16400-51-4

Basic information

• Product Name: 1-bromo-3-(3-bromophenyl)benzene
• Synonyms: 1-bromo-3-(3-bromophenyl)benzene;3,3'-Dibromo-1,1'-biphenyl;3,3'-Dibromobiphenyl;3,3'-Dibromodiphenyl;m,m'-Dibromobiphenyl;PBB 11;1,1'-Biphenyl,3,3'-dibroMo-;3,3'-DBB
• CAS NO: 16400-51-4
• Molecular Formula: C₁₂H₈Br₂
• Molecular Weight: 312.02
• Mol File: 16400-51-4.mol

Chemical Properties

• Melting Point: 171 °C
• Boiling Point: 338.6°Cat760mmHg
• Flash Point: 184.3°C
• Appearance: /
• Density: 1.667
• Vapor Pressure: 0.00019mmHg at 25°C
• Refractive Index: 1.625
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 1-bromo-3-(3-bromophenyl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-bromo-3-(3-bromophenyl)benzene(16400-51-4)
• EPA Substance Registry System: 1-bromo-3-(3-bromophenyl)benzene(16400-51-4)

Safety Data

• Hazardous Substances Data: 16400-51-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-bromo-3-(3-bromophenyl)benzene is utilized as a building block for the synthesis of various pharmaceuticals. Its unique structure and reactivity contribute to the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, 1-bromo-3-(3-bromophenyl)benzene serves as a key intermediate in the production of agrochemicals, such as pesticides and herbicides, due to its ability to be incorporated into complex organic molecules.
Used in Dye Production:
1-bromo-3-(3-bromophenyl)benzene is employed as a starting material in the synthesis of dyes, where its bromine-containing structure imparts specific color properties and stability to the final dye products.
Used in Polymer Industry:
1-bromo-3-(3-bromophenyl)benzene is also used in the polymer industry as a monomer or a precursor in the synthesis of polymers with tailored properties, such as thermal stability, mechanical strength, or specific chemical functionalities.
Used in Specialty Chemicals:
1-bromo-3-(3-bromophenyl)benzene is a valuable intermediate in the production of specialty chemicals, where its unique structure can be exploited to create novel compounds with specific applications in various industries.
Used in Chemical Research and Development:
Due to its unique structure and reactivity, 1-bromo-3-(3-bromophenyl)benzene is a valuable intermediate in the development of new chemical reactions and processes, contributing to advancements in synthetic chemistry and material science.

InChI:InChI=1/C12H8Br2/c13-11-5-1-3-9(7-11)10-4-2-6-12(14)8-10/h1-8H

Upstream product

• 34237-98-4 3,3'-dibromo-[1,1'-biphenyl]-4,4'-diamine 
• 108-36-1 1,3-dibromobenzene 
• 591-18-4 1-Bromo-3-iodobenzene 
• 89598-96-9 (3-bromophenyl)boronic acid 
• 591-50-4 iodobenzene 
• 594823-67-3 (3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)bromobenzene) 
• 635305-38-3 2,2-dimethylpropane-1,3-diyl [3-bromophenyl] boronate 
• 1316859-98-9 potassium 2-(2-nitrophenyl)acetate 
• 3740-52-1 2-(2-nitrophenyl)acetic acid 
• 1203709-76-5 3'-bromo-2,4,6-trimethyl(diphenyliodonium) trifluoromethanesulfonate 
• 2905-24-0 3-Bromobenzenesulfonyl chloride 
• 292638-85-8 acrylic acid methyl ester 
• 17984-89-3 triethoxy(thiophen-2-yl)silane 
• 577-19-5 2-nitrophenyl bromide 

Downstream Products

• 342638-54-4 3,3'-Bis(9H-carbozol-9-yl)-1,1'-biphenyl 
• 854952-41-3 9-(3’-bromo-[1,1’-biphenyl]-3-yl)-9H-carbazole 
• 1235880-28-0 9-(3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-3-yl)-9H-carbazole 
• 1408283-79-3 C₂₄H₁₆Br₂ 
• 850264-92-5 3,3'-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1'-biphenyl 
• 40642-08-8 C₇₀H₅₀O₂ 
• 18826-15-8 3,3'-Biphenylen-bis-(triphenylsilan) 

