2859-78-1

Basic information

• Product Name: 4-Bromoveratrole
• Synonyms: 4-BROMOVERATROLE;4-BROMOCATECHOL DIMETHYL ETHER;4-BROMO-1,2-DIMETHOXYBENZENE;3,4-DIMETHOXYBROMOBENZENE;1-BROMO-3,4-DIMETHOXYBENZENE;3,4-Dimethoxyphenyl bromide;4-bromo-1,2-dimethoxy-benzen;Bromoveratrole
• CAS NO: 2859-78-1
• Molecular Formula: C₈H₉BrO₂
• Molecular Weight: 217.06
• EINECS: 220-677-8
• Product Categories: Aromatic Ethers;Anisole;Anisoles, Alkyloxy Compounds & Phenylacetates;Bromine Compounds
• Mol File: 2859-78-1.mol

Chemical Properties

• Boiling Point: 255-256 °C(lit.)
• Flash Point: 229 °F
• Appearance: Clear colorless to slightly yellow/Liquid
• Density: 1.509 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.113mmHg at 25°C
• Refractive Index: n20/D 1.573(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: Soluble in benzene, ether, toluene.
• BRN: 2046884
• CAS DataBase Reference: 4-Bromoveratrole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromoveratrole(2859-78-1)
• EPA Substance Registry System: 4-Bromoveratrole(2859-78-1)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 23-24/25
• WGK Germany: 3
• TSCA: T
• Hazardous Substances Data: 2859-78-1(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
4-Bromoveratrole is used as a key intermediate in the synthesis of various organic compounds, particularly the isoquinoline alkaloid (-)-mesembrine. Its unique structure allows for its involvement in multiple chemical reactions, making it a valuable component in the production of specific alkaloids.
Used in Energy Storage:
In the energy storage industry, 4-Bromoveratrole serves as a redox shuttle additive, playing a crucial role in lithium batteries. It helps consume excess current during overcharging, thereby enhancing the safety and performance of these batteries.
Used in Pharmaceutical Research:
Due to its catechol moiety, 4-Bromoveratrole may also find applications in pharmaceutical research, potentially contributing to the development of new drugs or therapies that target specific biological pathways involving catechol-containing molecules.

Biological Functions

4-Bromoveratrole has been shown that this molecule binds to the receptor for acetylcholine, which is found in the central nervous system and on muscles. The binding of 4-bromoveratrole to this receptor leads to the release of chloride ions from the cell, which increases the activity of acetylcholine. The detection sensitivity of 4-bromoveratrole in solution was determined by adding malonic acid or hydrochloric acid, which led to an increase in fluorescence intensity. This molecule also has fatty acid and hydroxyl groups that have been shown to have anti-inflammatory properties.

InChI:InChI=1/C8H9BrO2/c1-10-7-5-3-4-6(9)8(7)11-2/h3-5H,1-2H3

Upstream product

• 91-16-7 1,2-dimethoxybenzene 
• 77-48-5 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione 
• 75-15-0 carbon disulfide 
• 7446-70-0 aluminium trichloride 
• 506-68-3 bromocyane 
• 122775-35-3 3,4-Dimethoxyphenylboronic acid 
• 6286-46-0 2-bromo-4,5-dimethoxybenzoic acid 
• 90-05-1 2-methoxy-phenol 
• 37942-01-1 5-bromo-2-methoxyphenol 
• 74-88-4 methyl iodide 
• 66037-04-5 1-acetoxy-5-bromo-2-methoxybenzene 
• 77-78-1 dimethyl sulfate 
• 7368-78-7 4-bromoguaiacol 
• 39416-48-3 pyridinium hydrobromide perbromide 

