Production Method 1

5467-74-3

92-86-4

Reaction Conditions

1.1 Reagents: Oxygen Catalysts: Cupric acetate ,  Palladium diacetate Solvents: Dimethyl sulfoxide ,  Water ;  14 h, rt

Reference

"Benchtop" Biaryl Coupling Using Pd/Cu Cocatalysis: Application to the Synthesis of Conjugated Polymers

Minus, Matthew B. ; Moor, Sarah R. ; Pary, Fathima F.; Nirmani, L. P. T.; Chwatko, Malgorzata; et al, Organic Letters, 2021, 23(8), 2873-2877

Production Method 2

5467-74-3

92-86-4

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Water ;  45 - 60 min, 120 - 130 °C

Reference

Organic synthesis via magnetic attraction: benign and sustainable protocols using magnetic nanoferrites

Nasir Baig, R. B.; Varma, Rajender S., Green Chemistry, 2013, 15(2), 398-417

Production Method 3

374564-35-9

92-86-4

Reaction Conditions

1.1 Reagents: Oxygen Catalysts: Gold (nanoclusters, poly(N-vinyl-2-pyrrolidone) supported) Solvents: Water ;  24 h, pH 6.86, 320 K

Reference

Oxidative homo-coupling of potassium aryltrifluoroborates catalyzed by gold nanocluster under aerobic conditions

Sakurai, Hidehiro; Tsunoyama, Hironori; Tsukuda, Tatsuya, Journal of Organometallic Chemistry, 2007, 692(1-3), 368-374

Production Method 4

28969-28-0

92-86-4

Reaction Conditions

1.1 Reagents: Lithium chloride Solvents: Hexamethylphosphoramide
1.2 Catalysts: Rhodium, tetracarbonyldi-μ-chlorodi-
1.3 Solvents: Water
1.4 Solvents: Diethyl ether ,  Benzene

Reference

Synthesis of symmetrical biaryls via rhodium catalyzed dimerization of arylmercurials and mechanism of the dimerization

Wang, Yu-Lan; Wu, Yang-Jie, Chemical Research in Chinese Universities, 2000, 16(2), 131-135

Production Method 5

589-87-7

92-86-4

Reaction Conditions

1.1 Reagents: DL-Glucose Catalysts: Gold triacetate Solvents: Tetrabutylammonium acetate ;  15 h, 90 °C

Reference

Ullmann homocoupling catalysed by gold nanoparticles in water and ionic liquid

Monopoli, Antonio; Cotugno, Pietro; Palazzo, Gerardo; Ditaranto, Nicoletta; Mariano, Bruno; et al, Advanced Synthesis & Catalysis, 2012, 354(14-15), 2777-2788

Production Method 6

92-86-4

Reaction Conditions

1.1 Reagents: Bromine ;  40 min, 40 °C; 5 h, 40 °C

Reference

Study of synthesis technology of 4, 4'-dibromobiphenyl

Wang, Yu-jing; Yan, Xing-li; Yuan, Li-li; Wang, Hong-ying; Li, Qin; et al, Hefei Gongye Daxue Xuebao, 2013, 36(6), 737-739

Production Method 7

106-37-6

92-86-4

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: Palladium Solvents: Dimethylformamide ;  20 h, 110 °C

Reference

Palladium nanoparticles immobilized on the magnetic few layer graphene support as a highly efficient catalyst for ligand free Suzuki cross coupling and homo coupling reactions

Rafiee, Fatemeh; Khavari, Parvaneh; Payami, Zahra; Ansari, Narges, Journal of Organometallic Chemistry, 2019, 883, 78-85

Production Method 8

5467-74-3

92-86-4

Reaction Conditions

1.1 Reagents: Sodium carbonate Catalysts: Palladium chloride Solvents: Water

Reference

Polydimethylsiloxane thimbles

Long, Tyler R.; Bowden, Ned B., e-EROS Encyclopedia of Reagents for Organic Synthesis, 2011, 1, 1-6

Production Method 9

5467-74-3

92-86-4

Reaction Conditions

1.1 Reagents: Cesium carbonate Catalysts: Gold (polystyrene-co-polymethacrylic acid microsphere-supported) Solvents: N-Methyl-2-pyrrolidone ,  Water ;  43 h, 110 °C

