2040-88-2

Usage

Uses

Used in Pharmaceutical Synthesis:
2-bromo-6-chloro-phenol is utilized as an intermediate in the production of pharmaceuticals, contributing to the development of new medications and therapeutic agents.
Used in Agrochemical Production:
In the agrochemical industry, 2-bromo-6-chloro-phenol serves as an intermediate, playing a crucial role in the synthesis of compounds that protect crops from pests and diseases.
Used in Dye Manufacturing:
2-bromo-6-chloro-phenol is also employed as an intermediate in the dye industry, where it aids in the creation of various colorants for different applications.
Used as a Disinfectant:
2-bromo-6-chloro-phenol is used for its disinfectant properties, helping to eliminate harmful microorganisms in various settings.
Used as a Fungicide:
Furthermore, it is applied as a fungicide to control fungal growth, which is beneficial in both agricultural and industrial contexts.

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

Upstream product

• 95-57-8 2-monochlorophenol 
• 4526-56-1 2,4-dibromo-6-chlorophenol 
• 108-95-2 phenol 
• 23951-01-1 <2-D>-phenol 
• 7305-01-3 o-chlorophenyl dimethylcarbamate 
• 1360939-08-7 2-deuterio-phenyl dimethylcarbamate 
• 6969-90-0 phenyl N,N-dimethylcarbamate 
• 7305-04-6 o-bromophenyl N,N-dimethylcarbamate 
• 1534364-16-3 2-bromo-6-chlorophenyl dimethylcarbamate 
• 95-56-7 2-hydroxybromobenzene 
• 104892-01-5 2-Bromo-6-chloro-phenol; compound with dimethyl-amine 

Downstream Products

• 21244-80-4 2-Brom-6-chlor-phenyl-oxyacetonitril 
• 1010390-50-7 C₈H₈BrClO 
• 1043912-15-7 2-bromo-6-chloro-1-trifluoromethanesulfonyloxybenzene 
• 1449472-59-6 2-chloro-6-(trimethylsilyl)phenyl trifluoromethanesulfonate 

Relevant academic research and scientific papers

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.

Ammonium Salt-Catalyzed Highly Practical Ortho-Selective Monohalogenation and Phenylselenation of Phenols: Scope and Applications

An ortho-selective ammonium chloride salt-catalyzed direct C-H monohalogenation of phenols and 1,1′-bi-2-naphthol (BINOL) with 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) as the chlorinating agent has been developed. The catalyst loading was low (down to 0.01 mol %) and the reaction conditions were very mild. A wide range of substrates including BINOLs were compatible with this catalytic protocol. Chlorinated BINOLs are useful synthons for the synthesis of a wide range of unsymmetrical 3-aryl BINOLs that are not easily accessible. In addition, the same catalytic system can facilitate the ortho-selective selenylation of phenols.

Regioselective monobromination of aromatics via a halogen bond acceptor-donor interaction of catalytic thioamide and N-bromosuccinimide

Regioselective monobromination of various aromatics was achieved at room temperature using N-bromosuccinimide and 5 mol% of thioamides in acetonitrile. With thiourea as catalyst, activated aromatics, such as anisole, acetanilide, benzamide and phenol analogues containing electron donating or withdrawing groups, were brominated with high regioselectivity. Room temperature brominations of weakly activated aromatics and deactivated 9-fluorenone were accomplished by 5 mol% thioacetamide, higher substrates concentrations and longer reaction times. A backbonding of the bromine lone pairs with the π*of C[dbnd]S group and a halogen bond between the halogen bond donor bromine and the halogen bond acceptor sulfur of the thioamide are thought to be the principal interactions and cause of N-bromosuccinimide activation.

Room-temperature Pd-catalyzed C-H chlorination by weak coordination: One-pot synthesis of 2-chlorophenols with excellent regioselectivity

A room-temperature Pd(ii)-catalyzed regioselective chlorination reaction has been developed for a facile one-pot synthesis of a broad range of 2-chlorophenols. The reaction demonstrates an excellent regioselectivity and reactivity for C-H chlorination. This reaction represents one of the rare examples of mild C-H functionalization at ambient temperature.

