2-Bromo-4,6-Dimethoxybenzaldehyde: Lab Handling Guide

2-Bromo-4,6-dimethoxybenzaldehyde is a halogenated aromatic aldehyde building block widely employed in organic synthesis for constructing complex molecular scaffolds via cross-coupling, condensation, and cyclization reactions.

CAS Number

Needs verification — not confirmed in source material

Molecular Formula

C9H9BrO3

Molecular Weight

245.07 g/mol (needs review)

Appearance

Solid (exact form needs review)

Key Functional Groups

Aldehyde (–CHO), bromine substituent, two methoxy groups (–OCH3)

Primary Use

Synthetic intermediate in pharmaceutical and fine-chemical research

Storage Condition

Cool, dry, well-ventilated area; away from light and moisture (exact conditions need review)

SKU

B691190

Chemical Identity and Physical Properties

2-Bromo-4,6-dimethoxybenzaldehyde (SKU: B691190) is an aryl aldehyde featuring a bromine atom at the ortho position relative to the aldehyde group, with methoxy substituents at the 4- and 6-positions of the benzene ring. This substitution pattern imparts distinct steric and electronic characteristics: the methoxy groups are electron-donating via resonance, while the bromine atom serves as a handle for metal-catalyzed cross-coupling reactions.

The compound belongs to the broader class of halogenated benzaldehydes and is classified as an aromatic aldehyde intermediate. Its molecular formula is C₉H₉BrO₃ with an approximate molecular weight of 245.07 g/mol. Specific physical constants including melting point, boiling point, density, and solubility profile should be confirmed against the certificate of analysis (CoA) supplied with each lot of B691190.

Synthetic Applications and Reactivity

The aldehyde functionality of 2-Bromo-4,6-dimethoxybenzaldehyde makes it reactive toward a broad range of transformations central to medicinal and synthetic chemistry:

• Palladium-catalyzed cross-coupling: The aryl–bromine bond undergoes Suzuki–Miyaura, Heck, Negishi, and Sonogashira couplings, enabling direct introduction of aryl, alkenyl, or alkynyl groups onto the ring.
• Nucleophilic addition to the aldehyde: Grignard reagents, organolithiums, and hydride reducing agents (e.g., NaBH₄, LiAlH₄) react at the carbonyl carbon to give secondary alcohols or the corresponding benzyl alcohol.
• Condensation reactions: The aldehyde participates in Knoevenagel, Wittig, and aldol-type condensations to generate extended conjugated systems useful in materials science.
• Cyclization: Combined aldehyde and halide functionality allows one-pot strategies for constructing heterocyclic scaffolds (e.g., benzofurans, isocoumarins) when paired with bifunctional coupling partners.

The electron-rich aromatic ring (due to methoxy groups) may also participate in electrophilic aromatic substitution under forcing conditions, though the steric environment should be considered when designing reactions.

Safe Handling, Storage, and Disposal

Personal Protective Equipment (PPE): Wear appropriate nitrile or neoprene gloves, safety goggles, and a lab coat when handling this compound. Work in a fume hood to avoid inhalation of dust or vapors, as aromatic aldehydes and brominated aromatics may be irritating to the respiratory tract, eyes, and skin.

Storage: Store B691190 in a tightly sealed container in a cool, dry, and well-ventilated area away from direct light, heat sources, and incompatible materials (strong oxidizers, strong bases). Exact recommended temperature range should be confirmed from the product label and CoA.

Stability: The aldehyde group can be susceptible to aerial oxidation over time. To preserve integrity, minimize exposure to air and moisture upon each use, and reseal promptly after weighing.

Disposal: Dispose of waste material and contaminated items in accordance with local, regional, and national regulations for halogenated organic waste. Consult the Safety Data Sheet (SDS) for B691190 for full hazard classification and emergency procedures.

Note: Specific GHS hazard classifications, H-statements, and P-statements are not confirmed in the available source material and must be verified against the official SDS before use.

Quality, Purity, and Ordering Information

Aladdin Scientific supplies 2-Bromo-4,6-dimethoxybenzaldehyde under SKU B691190. Each lot is accompanied by a Certificate of Analysis (CoA) detailing purity (typically assessed by GC or HPLC), appearance, and lot-specific analytical data. Researchers should verify purity specifications against their application requirements prior to ordering.

For demanding applications such as asymmetric catalysis or reference standard preparation, additional characterization by NMR or mass spectrometry is advisable. Contact Aladdin Scientific technical support for current stock availability, custom quantities, or bulk pricing inquiries.

Procurement teams should reference SKU B691190 in purchase orders to ensure accurate fulfillment. Updated SDS and CoA documents are available on request or through the Aladdin Scientific product portal.

Frequently asked questions

What reactions is 2-Bromo-4,6-dimethoxybenzaldehyde commonly used for?

This compound is primarily used as a bifunctional building block in palladium-catalyzed cross-coupling reactions (e.g., Suzuki, Heck, Sonogashira), nucleophilic additions to the aldehyde carbonyl, and condensation-cyclization strategies for heterocycle synthesis. The aldehyde and aryl bromide groups can be addressed independently or simultaneously in one-pot protocols.

How should 2-Bromo-4,6-dimethoxybenzaldehyde (B691190) be stored to maintain stability?

Store the compound in a tightly sealed container in a cool, dry, and well-ventilated area, protected from light and moisture. The aldehyde group is susceptible to aerial oxidation, so the container should be resealed promptly after each use. Confirm the specific temperature range from the product label or Certificate of Analysis.

What purity grade is available for SKU B691190, and how is it verified?

Aladdin Scientific provides a Certificate of Analysis with each lot of B691190, with purity typically determined by GC or HPLC analysis. Researchers requiring higher-specification material for reference standard or regulatory work should contact technical support for lot-specific data or request additional characterization.

Is 2-Bromo-4,6-dimethoxybenzaldehyde hazardous, and what precautions are required?

As a brominated aromatic aldehyde, this compound should be treated with appropriate caution. Use PPE including gloves, eye protection, and lab coat, and handle in a fume hood. Refer to the official Safety Data Sheet (SDS) for B691190 for confirmed GHS hazard classifications, first-aid measures, and disposal requirements, as specific hazard data were not available in the current source material.

References

1. Aladdin Scientific product page for 2-Bromo-4,6-dimethoxybenzaldehyde, SKU B691190.
2. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley, general reference for aldehyde and cross-coupling reactivity.
3. Miyaura, N.; Suzuki, A. Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds. Chemical Reviews, 1995. General reference for Suzuki coupling applicability to aryl bromides.

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.