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4,4'-Dibromobiphenyl, a brominated aromatic compound, is characterized by the presence of two bromine atoms attached to the 4,4' positions of a biphenyl molecule. This chemical structure endows it with unique properties, such as flame retardancy and plasticizing capabilities, making it a versatile compound for various industrial applications.

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  • 92-86-4 Structure
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    1. Product Name: 4,4'-Dibromobiphenyl
    2. Synonyms: 1,1’-(biphenyl,4,4’-dibromo-;1,1’-biphenyl,,4’-dibromo-(4,4’-bromobiphenyl);1,1’-biphenyl,,4’-dibromo-(4,4’-dibromobiphenyl);1,1’-Biphenyl,4,4’-dibromo-;4,4’-dibromo-1’-biphenyl;4,4'-Dibromo-1,1'-biphenyl;Biphenyl, 4,4'-dibromo-;P,P'-DIBROMOBIPHENYL
    3. CAS NO:92-86-4
    4. Molecular Formula: C12H8Br2
    5. Molecular Weight: 312
    6. EINECS: 202-198-6
    7. Product Categories: Aromatic Compounds;Light yellow crystalline powder;Alpha Sort;BromoVolatiles/ Semivolatiles;D;DAlphabetic;DIA - DIC;Aryl;C9 to C12;Halogenated Hydrocarbons;Method 625;500 Series Drinking Water Methods;600 Series Wastewater Methods;BromoEPA;Chemical Class;Halogenated;Method 508EPA;biphenyl
    8. Mol File: 92-86-4.mol
    9. Article Data: 142
  • Chemical Properties

    1. Melting Point: 163-165 °C(lit.)
    2. Boiling Point: 355-360 °C(lit.)
    3. Flash Point: 355-360°C
    4. Appearance: White to light yellow-beige/Liquid
    5. Density: 1.7243 (estimate)
    6. Refractive Index: 1.6000 (estimate)
    7. Storage Temp.: Store below +30°C.
    8. Solubility: N/A
    9. Water Solubility: INSOLUBLE
    10. BRN: 2044701
    11. CAS DataBase Reference: 4,4'-Dibromobiphenyl(CAS DataBase Reference)
    12. NIST Chemistry Reference: 4,4'-Dibromobiphenyl(92-86-4)
    13. EPA Substance Registry System: 4,4'-Dibromobiphenyl(92-86-4)
  • Safety Data

    1. Hazard Codes: Xi,Xn,N
    2. Statements: 36/37/38-37/38-36-40-50/53-41-22-67-52/53
    3. Safety Statements: 37/39-26-37-36/37-61-60-39-36/37/39
    4. RIDADR: 3152
    5. WGK Germany: 1
    6. RTECS:
    7. TSCA: Yes
    8. HazardClass: 9
    9. PackingGroup: II
    10. Hazardous Substances Data: 92-86-4(Hazardous Substances Data)

92-86-4 Usage

Uses

Used in Flame Retardants:
4,4'-Dibromobiphenyl is used as a flame retardant to enhance the fire resistance of materials. Its chemical structure allows it to interfere with the combustion process, thereby reducing the flammability of products and improving their safety in case of fire incidents.
Used in Plasticizers:
4,4'-Dibromobiphenyl serves as a plasticizer, which is added to polymers to increase their flexibility, workability, and durability. By incorporating this compound into plastics, manufacturers can achieve desired physical properties and improve the overall performance of the end product.
Used in Gas Chromatography:
In the field of analytical chemistry, 4,4'-Dibromobiphenyl is utilized in gas chromatography as a stationary phase or a component of a stationary phase. Its unique chemical properties enable the separation and analysis of complex mixtures, providing valuable information for research and quality control purposes.
Used in Liquid Chromatography:
Similarly, 4,4'-Dibromobiphenyl finds application in liquid chromatography, where it can be used as a stationary phase or part of a stationary phase to separate and analyze various compounds. Its selectivity and stability contribute to the efficiency and accuracy of the chromatographic process.

Purification Methods

Crystallise it from MeOH. [Beilstein 5 IV 1820.]

Check Digit Verification of cas no

The CAS Registry Mumber 92-86-4 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 2 respectively; the second part has 2 digits, 8 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 92-86:
(4*9)+(3*2)+(2*8)+(1*6)=64
64 % 10 = 4
So 92-86-4 is a valid CAS Registry Number.

