Chemist's Guide to 6-Bromo-2-Naphthol Functionalization
Chemist's Guide to 6-Bromo-2-Naphthol Functionalization
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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
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.
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