Vanadate-dependent bromoperoxidases from Ascophyllum nodosum in the synthesis of brominated phenols and pyrroles

Bromoperoxidases from the brown alga Ascophyllum nodosum, abbreviated as VBrPO(AnI) and VBrPO(AnII), show 41% sequence homology and differ by a factor of two in the percentage of α-helical secondary structures. Protein monomers organize into homodimers for VBrPO(AnI) and hexamers for VBrPO(AnII). Bromoperoxidase II binds hydrogen peroxide and bromide by approximately one order of magnitude stronger than VBrPO(AnI). In oxidation catalysis, bromoperoxidases I and II turn over hydrogen peroxide and bromide similarly fast, yielding in morpholine-4-ethanesulfonic acid (MES)-buffered aqueous tert-butanol (pH 6.2) molecular bromine as reagent for electrophilic hydrocarbon bromination. Alternative compounds, such as tribromide and hypobromous acid are not sufficiently electrophilic for being directly involved in carbon-bromine bond formation. A decrease in electrophilicity from bromine via hypobromous acid to tribromide correlates in a frontier molecular orbital (FMO) analysis with larger energy gaps between the π-type HOMO of, for example, an alkene and the σ*Br,X-type LUMO of the bromination reagent. By using this approach, the reactivity of substrates and selectivity for carbon-bromine bond formation in reactions mediated by vanadate-dependent bromoperoxidases become predictable, as exemplified by the synthesis of bromopyrroles occurring naturally in marine sponges of the genera Agelas, Acanthella, and Axinella. The Royal Society of Chemistry.

Selectivity enhancement of aromatic halogenation reactions at the micellar interface: Effect of highly ionic media

Halogenation (iodination and bromination) of various aromatic compounds has been studied in micellar media in order to observe the effect on regioselectivity and conversion of the reaction. The addition of surfactant causes a change in the chemical shifts of the aromatic proton resonance of phenol which proves the orientation of the aromatic compound on the micellar surface. However, increase in ionic strength of the reaction media affects the selectivity of reaction by disturbing this spatial orientation of the aromatic compound in the micelle. Selectivity towards particular isomers is dependent on the concentration of the surfactant. In bromination of chlorobenzene (deactivated aromatic compound) enhancement in selectivity and conversion towards the para isomer has been observed.

Facile p-toluenesulfonic acid-promoted para-selective monobromination and chlorination of phenol and analogues

para-Regioselective bromination of phenol and analogues, promoted by p-toluenesulfonic acid, is achieved in high to excellent yields at room temperature with N-bromosuccinimide. Chlorination with N-chlorosuccinimide and catalysed by p-toluenesulfonic acid also gives para-chlorinated phenol analogues in good yields at room temperature. para-Bromination of phenol, promoted by p-toluenesulfonic acid, is achieved in excellent yields at room temperature with N-bromosuccinimide. p-Toluenesulfonic acid is also effective as a promoter of para-chlorination with N-chlorosuccinimide.

Decoupling deprotonation from metalation: Thia-fries rearrangement

(Chemical Equation Presented) Label-enabled: Studies with 2H-, 18O-, and 34S-labeled aryl triflates show that lithium diisopropylamide-mediated thia-Fries rearrangement proceeds through an irreversible ortho deprotonation (see scheme; DIPA = diisopropylamine, LDA = lithium diisopropylamide). In contrast, ortho metalation results exclusively in the generation of a benzyne.

A new class of bradykinin B1 receptor antagonists with high oral bioavailability and minimal PXR activity

The design and synthesis of a novel class of human bradykinin B1 antagonists featuring difluoroethyl ether and isoxazole carboxamide moieties are disclosed. Compound 7g displayed excellent pharmacokinetic properties, efficient ex vivo receptor occupancy, and low potential for P450 induction via PXR activation.