17715-69-4

Basic information

• Product Name: 1-Bromo-2,4-dimethoxybenzene
• Synonyms: 1-BROMO-2,4-DIMETHOXYBENZENE;1,3-DIMETHOXY-4-BROMOBENZENE;2,4-DIMETHOXYBROMOBENZENE;4-BROMORESOCINOL DIMETHYL ETHER;4-BROMORESORCINOL DIMETHYL ETHER;2,4-Dimethoxyphenyl bromide;4-Bromo-1,3-dimethoxybenzene;1-BROMO-2 4-DIMETHOXYBENZENE 96%
• CAS NO: 17715-69-4
• Molecular Formula: C₈H₉BrO₂
• Molecular Weight: 217.06
• EINECS: 241-717-0
• Product Categories: Aromatic Ethers;Anisole;Alcohol& Phenol& Ethers;Benzene derivates;Anisoles, Alkyloxy Compounds & Phenylacetates;Bromine Compounds;Ethers;Organic Building Blocks;Oxygen Compounds
• Mol File: 17715-69-4.mol
• Article Data: 68

Chemical Properties

• Melting Point: 25-26 °C(lit.)
• Boiling Point: 153-155 °C18 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear slightly yellow/Liquid
• Density: 1.507 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00598mmHg at 25°C
• Refractive Index: n20/D 1.572(lit.)
• Storage Temp.: 0-6°C
• Water Solubility: insoluble
• BRN: 1867593
• CAS DataBase Reference: 1-Bromo-2,4-dimethoxybenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Bromo-2,4-dimethoxybenzene(17715-69-4)
• EPA Substance Registry System: 1-Bromo-2,4-dimethoxybenzene(17715-69-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 17715-69-4(Hazardous Substances Data)

Usage

Description

1-Bromo-2,4-dimethoxybenzene is an organic compound that belongs to the class of brominated aromatic compounds. It is characterized by the presence of a bromine atom attached to a benzene ring, which is substituted with two methoxy groups at the 2nd and 4th positions. 1-Bromo-2,4-dimethoxybenzene is a slightly yellow liquid and is commonly used as a synthetic intermediate in the production of various organic compounds.

Uses

1. Used in the Synthesis of 2,3-Disubstituted Benzo[b]furans:
1-Bromo-2,4-dimethoxybenzene is used as a synthetic intermediate for the production of 2,3-disubstituted benzo[b]furans. These compounds are important in the pharmaceutical industry due to their diverse range of biological activities, including anti-inflammatory, antifungal, and anticancer properties.
2. Used in the Synthesis of Dendrimers:
1-Bromo-2,4-dimethoxybenzene is also utilized in the synthesis of dendrimers, specifically in the preparation of dendrimer Si[CH2CH2Si(Me)2-2,4-(MeO)2-C6H3]4. Dendrimers are highly branched, nanoscale polymers with a well-defined structure and a large number of functional groups on their surface. They have a wide range of applications in various fields, including drug delivery, catalysis, and materials science.
3. Used in the Chemical Industry:
In the chemical industry, 1-Bromo-2,4-dimethoxybenzene can be used as a building block for the synthesis of various organic compounds, such as dyes, pigments, and pharmaceuticals. Its unique structure and reactivity make it a valuable starting material for the development of new molecules with specific properties and applications.
4. Used in Research and Development:
Due to its versatile chemical properties, 1-Bromo-2,4-dimethoxybenzene is also used in research and development for the exploration of new synthetic routes and the discovery of novel compounds with potential applications in various industries.

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

Upstream product

• 24988-36-1 4,6-dibromo-1,3-dimethoxybenzene 
• 6626-15-9 4-Bromoresorcinol 
• 77-78-1 dimethyl sulfate 
• 151-10-0 1,3-Dimethoxybenzene 
• 60-29-7 diethyl ether 
• 89-86-1 4-hydroxysalicylic acid 
• 870-63-3 prenyl bromide 
• 67-56-1 methanol 
• 458-50-4 1-bromo-2-fluoro-4-methoxybenzene 
• 2735-04-8 2,4-Dimethoxyaniline 
• 74-88-4 methyl iodide 
• 91-52-1 2,4 dimethoxybenzoic acid 
• 506-68-3 bromocyane 
• 348-57-2 2,4-difluorobromobenzene 

Downstream Products

• 3333-05-9 2-(5-bromo-2,4-dimethoxy-benzoyl)-benzoic acid 
• 108103-40-8 Butyl-(3,5-dimethoxy-phenyl)-methyl-amine 
• 65975-54-4 2-(2,4-Dimethoxy-phenyl)-butyronitrile 
• 116377-28-7 2-cyano-3-(3'-methoxybenzyl)-1,5-dimethoxybenzene 
• 108103-46-4 Dicyclohexyl-(3,5-dimethoxy-phenyl)-amine 
• 13388-75-5 3,5-dimethoxyphenylacetonitrile 
• 831-29-8 1-(2,4-dimethoxyphenyl)propan-2-one 
• 24988-36-1 4,6-dibromo-1,3-dimethoxybenzene 
• 151-10-0 1,3-Dimethoxybenzene 

Relevant articles and documents

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.

Catalytic SNAr Hydroxylation and Alkoxylation of Aryl Fluorides

Nucleophilic aromatic substitution (SNAr) is a powerful strategy for incorporating a heteroatom into an aromatic ring by displacement of a leaving group with a nucleophile, but this method is limited to electron-deficient arenes. We have now established a reliable method for accessing phenols and phenyl alkyl ethers via catalytic SNAr reactions. The method is applicable to a broad array of electron-rich and neutral aryl fluorides, which are inert under classical SNAr conditions. Although the mechanism of SNAr reactions involving metal arene complexes is hypothesized to involve a stepwise pathway (addition followed by elimination), experimental data that support this hypothesis is still under exploration. Mechanistic studies and DFT calculations suggest either a stepwise or stepwise-like energy profile. Notably, we isolated a rhodium η5-cyclohexadienyl complex intermediate with an sp3-hybridized carbon bearing both a nucleophile and a leaving group.