Downstream Products

• 51686-49-8 methyl 4-(3,4-dimethoxyphenyl)butanoate 
• 137744-77-5 methyl 4-(3,4-dimethoxyphenyl)-3-butenoate 
• 20036-53-7 3-<3,4-(dimethoxy)phenyl>-2-cyclohexen-1-one 
• 101432-12-6 bis(3, 4-dimethoxyphenyl)ether 
• 104756-76-5 dimethyl 4-hydroxy-6,7-dimethoxy-1-(3',4'-dimethoxyphenyl)naphthalene-2,3-dicarboxylate 
• 87282-15-3 tert-Butyl-(3,4-dimethoxy-phenyl)-amine 
• 123251-37-6 1,2-dimethoxythioxanthen-9-one 
• 109717-69-3 (+)-threo-hydroxynorlaudanosine 
• 700-96-9 3,4-dimethoxythiophenol 
• 158531-86-3 (tert-Butyldiphenylsiloxy)methyl 3,4-dimethoxyphenyl ketone 
• 155583-45-2 1,2-dimethoxy-4-(2-methylallyl)benzene 
• 210536-91-7 N-(3,4-dimethoxyphenyl) benzophenone hydrazone 
• 358369-06-9 4-(3,4-Dimethoxy-phenyl)-3-methyl-4-oxo-butyric acid 
• 358369-08-1 4-(3,4-dimethoxyphenyl)-2,3-dimethyl-4-oxobutyric acid 

Relevant articles and documents

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Anti-inflammatory, ulcerogenic and platelet activation evaluation of novel 1,4-diaryl-1,2,3-triazole neolignan-celecoxib hybrids

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Direct bromodeboronation of arylboronic acids with CuBr2 in water

An efficient and practical method has been developed for the preparation of aryl bromides via the direct bromodeboronation of arylboronic acids with CuBr2 in water. This strategy provides several advantages, such as being ligand-free, base-free, high yielding, and functional group tolerant.

Bis-selenonium Cations as Bidentate Chalcogen Bond Donors in Catalysis

Lewis acids are frequently employed in catalysis but they often suffer from high moisture sensitivity. In many reactions, catalysts are deactivated because of the problem that strong Lewis acids also bond to the products. In this research, hydrolytically stable bidentate Lewis acid catalysts derived from selenonium dicationic centers have been developed. The bis-selenonium catalysts are employed in the activation of imine and carbonyl groups in various transformations with good yields and selectivity. Lewis acidity of the bis-selenonium salts was found to be stronger than that of the monoselenonium systems, attributed to the synergistic effect of the two cationic selenonium centers. In addition, the bis-selenonium catalysts are not inhibited by strong bases or moisture.

Visible light-induced mono-bromination of arenes with BrCCl3

A highly efficient and regioselective bromination of electron-rich arenes and heteroarenes using commercially available BrCCl3as a “Br” source has been developed. The reaction was performed in air under mild conditions with photocatalyst Ru(bpy)3Cl2·6H2O, avoiding the usage of strong acids and strong oxidants. Mono-brominated products were obtained with medium to excellent yields (up to 94%). This strategy has shown good compatibility and highpara-selectivity, which will facilitate the complicated synthesis.

Eco-Friendly Methodology for the Formation of Aromatic Carbon–Heteroatom Bonds by Using Green Ionic Liquids

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Cooperativity within the catalyst: alkoxyamide as a catalyst for bromocyclization and bromination of (hetero)aromatics

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Oxybromination of aromatic compounds by high-valent metal-oxo intermediates has yet to be explored despite extensive studies on the oxybromination of aliphatic C-H bonds of hydrocarbons. Herein, we report the regioselective oxybromination of methoxy-substituted benzenes by a nonheme MnIV-oxo complex binding scandium ions, [(Bn-TPEN)MnIV(O)]2+-(Sc(OTf)3)2 (1), in the presence of tetrabutylammonium bromide. The regioselective oxybromination occurs at the carbon atom with the highest positive charge via electron transfer (ET) from the methoxy-substituted benzenes to 1. ET driving force dependence of the rate constants of ET from methoxy-substituted benzenes to 1 is well fitted in light of the Marcus theory of ET. Under photoirradiation, the oxybromination of benzene by 1 can be achieved via ET from benzene to the photoexcited state of 1, although no reaction occurs between benzene and the ground state of 1 in the dark. To the best of our knowledge, this is the first example of reporting the stoichiometric regioselective oxybromination of the benzene ring by a synthetic high-valent Mn(IV)-oxo complex and the catalytic regioselective oxybromination reaction with a Mn(II) complex and a terminal oxidant.

Atom-economical brominations with tribromide complexes in the presence of oxidants

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