6-Bromo-2-naphthol is an important halogenated naphthol derivative that plays a vital role as an intermediate in pharmaceutical, agrochemical, and dye chemistry. Known for its unique reactivity and functional groups, this compound is especially valued in synthetic organic chemistry, where it serves as a precursor to a wide variety of functionalized molecules.
Chemical Identity
Chemical Name: 6-Bromo-2-naphthol
Molecular Formula: C10H7BrO
Molecular Weight: 223.07 g/mol
CAS Number: 1806-23-1
Appearance: Off-white to light yellow crystalline powder
Solubility: Slightly soluble in water; soluble in organic solvents like ethanol, acetone, and chloroform
Structure and Properties
The compound consists of a naphthalene ring substituted with a hydroxyl (-OH) group at the 2-position and a bromine atom at the 6-position. This dual functionality makes it highly reactive in various chemical transformations including:
Electrophilic substitution
Nucleophilic aromatic substitution
Coupling reactions
Bromination and oxidation
The hydroxyl group provides potential for hydrogen bonding and metal coordination, while the bromine atom is a good leaving group, facilitating cross-coupling reactions like Suzuki, Heck, and Sonogashira reactions.
Applications of 6-Bromo-2-Naphthol
1. Pharmaceutical Intermediates
6-Bromo-2-naphthol is commonly used in the synthesis of bioactive compounds. It serves as a building block for the production of drugs targeting antibacterial, antifungal, anti-inflammatory, and anticancer pathways. Its naphthol backbone is part of several pharmacophores found in:
Kinase inhibitors
Non-steroidal anti-inflammatory drugs (NSAIDs)
Antimicrobial agents
2. Dye and Pigment Synthesis
Naphthol derivatives are extensively used in the dye industry. 6-Bromo-2-naphthol is used to prepare azo dyes, coupling components, and fluorescent dyes that are key in textile and ink formulations.
3. Organic Synthesis and Cross-Coupling Chemistry
Due to the presence of a bromine atom, 6-Bromo-2-naphthol is a valuable aryl halide for palladium-catalyzed cross-coupling reactions. Chemists use it in:
Suzuki-Miyaura couplings for forming C-C bonds
Buchwald-Hartwig aminations for introducing amine groups
Functionalized polyaromatics synthesis for material science applications
4. Agrochemicals and Specialty Chemicals
It is also used as an intermediate for producing herbicides, fungicides, and plant growth regulators, owing to its structural compatibility with biologically active compounds.
Handling and Safety
Stability: Stable under recommended storage conditions (cool, dry, well-ventilated area)
Toxicity: May cause skin and eye irritation; avoid inhalation
Protective Measures: Use gloves, goggles, and lab coats; follow standard laboratory protocols
Disposal: Dispose in accordance with local environmental regulations
Always consult the Material Safety Data Sheet (MSDS) for detailed safety, handling, and storage information.
Packaging and Availability
6-Bromo-2-naphthol is available in:
Research quantities (1g, 5g, 25g)
Bulk quantities (100g, 500g, 1kg, 5kg+)
Custom synthesis available for high-purity or specific specifications
Supplied with Certificate of Analysis (COA), MSDS, and TDS upon request. Custom packaging and purity grades (98%–99%+) available for pharmaceutical and industrial clients.
Conclusion
6-Bromo-2-naphthol is a key intermediate with diverse applications in pharmaceuticals, materials science, and dye chemistry. Its reactive sites enable advanced transformations in organic synthesis, while its structural versatility ensures utility in multiple industries.
Highlights:
Efficient building block in drug and dye synthesis
Useful in cross-coupling reactions due to bromine functionality
Compatible with a wide range of solvents and reagents
Commercially available in multiple grades and quantities
Structural Features
Naphthalene Core: Provides aromatic stability and electron-rich characteristics
Hydroxyl Group (-OH): Increases polarity and allows for hydrogen bonding
Bromo Substituent (-Br): Enables further electrophilic substitution or cross-coupling reactions
These features make 6-Bromo-2-naphthol a useful starting material or intermediate in complex syntheses.
Applications of 6-Bromo-2-naphthol
1. Pharmaceutical Intermediate
Used in the synthesis of naphthol-based therapeutic agents and bioactive heterocycles with potential antimicrobial and anticancer activity.
2. Dye and Pigment Industry
Acts as a precursor for azo dyes, reactive dyes, and other chromophores used in textiles and coatings.
3. Organic Synthesis
Useful in Suzuki, Heck, and Sonogashira coupling reactions, allowing extension and functionalization of the aromatic framework.
4. Analytical Chemistry
Sometimes employed as a reagent or derivatization agent in spectrophotometric analysis.
Safety and Handling
Hazards: May cause skin and eye irritation; harmful if swallowed or inhaled
Precautions: Use gloves, goggles, and appropriate protective clothing; operate in a fume hood
Storage: Store in a cool, dry, and well-ventilated place, away from heat and oxidizing agents
Packaging and Availability
Available in:
Laboratory Quantities: 1g, 5g, 25g
Bulk Quantities: 100g, 500g, 1kg, 5kg packs
Supplied with COA, MSDS, and compliance documentation on request.
Conclusion
6-Bromo-2-naphthol is a valuable compound for researchers and industries working in the areas of drug development, organic dye chemistry, and fine chemical synthesis. Its functional groups make it ideal for a wide range of synthetic applications.
Need bulk or custom-packed 6-Bromo-2-naphthol? Contact us for specifications, pricing, and delivery information tailored to your R&D or manufacturing requirements.
Introduction
6-Bromo-2-naphthol is a halogenated aromatic compound derived from naphthol, featuring a bromine atom at the 6-position and a hydroxyl group at the 2-position of the naphthalene ring. Due to its reactivity and structural versatility, it finds wide usage in pharmaceutical research, dye manufacturing, and fine chemical synthesis.
Chemical Identity
IUPAC Name: 6-Bromo-2-naphthol
Molecular Formula: C10H7BrO
Molecular Weight: 223.07 g/mol
CAS Number: 116057-18-6
Appearance: Pale yellow to off-white crystalline powder
Solubility: Slightly soluble in water, soluble in organic solvents such as ethanol, chloroform, and ether
