101-55-3

Usage

Uses

Used in Pharmaceutical Industry:
4-Bromophenoxybenzene is used as an intermediate for the synthesis of various pharmaceutical compounds due to its unique chemical structure and properties.
Used in Chemical Synthesis:
4-Bromophenoxybenzene is used as a starting material or intermediate in the synthesis of various organic compounds, including dyes, agrochemicals, and other specialty chemicals, due to its reactive bromo group and aromatic ether structure.
Used in Research and Development:
4-Bromophenoxybenzene is utilized as a research compound for studying the properties and reactivity of aromatic ethers and bromo-substituted compounds, contributing to the advancement of chemical knowledge and the development of new applications.
Used in Material Science:
4-Bromophenoxybenzene can be used as a component in the development of new materials, such as polymers or composites, that may have specific properties or applications due to the presence of the bromo group and aromatic ether structure.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

4-Bromophenoxybenzene oxidizes readily in air to form unstable peroxides that may explode spontaneously [Bretherick 1979 p.151-154, 164].

Fire Hazard

Combustible.

Environmental fate

Biological. Using settled domestic wastewater inoculum, 4-bromophenyl phenyl ether (5 and 10 mg/L) did not degrade after 28 d of incubation at 25 °C (Tabak et al., 1981). Chemical/Physical. At influent concentrations of 1.0, 0.1, 0.01, and 0.001 mg/L, the GAC adsorption capacities were 303, 112, 41, and 15 mg/g, respectively (Dobbs and Cohen, 1980).

InChI:InChI=1/C12H9BrO/c13-10-6-8-12(9-7-10)14-11-4-2-1-3-5-11/h1-9H

Upstream product

• 101-84-8 diphenylether 
• 139-59-3 4-phenoxyanilin 
• 106-37-6 1.4-dibromobenzene 
• 108-95-2 phenol 
• 139-02-6 sodium phenoxide 
• 59696-27-4 p-bromodiphenyliodonium bromide 
• 106-41-2 4-bromo-phenol 
• 1483-73-4 diphenyliodonium bromide 
• 56-23-5 tetrachloromethane 
• 7726-95-6 bromine 
• 7553-56-2 iodine 
• 100-67-4 potassium phenolate 
• 98-80-6 phenylboronic acid 
• 589-87-7 1,4-bromoiodobenzene 

Downstream Products

• 2215-77-2 4-Phenoxybenzoic acid 
• 2519-16-6 4,4'-diphenoxy-1,1'-biphenyl 
• 69199-84-4 2-phenoxy-5-bromobenzoic acid 
• 831-82-3 4-Phenoxyphenol 
• 30427-95-3 1-bromo-4-(4-chlorophenoxy)benzene 
• 61405-25-2 4-(4-bromophenoxy)-benzenesulfonyl chloride 
• 860515-97-5 4-(4-bromophenoxy)benzenesulfonamide 
• 34472-55-4 bis-(4-phenoxy-phenyl)-mercury 
• 17049-41-1 1-trimethylsilyl-4-phenoxybenzene 
• 25268-16-0 Dichloro-methyl-(4-phenoxy-phenyl)-silane 
• 25268-20-6 Dimethyl(p-phenoxyphenyl)silan 
• 15201-82-8 Dichlorbis-p-phenoxyphenylsilan 
• 15453-34-6 Trichloro-(4-phenoxy-phenyl)-silane 
• 25268-17-1 Dichloro-(4-phenoxy-phenyl)-phenyl-silane 

Relevant academic research and scientific papers

Halogenation of Aromatic Compounds by N-chloro-, N-bromo-, and N-iodosuccinimide

An efficient and mild method for the halogenation of aromatic compounds using N-chloro-, N-bromo-, and N-iodosuccinimide in the presence of NH 4NO3 or FeCl3 in acetonitrile was developed.

Nucleophilic reactions of 5-(aryl)thianthrenium bromides with sodium aryl oxides

Reactions between 5-(aryl)thianthrenium bromides (1a-e) with aryl (Ar) groups phenyl (a), p-tolyl (b), p-anisyl (c), p-chlorophenyl (d) and p-bromophenyl (e) and sodium aryl oxides (7a-c, Ar′ONa, Ar′ = phenyl, p-tolyl and p-chlorophenyl) were carried out in acetonitrile at 80°C. Results are compared with those of earlier reactions of 1a-e with corresponding sodium aryl thiolates (Ar′SNa). In contrast with the thiolate reactions, those with 7a-c were too slow at room temperature to be useful. Reactions of 1a-c at 80°C gave small amounts of benzene and toluene from la and b, small amounts of diaryl ethers ArOAr′ (9) and thianthrene (Th) and large amounts (90-97%) of 2-(ArS)-2′-(Ar′O)diphenyl sulfide (10). Compared with reactions of 1a-c, those of 1d and e gave larger amounts (10-17%) of 9, lesser amounts (25-30%) of 10 and substantial amounts (42-55%) of 2-[4-(Ar′O)-ArS]-2′-(Ar′O)diphenyl sulfide (12). Small amounts of 1,4-di(Ar′O)benzene (11) were also obtained from reactions of Id and e. Formation of 11 and 12 is preceded by replacement of halogen by Ar′O-. Structures of products 10 and 12 were deduced by comparison with earlier products from thiolate reactions, elemental analyses, mass spectrometry molecular masses and, in the case of 10, the crystal structure of 10d. It is proposed that products 9-12 are formed by nucleophilic reactions of Ar′O- at ipso positions in 1. Copyright

