5324-13-0

Basic information

• Product Name: 2,6-DIBROMO-4-CHLOROPHENOL
• Synonyms: 4-CHLORO-2,6-DIBROMOPHENOL;2,6-DIBROMO-4-CHLOROPHENOL;2,6-DIBROMO-4-CHLOROPHENOL 99%MIN;NSC 2863
• CAS NO: 5324-13-0
• Molecular Formula: C₆H₃Br₂ClO
• Molecular Weight: 286.35
• Product Categories: Bromine Compounds;Chlorine Compounds;Phenols;alkyl bromide|alkyl chloride
• Mol File: 5324-13-0.mol

Chemical Properties

• Melting Point: 92℃ (ethanol )
• Boiling Point: 245°C at 760 mmHg
• Flash Point: 102°C
• Appearance: /
• Density: 2.166g/cm³
• Vapor Pressure: 0.0188mmHg at 25°C
• Refractive Index: 1.653
• Storage Temp.: Room temperature.
• CAS DataBase Reference: 2,6-DIBROMO-4-CHLOROPHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-DIBROMO-4-CHLOROPHENOL(5324-13-0)
• EPA Substance Registry System: 2,6-DIBROMO-4-CHLOROPHENOL(5324-13-0)

Safety Data

• Hazardous Substances Data: 5324-13-0(Hazardous Substances Data)

Usage

Uses

Used in Chemical Production:
2,6-Dibromo-4-chlorophenol is used as an intermediate in the production of other chemicals, particularly pesticides. Its halogenated nature contributes to its reactivity, making it a valuable component in the synthesis of various chemical products.
Used in Water Treatment:
Due to its presence as a contaminant in surface waters, 2,6-dibromo-4-chlorophenol is often targeted for removal in water treatment procedures. Its semi-volatile nature and toxicity necessitate the development of effective methods to mitigate its environmental impact and protect water quality.

InChI:InChI=1/C6H3Br2ClO/c7-4-1-3(9)2-5(8)6(4)10/h1-2,10H

Upstream product

• 106-48-9 4-chloro-phenol 
• 1679-18-1 4-Chlorophenylboronic acid 
• 64-17-5 ethanol 
• 17587-83-6 2,4,6-tribromo-4-chloro-cyclohexa-2,5-dienone 
• 7782-99-2 sulphurous acid 
• 10035-10-6 hydrogen bromide 
• 106-47-8 4-chloro-aniline 
• 64-19-7 acetic acid 
• 7726-95-6 bromine 
• 67-66-3 chloroform 
• 62-53-3 aniline 

Downstream Products

• 1313182-82-9 2-bromo-4-chloro-6-(trimethylsilyl)phenol 
• 174913-44-1 2,6-dibromo-4-chloroanisole 
• 28719-55-3 dibromotriphenylbismuth 
• 851392-40-0 bis(2,6-dibromo-4-chlorophenoxy)triphenylbismuth 
• 861800-85-3 2,6-dibromo-4-chloro-3,5-dinitro-anisole 
• 116995-40-5 2,6-dibromo-4-chloro-3,5-dinitro-phenol 
• 15969-10-5 2-bromo-4-chloro-6-nitro-phenol 
• 17587-83-6 2,4,6-tribromo-4-chloro-cyclohexa-2,5-dienone 
• 19643-45-9 2,6-dibromo-1,4-benzoquinone 
• 20244-57-9 2,6-Dibrom-4,4-dichlor-2,5-cyclohexadienon-⁽¹⁾ 
• 140682-50-4 bis(2,6-dibromo-4-chlorophenoxy)trichlorophosphorane 
• 1570-64-5 2-methyl-4-chlorophenol 
• 1123-63-3 2,6-dimethyl-4-chlorophenol 
• 76800-28-7 5,5'-dichloro-2,2'-dihydroxy-3,3'-dimethylbiphenyl 

Relevant articles and documents

A scalable and green one-minute synthesis of substituted phenols

A mild, green and highly efficient protocol was developed for the synthesis of substituted phenols via ipso-hydroxylation of arylboronic acids in ethanol. The method utilizes the combination of aqueous hydrogen peroxide as the oxidant and H2O2/HBr as the reagent under unprecedentedly simple and convenient conditions. A wide range of arylboronic acids were smoothly transformed into substituted phenols in very good to excellent yields without chromatographic purification. The reaction is scalable up to at least 5 grams at room temperature with one-minute reaction time and can be combined in a one-pot sequence with bromination and Pd-catalyzed cross-coupling to generate more diverse, highly substituted phenols.