Relevant articles and documents

Host polymorphs and crystalline host-guest complexes of 3,3′-bis(9-hydroxy-9-fluorenyl)biphenyl

The diol host compound 2 featuring a structure with two 9-fluorenol moieties attached in 3,3′-position to a biphenyl core unit has been synthesized and is shown to form crystalline inclusion complexes with organic guest molecules. Aside from the single-crystal X-ray structures of unsolvated 2 in two polymorphous forms (2A, 2B), structures of five inclusion compounds with 1,4-dioxane (2a), DMSO (2b), diethylamine (2c), acetic acid (2d), and ethyl acetate (2e) are described and comparatively discussed in the interaction behavior including corresponding host compounds with different attachment mode of the biphenyl unit and the diphenylhydroxymethyl-substituted equivalent.

Soluble gold and palladium complexes heterogenized on MCM-41 are effective and versatile catalysts

Chiral Schiff base-gold and -palladium complexes were immobilized on ordered mesoporous silica supports (MCM-41), and their catalytic hydrogenation ability is studied and compared with that of their homogeneous counterparts. The high accessibility introduced by the structure of the supports allows the preparation of highly efficient immobilized catalysts with TOFs of up to 6000 h-1 for the hydrogenation of diethyl itaconate. The easily recoverable immobilized catalysts duplicate the activity of their homogeneous analogues, and no deactivation of the catalysts is observed after repeated recycling. Gold(III) homogeneous or heterogenized complexes also catalyze the homocoupling of arylboronic acids or alkynes to afford symmetrical biaryls, whereas the respective gold(I) and palladium(II) complexes catalyze the corresponding cross-coupling reaction. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Novel electron-transfer oxidation of Lipshutz cuprates with 1,4-benzoquinones: An efficient homo-coupling reaction of aryl halides and its application to the construction of macrocyclic systems

The electron transfer reaction from Lipshutz cuprates, which can be easily prepared from aryl bromides, to 1,4-benzoquinones was found to proceed smoothly, affording either the corresponding homo-coupling products, in modest to excellent yields, or macrocyclic products selectively.

Heterogenized gold(I), gold(III), and palladium(II) complexes for C-C bond reactions

Recycling of heterogenized gold(I), gold(III), and palladium(II) complexes could be achieved for Suzuki and Sonogashira cross-coupling reaction between iodo benzene and arylboronic acids or alkynes. Au(I) and Pd(II) afford selectively nonsymmetrical biaryl compounds, while gold(III) complexes can only catalyze the arylboronic or alkynes homocoupling. Recycling occurs without loss of the catalytic activity after several reaction cycles. Georg Thieme Verlag Stuttgart.

Phosphorescent OLED and hole transporting materials for phosphorescent OLEDS

The present invention relates to phosphorescent organic light-emitting diodes (OLEDs) including a hole-transporting or a hole-transporting and an electron-blocking layer including an N,N,N′,N′-tetraaryl-phenylene-3,5-diamine or an N,N,N′,N′-tetraaryl-1,1′-biphenyl-3,3′-diamine matrix compound and to new N,N,N′,N′-tetraarylsubstituted m-arylene diamine compounds useful as hole-transporting and electron-blocking layer matrices in phosphorescent OLEDs.

Diazcarbazole derivative, preparation method thereof, and application of diazcarbazole derivative as electroluminescent material

The invention belongs to the technical field of organic photoelectric material application, and particularly relates to a diazcarbazole derivative with different relative positions of N atoms and an application of the diazcarbazole derivative as an electroluminescent material. Carbazole-like group diazcarbazole with an electron-deficient property is introduced, and a triplet state of the materialcan be realized and the molecular orbital energy level can be adjustable through bonding with different groups, so that efficient recombination of carriers in an organic electroluminescent device is achieved fundamentally, an efficient and energy-saving organic light emitting diode (OLED) device is obtained, and the diazcarbazole derivative can be widely applied to the field of organic electroluminescence. The structural general formula of the material is as shown in the formula I, wherein a same diazcarbazole (diazcarbazole with N positions of 1,8, 1,7, 1,6, 2,7, 2,6, 2,5, 3,6, 3,5, and 4,5)is taken as a core, the L group is a bridging group for bonding the diazlocarbazole, the L group is selected from aromatic groups or aromatic heterocyclic groups containing heteroatoms, m and n are the numbers of the diazicarbazole, and the sum of m and n is greater than or equal to 1.

