, causes symmetrization of these cleavage products back to the original heterocycles in high yield.The terphenylenemercury dimer, (C6H4C6H4C6H4Hg)2, forms solvates with a wide variety of donor and non-donor solvents.Pyrolysis of mercuric 2,3,4,5-tetrafluorobenzoate at 190 deg.C. yields 2-mercurio-3,4,5,6-tetrafluorobenzoate and 2,3,4,5-tetrafluorobenzoic acid; at 300 deg.C. the former gives tetrafluorophenylenemercury, (C6F4Hg)3.

Fluorocarbanion Chemistry. Octafluorofluorene and Companions

Octafluoro-9-fluorenone (2) is obtained by reaction of 2-bromoctafluorobiphenyl-2'-carboxylic acid (4) with n-butyllithium.The reaction illustrates an unusual intramolecular nucleophilic arylation involving attack at a carboxylate salt.Catalytic reduction gives octafluoro-9-fluorenol, rather than octafluorofluorene (1). 1 is synthesized by a six-step procedure from 2-bromnonafluorobiphenyl (7).The key step involves an intramolecular nucleophilic alkylation to form ethyl octafluorofluorene-9-carboxylate (12), which rapidly undergoes decarboxylative hydrolysisin both alkaline and acidic media to form 1.Relative to the 9-fluorenyl system and open-chain polyfluorinated analogues, 1 and 12 exhibit anomalous reaction chemistry, owing to the exceptional stabilities of their anions.