Reference

A recyclable Au(I) catalyst for selective homocoupling of arylboronic acids: significant enhancement of nano-surface binding for stability and catalytic activity

Zhang, Xin; Zhao, Haitao; Wang, Jianhui, Journal of Nanoscience and Nanotechnology, 2010, 10(8), 5153-5160

Production Method 10

374564-35-9

92-86-4

Reaction Conditions

1.1 Reagents: Acetic acid ,  Quinone ,  Tetrabutylammonium tetrafluoroborate Catalysts: Palladium diacetate Solvents: Dimethylformamide ;  40 min, 80 °C

Reference

Pd(OAc)2/p-benzoquinone-catalyzed anaerobic electrooxidative homocoupling of arylboronic acids, arylboronates and aryltrifluoroborates in DMF and/or water

Amatore, Christian; Cammoun, Chama; Jutand, Anny, European Journal of Organic Chemistry, 2008, (27), 4567-4570

Production Method 11

92-86-4

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Catalysts: Silver hexafluoroantimonate ,  9,10-Dihydro-9-(methylthio)-9,10[1′,2′]-benzenoanthracene Solvents: 1,2-Dichloroethane ;  4 h, rt

Reference

Triptycenyl Sulfide: A Practical and Active Catalyst for Electrophilic Aromatic Halogenation Using N-Halosuccinimides

Nishii, Yuji ; Ikeda, Mitsuhiro; Hayashi, Yoshihiro ; Kawauchi, Susumu; Miura, Masahiro, Journal of the American Chemical Society, 2020, 142(3), 1621-1629

Production Method 12

5467-74-3

92-86-4

Reaction Conditions

1.1 Reagents: Oxygen Catalysts: Copper, bis[μ-(1,10-phenanthrolin-2-olato-κN1,κN10:κO2)]di-, (Cu-Cu), stereoisom… Solvents: Dimethylformamide ;  20 h, rt

Reference

Three-coordinate copper(I) 2-hydroxy-1,10-phenanthroline dinuclear complex catalyzed homocoupling of arylboronic acids towards biphenyls under air condition

Wang, Yan-Hong; Xu, Mei-Chen; Liu, Jie; Zhang, Ling-Juan; Zhang, Xian-Ming, Tetrahedron, 2015, 71(52), 9598-9601

Production Method 13

92-86-4

Reaction Conditions

1.1 Reagents: Sodium bicarbonate ,  Silver carbonate ,  Cuprous iodide Catalysts: Triphenylphosphine ,  Palladium diacetate Solvents: 1,4-Dioxane ;  4 h, reflux

Reference

Pd(OAc)2/PPh3-Catalyzed Desulfonylative Homocoupling of Arylsulfonyl Chlorides

Zhao, Qiao; Chen, Liangshun; Lang, Hongyue; Wu, Shengying; Wang, Limin, Chinese Journal of Chemistry, 2015, 33(5), 535-538

Production Method 14

5467-74-3

92-86-4

Reaction Conditions

1.1 Reagents: Sodium carbonate Catalysts: Tosyl chloride ,  Palladium chloride Solvents: Ethanol ,  Water

Reference

Ligandless palladium chloride-catalyzed homo-coupling of arylboronic acids in aqueous media

Kabalka, George W.; Wang, Lei, Tetrahedron Letters, 2002, 43(16), 3067-3068

Production Method 15

5467-74-3

92-86-4

Reaction Conditions

1.1 Reagents: Oxygen Catalysts: Palladium diacetate Solvents: Water ;  15 min, rt

Reference

Pd-catalyzed oxidative homocoupling of arylboronic acids in WEPA: A sustainable access to symmetrical biaryls under added base and ligand-free ambient conditions

Appa, Rama Moorthy; Lakshmidevi, Jangam; Naidu, Bandameeda Ramesh; Venkateswarlu, Katta, Molecular Catalysis, 2021, 501,

