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2-Bromophenol is an aromatic halogenated phenol compound commonly used as a building block in organic synthesis. It is an ortho-substituted bromophenol, where a bromine atom is attached to the benzene ring at the second position relative to the hydroxyl group (-OH). The presence of both hydroxyl and halogen groups makes it a versatile reagent in the synthesis of pharmaceuticals, agrochemicals, and fine chemicals.
Chemical Structure and Properties
Chemical Structure
The structure of 2-bromophenol consists of a benzene ring with two functional groups:
This combination gives the molecule unique chemical and physical properties, including polarity, reactivity, and solubility.
Synthesis of 2-Bromophenol
2-Bromophenol can be synthesized by:
Applications of 2-Bromophenol
Reactivity of 2-Bromophenol
2-Bromophenol exhibits both nucleophilic and electrophilic reactivity due to the presence of the hydroxyl and bromine groups:
Safety and Handling
2-Bromophenol is classified as a hazardous substance and should be handled with care.
Hazards:
Precautions:
First Aid Measures:
Environmental Impact
2-Bromophenol can be toxic to aquatic life and should not be released into the environment. Proper waste disposal methods must be followed in compliance with local regulations.
Conclusion
2-Bromophenol is a valuable reagent in organic synthesis, particularly in the pharmaceutical and agrochemical industries. Its unique structure and reactivity make it an important intermediate in various chemical transformations. While it is a useful compound, appropriate safety precautions should be taken to handle it safely due to its hazardous properties.
Chemical Structure and Properties
| Chemical Name | 2-Bromophenol |
| Molecular Formula | C₆H₅BrO |
| Molecular Weight | 173.01 g/mol |
| CAS Number | 95-56-7 |
| Appearance | White to pale yellow crystalline solid |
| Boiling Point | 210°C |
| Melting Point | 7°C |
| Density | 1.77 g/cm³ |
| Solubility | Slightly soluble in water, soluble in organic solvents like ethanol, ether, and chloroform |
Chemical Structure
The structure of 2-bromophenol consists of a benzene ring with two functional groups:
- Hydroxyl group (-OH) at the first position.
- Bromine atom (Br) at the second position (ortho position).
This combination gives the molecule unique chemical and physical properties, including polarity, reactivity, and solubility.
Synthesis of 2-Bromophenol
2-Bromophenol can be synthesized by:
- Bromination of Phenol:
- Phenol undergoes electrophilic aromatic substitution with bromine in the presence of a catalyst (like FeBr₃), resulting in bromophenol. By controlling the reaction conditions, the ortho isomer (2-bromophenol) can be selectively produced.
Reaction:
C6H5OH+Br2→C6H4BrOH+HBr\text{C}_6\text{H}_5\text{O H} + \text{Br}_2 \rightarrow \text{C}_6\text{H}_4\text{BrOH} + \text{HBr}C6H5OH+Br2→C6H4BrOH+HBr - Direct Bromination with NBS (N-Bromosuccinimide):
- NBS is used as a brominating agent in the presence of a radical initiator (like light or peroxide) to selectively brominate phenol derivatives at the ortho position.
Applications of 2-Bromophenol
- Intermediate in Pharmaceutical Synthesis:
- 2-Bromophenol is a key starting material in the production of antifungal agents, analgesics, and anti-inflammatory drugs.
- It is used to prepare brominated benzodiazepines and other heterocyclic compounds.
- Building Block in Organic Synthesis:
- It is used as a precursor for the synthesis of aryl ethers, aryl amines, and aryl halides.
- The hydroxyl and bromine groups facilitate substitution and coupling reactions, such as:
- Suzuki coupling
- Buchwald-Hartwig amination
- Ullmann reaction
- Agrochemical Synthesis:
- Used in the preparation of fungicides, herbicides, and pesticides.
- Polymer Chemistry:
- It is employed in the modification of polymers and resins, improving their chemical and thermal properties.
- Dye and Pigment Manufacturing:
- The compound is used in the synthesis of azo dyes and organic pigments.
- Biochemical Studies:
- It serves as a model compound in studying the interaction of phenolic compounds with biological systems, particularly their role in enzyme inhibition and antioxidant activity.
Reactivity of 2-Bromophenol
2-Bromophenol exhibits both nucleophilic and electrophilic reactivity due to the presence of the hydroxyl and bromine groups:
- Nucleophilic Substitution (SNAr):
- The bromine atom can be displaced by a nucleophile (e.g., amine, thiol, or alkoxide) to form various derivatives.
- Electrophilic Substitution:
- The hydroxyl group activates the benzene ring, making it more susceptible to further electrophilic substitutions, such as nitration, sulfonation, or alkylation.
- Oxidation:
- The hydroxyl group can be oxidized to form quinones or other oxidized phenol derivatives.
Safety and Handling
2-Bromophenol is classified as a hazardous substance and should be handled with care.
Hazards:
- Causes skin and eye irritation.
- Harmful if inhaled or ingested.
- Can cause environmental damage if released into water bodies.
Precautions:
- Wear PPE: Gloves, goggles, and a lab coat should be worn while handling.
- Work in a fume hood: Avoid inhaling vapors.
- Proper storage: Keep in a cool, dry place, away from heat, moisture, and incompatible substances (e.g., strong oxidizers).
First Aid Measures:
- Skin contact: Wash thoroughly with soap and water.
- Eye contact: Rinse with water for at least 15 minutes and seek medical attention.
- Inhalation: Move to fresh air immediately and seek medical help if symptoms persist.
Environmental Impact
2-Bromophenol can be toxic to aquatic life and should not be released into the environment. Proper waste disposal methods must be followed in compliance with local regulations.
Conclusion
2-Bromophenol is a valuable reagent in organic synthesis, particularly in the pharmaceutical and agrochemical industries. Its unique structure and reactivity make it an important intermediate in various chemical transformations. While it is a useful compound, appropriate safety precautions should be taken to handle it safely due to its hazardous properties.