14472-14-1

Usage

Uses

Phenol,4-bromo-3-methylis used as a chemical intermediate in the synthesis of various organic compounds, particularly in the production of bromo[2-methyl-4-[2-(t-butyldimethylsilyloxy)ethyloxy]phenyl]bis(triphenylphopshine)nickel(II) and bromo-[2-methyl-4-[6-(t-butyldimethylsilyloxy)hexyloxy]phenyl] bis(triphenylphosphine) nickel. These are protected alcohol-functionalized initiators and are utilized in the field of polymer chemistry.
Used in Polymer Chemistry:
Phenol,4-bromo-3-methylis used as a key component in the synthesis of initiators for polymerization reactions. These initiators are crucial in the production of polymers with specific properties and structures, which can be tailored for various applications in different industries.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, due to its chemical structure, Phenol,4-bromo-3-methylmay also have potential applications in the pharmaceutical industry as a starting material for the synthesis of various drugs or drug candidates. Its reactivity and functional groups can be exploited to create new molecules with desired biological activities.
Used in Chemical Research:
Phenol,4-bromo-3-methylis also likely to be used in chemical research for studying the properties and reactivity of brominated phenols. This can contribute to the development of new synthetic methods, understanding reaction mechanisms, and discovering novel applications in various fields.

InChI:InChI=1/C7H7BrO/c1-5-4-6(9)2-3-7(5)8/h2-4,9H,1H3

Upstream product

• 108-39-4 3-methyl-phenol 
• 27060-75-9 4-bromo-3-methylanisole 
• 56-23-5 tetrachloromethane 
• 7726-95-6 bromine 
• 1972-28-7 diethylazodicarboxylate 
• 6933-10-4 amino-5-bromo-2-toluene 
• 139125-86-3 Cyclopentanone O-(4-bromo-3-methyl-phenyl)-oxime 
• 95-46-5 2-methylphenyl bromide 
• 1193-18-6 3-methylcyclohexen-2-one 
• 67-66-3 chloroform 
• 93684-15-2 3-methyl-4-bromo-2,5-cyclohexadienone 
• 125029-51-8 2,5-Dimethyl-cyclopentanone O-(4-bromo-3-methyl-phenyl)-oxime 
• 2973-80-0 2-bromo-5-hydroxybenzaldehyde 

Downstream Products

• 182500-28-3 4-bromo-5-methyl-2-nitrophenol 
• 56037-74-2 4-bromo-2,6-dichloro-3-methyl-phenol 
• 26177-63-9 carbonic acid ethyl ester-(4-bromo-3-methyl-phenyl ester) 
• 90971-89-4 4-Brom-3-methyl-1-phenoxyessigsaeure 
• 860559-48-4 benzenesulfonic acid-(4-bromo-3-methyl-phenyl ester) 
• 27060-75-9 4-bromo-3-methylanisole 
• 808134-00-1 5-bromo-2-methoxy-4-methylbenzenesulfonyl chloride 
• 97151-08-1 2-methyl-4-(tetrahydropyranyloxy)phenyl bromide 
• 52431-61-5 5-chloro-8-hydroxy-6-methylnaphthalene-1,4-dione 
• 22012-59-5 4-bromo-3-methylphenyl acetate 

Relevant academic research and scientific papers

METHOD FOR PREPARING CRISABOROLE

The invention relates to a method for preparing Crisaborole of Formula I, comprising using m-methylphenol as the starting material to obtain a target product through a five-step reaction. The starting materials and the raw materials used in each step of the method according to the present invention are cheap and easy to obtain, and the process is simple. The reaction of introducing boron atoms into the benzene ring to form an oxygen boron heterocycle is novel, with high yield and mild conditions, and is suitable for industrial production.

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.

SELECTIVE BTK IRREVERSIBLE INHIBITORS

The invention provides a series of conformationally stable and selective, irreversible kinase inhibitors, and methods of using the kinase inhibitors. The effect of atropisomerism on kinase selectivity was assessed, finding improved selectivity compared to rapidly interconverting parent compounds. The compounds herein are atropisomers having increased kinase selectivity and are for use in treating conditions that benefit from selective BTK kinase inhibition.

Synthesis of natural product inulavosin via Ga(OTf)3-Catalyzed Hetero Diels–Alder Dimerization of salicyl alcohol derivative

Inulavosin, a natural melanogenesis inhibitor, has been synthesized smoothly from readily available and inexpensive starting materials by using a Ga(OTf)3-catalyzed room temperature hetero Diels–Alder dimerization of salicyl alcohol derivative and a regioselective phenol monobromination as the key steps.

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.

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.

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.

Ultrasonically assisted halogenation of aromatic compounds using isoquinolinium bound hypervalent chromium and tetrabutylammonium halides in PEG-600 solutions under acid free and solvent-free conditions

Isoquinolinium bound Cr(VI) reagents like isoquinolinium dichromate (IQDC) and isoquinolinium chlorochromate (IQCC) have been successfully accomplished as efficient reagents for oxidative halogenation of aromatic compounds using tetrabutylammonium halide (TBAX) as halogenating agents in aqueous polyethylene glycol (PEG-600) under acid free conditions. Tetrabutylammonium bromide (TBAB) has been used for bromination and tetrabutylammonium iodide (TBAI) for iodination. The halogenation reactions that occurred smoothly in 2 to 7 h under conventional conditions are accelerated magnificently under sonication with few minutes (25 to 70 min) of reaction time and fairly good yields. The reactions occurred at moderate temperature under mild and environmentally safe conditions with simple work up.

Regioselective Halogenation of Arenes and Heterocycles in Hexafluoroisopropanol

Regioselective halogenation of arenes and heterocycles with N-halosuccinimides in fluorinated alcohols is disclosed. Under mild condition reactions, a wide diversity of halogenated arenes are obtained in good yields with high regioselectivity. Additionally, the versatility of the method is demonstrated by the development of one-pot sequential halogenation and halogenation-Suzuki cross-coupling reactions.