10386-84-2

Basic information

• Product Name: 4,4'-DIBROMOOCTAFLUOROBIPHENYL
• Synonyms: 4,4'-Dibromooctafluorobiphenyl,2.0 mg/mL in CH2Cl2;2,2',3,3',5,5',6,6'-Octafluoro-4,4'-dibromobiphenyl;Octafluorobiphenyl-4,4'-diyl dibromide;4,4'-Dibromooctafluorobiphenyl 100mg [10386-84-2];OCTAFLUORO-4,4'-DIBROMOBIPHENYL;4,4'-DIBROMOOCTAFLUOROBIPHENYL;F-PBB;4,4'-dibromo-2,2',3,3',5,5',6,6'-octafluoro-1,1'-biphenyl
• CAS NO: 10386-84-2
• Molecular Formula: C₁₂Br₂F₈
• Molecular Weight: 455.92
• EINECS: 233-847-1
• Product Categories: Method 515EPA;500 Series Drinking Water Methods;8000 Series Solidwaste Methods;BromoEPA;Chemical Class;Halogenated;Method 8150/8151;Biphenyls (for High-Performance Polymer Research);Functional Materials;Reagent for High-Performance Polymer Research;Aryl;C9 to C12;Halogenated Hydrocarbons;600 Series Wastewater Methods;Alpha Sort;BromoVolatiles/ Semivolatiles;D;DAlphabetic;DIA - DICEPA;Method 625
• Mol File: 10386-84-2.mol

Chemical Properties

• Melting Point: 113-115 °C(lit.)
• Boiling Point: 295.4 °C at 760 mmHg
• Flash Point: 132.4 °C
• Appearance: white crystalline powder
• Density: 2.065 g/cm³
• Storage Temp.: room temp
• Solubility: soluble in Toluene
• Stability: Stable. Incompatible with strong oxidizing agents.
• CAS DataBase Reference: 4,4'-DIBROMOOCTAFLUOROBIPHENYL(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-DIBROMOOCTAFLUOROBIPHENYL(10386-84-2)
• EPA Substance Registry System: 4,4'-DIBROMOOCTAFLUOROBIPHENYL(10386-84-2)

Safety Data

• Hazard Codes: Xi,F,T,Xn
• Statements: 36/37/38-67-36-11-63-43-23/24/25-45-40-66
• Safety Statements: 26-36-16-9-36/37-24/25-23-53
• RIDADR: UN 3152 9/PG 2
• WGK Germany: 3
• HazardClass: 9
• PackingGroup: II
• Hazardous Substances Data: 10386-84-2(Hazardous Substances Data)

Usage

Uses

Used in Environmental and Analytical Chemistry:
4,4'-DIBROMOOCTAFLUOROBIPHENYL is used as a reference compound for the detection and quantification of brominated flame retardants and phenolic endocrine disrupters in environmental and biological samples. Its application is crucial in understanding the presence and impact of these harmful substances on human health and the environment.
Used in Finnish Human Adipose Tissue Screening:
In the specific context of Finnish human adipose tissue, 4,4'-DIBROMOOCTAFLUOROBIPHENYL is used as a screening agent to identify and analyze the presence of brominated flame retardants and phenolic endocrine disrupters. This helps in assessing the exposure levels and potential health risks associated with these contaminants in the Finnish population.
Used in Research and Development:
4,4'-DIBROMOOCTAFLUOROBIPHENYL is also utilized in research and development for the creation of new flame retardants with reduced environmental and health impacts. Its properties and behavior can provide valuable insights into the design and synthesis of safer alternatives to existing brominated flame retardants.
Used in Quality Control and Regulatory Compliance:
In the manufacturing and production of materials and products containing flame retardants, 4,4'-DIBROMOOCTAFLUOROBIPHENYL is used as a quality control standard to ensure compliance with regulatory guidelines and safety standards. This helps in maintaining the quality and safety of products in the market, reducing the risk of exposure to harmful substances.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Simple aromatic halogenated organic compounds, such as 4,4'-DIBROMOOCTAFLUOROBIPHENYL, are very unreactive. Reactivity generally decreases with increased degree of substitution of halogen for hydrogen atoms. Materials in this group may be incompatible with strong oxidizing and reducing agents. Also, they may be incompatible with many amines, nitrides, azo/diazo compounds, alkali metals, and epoxides.

Fire Hazard

Flash point data for 4,4'-DIBROMOOCTAFLUOROBIPHENYL are not available, however, 4,4'-DIBROMOOCTAFLUOROBIPHENYL is probably combustible.