Cu(I)-PNF, an organic-based nanocatalyst, catalyzed C-O and C-S cross-coupling reactions

Peptide nanofiber has been prepared via a self-assembly protocol and decorated with Cu(I) to prepare a nanostructural catalyst. The catalytic activity of this prepared nanomaterial (Cu(I)-PNF) was examined in C-O and C-S cross-coupling reactions. Compared with conventional copper-ligand catalytic systems, CuNP-PNF has unique advantages such as water solubility, high efficiency, and low cost, which makes it a highly efficient and beneficial catalyst to reuse in cross-coupling reactions.

An efficient and regioselective monobromination of electron-rich aromatic compounds using catalytic hypervalent iodine(III) reagent

An efficient and regioselective monobromination of electron-rich aromatic compounds is reported in which iodobenzene is used as the recyclable catalyst in combination with m-chloroperbenzoic acid as the terminal oxidant. The bromination of electron-rich aromatic compounds with lithium bromide was fast in tetrahydrofuran at room temperature, providing regioselective monobrominated products in good yields.

Diaza crown-type macromocycle (kryptofix 22) functionalised carbon nanotube for efficient Ni2+ loading; A unique catalyst for cross-coupling reactions

Raising the capability of supporting and suppressing the leaching possibility to a very insignificant level has still remained challenging for some class of transition metals, i.e. Ni2+. Here we present the covalent functionalisation of macrocyclic ligand, 4,13-diaza-18-crown-6 (kryptofix 22), on the surface of carbon nanotube (CNT), leading to a unique adsorptive capability for supporting Ni2+. This material was incorporated as a promising catalyst in coupling reactions including C[sbnd]C, CN, and CO[sbnd][sbnd] cross-coupling reactions. We demonstrate that the kryptofix 22 functionalisation on the surface of CNT has a key role in the enhancement of the adsorption capability Ni2+ and subsequent catalytic activity. We further prove that this ligand causes a significant boost in the recyclability of the reactions due to the extremely trivial Ni2+ leaching from the CNT's surface during the reactions.

Synthesis of arylbromides from arenes and Nbromosuccinimide bromosuccinimide (NBS) in acetonitrile - A convenient method for aromatic bromination

Regioselective and chemoselective electrophilic bromination of a wide series of activated arenes using N-bromosuccinimide (NBS) in acetonitrile occurs readily. Environmentally friendly conditions, large substrate scope, and ease of synthesis enhance the utility of this method over other electrophilic bromination conditions.

Recyclable heterogeneous copper oxide on alumina catalyzed coupling of phenols and alcohols with aryl halides under ligand-free conditions

An efficient alumina-supported CuO-catalyzed O-arylation of phenols and aliphatic alcohols with various aryl as well as heteroaryl halides under ligand-free conditions are reported. This protocol provides a variety of diaryl ether and bis-diaryl ether motifs by reacting different aryl/aliphatic halides with differently substituted phenols and saturated alcohols in the presence of a catalytic amount of CuO on alumina and KOH as a base at moderate temperature under nitrogen atmosphere. The described methodology is simple, straightforward and efficient to afford the cross-coupled products in high yields under ligand-free conditions. The explored catalyst is inexpensive, air-stable and recyclable up to three cycles.

Betti base as an efficient ligand for copper-catalyzed ullmann coupling of phenol with aryl halides

GRAPHICAL ABSTRACT A simple, general, and highly efficient Betti base ligand has been developed for copper-catalyzed Ullmann coupling of phenol with aryl halides without the protection of an inert atmosphere. The reaction proceeds smoothly in the presence of K2CO3 as the base and dimethylsulfoxide as the solvent. The catalyst was reused several times with no evident loss of catalytic activity and is environmentally friendly.

Synthesis of diaryl ethers through the copper-catalyzed arylation of phenols with aryl iodides using KF/Al2O3

An efficient synthesis of diaryl ethers by the copper-catalyzed arylation of phenols with a variety of aryl iodide susing KF/Al2O3 as a suitable base and CuI and 1,3 diphenyl-1,3 propandione as the catalyst is described. Copyright Taylor & Francis Group, LLC.

Synthetic Methods and Reactions; 127. Regioselective para Halogenation of Phenols, Phenol Ethers and Anilines with Halodimethylsulfonium Halides

Halodimethylsulfonium halides are efficient regioselective para halogenating agent for activated aromatics, such as phenol, anisole, diphenyl ether and N-alkylanilines.Dihalo and monohalo derivatives of diphenyl ethers were obtained depending upon the reaction conditions.Aniline itself is not suitable in the reaction due to the strong complexation of the lone electron pair of nitrogen with the sulfonium reagent.