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.

Method for photocatalytic synthesis of polybrominated phenol compound in water phase

The invention discloses a method for photocatalytic synthesis of a polybrominated phenol compound in a water phase, comprising the following steps: adding a catalytic amount of a radical initiator, aphenol derivative and low-toxic and cheap bromide salt and water into a reaction vessel, reacting at room temperature at 5 W power in a photocatalytic reactor for a certain period, extracting with ethyl acetate and then re-crystallizing to obtain a polybrominated phenol compound. The above radical initiator is eosin, azobisisobutanol, sodium persulfate, ammonium persulfate or potassium persulfate.The free radical initiator and the bromine salt are cheap and easily available, and the method is an ideal synthesis method of the polybrominated phenol compound. According to the method, low-toxicity bromine salt instead of liquid bromine is used to carry out a bromination reaction, unstable and explosive hydrogen peroxide is replaced with the cheap and easily-available free radical initiator, and an emerging photocatalytic method is used. The polybrominated phenol compound can be obtained in a high yield by only using a 5W power lamp for the reaction, the reaction selectivity is high, by-products are less, and the post-treatment is simple.

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.

Aerobic oxybromination of phenols catalyzed by sodium nitrite under mild conditions

An efficient catalytic system for oxybromination of phenols under mild conditions has been developed, which utilizes sodium nitrite as the catalyst, dioxygen or air as the terminal oxidant, aqueous hydrobromic acid or molecular bromine as the bromine resource. From both the atom-economic and environmental points of view, the developed protocol is expected to provide a valuable synthetic method for practical applications in laboratory or industry. Georg Thieme Verlag Stuttgart - New York.

Regioselective synthesis of phenols and halophenols from arylboronie acids using solid poly(N-vinylpyrrolidone)/hydrogen peroxide and poly(4-vinylpyridine) /hydrogen peroxide complexes

Solid hydrogen peroxide complexes based on poly(N-vinylpyrrolidone) and poly(4-vinylpyridine) were prepared and used as solid hydroxylating reagents. These solid hydrogen peroxide equivalents are found to be much safer, convenient and efficient reagent systems for the ipso-hydroxylation of arylboronie acids to the corresponding phenols in high yields at a faster rate. The versatility of the reagents has been further expanded for the one-pot synthesis of halophenols. Density functional theory calculations were carried out on hydrogen peroxide complexes of N-ethylpyrrolidone and 4-ethylpyridine as models to get a better understanding of structure and behavior of hydrogen peroxide complexes of the polymers poly(N-vinylpyrrolidone) and poly(4-vinylpyridine) compared to aqueous hydrogen peroxide.

Regioselective monobromination of substituted phenols in the presence of β-cyclodextrin

Cyclodextrin acts as a restricting nanovessel to enhance regioselectivity in bromination of substituted phenols such as 3-nitrophenol, 2-chlorophenol, 3-chlorophenol, and 4-chlorophenol. In contrast to solution bromination, cyclodextrin facilitates regioselective monobromination and formation of polybrominated products are substantially reduced. Selectivities in brominations are also observed in water and in the solid state. The observed results are rationalized on the basis of specific modes of inclusion of substituted phenols inside the cyclodextrin cavity and find strong support from energy minimization studies and 1H-1H NOESY.

Chemical modification of chlorophenols for their gas-chromatographic determination in water

A two-stage chemical modification involving bromination in aqueous solution followed by acylation of the resulting bromochlorophenols in the extract was studied as a way to decrease the detection limit of chlorophenols in water.

Synthesis and Structural Characterization of Poly(dihalophenylene oxide)s Based on the Thermal Decomposition of Bis (4-chloro-2-6-dibromophenoxo) Ethylenediamine Copper (II) Complex in Toluene

Synthesis of poly (dihalophenylene oxides) by thermal decomposition of bis (4-chloro-2,6-dibromophenoxo) ethylenediamine copper (II) complex was achieved in toluene at 70 deg C.The structural characterization of polymer were carried out by FTIR, 1H-NMR an