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

Uses

Different sources of media describe the Uses of 16400-50-3 differently. You can refer to the following data:
1. PBB 80 is a related compound of PBB 37 (P215150), a brominated biphenyls that can be used as a flame retardant and often incorporated into consumer products including appliances, electronics and plastics.
2. 3,3',5,5'-TETRABROMOBIPHENYL can be used as organic synthesis intermediates and pharmaceutical intermediates, mainly used in laboratory research and development processes and chemical production processes.

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

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

Downstream Products

• 2266619-47-8 C₃₂H₂₂N₄ 
• 150239-90-0 3,3',5,5'-tetra-(pyrid-2-yl)biphenyl 
• 1373155-12-4 3,3′,5,5′-tetra(1H-imidazol-1-yl)-1,1′-biphenyl 
• 1185909-06-1 3,5,3',5'-tetrakis(pyridylethynyl)biphenyl 
• 1009033-95-7 3,5,3',5'-tetra(p-pyridin-3-yl)phenyl-[1,1']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.

Oxidative homocoupling reaction of aryltrimethylsilanes by Pd/o-chloranil catalysis

A practical oxidative homocoupling reaction of aryltri-methylsilanes has been achieved by Pd/o-chloranil catalytic system. The reaction shows the good functional group tolerability toward bromo, fluoro, ester, and methoxy groups to give a series of biaryls bearing electron-withdrawing and -donating groups. The boronate group is also retained on biaryls without any ArB bond cleavage, which is highly advantageous for orthogonal coupling.

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