Production Method 16

589-21-9

92-86-4

Reaction Conditions

1.1 Reagents: Sodium acetate Catalysts: Palladium diacetate Solvents: Methyl ethyl ketone ;  3 h, 50 °C

Reference

Method for synthesizing symmetric biphenyl with aromatic hydrazine

, China, , ,

Production Method 17

589-87-7

92-86-4

Reaction Conditions

1.1 Catalysts: Palladium, bis(acetonitrile)dichloro- ,  [[2,2′-Bipyridine]-5,5′-dicarboxylato(2-)-κO5]hydroxyaluminum Solvents: Dimethylformamide ;  24 h, 65 °C
1.2 Reagents: Potassium acetate Solvents: Ethanol ,  Dimethyl sulfoxide ;  14 h, 120 °C

Reference

Immobilization of Pd(II) on MOFs as a highly active heterogeneous catalyst for Suzuki-Miyaura and Ullmann-type coupling reactions

Chen, Liyu; Gao, Zhiqiang; Li, Yingwei, Catalysis Today, 2015, 245, 122-128

Production Method 18

5467-74-3

92-86-4

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: Gold(1+), [2-[[[(1S)-2′-[[[5-(2-aminoethyl)-3-(1,1-dimethylethyl)-2-(hydroxy-κO)… (MCM-41-supported) Solvents: Xylene ;  24 h, 130 °C

Reference

Homogeneous and heterogenized Au(III) Schiff base-complexes as selective and general catalysts for self-coupling of arylboronic acids

Gonzalez-Arellano, C.; Corma, A.; Iglesias, M.; Sanchez, F., Chemical Communications (Cambridge, 2005, (15), 1990-1992

Production Method 19

92-86-4

Reaction Conditions

1.1 Reagents: Bromine Catalysts: Aluminum chloride Solvents: Ethyl acetate ;  6 h, 30 °C

Reference

Green preparation of 4-alkyl-4'-cyanobiphenyls

, China, , ,

Production Method 20

589-87-7

92-86-4

Reaction Conditions

1.1 Reagents: Tripotassium phosphate ,  Oxygen Catalysts: Gold Solvents: Dimethylformamide ;  48 h, 130 °C

Reference

Synthesis of DMF-protected Au NPs with different size distributions and their catalytic performance in the Ullmann homocoupling of aryl iodides

Yao, Wang; Gong, Wei-Jie; Li, Hong-Xi; Li, Fei-Long; Gao, Jun; et al, Dalton Transactions, 2014, 43(42), 15752-15759

4,4'-Dibromobiphenyl Raw materials

• (4-bromophenyl)boronic acid
• 1,4-Dibromobenzene
• (4-Bromophenyl)hydrazine
• 1-Bromo-4-iodobenzene
• Potassium 4-Bromophenyltrifluoroborate
• Mercury, (4-bromophenyl)chloro-

4,4'-Dibromobiphenyl Preparation Products

• 4,4'-Dibromobiphenyl (92-86-4)

• 1. Aggregation dynamics, structure, and mechanical properties of bigels
  L. Di Michele,D. Fiocco,F. Varrato,E. Eiser,G. Foffi Soft Matter, 2014,10, 3633-3648
• 2. An insight into the role of side chains in the microstructure and carrier mobility of high-performance conjugated polymers?
  Jianyao Huang,Dong Gao,Zhihui Chen,Weifeng Zhang Polym. Chem., 2021,12, 2471-2480
• 3. An integrated digital microfluidic chip for multiplexed proteomic sample preparation and analysis by MALDI-MS?
  Hyejin Moon,Aaron R. Wheeler,Robin L. Garrell,Chang-Jin “CJ” Kim Lab Chip, 2006,6, 1213-1219
• 4. An arsenic trioxide nanoparticle prodrug (ATONP) potentiates a therapeutic effect on an aggressive hepatocellular carcinoma model via enhancement of intratumoral arsenic accumulation and disturbance of the tumor microenvironment?
  Xin Fu,Qing-rong Liang,Rong-guang Luo,Yan-shu Li,Xiao-ping Xiao,Lu-lu Yu,Wen-zhe Shan,Guang-qin Fan J. Mater. Chem. B, 2019,7, 3088-3099
• 5. An asymmetric supercapacitor based on controllable WO3 nanorod bundle and alfalfa-derived porous carbon?
  Kanjun Sun,Fengting Hua,Shuzhen Cui,Yanrong Zhu,Hui Peng,Guofu Ma RSC Adv., 2021,11, 37631-37642

