3,5-Dimethoxybenzyl bromide
[CAS# 877-88-3]

Identification

• Classification: Chemical reagent >> Organic reagent >> Aromatic hydrocarbon reagent
• Name: 3,5-Dimethoxybenzyl bromide
• Synonyms: 1-(bromomethyl)-3,5-dimethoxybenzene
• Molecular Formula: C₉H₁₁BrO₂
• Molecular Weight: 231.09
• CAS Registry Number: 877-88-3
• EC Number: 618-071-7
• SMILES: COC1=CC(=CC(=C1)CBr)OC

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*
• Melting point: 69-70 °
• Index of Refraction: 1.539, Calc.^*
• Boiling Point: 292.1±25.0 °C (760 mmHg), Calc.^*
• Flash Point: 129.9±18.7 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS05 Danger
• Risk Statements: H314-H318
• Safety Statements: P260-P264-P264+P265-P280-P301+P330+P331-P302+P361+P354-P304+P340-P305+P354+P338-P316-P317-P321-P363-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Serious eye damage	Eye Dam.	1	H318
Skin corrosion	Skin Corr.	1B	H314
Substances or mixtures corrosive to metals	Met. Corr.	1	H290

• Transport Information: UN 3261

Discovery and Applications

3,5-Dimethoxybenzyl bromide is an organic compound that serves as an important intermediate in synthetic organic chemistry. With a molecular formula of C10H13BrO2, this compound features a benzene ring substituted with two methoxy groups (-OCH3) at the 3 and 5 positions, along with a bromomethyl group (-CH2Br) attached to the benzene. This particular structure makes 3,5-dimethoxybenzyl bromide a versatile building block for various chemical transformations, including nucleophilic substitutions and coupling reactions.

The discovery of 3,5-dimethoxybenzyl bromide can be attributed to advances in synthetic organic chemistry in the mid-20th century, where researchers sought to develop more efficient methods for constructing complex organic molecules. The introduction of methoxy groups in the benzyl position enhances the electron density of the aromatic ring, making it more reactive towards nucleophiles. The bromine atom, a good leaving group, allows for the substitution reactions that facilitate the formation of new carbon-carbon or carbon-heteroatom bonds.

3,5-Dimethoxybenzyl bromide finds applications in various fields, including pharmaceuticals, agrochemicals, and materials science. In medicinal chemistry, it is utilized as a precursor for synthesizing biologically active compounds. The methoxy groups not only influence the electronic properties of the molecule but also affect its lipophilicity and pharmacokinetic profiles, making it an attractive candidate for drug design. Researchers have explored derivatives of 3,5-dimethoxybenzyl bromide that exhibit potent biological activities, including anticancer and antimicrobial properties.

Additionally, this compound plays a role in the development of novel materials. Its ability to undergo various chemical reactions enables the synthesis of polymers, resins, and other materials with tailored properties. The incorporation of 3,5-dimethoxybenzyl bromide into polymer backbones or as a side chain can enhance the thermal stability and mechanical properties of the resulting materials.

Furthermore, 3,5-dimethoxybenzyl bromide is used in the field of organic synthesis as a reagent in cross-coupling reactions, such as Suzuki and Heck reactions. These reactions are pivotal in constructing complex molecules and are widely employed in the synthesis of natural products and pharmaceutical compounds. The versatility of the compound allows chemists to explore a wide array of functionalized products, contributing to advancements in organic chemistry.

In summary, 3,5-dimethoxybenzyl bromide is a significant compound in synthetic organic chemistry, serving as a valuable building block in the development of pharmaceuticals and advanced materials. Its unique structure, which features methoxy substituents and a reactive bromomethyl group, enables diverse chemical transformations and applications across various scientific fields.

References

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DOI: 10.1134/s0012500816080036

2016. Polyarenes prepared by Suzuki–Miyaura reaction via condensation of sumanene and 3,4:9,10-perylenetetracarboxydiimide derivatives: Synthesis and chemical transformations. Doklady Chemistry, 470(2).
DOI: 10.1134/s0012500816100037

2015. Anti-tumor properties of cis-resveratrol methylated analogs in metastatic mouse melanoma cells. Molecular and Cellular Biochemistry, 402(1).
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