15969-09-2

Usage

Uses

Used in Dye and Pigment Manufacturing:
2,4-Dibromo-6-nitrophenol is utilized as a key intermediate in the production of various dyes and pigments. Its chemical structure allows for the creation of a diverse range of colorants that are used in different industries, such as textiles, plastics, and paints. The versatility of 2,4-DIBROMO-6-NITROPHENOL in organic synthesis makes it an essential component in the formulation of these colorants.
Used in Organic Synthesis:
In the field of organic chemistry, 2,4-dibromo-6-nitrophenol serves as a valuable building block for the synthesis of more complex molecules. Its reactivity and the presence of multiple functional groups make it a suitable candidate for various chemical reactions, such as substitution, addition, and coupling reactions. This allows chemists to create a wide array of compounds with potential applications in pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Research and Development:
2,4-Dibromo-6-nitrophenol is also employed in research settings, where it is used as a model compound to study the effects of bromination and nitration on the properties of phenolic compounds. This helps in understanding the reactivity and behavior of similar compounds, which can be crucial for the development of new synthetic routes and the discovery of novel compounds with potential applications in various industries.

InChI:InChI=1/C6H3Br2NO3/c7-3-1-4(8)6(10)5(2-3)9(11)12/h1-2,10H

Upstream product

• 104-91-6 p-nitrosophenol 
• 615-58-7 2,4-dibromophenol 
• 616-85-3 4-hydroxy-3-nitrobenzene sulfonic acid 
• 88-28-8 4-hydroxy-5-nitro-benzene-1,3-disulfonic acid 
• 109-95-5 ethyl nitrite 
• 118-79-6 2,4,6-tribromophenol 
• 7726-95-6 bromine 
• 7727-15-3 aluminium bromide 
• 88-75-5 2-hydroxynitrobenzene 
• 60-29-7 diethyl ether 
• 64-17-5 ethanol 
• 64-19-7 acetic acid 
• 7697-37-2 nitric acid 
• 29906-33-0 4-diazo-2-nitrophenol 

Downstream Products

• 99-28-5 2,6-dibromo-4-nitrophenol 
• 10539-14-7 2‐amino‐4,6‐dibromophenol 
• 2316-50-9 2-bromo-4,6-dinitrophenol 
• 55229-73-7 acetic acid-(2,4-dibromo-6-nitro-phenyl ester) 
• 121056-06-2 <3,5-(2)H2>-2-Hydroxyaniline 
• 35153-86-7 2,4-Dibrom-6-nitro-phenyl-iminocarbonat 
• 488-48-2 tetrabromobenzoquinone 
• 5847-59-6 2-bromo-4-nitrophenol 
• 55202-09-0 2-acetamido-4,6-dibromophenol 
• 857949-26-9 2-acetoxy-1-acetylamino-3,5-dibromo-benzene 
• 87013-12-5 2-acetamido-6-bromo-1,4-benzoquinone 
• 55229-71-5 acetic acid-(2-bromo-4,6-dinitro-phenyl ester) 
• 725241-64-5 4,6-dibromo-2-nitroanisole 
• 6161-61-1 2,3,4,5-tetrabromoanisole 

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.

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.

Graphene Oxide Promoted Oxidative Bromination of Anilines and Phenols in Water

The mildly acidic and oxidative nature of graphene oxide, with its large surface area available for catalytic activity, has been explored in aromatic nuclear bromination chemistry for the first time. The versatile catalytic activity of graphene oxide (GO) has been used to selectively and rapidly brominate anilines and phenols in water. The best results were obtained at ambient temperatures using molecular bromine in a protocol promoted by oxidative bromination catalyzed by GO; these transformations proceeded with 100% atom economy with respect to bromine and high selectivities for the tribromoanilines and -phenols. Reduced graphene oxide (r-GO) was observed to form after the second recycle (third use) of GO. This technique is also effective with N-bromosuccinimide (NBS) as the brominating reagent. In the case of NBS, reactions were instantaneous and the GO displayed excellent recyclability without any loss of activity over several cycles.