92-86-4 Well-known Company Product Price

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  • TCI America

  • (D1695)  4,4'-Dibromobiphenyl  >98.0%(GC)

  • 92-86-4

  • 25g

  • 80.00CNY

  • Detail
  • TCI America

  • (D1695)  4,4'-Dibromobiphenyl  >98.0%(GC)

  • 92-86-4

  • 250g

  • 329.00CNY

  • Detail
  • Alfa Aesar

  • (A14139)  4,4'-Dibromobiphenyl, 98+%   

  • 92-86-4

  • 50g

  • 275.0CNY

  • Detail
  • Alfa Aesar

  • (A14139)  4,4'-Dibromobiphenyl, 98+%   

  • 92-86-4

  • 250g

  • 1214.0CNY

  • Detail

92-86-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 4,4'-Dibromobiphenyl

1.2 Other means of identification

Product number -
Other names 1,1‘-Biphenyl, 4,4‘-dibromo-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:92-86-4 SDS

92-86-4Relevant articles and documents

Functionalized NHC-incorporated Te?Fe?Cu clusters: Facile synthesis, electrochemistry, and catalytic reaction

Shieh, Minghuey,Liu, Yu-Hsin,Li, Yu-Huei,Lin, Chien-Nan,Wang, Chih-Chin

, p. 161 - 169 (2018)

Two novel TeFe3(CO)9-containing functionalized NHC dicopper complexes, [TeFe3(CO)9{Cu(Me2-bimy)}2] (1) and [TeFe3(CO)9{Cu(iPr2-bimy)}2] (2), were prepared from the reaction of the ternary Te?Fe?Cu complex [TeFe3(CO)9{Cu(MeCN)}2] with bis-N-methyl- or bis-N-isopropyl-substituted benzimidazol-2-ylidene (Me2-bimy or iPr2-bimy) under appropriate conditions, respectively. X-ray analysis showed that Me2-bimy-introduced complex 1 displayed a TeFe3(CO)9Cu(Me2-bimy) trigonal-bipyramidal core geometry having the Fe2Cu face capped by a Cu(Me2-bimy) fragment with the two bonded Cu atoms, whereas the bulkier iPr2-bimy-incorporated complex 2 exhibited a similar TeFe3(CO)9Cu(iPr2-bimy) core having the Fe3 triangle coordinated by a Cu(iPr2-bimy) fragment with the two unbonded Cu atoms. On the other hand, when [TeFe3(CO)9{Cu(MeCN)}2] reacted with the 4,5-dichloro-substituted 1,3-dimethylimidazolium salt (Me2-Cl2-imy·HI) in the presence of KOtBu, a different type of [TeFe3(CO)9{Cu(Me2-Cl2-imy)}2] (3) was produced in good yields. Cluster 3 was shown to possess a tetrahedral TeFe3 core geometry in which the two Fe?Fe edges were each bridged by a Cu(Me2-Cl2-imy) group. According to solid-state packings, complex 1 revealed a cluster-based 3D-supramolecular framework and complexes 2 and 3 each formed a 1D-supramolecular chain, which was stabilized by intermolecular C?H…O interactions between COs and CH moieties of the corresponding NHC ligands. Further, these di-Cu(I) based complexes 1?3 exhibited catalytic activities toward the homocoupling of arylboronic acid with high yields. Importantly, the catalytic efficiencies of this series of functionalized NHC-incorporated TeFe3(CO)9Cu2-based complexes perfectly paralleled the ease of their first oxidation and the greater electron density of the carbene atom in the NHC ligands, which was elucidated by electrochemistry, 13C NMR, and DFT calculations.

Pd-Catalyzed desulfitative arylation of olefins by: N -methoxysulfonamide

Ojha, Subhadra,Panda, Niranjan

supporting information, p. 1292 - 1298 (2022/02/19)

A novel Pd-catalyzed protocol for the desulfitative Heck-type reaction of N-methoxy aryl sulfonamides with alkenes was reported. The cross-coupling reaction was performed successfully with a variety of olefins to obtain aryl alkenes. Different substituents on the aromatic ring of N-methoxysulfonamides were also found to be compatible with the reaction conditions. Expectedly, the reaction proceeds through CuCl2-promoted generation of the nitrogen radical and subsequent desulfonylation under thermal conditions to afford the aryl radical for the Pd-catalyzed coupling reaction. N-Methoxysulfonamide was further exploited for the synthesis of symmetrical biaryls in the presence of CuCl2. This journal is