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Biphenyls and derivatives Brominated biphenyls
• Pesticide Chemicals Pesticide Active Ingredients Standard Substances
• Solvents and Organic Chemicals Organic Compounds Organic Halides

Professional Introduction to 4,4'-Dibromobiphenyl (CAS No. 92-86-4)

4,4'-Dibromobiphenyl, with the chemical formula C₁₂H₈Br₂, is a brominated derivative of biphenyl. Its CAS number, CAS No. 92-86-4, uniquely identifies it in the chemical industry and research communities. This compound has garnered significant attention due to its versatile applications in organic synthesis, material science, and pharmaceutical research.

The structure of 4,4'-Dibromobiphenyl consists of two benzene rings connected by a bromine atom at each position on the para-substituted sites. This symmetrical arrangement imparts unique electronic and steric properties, making it a valuable intermediate in the synthesis of more complex molecules. The presence of bromine atoms enhances its reactivity, allowing for further functionalization through various chemical reactions such as cross-coupling, substitution, and polymerization.

In recent years, 4,4'-Dibromobiphenyl has been extensively studied for its potential applications in the development of advanced materials. Its ability to form stable radicals and participate in electron transport processes has made it a candidate for use in organic semiconductors and light-emitting diodes (OLEDs). Researchers have demonstrated its efficacy in creating high-performance charge transport layers, which are crucial for improving the efficiency of electronic devices.

Moreover, the pharmaceutical industry has shown interest in 4,4'-Dibromobiphenyl due to its structural similarity to certain bioactive compounds. Studies have indicated that derivatives of this molecule may exhibit promising biological activities, including anti-inflammatory and antimicrobial properties. While further research is needed to fully elucidate its therapeutic potential, preliminary findings suggest that modifications to the bromine substituents could lead to novel drug candidates.

The synthesis of 4,4'-Dibromobiphenyl typically involves the bromination of biphenyl using bromine or N-bromosuccinimide (NBS) as the brominating agent. The reaction is often carried out under controlled conditions to ensure high yield and purity. Advances in synthetic methodologies have enabled the production of this compound on an industrial scale, facilitating its use in various applications without compromising quality.

In material science, 4,4'-Dibromobiphenyl has been explored as a precursor for flame-retardant additives. Its bromine content makes it effective in enhancing the fire resistance of polymers and other materials. By incorporating this compound into polymer matrices, manufacturers can improve safety standards without significantly altering the physical properties of the final product.

The environmental impact of using CAS No. 92-86-4, or 4,4'-Dibromobiphenyl, is another area of concern. While it offers numerous benefits in industrial and research settings, its persistence in the environment and potential toxicity must be carefully managed. Regulatory agencies have established guidelines for its handling and disposal to minimize ecological risks. Ongoing research aims to develop more sustainable alternatives while maintaining its advantageous properties.

In conclusion, 4,4'-Dibromobiphenyl is a multifaceted compound with significant applications across multiple industries. Its unique structural features and reactivity make it indispensable in organic synthesis, material science, and pharmaceutical research. As scientific understanding advances, new uses for this molecule are likely to emerge, further solidifying its importance in modern chemistry.

• 7511-49-1(1,3,5-Tris(4-bromophenyl)benzene)
• 149248-33-9(1,1':4',1''-Terphenyl, 4-bromo-4''-methyl-)
• 56961-07-0(4'-Bromo-3-methylbiphenyl)
• 17788-94-2(4,4''-Dibromo-p-terphenyl)
• 50670-49-0(4-Bromo-4'-methylbiphenyl)
• 92-66-0(4-Bromobiphenyl)
• 1762-84-1(4-Bromo-p-terphenyl)
• 98905-03-4(3-Bromo-m-terphenyl)
• 80523-79-1(4,4'-Dibromobiphenyl-D8)
• 116941-52-7(4-Bromo-5'-phenyl-1,1':3',1''-terphenyl)