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
• Article Data: 51

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

Chemical Properties

Colorless to Yellow liquid

Uses

4-Bromoveratrole is a metabolite of bromobenzene, with a catechol moiety in the substructure. It also has use as a redox shuttle additive, essentially a component in lithium batteries that consumes excess current during overcharge. It is also used in the synthesis of the isoquinoline alkaloid (-)-mesembrine.

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 
• 7368-78-7 4-bromoguaiacol 
• 77-78-1 dimethyl sulfate 
• 75-15-0 carbon disulfide 
• 7446-70-0 aluminium trichloride 
• 506-68-3 bromocyane 
• 6286-46-0 2-bromo-4,5-dimethoxybenzoic acid 
• 122775-35-3 3,4-Dimethoxyphenylboronic 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 
• 39416-48-3 pyridinium hydrobromide perbromide 

Downstream Products

• 111770-90-2 5-bromo-2-(3,4-dimethoxyphenyl)pyridine 
• 51686-49-8 methyl 4-(3,4-dimethoxyphenyl)butanoate 
• 137744-77-5 methyl 4-(3,4-dimethoxyphenyl)-3-butenoate 
• 87282-17-5 Butyl-(3,4-dimethoxy-phenyl)-methyl-amine 
• 20036-53-7 3-<3,4-(dimethoxy)phenyl>-2-cyclohexen-1-one 
• 91-16-7 1,2-dimethoxybenzene 
• 107770-10-5 1-benzyl-3-(3,4-dimethoxyphenyl)-2-pyrrolidinone 
• 138207-01-9 3-(3,4-Dimethoxy-phenyl)-4-methoxy-pyridine 
• 80245-45-0 9-(3,4-dimethoxyphenyl)-1H-phenalen-1-one 
• 93-17-4 3,4-dimethoxyphenylacetonitrile 
• 7250-04-6 bis(3,4-dimethoxyphenyl)acetonitrile 
• 6258-35-1 3-(3,4-dimethoxyphenyl)prop-2-yn-1-ol 
• 160360-45-2 4-(3,4-dimethoxyphenyl)but-3-yn-1-ol 
• 700-96-9 3,4-dimethoxythiophenol 

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

This study reports the synthesis of novel neolignans-celecoxib hybrids and the evaluation of their biological activity. Analogs 8–13 (L13-L18) exhibited anti-inflammatory activity, inhibited glycoprotein expression (P-selectin) related to platelet activation, and were considered non– ulcerogenic in the animal model, even with the administration of 10 times higher than the dose used in reference therapy. In silico drug-likeness showed that the analogs are compliant with Lipinski's rule of five. A molecular docking study showed that the hybrids 8–13 (L13-L18) fitted similarly with celecoxib in the COX-2 active site. According to this data, it is possible to infer that extra hydrophobic interactions and the hydrogen interactions with the triazole core may improve the selectivity towards the COX-2 active site. Furthermore, the molecular docking study with P-selectin showed the binding affinity of the analogs in the active site, performing important interactions with amino acid residues such as Tyr 48. Whereas the P-selectin is a promising target to the design of new anti-inflammatory drugs with antithrombotic properties, a distinct butterfly-like structure of 1,4-diaryl-1,2,3-triazole neolignan-celecoxib hybrids synthesized in this work may be a safer alternative to the traditional COX-2 inhibitors.

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.

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.