615-58-7

Usage

Uses

Used in Marine Environmental Applications:
2,4-Dibromophenol is used as an inhibitor for controlling microbial activity in marine sediments, which can be beneficial for maintaining the balance of marine ecosystems and preventing the overgrowth of certain microorganisms that may disrupt the natural environment.
Used in Chemical Synthesis:
2,4-Dibromophenol can be utilized as a starting material or intermediate in the synthesis of various organic compounds, particularly those requiring a brominated aromatic ring. Its electrochemical properties make it a candidate for green chemistry approaches to produce environmentally friendly products.
Used in Pharmaceutical Research:
Given its ability to inhibit microbial activity, 2,4-Dibromophenol may be investigated for its potential use in the development of new antimicrobial agents, particularly for applications where traditional antibiotics may be less effective.
Used in Electrochemical Studies:
As a subject of electrochemical hydrodehalogenation research, 2,4-Dibromophenol can be used in the development of new electrochemical cell technologies, potentially contributing to advancements in energy storage and conversion systems.
Used in Material Science:
The electrochemical properties of 2,4-Dibromophenol may also find applications in the development of new materials with specific electronic or conductive properties, particularly in the field of organic electronics and sensors.

Synthesis Reference(s)

Tetrahedron, 45, p. 7869, 1989 DOI: 10.1016/S0040-4020(01)85800-2

Purification Methods

Crystallise the phenol from CHCl3 at -40o, or distil it in a vacuum. [Beilstein 6 H 202, 6 I 106, 6 II 188, 6 III 753, 6 IV 1061.]

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

Upstream product

• 93-99-2 benzoic acid phenyl ester 
• 106-41-2 4-bromo-phenol 
• 615-57-6 2,4-dibromo-aniline 
• 3147-55-5 3,5-dibromosalicylic acid 
• 13130-23-9 3,5-dibromo-2-methoxybenzoic acid 
• 142-04-1 aniline hydrochloride 
• 62-53-3 aniline 
• 118-79-6 2,4,6-tribromophenol 
• 108-95-2 phenol 
• 95-56-7 2-hydroxybromobenzene 
• 917-54-4 methyllithium 
• 74-88-4 methyl iodide 
• 64-19-7 acetic acid 
• 7726-95-6 bromine 

Downstream Products

• 81-52-7 2-bromoquinizarine 
• 89-55-4 5-bromosalicyclic acid 
• 2183-54-2 2-hydroxy-3,5-dibromobenzenemethanol 
• 129633-41-6 2,4-Dibromo-1-butoxybenzene 
• 121-69-7 N,N-dimethyl-aniline 
• 15969-09-2 2,4-dibromo-6-nitrophenol 
• 615-54-3 1,2,4-tribromobenzene 
• 53872-06-3 2,4-dibromo-6-iodophenol 
• 21702-84-1 2,4-dibromoanisole 
• 19430-77-4 dichlorophosphoric acid-(2,4-dibromo-phenyl ester) 
• 4526-56-1 2,4-dibromo-6-chlorophenol 

Relevant academic research and scientific papers

Halogenated method of aromatic compound

The invention belongs to the field of organic synthesis, and particularly relates to synthesis of aromatic halogens, in particular to arylamine. The invention discloses a synthesis method of a corresponding ortho-halogenated product from aromatic compounds such as carbazole and phenol. The method comprises the following steps: adding a metal sulfonate salt catalyst, aromatic amine, carbazole, phenol and other hydrogen - heteroatom-containing aromatic compound reaction substrates, a halogenation reagent and a reaction solvent at a specific reaction temperature. After the drying agent is dried, the yield of the reaction product and the nuclear magnetic characterization determining structure are determined by column chromatography. The reaction product yield is determined by gas chromatography. By adopting the method, under the cheap metal salt catalyst, a plurality of ortho-substituted brominated and chloro products can be obtained with moderate to excellent yield.

A convenient and efficient H2SO4-promoted regioselective monobromination of phenol derivatives using N-bromosuccinimide

A convenient, rapid H2SO4-promoted regioselective monobromination reaction with N-bromosuccinimide was developed. The desired para-monobrominated or ortho-monobrominated products of phenol derivatives were obtained in good to excellent yields with high selectivity. Regioselective chlorination and iodination were also achieved in the presence of H2SO4 using N-chlorosuccinimide and N-iodosuccinimide, respectively.

Regioselective monobromination of phenols with KBr and ZnAl–BrO3?–layered double hydroxides

The regioselective mono-bromination of phenols has been successfully developed with KBr and ZnAl–BrO3?–layered double hydroxides (abbreviated as ZnAl–BrO3?–LDHs) as brominating reagents. The para site is much favorable and the ortho site takes the priority if para site is occupied. This reaction featured with excellent regioselectivity, cheap brominating reagents, mild reaction condition, high atom economy, broad substrate scope, and provided an efficient method to synthesize bromophenols.

Preparation method of monobrominated aromatic hydrocarbon compound

The invention discloses a preparation method of a monobrominated aromatic hydrocarbon compound, which comprises the following steps: by using an aromatic hydrocarbon compound as a raw material, wateras a solvent and liquid bromine as a bromine source, reacting at room temperature for 4.5 hours, and after the reaction is finished, carrying out aftertreatment on the obtained reaction mixed solutionto obtain the monobrominated target product. According to the method, a high-selectivity bromination method is realized on the aromatic hydrocarbon compound under the action of water, and the monobrominated aromatic hydrocarbon compound is prepared. The method is high in reaction applicability, mild in condition, high in yield, green and environment-friendly.

