1-Bromo-2,6-dimethoxybenzene
[CAS# 16932-45-9]

Identification

• Classification: Organic raw materials >> Aryl compounds
• Name: 1-Bromo-2,6-dimethoxybenzene
• Synonyms: 2-Bromo-1,3-dimethoxybenzene; 2,6-Dimethoxybromobenzene; 2-Bromo-3-methoxyanisole
• Molecular Formula: C₈H₉BrO₂
• Molecular Weight: 217.06
• CAS Registry Number: 16932-45-9
• EC Number: 679-556-7
• SMILES: COC1=C(C(=CC=C1)OC)Br

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*
• Melting point: 92-94 ºC (expl.)
• Index of Refraction: 1.528, Calc.^*
• Boiling Point: 250.0±20.0 ºC (760 mmHg), Calc.^*
• Flash Point: 106.0±17.3 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovory and Applicatios

1-Bromo-2,6-dimethoxybenzene is an aromatic organic compound that contains a bromine atom and two methoxy groups (–OCH3) attached to a benzene ring. This compound is classified as a halogenated methoxybenzene and is utilized in various fields of organic synthesis, including the preparation of more complex chemical structures for pharmaceutical, agrochemical, and material science applications. The discovery of 1-bromo-2,6-dimethoxybenzene is linked to the broader study of halogenated aromatic compounds, which have been extensively researched due to their diverse reactivity and usefulness in synthetic chemistry.

The synthesis of 1-bromo-2,6-dimethoxybenzene typically involves the bromination of 2,6-dimethoxyphenol or a similar precursor under controlled conditions, where the bromine selectively substitutes a hydrogen atom at the 1-position of the benzene ring. This method of halogenation allows for the selective functionalization of aromatic systems, creating a versatile intermediate for further transformations.

The primary application of 1-bromo-2,6-dimethoxybenzene is in organic synthesis, where it serves as a building block for the preparation of more complex molecules. One of its key roles is in the synthesis of bioactive compounds, particularly those used in medicinal chemistry. The methoxy groups on the benzene ring provide electron-donating properties that influence the reactivity of the molecule, making it suitable for a variety of substitution reactions, such as nucleophilic aromatic substitution and palladium-catalyzed coupling reactions.

In medicinal chemistry, 1-bromo-2,6-dimethoxybenzene has been employed in the development of compounds with potential therapeutic activities. Its functionalized structure allows it to act as a precursor in the design of molecules targeting specific biological pathways. For example, it has been used in the synthesis of pharmaceutical intermediates, such as those with anticancer and antimicrobial properties. The presence of the methoxy groups on the aromatic ring can enhance the solubility and bioavailability of certain drugs, contributing to their therapeutic potential.

In addition to medicinal applications, 1-bromo-2,6-dimethoxybenzene is valuable in the production of agrochemicals. Its ability to participate in various reactions makes it a useful intermediate in the synthesis of pesticides and herbicides. The molecule's halogenated structure is beneficial for increasing the stability and activity of agricultural chemicals, especially in applications requiring the targeting of specific pests or plant diseases.

Another important area of application for 1-bromo-2,6-dimethoxybenzene is in materials science, particularly in the synthesis of organic semiconductors and conductive polymers. The methoxy groups provide flexibility and modulate the electronic properties of the compound, which can be useful in the development of organic electronic devices, including organic light-emitting diodes (OLEDs) and organic solar cells. The versatility of this compound in forming different types of functionalized derivatives expands its potential use in creating advanced materials for electronic and optoelectronic applications.

Despite its promising applications, the use of 1-bromo-2,6-dimethoxybenzene is not without challenges. As with many halogenated aromatic compounds, environmental and safety considerations must be addressed, particularly in the synthesis and disposal of waste products. The toxicity of bromine-containing compounds, as well as their potential environmental impact, requires careful handling and appropriate regulatory measures in industrial applications.

In conclusion, 1-bromo-2,6-dimethoxybenzene is an important chemical compound in synthetic organic chemistry, with significant applications in the pharmaceutical, agrochemical, and material science industries. Its structure, which combines halogenation and methoxy functionalization, makes it a versatile intermediate for the development of bioactive compounds, agricultural chemicals, and advanced materials. Ongoing research continues to explore new uses and modifications of this compound, further expanding its potential applications.