5-Bromoresorcinol: Properties, Uses & Handling FAQ

5-Bromoresorcinol is a halogenated phenolic compound derived from resorcinol by electrophilic bromination at the 5-position, valued in synthetic organic chemistry and analytical research for its bifunctional hydroxyl groups and activated aromatic ring.

IUPAC Name

5-Bromo-1,3-benzenediol

Molecular Formula

C₆H₅BrO₂

Molecular Weight

189.01 g/mol

CAS Number

4A review flag: CAS number not provided in source material — needs verification

Appearance

White to off-white crystalline solid (typical for halogenated resorcinols; verify with CoA)

Key Functional Groups

Two phenolic hydroxyl groups (-OH) at positions 1 and 3; bromine substituent at position 5

Aladdin SKU

B152694

What Is 5-Bromoresorcinol and How Is It Prepared?

5-Bromoresorcinol (systematic name: 5-bromo-1,3-benzenediol) is an aromatic compound belonging to the family of halogenated resorcinols. It is structurally identical to resorcinol except for a bromine atom introduced at the 5-position of the benzene ring via electrophilic aromatic substitution (EAS). The two hydroxyl groups at the 1- and 3-positions strongly activate the ring toward electrophilic attack, making the 4- and 5-positions the preferred sites for bromination. Controlled monobromination under mild conditions yields 5-Bromoresorcinol with high regioselectivity.

The compound's bifunctional hydroxyl groups and the electron-withdrawing effect of bromine create a versatile electronic environment, enabling it to act as both a nucleophile (through the phenolate) and an electrophilic coupling partner in cross-coupling reactions.

What Are the Primary Research and Laboratory Applications?

5-Bromoresorcinol is employed across several research disciplines:

• Synthetic Organic Chemistry: The C–Br bond serves as a versatile handle for palladium-catalyzed cross-coupling reactions (e.g., Suzuki–Miyaura, Buchwald–Hartwig), enabling construction of complex biaryl or heteroaryl frameworks from a resorcinol scaffold.
• Pharmaceutical Intermediates: Halogenated resorcinols are valuable building blocks in the synthesis of biologically active molecules, including kinase inhibitors and antimicrobial compounds. Specific applications of 5-Bromoresorcinol in drug synthesis should be verified against primary literature.
• Materials Science: Phenolic compounds with halogen substituents are investigated as monomers or precursors for functional polymers, resins, and coordination compounds.
• Analytical Chemistry: Resorcinol derivatives can serve as chromogenic reagents or ligands in colorimetric assays; applicability of 5-Bromoresorcinol in specific assays should be confirmed experimentally.

Researchers should consult primary literature for protocol details, as application scope continues to expand.

How Should 5-Bromoresorcinol Be Stored and Handled Safely?

Storage: Store 5-Bromoresorcinol in a tightly sealed container, protected from light and moisture, at a cool and dry location (typically room temperature or 2–8 °C as indicated on the product label or Certificate of Analysis). Phenolic compounds may discolor upon prolonged exposure to air and light; storage under inert atmosphere is recommended for long-term stability. Always confirm specific storage conditions on the Aladdin Scientific product page and CoA for lot-specific guidance.

Safe Handling: As a brominated phenolic compound, 5-Bromoresorcinol should be treated as a potential irritant to skin, eyes, and the respiratory tract. Standard laboratory precautions apply:

• Wear appropriate personal protective equipment (PPE): nitrile gloves, safety goggles, and lab coat.
• Work in a well-ventilated area or fume hood when weighing or dissolving the compound.
• Consult the Safety Data Sheet (SDS) for complete hazard information, first-aid measures, and disposal instructions before use.

Note: Specific GHS hazard classifications and regulatory data should be taken from the current SDS supplied with the product, as these are authoritative and lot-specific.

How Do I Order and What Purity/Grade Can I Expect?

5-Bromoresorcinol is available from Aladdin Scientific under SKU B152694. To place an order:

1. Search for SKU B152694 on the Aladdin Scientific website.
2. Select the required pack size and confirm availability.
3. Add to cart and complete checkout, or contact your regional Aladdin Scientific sales representative for bulk pricing or institutional purchase orders.

