615-56-5

Usage

Uses

Used in Environmental Testing and Research:
3,4-Dibromophenol is used as a standard in environmental testing and research for the determination of urinary bromophenols (BrPs). These bromophenols serve as potential biomarkers for human exposure to polybrominated diphenyl ethers (PBDEs), which are a group of persistent organic pollutants known for their adverse effects on human health and the environment.
The application of 3,4-dibromophenol in this context is crucial for understanding the extent of human exposure to PBDEs and the potential health risks associated with them. Gas chromatography-tandem mass spectrometry (GC-MS/MS) is a widely used analytical technique for the detection and quantification of BrPs in biological samples, such as urine.

InChI:InChI=1/C6H4Br2O/c7-5-2-1-4(9)3-6(5)8/h1-3,9H

Upstream product

• 583-53-9 2,3-dibromobenzene 
• 56-23-5 tetrachloromethane 
• 591-20-8 3-Bromophenol 
• 7726-95-6 bromine 
• 98-95-3 nitrobenzene 
• 1086964-79-5 tert-butyl(3,4-dibromophenoxy)dimethylsilane 
• 108-95-2 phenol 
• 634603-83-1 3-bromo-4-nitrosophenol 
• 57383-80-9 2,3-dibromophenol 
• 615-55-4 3,4-dibromoaniline 

Downstream Products

• 14400-94-3 2,3,4,6-tetrabromophenol 
• 30757-50-7 4-hydroxy-1,2-benzenedicarbonitrile 
• 14401-61-7 2,4,5-tribromophenol 
• 138507-65-0 2,3,4-tribromo-phenol 
• 886748-36-3 2,3,4-tribromophenyl acetate 
• 855429-70-8 2,4,5-tribromophenyl acetate 
• 182677-30-1 2,2',3,4,4'5'-hexabromodiphenyl ether 
• 207122-16-5 2,3,4,6-tetrabromophenyl 2,4,5-tribromophenyl ether 
• 80323-72-4 4-methoxyphthalonitrile 
• 62415-74-1 3,4-dibromoanisole 

Relevant academic research and scientific papers

Synthetic method of 2-(3,4-dibromophenoxy)acetic acid

The invention discloses a synthetic method of 2-(3,4-dibromophenoxy)acetic acid, belonging to the technical field of organic synthesis. Aiming at the problems that at present, hydrogen chloride is continuously filled in the reaction process of 2-(3,4-dibr

Regioselectivity in the aryne cross-coupling of aryllithiums with functionalized 1,2-dibromobenzenes

Tri- and tetrasubstituted ortho-bromobiaryls have been synthesized in good-to-excellent yields by aryne cross-coupling reactions starting from 1,3-dimethoxybenzene and functionalized 1,2-dibromobenzenes. This study outlines the influence of the 1,2-dibromobenzene precursor as well as the reaction temperature on the outcome of the aryl-aryl bond formation and indicates, in the case of dissymmetrical benzyne precursors, how structural parameters (electronic effects, steric hindrance, temperature, etc.) control the regioselectivity of the aryne cross-coupling reactions. A wide range of o,o′-tri- and-tetrasubstituted biphenyls have been prepared by a transition-metal-free "aryne" cross-coupling starting from 2,6-dimethoxyphenyllithium and various functionalized 1,2-dibromobenzenes. Mechanistic investigations outline the key parameters that govern both the aryl-aryl bond formation and the regioselectivity of the reaction with dissymmetrical aryne precursors. Copyright

Synthesis of phthalonitriles using a palladium catalyst

An easy synthetic method to obtain phthalonitriles from o-dibromobenzenes under mild conditions in high yields using Zn(CN)2 and a catalytic amount of tris(dibenzylideneacetone)dipalladium and 1,1′- bis(diphenylphosphino)ferrocene is described. Georg Thieme Verlag Stuttgart.

Polybrominated diphenyl ethers (BDEs); preparation of reference standards and fluorinated internal analytical standards

Four new difluorinated tetra- and pentabromo BDE internal standards for GC-MS/GC-ECD analysis, 2F-BDE 47, 2F-BDE 85, 2F-BDE 99 and 2F-BDE 119, have been prepared in 98-99.0% purity, mainly by coupling of the new tribromodifluorophenols (19-21) and symmetr

Synthesis of polybrominated diphenyl ethers and their capacity to induce CYP1A by the Ah receptor mediated pathway

Polybrominated diphenyl ethers (PBDEs) have become widely distributed as environmental contaminants due to their use as flame retardants. Their structural similarity to other halogenated aromatic pollutants has led to speculation that they might share toxicological properties such as hepatic enzyme induction. In this work we synthesized a number of PBDE congeners, studied their affinity for rat hepatic Ah receptor through competitive binding assays, and determined their ability to induce hepatic cytochrome P-450 enzymes by means of EROD (ethoxyre-sorufin-O-deethylase) assays in human, rat, chick, and rainbow trout cells. Both pure PBDE congeners and commercial PBDE mixtures had Ah receptor binding affinities 10-2-10-5 times that of 2,3,7,8-tetrachlorodibenzo-p-dioxin. In contrast with polychlorinated biphenyls, Ah receptor binding affinities of PBDEs could not be related to the planarity of the molecule, possibly because the large size of the bromine atoms expands the Ah receptor's binding site. EROD activities of the PBDE congeners followed a similar rank order in all cells. Some congeners, notably PBDE 85, did not follow the usual trend in which strength of Ah receptor binding affinity paralleled P-450 induction potency. Use of the gel retardation assay with a synthetic oligonucleotide indicated that in these cases the liganded Ah receptor failed to bind to the DNA recognition sequence.

Selective and one-pot formation of phenols by anodic oxidation

Direct monohydroxylation of benzene and substituted benzenes was successfully performed by anodic oxidation to form the corresponding phenol derivatives in good yields. The anodic oxidation was generally carried out in a mixed solvent of trifluoroacetic acid and dichloromethane containing triethylamine using a divided cell equipped with a platinum plate as the anode, a carbon rod as the cathode. Benzene derivatives having electron withdrawing groups were suitable for the present electrochemical oxidation. It was clarified that aryltrifluoroacetates were formed as the initial products from the reaction of the radical cations, generated by one electron transfer from the substrates, with trifluoroacetic acid, followed by hydrolysis during work-up to give the corresponding phenols.

Copper(I)-Induced Bromo-Hydrogen Exchange of 2,3-Dibromoanilines

The copper(I)-induced bromine-hydrogen exchange reaction of 2,3-dibromoaniline and 5-substituted 2,3-dibromoanilines in the 2-position has been kinetically studied in water-acetic acid-hydrochloric acid medium at 90 deg C.The dehalogenation reaction is of second order, first order in both substrate and Cu+, and may be interpreted as a reductive substitution, composed of two one-electron steps.The 2,3-dibromophenol was only qualitatively investigated, but gave similar results.

Process for producing polyhalogenated phenols

A process for producing polyhalogenated phenol by mixing a polyhalogenated aniline with an aqueous sulfuric acid solution to obtain a suspension of fine particles of polyhalogenated aniline sulfate having the particle size of 50 μ or less, diazotizing the polyhalogenated aniline sulfate to obtain polyhalogenate benzenediazonium sulfate, hydrolyzing the resulting benzenediazonium sulfate by heating it as such, recycling to the diazotization step the aqueous sulfuric acid solution from which the desired polyhalogenated phenol has been separated.