2887-72-1

Usage

Uses

Used in Pharmaceutical Industry:
3',5'-Dibromo-4'-hydroxyacetophenone is used as an intermediate compound for the synthesis of various pharmaceuticals. Its unique structural features make it a valuable building block in the development of new drugs, particularly those targeting specific biological pathways or receptors.
Used in Chemical Synthesis:
In the field of organic chemistry, 3',5'-Dibromo-4'-hydroxyacetophenone serves as a key intermediate in the synthesis of a range of chemical products. Its bromine atoms and hydroxyl group can be further functionalized or modified to produce a variety of compounds with different applications.
Used in Material Science:
3',5'-Dibromo-4'-hydroxyacetophenone can be utilized in the development of novel materials with specific properties, such as those with enhanced thermal stability, chemical resistance, or optical characteristics. Its unique molecular structure allows for the creation of new polymers, coatings, or additives with tailored properties for various applications.
Used in Research and Development:
As a versatile compound, 3',5'-Dibromo-4'-hydroxyacetophenone is also employed in research and development settings. It can be used to study the effects of structural modifications on the properties and reactivity of molecules, as well as to explore new reaction pathways and mechanisms in organic chemistry.

Preparation

Preparation by bromination of 4-hydroxyacetophenone in dilute acetic acid (94%)，(80%), (75%) (62%).

Upstream product

• 28165-72-2 1-acetoxy-2,6-dibromobenzene 
• 99-93-4 4-Hydroxyacetophenone 
• 149104-90-5 4-acetylphenylboronic acid 
• 57018-12-9 2,6-dibromo-4-ethylphenol 
• 108-95-2 phenol 
• 608-33-3 2,6-dibromophenol 

Downstream Products

• 34969-79-4 2-bromo-1-(3,5-dibromo-4-hydroxyphenyl)ethanone 
• 69299-25-8 1-(3,5-dibromo-4-hydroxyphenyl)-3-phenyl-2-propen-1-one 
• 92853-23-1 3',5'-Dibrom-4'-hydroxy-4-methoxychalcon 
• 478978-59-5 4-acetyl-2-allyl-6-bromo-phenol 
• 115929-62-9 3-bromo-2,5-dimethoxyaniline 
• 130740-41-9 1-(3-Amino-5-bromo-4-methoxy-phenyl)-ethanone 
• 130740-42-0 1-(3-Bromo-2,5-dimethoxy-phenyl)-2,5-dimethyl-1H-pyrrole 
• 130740-43-1 (E)-(1R,2R,4R,5S,6R,9S,10R)-9,11-Bis-(tert-butyl-dimethyl-silanyloxy)-1-[3-(2,5-dimethyl-pyrrol-1-yl)-2,5-dimethoxy-phenyl]-5-methoxy-2,6,8,10-tetramethyl-undec-7-ene-1,4-diol 
• 130740-43-1 (E)-(1R,2S,4S,5R,6S,9R,10S)-9,11-Bis-(tert-butyl-dimethyl-silanyloxy)-1-[3-(2,5-dimethyl-pyrrol-1-yl)-2,5-dimethoxy-phenyl]-5-methoxy-2,6,8,10-tetramethyl-undec-7-ene-1,4-diol 
• 133455-15-9 1-[4-(3-bromopropoxy)-3,5-dibromophenyl]ethanone 
• 122637-77-8 3,5-dibromo-4-acetoxyacetophenone 
• 129527-07-7 2,6-dibromo-4-acetylphenol sodium salt 
• 1068709-29-4 (E)-4-(3,5-dibromo-4-hydroxyphenyl)-4-oxobut-2-enoic acid 

Relevant academic research and scientific papers

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.

Magnesium tetrapyrazinoporphyrazines: Tuning of the pKa of red-fluorescent pH indicators

Magnesium(ii) tetrapyrazinoporphyrazines (TPyzPzs) are excellent red fluorophores (λF ～ 663 nm, ΦF ～ 0.53 in THF). In this work, a series of magnesium(ii) complexes of unsymmetrical TPyzPzs bearing one or two phenol substituents was prepared. Suitable substitutions on the phenolic moiety tuned its pKa in the range of 5.5 to 13. Deprotonation of the phenolic group at higher pH induced a strong donor (phenolate) in the macrocycle that led to pH-dependent quenching of the red fluorescence of these indicators. pH sensing was proved in water solutions after the incorporation of TPyzPzs into two delivery systems-microemulsions and liposomes. The latter also serves as a simple model of biomembranes. Finally, a wavelength-ratiometric probe was constructed by the incorporation of a TPyzPz indicator and lipophilic pH-nonsensitive BODIPY dye into liposomes. Synthetic precursors for TPyzPzs, substituted pyrazine-2,3-dicarbonitriles, also represent donor-acceptor systems and the pH-dependent changes in absorption spectra may be easily visible to the naked eye.

Synthesis and antibacterial activities of cadiolides A, B and C and analogues

The one-pot multicomponent synthesis of natural butenolides named cadiolides A, B, C and analogues has been realized. The antibacterial structure activity relationship shows that the presence of phenolic hydroxyl groups and the number and position of bromine atoms on the different aromatic rings are important features for antibacterial activity, besides it was demonstrated the tolerance of both benzene and furan ring at position 3 of the butenolide nucleus. Furthermore, none of the most relevant antibacterial compounds showed any cytotoxicity in freshly isolated human neutrophils.