Silk?Fibroin-Supported Palladium Catalyst for Suzuki-Miyaura and Ullmann Coupling Reactions of Aryl Chlorides

Albano, Gianluigi,Farinola, Gianluca M.,Giannini, Cinzia,Musio, Roberta,Omenetto, Fiorenzo G.,Rizzo, Giorgio,Sibillano, Teresa

supporting information, (2022/02/03)

Recently, we have reported the preparation of a silk fibroin-supported Palladium catalyst (Pd/SF) and its use in the Suzuki-Miyaura cross-coupling of aryl iodides. Since its synthetic applicability and structural features are still far from being fully ex

Porphyrin n-pincer pd(Ii)-complexes in water: A base-free and nature-inspired protocol for the oxidative self-coupling of potassium aryltrifluoroborates in open-air

Hanafiah, Marlia M.,Lakkaboyana, Sivarama Krishna,Lakshmidevi, Jangam,Marella, Ravi Kumar,Naidu, Bandameeda Ramesh,Prasad, Sana Siva,Venkateswarlu, Katta

, (2021/09/13)

Metalloporphyrins (and porphyrins) are well known as pigments of life in nature, since representatives of this group include chlorophylls (Mg-porphyrins) and heme (Fe-porphyrins). Hence, the construction of chemistry based on these substances can be based on the imitation of biological systems. Inspired by nature, in this article we present the preparation of five different porphyrin, meso-tetraphenylporphyrin (TPP), meso-tetra(p-anisyl)porphyrin (TpAP), tetra-sodium meso-tetra(p-sulfonatophenyl)porphyrin (TSTpSPP), meso-tetra(m-hydroxyphenyl)porphyrin (TmHPP), and meso-tetra(m-carboxyphenyl)porphyrin (TmCPP) as well as their N-pincer Pd(II)-complexes such as Pd(II)-meso-tetraphenylporphyrin (PdTPP), Pd(II)-meso-tetra(p-anisyl)porphyrin (PdTpAP), Pd(II)-tetrasodium meso-tetra(p-sulfonatophenyl)porphyrin (PdTSTpSPP), Pd(II)-meso-tetra(m-hydroxyphenyl)porphyrin (PdTmHPP), and Pd(II)-meso-tetra(m-carboxyphenyl)porphyrin (PdTmCPP). These porphyrin N-pincer Pd(II)-complexes were studied and found to be effective in the base-free self-coupling reactions of potassium aryltrifluoroborates (PATFBs) in water at ambient conditions. The catalysts and the products (symmetrical biaryls) were characterized using their spectral data. The high yields of the biaryls, the bio-mimicking conditions, good substrate feasibility, evading the use of base, easy preparation and handling of catalysts, and the application of aqueous media, all make this protocol very attractive from a sustainability and cost-effective standpoint.

N-Methylphenothiazine S-Oxide Enabled Oxidative C(sp2)–C(sp2) Coupling of Boronic Acids with Organolithiums via Phenothiaziniums

Yoshida, Tatsuki,Honda, Yuki,Morofuji, Tatsuya,Kano, Naokazu

supporting information, p. 9664 - 9668 (2021/12/17)

Herein, we report the development of a transition-metal-free oxidative C(sp2)–C(sp2) coupling of readily available boronic acids and organolithiums via phenothiazinium ions. Various biaryl, styrene, and diene derivatives were obtained using this reaction system. The key to this process is N-methylphenothiazine S-oxide (PTZSO), which allows efficient conversion of boronic acids to phenothiazinium ions. The mechanism of phenothiazinium formation using PTZSO was investigated using theoretical calculations and experiments, which provided insight into the unique reactivity of PTZSO.

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

, (2021/01/11)

Symmetrical and unsymmetrical biaryls comprises a diverse class of biologically eloquent organic compounds. We herein report, a quick and eco-friendly protocol for the synthesis of biaryls by an oxidative (aerobic) homocoupling of arylboronic acids (ABAs) using Pd(OAc)2 in water extract of pomogranate ash (WEPA) as an efficient agro-waste(bio)-derived aqueous (basic) media. The reactions were executed at ambient aerobic conditions in the absence of external base and ligand to result symmetrical biaryls in excellent yields. The use of renewable media with an effective exploitation of waste, short reaction times, excellent yields of products, easy separation of the products, unnecessating the external base, oxidant, ligand or volatile organic solvents and ambient reaction conditions are the vital insights of the present protocol.