Decarboxylative Benzylation of Aryl and Alkenyl Boronic Esters

The copper-catalyzed decarboxylative benzylation of aryl and alkenyl boronic esters with electron-deficient aryl acetates is reported. The oxidative coupling proceeds under mild, aerobic conditions and tolerates a host of potentially reactive electrophilic functional groups that would be problematic with traditional benzylation methods (aryl iodides and bromides, protic heteroatoms, aldehydes, Michael acceptors). A reaction pathway in which a benzylic nucleophile is generated by aryl acetate decarboxylation and in turn is intercepted by the catalyst to form diarylmethane products is supported by mechanistic studies.

A ligand free protocol using Cu(OAc)2@Mont K-10 as versatile reusable catalyst for efficient homocoupling of arylboronic acids for synthesis of symmetric biaryls

Biaryls are an important class of organic compounds that occur in many natural products and they have a wide variety of applications in drugs, agrochemicals, dyes, semi-conductors, and asymmetric syntheses. A versatile, eco-friendly, recyclable, heterogeneous catalyst has been developed for the efficient synthesis of symmetric biaryls from aryl boronic acids. The developed protocol for homocoupling of aryl boronic acid to symmetric biaryls is based on copper acetate supported on acid activated Mont K-10 which is ligand free, mild, inexpensive and compatible with wide range of functional groups and exhibit excellent yields. The catalyst is characterised by FTIR, ESR, XRD, SEM-EDX, BET surface area measurement and the catalyst can be separated from the reaction mixture by simple centrifugation and reused upto five cycles without significant loss in activity.

Ligand- and Base-Free Access to Diverse Biaryls by the Reductive Coupling of Diaryliodonium Salts

A ligand- and base-free, Pd-catalyzed protocol to access a wide range of symmetrical and unsymmetrical biaryls from stable diaryliodonium salts was developed. The reaction involved the use of an effective and recyclable Pd/polyethylene glycol-400 catalyst system to harness the aryl moieties of two diaryliodonium salts; the ensuing biaryls may be utilized to synthesize an array of useful compounds, including 5-aryluracils, carbazoles, chromenones, fluorenones, phenathridines, and boscalid analogues.

Design, synthesis, characterization and application of a novel electron-deficient moiety 1,5-diazacarbazole in high triplet energy host materials

A novel electron deficient, high triplet energy moiety 1,5-diazacarbazole (NCz) was designed, synthesized and firstly introduced for the construction of phosphorescent host materials. And the two synthesized NCz derivatives NCzBPhCz and NCzBPhNCz possessed high triplet energy (ET = 2.85 eV) and bipolar transporting ability. The structure and nitrogen atom position in the diazacarbazole unit were verified by crystallographic analysis of their single crystals and by 2D-NMR. The frontier molecular orbital distribution, electrochemical, thermal and photophysical properties, and electroluminescence of the two new host materials were systematically investigated. Finally, the bis(3,5-difluoro-2-(2-pyridyl)phenyl-(2-carboxypyridyl)iridium(iii)) (FIrpic)-doped NCzBPhCz based blue device exhibited high efficiencies with a ηEQE,max of 24.0%, a ηC,max of 47.8 cd A-1 and a ηP,max of 45.6 lm W-1. Furthermore, a two-color, all-phosphor single layer white device displayed a ηEQE,max of 20.7%, a ηC,max of 62.1 cd A-1 and a ηP,max of 49.5 lm W-1. This study definitely demonstrates that the novel electron deficient unit NCz has great potential for the fabrication of host materials and provides a useful strategy in the design of new high triplet energy and good charge-transporting hosts.