16400-50-3

Basic information

• Product Name: 3,3',5,5'-TETRABROMOBIPHENYL
• Synonyms: PBB NO 80;3,3',5,5'-TETRABROMOBIPHENYL;1,3-Dibromo-5-phenylbenzene;pbb 80;3,3',5,5'-Tetrabromo-1,1'-biphenyl;3,5,3',5'-TetrabroMo-biphenyl;3,3',5,5'-Tetrabromobiphenyl, 35μg /mL in Isooctane;-Tetrabromo-1,1′
• CAS NO: 16400-50-3
• Molecular Formula: C₁₂H₆Br₄
• Molecular Weight: 469.79
• Product Categories: Aryl;Building Blocks;C9 to C12;Chemical Synthesis;Halogenated Hydrocarbons;Liquid Crystals;Materials Science;Organic and Printed Electronics;Organic Building Blocks
• Mol File: 16400-50-3.mol
• Article Data: 14

Chemical Properties

• Melting Point: 185-190℃
• Boiling Point: 401.8 °C at 760 mmHg
• Flash Point: 190.7 °C
• Appearance: /
• Density: 2.14 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Dichloromethane (Slightly)
• CAS DataBase Reference: 3,3',5,5'-TETRABROMOBIPHENYL(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3',5,5'-TETRABROMOBIPHENYL(16400-50-3)
• EPA Substance Registry System: 3,3',5,5'-TETRABROMOBIPHENYL(16400-50-3)

Safety Data

• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-39
• WGK Germany: 3
• Hazardous Substances Data: 16400-50-3(Hazardous Substances Data)

Usage

Description

3,3',5,5'-TETRABROMOBIPHENYL, also known as PBB 80, is a brominated biphenyl compound related to PBB 37 (P215150). It is characterized by its chemical structure, which includes four bromine atoms attached to the biphenyl molecule. 3,3',5,5'-TETRABROMOBIPHENYL has various applications in different industries due to its unique properties.

Uses

Used in Flame Retardancy:
3,3',5,5'-TETRABROMOBIPHENYL is used as a flame retardant for enhancing the fire resistance of various consumer products. It is commonly incorporated into appliances, electronics, and plastics to reduce the risk of fire and improve safety.
Used in Organic Synthesis:
3,3',5,5'-TETRABROMOBIPHENYL serves as an organic synthesis intermediate, playing a crucial role in the development of new chemical compounds. Its unique structure allows for further chemical reactions and modifications, leading to the creation of a wide range of products.
Used in Pharmaceutical Industry:
As a pharmaceutical intermediate, 3,3',5,5'-TETRABROMOBIPHENYL is utilized in the research and development of new drugs. Its properties make it a valuable component in the synthesis of various pharmaceutical compounds, contributing to the advancement of medical treatments.
Used in Laboratory Research and Development:
3,3',5,5'-TETRABROMOBIPHENYL is also employed in laboratory research and development processes. Its unique chemical structure and properties make it an essential tool for scientists and researchers working on various projects, including the development of new materials, chemicals, and pharmaceuticals.
Used in Chemical Production Processes:
In the chemical production industry, 3,3',5,5'-TETRABROMOBIPHENYL is used as an intermediate in the manufacturing of various chemicals. Its versatility and unique properties make it a valuable component in the production of a wide range of chemical products.

Preparation

1,3,5-tribromobenzene (6.3 g, 20 mmol) was dissolved in diethylether (50 ml). The reaction solution was cooled to -78° C., and n-butyllithium (8.8 ml, 22 mmol, 2.5M in hexane) was gradually added thereto. The reaction mixture was stirred at -78° C. for one hour, and copper chloride (II) (2.96 g, 22 mmol) was added thereto at -78° C. The reaction solution was stirred for five hours and washed with distilled water and ethylacetate at room temperature. The obtained ethylacetate layer was dried over MgSO4, and then dried under a reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography to give intermediate A as a white solid (3.74 g, yield: 80%).