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

Minus, Matthew B.,Moor, Sarah R.,Pary, Fathima F.,Nirmani,Chwatko, Malgorzata,Okeke, Brandon,Singleton, Josh E.,Nelson, Toby L.,Lynd, Nathaniel A.,Anslyn, Eric V.

supporting information, p. 2873 - 2877 (2021/05/05)

Typically, Suzuki couplings used in polymerizations are performed at raised temperatures in inert atmospheres. As a result, the synthesis of aromatic materials that utilize this chemistry often demands expensive and specialized equipment on an industrial scale. Herein, we describe a bimetallic methodology that exploits the distinct reactivities of palladium and copper to perform high yielding aryl-aryl dimerizations and polymerizations that can be performed on a benchtop under ambient conditions. These couplings are facile and can be performed by simple mixing in the open vessel. To demonstrate the utility of this method in the context of polymer synthesis: polyfluorene, polycarbazole, polysilafluorene, and poly(6,12-dihydro-dithienoindacenodithiophene) were created at ambient temperature and open to air.

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

Nishii, Yuji,Ikeda, Mitsuhiro,Hayashi, Yoshihiro,Kawauchi, Susumu,Miura, Masahiro

supporting information, p. 1621 - 1629 (2020/02/04)

A Lewis base catalyst Trip-SMe (Trip = triptycenyl) for electrophilic aromatic halogenation using N-halosuccinimides (NXS) is introduced. In the presence of an appropriate activator (as a noncoordinating-anion source), a series of unactivated aromatic compounds were halogenated at ambient temperature using NXS. This catalytic system was applicable to transformations that are currently unachievable except for the use of Br2 or Cl2: e.g., multihalogenation of naphthalene, regioselective bromination of BINOL, etc. Controlled experiments revealed that the triptycenyl substituent exerts a crucial role for the catalytic activity, and kinetic experiments implied the occurrence of a sulfonium salt [Trip-S(Me)Br][SbF6] as an active species. Compared to simple dialkyl sulfides, Trip-SMe exhibited a significant charge-separated ion pair character within the halonium complex whose structural information was obtained by the single-crystal X-ray analysis. A preliminary computational study disclosed that the πsystem of the triptycenyl functionality is a key motif to consolidate the enhancement of electrophilicity.

Arylation of aryllithiums with: S-arylphenothiazinium ions for biaryl synthesis

Morofuji, Tatsuya,Yoshida, Tatsuki,Tsutsumi, Ryosuke,Yamanaka, Masahiro,Kano, Naokazu

, p. 13995 - 13998 (2020/11/21)

Aryllithiums are one of the most common and important aryl nucleophiles; nevertheless, methods for arylation of aryllithums to produce biaryls have been limited. Herein, we report arylation of aryllithiums with S-arylphenothiazinium ions through selective

Modular and Selective Arylation of Aryl Germanes (C?GeEt3) over C?Bpin, C?SiR3 and Halogens Enabled by Light-Activated Gold Catalysis

Dahiya, Amit,Fricke, Christoph,Funes-Ardoiz, Ignacio,Gevondian, Avetik G.,Schoenebeck, Franziska,Sherborne, Grant J.

supporting information, p. 15543 - 15548 (2020/06/22)

Selective C (Formula presented.) –C (Formula presented.) couplings are powerful strategies for the rapid and programmable construction of bi- or multiaryls. To this end, the next frontier of synthetic modularity will likely arise from harnessing the coupling space that is orthogonal to the powerful Pd-catalyzed coupling regime. This report details the realization of this concept and presents the fully selective arylation of aryl germanes (which are inert under Pd0/PdII catalysis) in the presence of the valuable functionalities C?BPin, C?SiMe3, C?I, C?Br, C?Cl, which in turn offer versatile opportunities for diversification. The protocol makes use of visible light activation combined with gold catalysis, which facilitates the selective coupling of C?Ge with aryl diazonium salts. Contrary to previous light-/gold-catalyzed couplings of Ar–N2+, which were specialized in Ar–N2+ scope, we present conditions to efficiently couple electron-rich, electron-poor, heterocyclic and sterically hindered aryl diazonium salts. Our computational data suggest that while electron-poor Ar–N2+ salts are readily activated by gold under blue-light irradiation, there is a competing dissociative deactivation pathway for excited electron-rich Ar–N2+, which requires an alternative photo-redox approach to enable productive couplings.

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