695-96-5

Usage

Chemical Properties

White to slightly beige low melting solid

InChI:InChI=1/C6H4BrClO/c7-5-3-4(8)1-2-6(5)9/h1-3,9H

Upstream product

• 106-48-9 4-chloro-phenol 
• 95-56-7 2-hydroxybromobenzene 
• 17005-59-3 4-chlorophenoxytrimethylsilane 
• 121767-82-6 2-Bromo-4-chloro-1-(2-chloro-ethoxy)-benzene 
• 5324-13-0 2,6-dibromo-4-chlorophenol 

Downstream Products

• 13659-24-0 3-bromo-4-chlorophenol 
• 15969-10-5 2-bromo-4-chloro-6-nitro-phenol 
• 33076-44-7 C₁₃H₉BrClNO₄ 
• 32862-04-7 C₁₅H₁₃BrClNO₄ 
• 32862-03-6 C₁₄H₁₁BrClNO₄ 
• 34704-80-8 C₁₁H₁₄BrClNO₂PS 
• 71642-98-3 C₂₀H₁₃Br₃Cl₂O₃ 
• 32862-05-8 C₁₅H₁₃BrClNO₄ 
• 88252-68-0 4-Chloro-2-(1-hydroxy-3-methyl-but-2-enyl)-phenol 
• 73050-84-7 chloro-4 <(hydroxy-1) cyclohexyl>-2 phenol 
• 121767-82-6 2-Bromo-4-chloro-1-(2-chloro-ethoxy)-benzene 
• 76429-65-7 1-(2-bromoethoxy)-2-bromo-4-chlorobenzene 
• 76429-75-9 2-Bromo-1-(3-bromo-propoxy)-4-chloro-benzene 
• 68224-01-1 2-((2-bromo-4-chlorophenoxy)methyl)oxirane 

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.

Directed regioselectiveortho,ortho′-magnesiations of aromatics and heterocycles usingsBu2Mg in toluene

Aryl azoles are ubiquitous as bioactive compounds and their regioselective functionalization is of utmost synthetic importance. Here, we report the development of a toluene-soluble dialkylmagnesium basesBu2Mg. This new reagent allows mild and regioselectiveortho-magnesiations of variousN-arylated pyrazoles and 1,2,3-triazoles as well as arenes bearing oxazoline, phosphorodiamidate or amide directing groups. The resulting diarylmagnesium reagents were further functionalized either by Pd-catalyzed arylation or by trapping reactions with a broad range of electrophiles (aldehydes, ketones, allylic halides, acyl chlorides, Weinreb amides, aryl halides, hydroxylamine benzoates, terminal alkynes). Furthermore, several doubleortho,ortho′-magnesiations were realized in the case of aryl oxazolines,N-aryl pyrazoles as well as 2-aryl-2H-1,2,3-triazoles by simply repeating the magnesiation/electrophile trapping sequence allowing the preparation of valuable 1,2,3-functionalized arenes.

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.

Catalyst-Controlled Regioselective Chlorination of Phenols and Anilines through a Lewis Basic Selenoether Catalyst

We report a highly efficient ortho-selective electrophilic chlorination of phenols utilizing a Lewis basic selenoether catalyst. The selenoether catalyst resulted in comparable selectivities to our previously reported bis-thiourea ortho-selective catalyst, with a catalyst loading as low as 1%. The new catalytic system also allowed us to extend this chemistry to obtain excellent ortho-selectivities for unprotected anilines. The selectivities of this reaction are up to >20:1 ortho/para, while the innate selectivities for phenols and anilines are approximately 1:4 ortho/para. A series of preliminary studies revealed that the substrates require a hydrogen-bonding moiety for selectivity.

Bioinspired catalysis and bromoperoxidase like activity of a multistimuli-responsive supramolecular metallogel: Supramolecular assembly triggered by pi-pi stacking and hydrogen bonding interactions

We report the synthesis and characterization of a new self-assembled VO2-L metallogel. Gel formation was investigated by dissolving VO2-L in various solvents and it was found that water/methanol (1?:?9 (v/v) ratio) induces gel formation. The single crystal X-ray structure of the VO2-L metallogel exhibits C-H?O and N-H?O hydrogen bonding interactions and pi-pi stacking. The VO2-L xerogel obtained after removing the solvents was found to exhibit outstanding performance in catalysis. Bromoperoxidase-like activity of the VO2-L metallogel was also reported. The present catalytic studies are simple and proceed under mild conditions.

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.

o-xylylene bis(triethyl ammonium tribromide) as a mild and recyclable reagent for rapid and regioselective bromination of anilines and phenols

Background: o-Xylylene bis(triethyl ammonium tribromide) (OXBTEATB) as a recyclable and high bromine containing di-(tribromide) reagent has been employed for the bromination of various organic substrates such as phenol and aniline or its derivatives. This catalyst can be recovered and reused several times. Methods: Aryl bromides shown in Table 1, were easily produced from bromination of aromatic compounds by OXBTEATB. This high-yield process lets the reagents to be recycled and reused. Results: As shown in Table 1, substituted anilines, phenols and β-naphthol were found to be the most reactive and immediately converted to the corresponding mono-brominated products by OXBTEATB. Conclusion: OXBTEATB can be considered a solidified bromine. This novel reagent has variable solubility in different polar protic and aprotic solvents but insoluble in non-polar aprotic solvent. Subsequently, OXBTEATB can be recognized as a more useful brominating and regioselective catalyst than the liquid bromine.

Synthesis, kinetics, and mechanism of bromophenols by N-bromophthalimide in aqueous acetic acid

The kinetics and mechanism of bromination of phenol and its substituents, viz. 4-chlorophenol, 4-bromophenol, 4-methylphenol, and 4-methoxyphenol by N-bromophthalimide (NBP) in the presence of mercuric acetate in the temperature range of 303–318?K in aqueous acetic acid medium have been investigated. The reaction follows first-order dependence on [NBP] and fractional order dependence of rate on [Phenol]. The activation parameters have been evaluated, and based on the observed kinetic results the probable mechanism has been proposed. Observed kinetic features and Hammett's reaction constant (ρ) suggests that bromination occurs through electrophilic substitution of bromonium ion (Br+) into the aromatic ring in the transition state. Large negative entropy of activation values probably suggests the rigid nature of transition state.

Expedient Access to 2-Benzazepines by Palladium-Catalyzed C?H Activation: Identification of a Unique Hsp90 Inhibitor Scaffold

Bioactive 2-benzazepines were accessed in an atom- and step-economical manner through a versatile palladium-catalyzed C?H activation strategy. The C?H arylation required low catalyst loading and a mild base, which was reflected by a broad scope and high functional-group tolerance. The benzotriazolodiazepinones were identified as new heat shock protein 90 (Hsp90) inhibiting lead compounds, with considerable potential for anti-cancer applications.

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.