2887-72-1

Basic information

• Product Name: 3',5'-Dibromo-4'-hydroxyacetophenone
• Synonyms: 3,5-Dibromo-p-hydroxyhypnone;3',5'-DIBROMO-4'-HYDROXYACETOPHENONE;3,5-DIBROMO-4-HYDROXYACETOPHENONE;AKOS BC-1523;1-(3,5-dibromo-4-hydroxyphenyl)ethan-1-one;3,5-dibrom0-4-hydroxyacetophenone;3'',5''-Dibromo-4''-hydroxyacetophenoe;2,6-Dibromo-4-acetylphenol
• CAS NO: 2887-72-1
• Molecular Formula: C₈H₆Br₂O₂
• Molecular Weight: 293.94
• EINECS: 220-750-4
• Product Categories: Aromatic Acetophenones & Derivatives (substituted);Building Blocks for Dendrimers;Functional Materials;C7 to C8;Carbonyl Compounds;Ketones;Building Blocks;C7 to C8;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 2887-72-1.mol
• Article Data: 21

Chemical Properties

• Melting Point: 182-187 °C(lit.)
• Boiling Point: 337.7 °C at 760 mmHg
• Flash Point: 158 °C
• Appearance: /
• Density: 1.936 g/cm³
• Solubility: very faint turbidity in hot Methanol
• PKA: 5.11±0.23(Predicted)
• CAS DataBase Reference: 3',5'-Dibromo-4'-hydroxyacetophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 3',5'-Dibromo-4'-hydroxyacetophenone(2887-72-1)
• EPA Substance Registry System: 3',5'-Dibromo-4'-hydroxyacetophenone(2887-72-1)

Safety Data

• Hazard Codes: C,Xi
• Statements: 22-34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 1759 8/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 2887-72-1(Hazardous Substances Data)

Usage

Preparation

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

General Description

3′,5′-Dibromo-4′-hydroxyacetophenone (3,5-dibromo-4-hydroxyacetophenone) can be obtained from 4-hydroxyacetophenone, via bromination by N-bromosuccinimide in the presence of LiClO4-SiO2.

Upstream product

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

Downstream Products

• 133455-15-9 1-[4-(3-bromopropoxy)-3,5-dibromophenyl]ethanone 
• 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 
• 1191243-62-5 1-(3-5-dibromo-4-(4-methoxybenzyloxy)phenyl)ethanone 
• 1191248-82-4 2-(3,5-dibromo-4-hydroxyphenyl)-2-oxoacetaldehyde 
• 1191248-84-6 2-(3,5-dibromo-4-hydroxyphenyl)-2-oxoacetaldehyde oxime 
• 1422285-76-4 C₁₈H₁₄Br₃NO₅ 
• 1422285-77-5 C₁₈H₁₃Br₃N₂O₃ 
• 1422285-78-6 C₁₈H₁₂Br₃ClN₂O₂ 
• 1422285-79-7 C₂₃H₂₃Br₃ClN₃O₂ 
• 1422285-80-0 C₂₂H₂₁Br₃ClN₃O₂ 
• 1422285-81-1 C₂₁H₁₇Br₄ClN₂O₂ 
• 1422285-82-2 C₂₆H₃₀Br₄N₂O₆ 
• 1422285-84-4 C₂₁H₂₂Br₄N₂O₄ 

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.

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.

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.