An eco-friendly Co(OAc)2-catalyzed aerobic oxidation of 4-benzylphenols into 4-hydroxybenzophenones

An undecorated Co(OAc)2-catalyzed aerobic oxidation system has been reported that enables direct transformation of 4-benzylphenols into the corresponding 4-hydroxybenzophenones. The procedure is especially suitable for electron-withdrawing group-containing substrates, which are commonly inefficient to conduct this category of oxidation. Based on well-defined p-benzoquinone methides and the confirmed ethereal intermediate, a plausible mechanism was depicted.

Cu(OAc)2-catalyzed remote benzylic C(sp3)-H oxyfunctionalization for C=O formation directed by the hindered para-hydroxyl group with ambient air as the terminal oxidant under ligand- and additive-free conditions

A hindered para-hydroxyl group-directed remote benzylic C(sp3)-H oxyfunctionalization has been developed for the straightforward transformation of 2,6-disubstituted 4-cresols, 4-alkylphenols, 4-hydroxybenzyl alcohols and 4-hydroxybenzyl alkyl ethers into various aromatic carbonyl compounds. The ligand- and additive-free Cu(OAc)2-catalyzed atmospheric oxidation mediated by ethylene glycol unlocks a facile, atom-economical, and environmentally benign C=O formation for the functionalization of primary and secondary benzyl groups. Due to the pharmaceutical importance of 4-hydroxybenzaldehydes and 4-hydroxyphenones, the methodology is expected to be of significant value for both fundamental research and practical applications.

Total synthesis and biological activity of marine alkaloid eudistomins Y1-Y7 and their analogues

Eudistomin Y class compounds are a series of β-carbolines which was originally isolated from a marine turnicate or ascidian near the South Korea Sea. These compounds contain bromo-substituted groups, which is one of the typical characters of marine natural products. We report herein the chemical synthesis and biological evaluation of seven new β-carboline-based metabolites, Eudistomins Y1-Y7, and their hydroxyl-methylated phenyl derivatives. Using bromo-substituted tryptamines and bromo-substituted phenylglyoxals as the key intermediates, Eudistomins Y 1-Y7 and their derivatives were synthesized via the acid-catalyzed Pictet-Spengler reaction and fully characterized by 1H- and 13C-NMR and mass spectroscopy. Biological studies revealed that all of the compounds showed moderate growth inhibitory activity against breast carcinoma cell line MDA-231 with IC50 of 15-63 μM and the inhibitory activities of hydroxyl-methylated phenyl products were higher than that of the corresponding natural products Eudistomins Y 1-Y7.

Synthesis and SAR studies of marine natural products ma'edamines A, B and their analogues

The synthesis of several analogues of ma'edamines A and B are reported. The synthesized compounds were tested on hormone receptor positive and HER2 positive breast cancer cell lines, by MTT assay. MED-114, 115, 117, 119, 120, 124, 128 and 131 were found to be equally active as Lapatinib on HER2 +ve cell line SKBR3.

The first total synthesis and biological evaluation of marine natural products ma'edamines A and B

We have developed the first total syntheses of marine natural products ma'edamines A (18) and B (20). Structurally, they contain a pyrazine-2-(1H)-one core and were screened for antiproliferative activity on several cancer cell lines. Out of the six cell lines tested, ma'edamines A and B showed significant cytotoxicity against human colon cancer line COLO 205 (IC50 7.9 and 10.3 μM, respectively), breast cancer cell line MCF-7 (IC50: 6.9 and 10.5 μM, respectively) and human lung adenocarcinoma cell line A549 (IC50: 12.2 and 15.4 μM, respectively). The apoptotic effect of ma'edamines was confirmed by comet assay. Hence ma'edamines are likely to be useful as leads for development of a new class of anti-cancer agents.

Synthesis, biochemical evaluation and rationalisation of a series of 3,5- dibromo derivatives of 4-hydroxyphenyl ketone-based compounds as probes of the active site of type 3 of 17β-hydroxysteroid dehydrogenase (17β-hsd3) and the role of hydrogen bonding interaction in the inhibition of 17β-HSD3

We report the synthesis, evaluation and rationalisation of the inhibitory activity of a series of 3,5-dibromo derivatives of 4-hydroxyphenyl ketone as probes of the active site of the type 3 of 17β-hydroxysteroid dehydrogenase (17β-HSD3). The results support the important role of hydrogen bonding interaction in the inhibition of 17β-HSD3.

Synthesis and biological evaluation of some 3,5-dibromo-4-hydroxy enoness

Enones having an a,b-unsaturated carbonyl systems are important as Michael acceptors and constitute an important class of biologically active compounds. Enones are one of the most versatile synthons for various chemical transformations leading to the synthesis of several biodynamic heterocyclic compounds. Therefore, the chemistry of synthetic enones is most dynamic and challenging area embracing a vast spectrum of advances of both theoretical and practical relevance. In view of this, in the present paper synthesis of some 3,5-dibromo- 4-hydroxyphenyl enones are reported along with their herbicidal, fungicidal, insecticidal, animal health and antibacterial activities. Some of the compounds showed promising biological activities.