13029-09-9

  • Product Name2,2'-Dibromobiphenyl
  • Molecular FormulaC12H8Br2
  • Molecular Weight312
  • Purity99%
  • Appearancewhite crystalline powder
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Product Details

Quick Details

  • CasNo: 13029-09-9
  • Molecular Formula: C12H8Br2
  • Appearance: white crystalline powder
  • Purity: 99%

2,2'-DibroMobiphenyl 13029-09-9 Crystalline Powder In Bulk Supply

  • Molecular Formula:C12H8Br2
  • Molecular Weight:312.004
  • Appearance/Colour:white crystalline powder 
  • Vapor Pressure:0.007-0.27Pa at 20-50℃ 
  • Melting Point:79-83 °C 
  • Boiling Point:332.884 °C at 760 mmHg 
  • Flash Point:180.005 °C 
  • PSA:0.00000 
  • Density:1.668 g/cm3 
  • LogP:4.87860 

2,2'-Dibromobiphenyl(Cas 13029-09-9) Usage

Description

2,2'-Dibromobiphenyl is a polybrominated biphenyl (PBB) with two bromine atoms attached to the biphenyl structure.

Uses

PBBs, including 2,2'-dibromobiphenyl, have historically been used as flame retardants in various materials such as plastics for electronics, textiles, and foams. However, due to their environmental persistence and toxicity, the use of PBBs is now restricted or banned in many regions. Chemically, 2,2'-dibromobiphenyl is an important intermediate in organic synthesis. It is utilized in the production of compounds like 5,5-dimethyl-5H-dibenzosilole under specific conditions involving reagents like n-BuLi and solvents such as diethyl ether and hexane. This compound also plays a crucial role in constructing the molecular frameworks of organic luminescent materials and conjugated macromolecules, participating in Suzuki coupling reactions either individually or concurrently through its bromine atoms. Additionally, 2,2'-dibromobiphenyl is employed in copper-catalyzed synthesis of carbazole derivatives through double C-N coupling reactions with amines, and in nickel-catalyzed electroreductive syntheses of triphenylenes, showcasing its versatility and importance in advanced synthetic methodologies.

Canonical SMILES C1=CC=C(C(=C1)C2=CC=CC=C2Br)Br
XLogP3 5.1
Exact Mass 311.89723 g/mol
Monoisotopic Mass 309.89928 g/mol
Complexity 161

 

13029-09-9 Relevant articles

Efficient Copper-Catalysed Synthesis of Carbazoles by Double N-Arylation of Primary Amines with 2, 2′-Dibromobiphenyl in the Presence of Air

Ha Nam Do  , Nguyen Minh Quan , Ban Van Phuc , Dinh Van Tinh , Nguyen Quyet Tien , Truong Thi Thanh Nga , Van Tuyen Nguyen , Tran Quang Hung∗ , Tuan Thanh Dang∗ , Peter Langer∗

, Synlett 2021; 32(06): 611-615

An efficient Cu-catalyzed synthesis of carbazole derivatives is reported, which proceeds by double C–N coupling reactions of 2,2′-dibromobiphenyl and amines in the presence of air. …

Cu (i)-catalyzed cross-coupling of primary amines with 2, 2′-dibromo-1, 1′-biphenyl for the synthesis of polysubstituted carbazole

YN Niu, Y Qiao, KY Wang, BX Sha, GQ Li

, RSC advances, 2022

However, only one example was reported, and the cheaper 2,2-dibromobiphenyl was … synthesis of carbazole to use the cheaper 2,2-dibromobiphenyl as substrates in the copper-…

A highly efficient methodology for the preparation of N-methoxycarbazoles and the total synthesis of 3,3′-[oxybis(methylene)]bis(9-methoxy-9H-carbazole)

Y Zhang, S Wang, Y Huang

, Frontiers of Chemical Science and Engineering volume 15, pages679–686 (2021)

From different 2,2′-dibromobiphenyl compounds with sterically hindered or strongly electron-donating orwithdrawing substituents, or even 3,3′-dibromo-2,2′binaphthyl, various N-…

13029-09-9 Process route

bromobenzene
108-86-1,52753-63-6

bromobenzene

phenol
108-95-2,27073-41-2

phenol

3,3'-dibromobiphenyl
16400-51-4

3,3'-dibromobiphenyl

4-(4-bromophenyl)bromobenzene
92-86-4

4-(4-bromophenyl)bromobenzene

2,2'-dibromobiphenyl
13029-09-9

2,2'-dibromobiphenyl

2,3′-dibromo-1,1′-biphenyl
49602-90-6

2,3′-dibromo-1,1′-biphenyl

2-bromo-4'-bromobiphenyl
49602-91-7

2-bromo-4'-bromobiphenyl

3,4’-dibromobiphenyl
57186-90-0

3,4’-dibromobiphenyl

Conditions
Conditions Yield
With tert.-butylhydroperoxide; iodine; at 289.9 ℃; for 0.0272222h; Product distribution;
12.5%
30.9%
16%
17%
19.3%
4.3%
bromobenzene
108-86-1,52753-63-6

bromobenzene

2,3-dibromobenzene
583-53-9

2,3-dibromobenzene

2-Bromobiphenyl
2052-07-5

2-Bromobiphenyl

2,2'-dibromobiphenyl
13029-09-9

2,2'-dibromobiphenyl

Conditions
Conditions Yield
bromobenzene; With tert.-butyl lithium; In tetrahydrofuran; at -80 ℃; for 1h; Inert atmosphere;
2,3-dibromobenzene; In tetrahydrofuran; at -50 ℃; for 2h; Inert atmosphere;
44%
9%

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13029-09-9 Downstream products

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