Mild and Regioselective Bromination of Phenols with TMSBr

In this work, an unexpected promoting effect of by-product thioether was observed, leading to a mild and regioselective bromination of phenols with TMSBr. This method can tolerate a series of functional groups such as the reactive methoxyl, amide, fluoro, chloro, bromo, aldehyde, ketone and ester groups, and has the potential to recycle the by-product thioether and isolate the desired product under column chromatography-free conditions. Mechanism studies revealed that O–H···S hydrogen bond may be formed between phenol and by-product thioether. Possibly owing to the steric hindrance effect from by-product thioether, the electrophilic bromination at para-position of phenols is much favorable.

A phenol compound high regioselective bromination method

The invention discloses a phenol compound high regioselective bromination of the method, the method to trimethyl silane as brominating agent, in order to aryl sulfoxide as activator, with the phenol compound in the 0 - 50 °C lower, in a solvent, the reaction is stirred under an atmosphere of nitrogen at 1 - 12 hours, to realize the phenol compound high regioselective bromination, filtered, extraction columns chromatography separation to obtain the bromo phenol compound. This invention adopts the aryl sulfoxide as activator, sulfoxide substituted Kiev, on the one hand so that the phenol compound bromo the higher selectivity of the reaction region, and when the phenol compound hydroxy alignment not substituted basetime, regional selective para - bromo product, when the phenol compound hydroxy position there is substituted basetime, selective ortho - bromo product obtained; on the other hand if it through the filter, the extraction can be realized at the same time the isolation and purification of the recycling of the by-product, compared with column chromatography, reduces the separation and purification cost.

Synthesis of new oxido-vanadium complexes: Catalytic properties and cytotoxicity

Reaction of 2,3-dihydroxy benzaldehyde with 2-({2-amino phenyl}diazenyl)phenol afforded the ligand 3-(2-(2-hydroxyphenyl)diazenyl)- 4-alkylphenyliminomethyl)benzene-1,2-diol. Reaction of H2L with VOSO4. 5H2O gave the oxido-vanadium(IV) complexes [(L)VO], which exhibited a quasi-reversible oxidative cyclic voltammetric response in a V(IV)/V(V) oxidative process. The complexes act as catalysts in the oxidation of organic thioethers and bromination of phenol. Their cytotoxic properties were examined for three cancer cell lines.

A bromo-capped diruthenium(i,i) N-heterocyclic carbene compound for in situ bromine generation with NBS: Catalytic olefin aziridination reactions

A bromo-capped metal-metal bonded diruthenium(i,i) complex Ru2(CO)4(PIN)2Br2 (1) (PIN = 1-isopropyl-3-(5,7-dimethyl-1,8-naphthyrid-2-yl)imidazol-2-ylidene) generates bromine with N-bromosuccinimide (NBS) at room temperature. Cycloalkene and stilbene are readily brominated by stoichiometric reactions with 1 and NBS. An analysis of the dibrominated products suggests the formation of cyclic bromonium intermediates indicating in situ Br2 generation. Complex 2, an iodide analogue of 1, is also synthesized. The reaction of 2 with N-iodosuccinimide releases I2, which is confirmed by the starch-iodine test. The catalytic utility of 1 is examined for the bromination of phenol. Catalyst 1, in combination with NBS and base, exhibits regioselectivity towards monobrominated products. Furthermore, efficient olefin aziridination is demonstrated utilizing catalyst 1 in the presence of NBS, K2CO3 and TsNH2.

1,1,2,2-Tetrahydroperoxy-1,2-Diphenylethane: An efficient and high oxygen content oxidant in various oxidative reactions

Several oxidative approaches namely thiocyanation of aromatic compounds, epoxidation of alkenes, amidation of aromatic aldehydes, epoxidation of α β-unsaturated ketones, oxidation of sulfides to sulfoxides and sulfones, bayer-villeger reaction, bromination and iodation of aniline and phenol derivatives oxidative esterification, oxidation of pyridines and oxidation of secondary, allylic and benzyllic alcohols were carried out using 1,1,2,2-Tetrahydroperoxy-1,2-Diphenylethane as the potential solid oxidant which can be stored for several months without any loss in its activity. All of the procedures were accomplished via mild reaction conditions and the products were afforded in high yields and short reaction times.

Practical, mild and efficient electrophilic bromination of phenols by a new I(iii)-based reagent: The PIDA-AlBr3 system

A practical electrophilic bromination procedure for phenols and phenol-ethers was developed under efficient and very mild reaction conditions. A broad scope of arenes was investigated, including the benzimidazole and carbazole core as well as analgesics such as naproxen and paracetamol. The new I(iii)-based brominating reagent PhIOAcBr is operationally easy to prepare by mixing PIDA and AlBr3. Our DFT calculations suggest that this is likely the brominating active species, which is prepared in situ or isolated after centrifugation. Its stability at 4 °C after preparation was confirmed over a period of one month and no significant loss of its reactivity was observed. Additionally, the gram-scale bromination of 2-naphthol proceeds with excellent yields. Even for sterically hindered substrates, a moderately good reactivity is observed.