Upstream product

• 62477-23-0 4,4′-diaminobiphenyl-3,3′,5,5′-tetrabromide 
• 626-39-1 1,3,5-trisbromobenzene 
• 619-44-3 methyl 4-iodobenzoate 
• 408492-26-2 2-(3,5-dibromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 117695-55-3 3,5-dibromophenylboronic acid 
• 1041479-71-3 C₂₄H₅₁In 
• 1205517-08-3 (3,5-dibromophenyl)zinc(II) chloride 
• 1041479-72-4 C₂₄H₅₁In 
• 17878-23-8 3,5-dibromo-1-trimethylsilylbenzene 
• 108-36-1 1,3-dibromobenzene 

Downstream Products

• 586960-01-2 5,5''-bis(3-nitrophenyl)-1,1':3',1'':3'',1'''-quaterphenyl 
• 586960-06-7 tetraethyl 3,3',3'',3'''-(1,1'-biphenyl-3,3',5,5'-tetrayl)tetrakis(benzenecarboxylate) 
• 1185909-06-1 3,5,3',5'-tetrakis(pyridylethynyl)biphenyl 
• 2411406-15-8 3,3',5,5'-tetra(p-aminophenyl)-biphenyl 
• 2266619-47-8 C₃₂H₂₂N₄ 
• 150239-90-0 3,3',5,5'-tetra-(pyrid-2-yl)biphenyl 

Relevant articles and documents

Sterically controlled C-H/C-H homocoupling of arenes: Via C-H borylation

A mild one-pot protocol for the synthesis of symmetrical biaryls by sequential Ir-catalyzed C-H borylation and Cu-catalyzed homocoupling of arenes is described. The regiochemistry of the biaryl formed is sterically controlled as dictated by the C-H borylation step. The methodology is also successfully extended to heteroarenes. Some of the products obtained by this approach are impossible to obtain via the Ullmann or the Suzuki coupling protocols. Finally, we have shown a one-pot sequence describing C-H borylation/Cu-catalyzed homocoupling/Pd-catalyzed Suzuki coupling to obtain π-extended arene frameworks.

Robust Multifunctional Yttrium-Based Metal-Organic Frameworks with Breathing Effect

Phosphonate- and yttrium-based metal-organic frameworks (MOFs), formulated as [Y(H5btp)]·5.5H2O (1), [Y(H5btp)]·2.5H2O (2), (H3O)[Y2(H5btp)(H4btp)]·H2O (3), and [Y(H5btp)]·H2O·0.5(MeOH) (4), were prepared using a “green” microwave-assisted synthesis methodology which promoted the self-assembly of the tetraphosphonic organic linker [1,1′-biphenyl]-3,3′,5,5′-tetrayltetrakis(phosphonic acid) (H8btp) with Y3+ cations. This new family of functional materials, isolated in bulk quantities, exhibits a remarkable breathing effect. Structural flexibility was thoroughly studied by means of X-ray crystallography, thermogravimetry, variable-temperature X-ray diffraction, and dehydration and rehydration processes, ultimately evidencing a remarkable reversible single-crystal to single-crystal (SC-SC) transformation solely through the loss and gain of crystallization solvent molecules. Topologically, frameworks remained unaltered throughout this interconversion mechanism, with all compounds being binodal 6,6-connected network with a Scha?fli symbol of {413.62}{48.66.8}. Results show that this is one of the most stable and thermally robust families of tetraphosphonate-based MOFs synthesized reported to date. Porous materials 2 and 3 were further studied to ascertain their performance as heterogeneous catalysts and proton conductors, respectively, with outstanding results being registered for both materials. Compound 2 showed a 94% conversion of benzaldehyde into (dimethoxymethyl)benzene after just 1 h of reaction, among the best results registered to date for MOF materials. On the other hand, the protonic conductivity of compound 3 at 98% of relative humidity (2.58 × 10-2 S cm-1) was among the highest registered among MOFs, with the great advantage of the material to be prepared using a simpler and sustainable synthesis methodology, as well as exhibiting a good stability at ambient conditions (temperature and humidity) over time when compared to others.

Tetraarylbiphenyl as a new lattice inclusion host by structure reductionism: Shape and size complementarity based on torsional flexibility

3,3′,5,5′-Tetrakis(2,6-dimethyl-4-methoxyphenyl)biphenyl (TB) was designed as a lattice inclusion host based on a structure reductionistic approach. TB binds guests in two different domains based on the premise that the two phenyl rings of the biphenyl co