samir12
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Mar 09, 2025
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6-bromo-2-naphthol
is an important halogenated naphthol derivative widely used in organic synthesis, dye manufacturing, and pharmaceutical research. This compound, derived from naphthalene, features a bromine atom at position 6 and a hydroxyl group (-OH) at position 2 of the naphthalene ring system. This specific positioning gives 6-bromo-2-naphthol its unique reactivity, making it valuable in chemical and industrial applications.
Chemical Information
Property Details
Chemical Name 6-Bromo-2-Naphthol
Molecular Formula C??H?BrO
Molecular Weight 223.07 g/mol
CAS Number 4282-15-5
Appearance Off-white to light brown solid
Melting Point ~140-145°C
Solubility Slightly soluble in water, soluble in organic solvents (ethanol, acetone, DMSO)
Structure of 6-Bromo-2-Naphthol
6-Bromo-2-Naphthol contains a naphthalene ring, which is a fused aromatic system, with:
A hydroxyl group (-OH) at position 2.
A bromine atom (Br) at position 6.
Structural Formula:
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Br
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OH
Synthesis of 6-Bromo-2-Naphthol
6-Bromo-2-Naphthol can be synthesized by:
1. Bromination of 2-Naphthol
2-Naphthol is treated with bromine (Br?) or N-bromosuccinimide (NBS) under controlled conditions to selectively introduce bromine at position 6.
This reaction is an example of electrophilic aromatic substitution, where the activated aromatic ring undergoes substitution due to the electron-donating -OH group.
Reaction:
?
BrOH+HBr
Applications of 6-Bromo-2-Naphthol
1. Intermediate in Dye Manufacturing
Naphthol derivatives, especially halogenated naphthols, are essential building blocks for azo dyes, pigments, and colorants.
6-Bromo-2-naphthol can undergo diazotization and coupling reactions to produce vibrant dyes.
2. Pharmaceutical Intermediate
Used as a precursor for synthesizing bioactive compounds, especially those with antibacterial, anti-inflammatory, or anticancer properties.
Halogenated aromatic systems like this are important in designing drug scaffolds with enhanced activity.
3. Ligand and Organic Synthesis
The -OH and -Br functional groups offer versatility in synthesis.
It can act as a precursor for forming ethers, esters, and aryl halides.
It also finds use in metal coordination complexes, serving as a ligand in catalytic applications.
4. Materials Chemistry
Researchers use 6-bromo-2-naphthol in modifying polymers or surfaces to improve hydrophobicity, adhesion, or optical properties.
Chemical Reactivity
Bromine (Br): Acts as a leaving group, enabling nucleophilic substitution reactions (e.g., forming ethers, amines, or thiols).
Hydroxyl Group (-OH): Activates the aromatic ring towards electrophilic substitution and can form esters, ethers, or undergo oxidation.
Safety and Handling
Hazard Category Details
Irritation May cause skin, eye, and respiratory irritation
Toxicity Harmful if swallowed or inhaled
Environmental Impact Toxic to aquatic life; avoid uncontrolled release
Precautionary Measures:
Use in a fume hood.
Wear gloves, safety goggles, and a lab coat.
Store away from heat, moisture, and incompatible materials such as strong oxidizing agents.
Environmental Impact
As with most halogenated aromatic compounds, 6-bromo-2-naphthol is persistent in the environment.
Proper disposal methods should be followed in accordance with local regulations.
Conclusion
6-Bromo-2-Naphthol stands out as a highly useful synthetic building block for dyes, pharmaceuticals, and specialty chemicals. Its bromine and hydroxyl groups enable rich chemical functionality, while its aromatic core offers stability and versatility. Despite its usefulness, care must be taken to handle and dispose of it safely to protect both health and the environment.
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