Upstream product

• 344-04-7 bromopentafluorobenzene 
• 344-03-6 1,4-dibromotetrafluorobenzene 
• 434-90-2 decafluorobiphenyl 
• 328534-10-7 nonafluoro-1,1′-biphenyl-4-thiol 
• 21386-21-0 octafluoro-1,1′-biphenyl-4,4′-dithiol 
• 1038-65-9 4-bromo-2,2',3,3',4',5,5',6,6'-nonafluoro-1,1'-biphenyl 

Downstream Products

• 3883-86-1 2,2',3,3',5,5',6,6'-octafluoro-1,1'-biphenyl 
• 63107-92-6 2,3,5,6,2',3',5',6',2'',3'',5'',6'',2''',3''',5''',6'''-hexadecafluoro-<1,1';4',1'';4'',1'''>-quaterphenyl 
• 5492-84-2 perfluoro-4-bromo-p-quaterphenyl 
• 90635-26-0 (HC₆F₄C₆F₄)Au(C₄H₈S) 
• 90635-27-1 [(μ-4,4'-C6F4C6F4)(Au(tetrahydrothiophene))2] 
• 1106998-60-0 Au(C₆F₄C₆F₄Br)(CNC₆H₄CO₂H) 
• 90635-35-1 4,4'-bis-(triphenylphoshine)gold(I)-μ-2,3,5,6,2',3',5',6'-octafluoro-1,1'-biphenyl 
• 90635-32-8 [Au(C₆H₄(As(CH₃)2)2)2]⁽¹⁺⁾*[Au(C₆F₄C₆F₄H)2]^(1-)=[Au(C₆H₄(As(CH₃)2)2)2][Au(C₆F₄C₆F₄H)2] 
• 90635-28-2 (Ph₃P)Au(octafluorobiphenyl) 
• 90653-89-7 (HC₆F₄C₆F₄)Au(C₁₂H₈N₂) 
• 90635-34-0 [N(P(C₆H₅)3)2]⁽¹⁺⁾*[(HC₆F₄C₆F₄)AuCl]^(1-)=[N(P(C₆H₅)3)2][(HC₆F₄C₆F₄)AuCl] 
• 90635-29-3 [((HC₆F₄C₆F₄)Au)2(CH₂(P(C₆H₅)2)2)] 
• 967-95-3 1,1′-sulfanediylbis(2,3,5,6-tetrafluorobenzene) 
• 18707-14-7 bis(pentafluorophenyl) sulphone 

Relevant articles and documents

One-pot route to X-perfluoroarenes (X = Br, I) based on FeIII-assisted C-F functionalization and utilization of these arenes as building blocks for crystal engineering involving halogen bonding

Perfluorinated arenes (benzeneF derivatives, diphenylF, naphthaleneF) were converted into X-perfluoroarenes (X = Br, I) via the developed one-pot protocol based on [Fe(acetylacetonate)3]-assisted C-F functionalization. The syntheses proceed under mild conditions and employ readily available perfluorinated arenes, which are treated with EtMgBr followed by addition of X2/[Fe(acetylacetonate)3] (0.8 mol %); yields range from good to moderate. The σ-hole donor properties of the obtained mono- and di-X-perfluoroarenes and the significance of these species for halogen-bonding-based crystal engineering was illustrated in a series of postsynthetic experiments, all supported by density functional theory (DFT) energy calculations, molecular electrostatic potential (MEP) surface analysis, and the quantum theory of atoms in molecules (QTAIM). These include (i) a solid-state X-ray diffraction study of X-perfluoroarene self-association (dimerization) via iodine σ-hole - electron belt interactions (three X-ray structures) and (ii) verification of X-perfluoroarene σ-hole donor abilities by their interactions with iodides acting as external σ-hole acceptors (five X-ray structures); a Hirshfeld surface analysis was performed for all eight structures.

Synthesis of Bromochloropolyfluorobiphenyls Containing Bromine and Chlorine Atoms in the 4 and 4,4′ Positions

Abstract: A new method for the synthesis of 4-chlorononafluoro- and 4-bromononafluorobiphenyl by the reactions of nonafluorobiphenyl-4-thiol with Cl2, PCl5, and Br2, as well as of 4,4′-dichlorooctafluorobiphenyl from octafluorobiphenyl-4,4′-dithiol, 4′-chlorooctafluorobiphenyl-4-thiol, Cl2, and PCl5 was developed. 4-Bromo-4′-chlorooctafluorobiphenyl was synthesized for the first time from 4′-chlorooctafluorobiphenyl-4-thiol and Br2. 4,4′-Dichlorooctafluorobiphenyl was obtained as the main product in the reaction of 4′-bromooctafluorobiphenyl-4-thiol with PCl5. [Figure not available: see fulltext.].

Synthesis method of 2, 2', 3, 3', 5, 5', 6, 6'-octafluoro-4, 4'-dibromobiphenyl

The invention discloses a synthesis method of 2, 2', 3, 3', 5, 5', 6, 6'-octafluoro-4, 4'-dibromobiphenyl, and belongs to the technical field of chemical synthesis. The method comprises the followingsteps: reacting 2, 3, 5, 6-tetrafluoro-1, 4-dibromobenzene with magnesium metal in an inert solvent to obtain 2, 3, 5, 6-tetrafluoro-4-bromophenyl magnesium bromide, and then carrying out self-coupling reaction in the inert solvent under the action of a copper catalyst to obtain 2, 2', 3, 3', 5, 5', 6, 6'-octafluoro-4, 4'-dibromobiphenyl. The method has the advantages of cheap and easily availableraw materials, short reaction steps, high synthesis yield, good product quality and the like, and is suitable for industrial production and application.