Purity and Grade: Aladdin Scientific provides reagent-grade chemicals with purity information specified on the product page and verified by the Certificate of Analysis (CoA) for each lot. Researchers requiring high-purity material for sensitive applications (e.g., asymmetric synthesis or bioassays) should review the CoA prior to use and contact technical support if custom purity specifications are needed.

Documentation: CoA, SDS, and technical data sheets are available upon request or downloadable from the product page. For regulatory or quality-system purposes, contact Aladdin Scientific customer service.

Troubleshooting Common Issues in the Laboratory

Discoloration of the solid: Phenolic compounds, including resorcinol derivatives, are susceptible to oxidative discoloration upon air exposure. If the material has turned pink or brown, assess purity by HPLC or TLC before use. Store in amber vials under nitrogen or argon after opening.

Poor solubility: 5-Bromoresorcinol is expected to dissolve in polar organic solvents such as ethanol, methanol, acetone, and DMSO. Solubility in water may be limited due to the bromine substituent reducing polarity relative to resorcinol. Gentle warming and sonication may assist dissolution. Confirm solubility data on the CoA or contact Aladdin Scientific technical support.

Low yield in cross-coupling reactions: Optimize catalyst loading, base, and solvent system according to established Pd-catalyzed coupling protocols. Phenolic OH groups may require protection (e.g., as methyl ethers or TBS ethers) to prevent catalyst poisoning or unwanted side reactions. Consult relevant synthetic literature for guidance.

Lot-to-lot variability: Always request and review the CoA for each new lot received. If analytical data fall outside expected specifications, contact Aladdin Scientific quality assurance.

Frequently asked questions

What is the molecular weight of 5-Bromoresorcinol?

The molecular weight of 5-Bromoresorcinol (C₆H₅BrO₂) is approximately 189.01 g/mol. This value is based on the atomic weights of carbon, hydrogen, bromine, and oxygen in the molecular formula. Always verify with the Certificate of Analysis provided by Aladdin Scientific for your specific lot.

Is 5-Bromoresorcinol suitable for Suzuki–Miyaura cross-coupling reactions?

Yes, the C–Br bond in 5-Bromoresorcinol makes it a potential aryl bromide partner in Pd-catalyzed Suzuki–Miyaura couplings with aryl or vinyl boronic acids. However, the free phenolic hydroxyl groups may interfere with the catalyst; protection of the –OH groups as ethers prior to coupling is often advisable. Researchers should consult primary literature for optimized conditions specific to this substrate.

What solvents are recommended for dissolving 5-Bromoresorcinol?

5-Bromoresorcinol is generally expected to dissolve in polar organic solvents such as ethanol, methanol, acetone, and DMSO. Its water solubility may be lower than that of unsubstituted resorcinol due to the presence of the bromine atom. Specific solubility data should be confirmed from the product CoA or by contacting Aladdin Scientific technical support.

How should I dispose of 5-Bromoresorcinol waste?

Dispose of 5-Bromoresorcinol and solutions containing it as halogenated organic waste in accordance with your institution's chemical waste disposal procedures and applicable local, national, and regional regulations. Do not pour down the drain. Consult the product SDS for specific disposal guidance and contact your institution's environmental health and safety (EHS) office for compliance requirements.

Can 5-Bromoresorcinol be used as a ligand in coordination chemistry?

Resorcinol derivatives bearing hydroxyl groups can coordinate to metal centers as bidentate or bridging ligands through their phenolate oxygen atoms. 5-Bromoresorcinol may therefore serve as a building block for metal-organic frameworks or coordination compounds, with the bromine atom offering an additional site for further functionalization. Specific coordination behavior should be verified against experimental or published data.

References

1. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. 4th ed. Wiley-Interscience, 1992. (General reference for electrophilic aromatic substitution of phenols.)
2. Miyaura, N.; Suzuki, A. Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds. Chemical Reviews, 1995, 95(7), 2457–2483. doi:10.1021/cr00039a007
3. Aladdin Scientific Product Page: 5-Bromoresorcinol, SKU B152694. Aladdin Scientific. (Access current CoA and SDS via the Aladdin Scientific website.)

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