A formal synthesis of lavendamycin methyl ester, nitramarine, and their analogues: A povarov approach

A convergent formal synthesis of lavendamycin methyl ester and synthesis of its analogues have been delineated through the Povarov approach. This protocol is also applied to the formal synthesis of nitramarine (3) in good yield.

Fast and efficient bromination of aromatic compounds with ammonium bromide and Oxone

A highly efficient, rapid and regioselective protocol was developed for the ring bromination of aromatic compounds under mild conditions with ammonium bromide as a source of bromine source and Oxone (potassium peroxysulfate) as an oxidant. No metal catalyst or acidic additive is required. A variety of aromatic compounds, including methoxy, hydroxy, amino, and alkyl arenes, reacted smoothly to give the corresponding monobrominated products in good to excellent yields in very short reaction times. Moreover, dibromination of deactivated anilines to give the corresponding dibromides proceeded in high yields. Interestingly, 1-(2-naphthyl)ethanone provided a ring-brominated product. Georg Thieme Verlag Stuttgart . New York.

Solvent-free bromination reactions with sodium bromide and oxone promoted by mechanical milling

New solvent-free brominations of 1,3-dicarbonyl compounds, phenols, various alkenes including chalcones, azachalcones, 4-phenylbut-3-en-2-one, methyl cinnamate, styrene and 1,3-cyclohexadiene were efficiently achieved by employing sodium bromide and oxone under mechanical milling conditions. The brominated products were obtained in good to excellent yields.

An instant and facile bromination of industrially-important aromatic compounds in water using recyclable CaBr2-Br2 system

Various industrially-important brominated intermediates have been instantly synthesized using aq. CaBr2-Br2 system as an efficient and recyclable brominating reagent under aqueous conditions at room temperature without the need for metal catalysts or acidic additives. Structurally-diverse phenol and aniline derivatives with strong electron-withdrawing groups such as carboxylic, nitro and formyl show remarkable reactivity to the brominating reagent and brominated in 92-98% yield with high purity (>99%) in a very short reaction time. Organic solvent-free conditions, a feature of the green chemistry, were successively used not only for the reactions but also for the isolation of products at the end of the reaction. The recycling of HBr by its neutralization, thereby generating additional amounts of industrially-important CaBr2 has been designed and developed. The brominating reagent has been recycled and regenerated, and the process was repeated up to 4 cycles after the fresh batch using the regenerated brominating reagent having almost identical selectivity and isolated yields, which seems to be the most promising methodology from the viewpoint of the green approach to organic synthesis.

Rearrangements during nitrosodecarboxylation of isomeric dibromohydroxybenzoic acids

The reaction of 3,5-dibromo-4-hydroxybenzoic acid, its sodium salt, and also sodium 3,5-dibromo-2-hydroxybenzoate with NaNO2 in a glacial acetic acid at room temperature led to the formation of a mixture of dibromonitrophenol resulting from nitrosodecarboxylation accompanied by a rearrangement processes and followed by oxidation of the arising nitrosophenols.

Nitration of phenolic compounds by metal-modified montmorillonite KSF

The nitration of phenolic compounds with 60% nitric acid (1.2 equiv) has been carried out in the presence of metal-modified montmorillonite KSF, prepared from different metals (V, Mo, W; Sc, La, Yb, Eu, In, Bi, Ti, Zr, Hf) and KSF or nitric acid treated HKSF, as catalysts. These catalysts showed good stabilities and high catalytic activities in nitration process. In addition, these catalysts can be recovered easily and reused for many times in nitration. This process is an eco-safer and environment-benign way for clean synthesis of nitrated phenolic compounds.

Pyridinium dichlorobromate: A new stable brominating agent for aromatic compounds

Pyridinium dichlorobromate (PyHBrCl2, 1) is a new example of iminium-trihalide complexes. The compound is prepared from pyridine and chlorine in the presence of aqueous hydrogen bromide. The crystalline trihalide is quite stable and acts as a safe source of positive bromine. It shows a remarkable reactivity towards aromatic compounds compared with other bromine complexes. It is also considered as a potential source for bromine chloride BrCl.