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2-Bromophenol, also known as ortho bromophenol, is an organic compound. The appearance is a colorless to yellow liquid with an unpleasant odor. It is slightly soluble in water and soluble in organic solvents such as ethanol and ether. It is stable at room temperature and pressure and avoids heating. Do not come into contact with acyl chlorides, acid anhydrides, strong oxidants, etc. It is flammable in the presence of open flames and high heat, and can decompose into toxic bromide gases under high heat. It is an important organic synthetic intermediate widely used in the synthesis of fine chemicals such as pharmaceuticals, pesticides, plastic and rubber additives, disinfectants and preservatives. It can also be used as an intermediate in the preparation of drugs such as tamoxifen and as a solvent.
Additional information of chemical compound:
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Chemical Formula |
C6H5BrO |
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Exact Mass |
171.95 |
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Molecular Weight |
173.01 |
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m/z |
171.95(100.0%),173.95(97.3%),172.96(6.5%),174.95(6.3%) |
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Elemental Analysis |
C, 41.65; H, 2.91; Br, 46.18; O, 9.25 |
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Melting point |
5℃ |
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Boiling point |
195℃(lit.) |
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Density |
1.492 g/mL at 25℃(lit.) |
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2-Bromophenol, also known as ortho bromophenol, is an important organic compound with wide applications in various industrial fields. The following is a detailed analysis of its use:
Organic synthesis intermediates
N-bromophenol is an important intermediate in the synthesis of various anti-tumor drugs. For example, in the synthesis of tamoxifen, ortho bromophenol was involved as a key intermediate in multiple critical steps. Tamoxifen is a non steroidal anti estrogen drug, widely used in the treatment of breast cancer and other diseases. By introducing and converting ortho bromophenol, tamoxifen molecules with specific pharmacological activities can be efficiently synthesized. In addition to anti-tumor drugs, ortho bromophenol can also be used to synthesize various other types of drugs.
For example, in the synthesis of certain antibacterial, antiviral, or anti-inflammatory drugs, ortho bromophenol can be used as a starting material or intermediate to obtain the target product through a series of chemical reactions. In the synthesis process of certain drugs, structural modifications of drug molecules are required to enhance their efficacy or reduce their toxic side effects. Ortho bromophenol can modify the structure of drug molecules through substitution, addition, and other reactions, thereby obtaining new drug molecules with better efficacy or lower toxicity. Chiral drugs have unique pharmacological activities, but their synthesis is often complex.
Pesticide field
O-Bromophenol is an important intermediate in the synthesis of various insecticides. For example, in the synthesis of certain organophosphorus, organochlorine, or carbamate insecticides, o-bromophenol can be used as a starting material or intermediate to obtain the target product through a series of chemical reactions. These insecticides play an important role in agricultural production, helping to protect crops from pests and diseases. In addition to insecticides, ortho bromophenol can also be used to synthesize fungicides and herbicides.
These pesticides also have significant importance in agricultural production, as they can increase crop yield and quality. By introducing and converting ortho bromophenol, pesticide molecules can be structurally modified to enhance their efficacy or reduce their dosage. This is of great significance for reducing pesticide pollution to the environment and improving agricultural production efficiency. Some pesticide molecules have high toxicity and pose potential threats to human health and the environment. By modifying and modifying with ortho bromophenol, the toxicity of pesticide molecules can be reduced, thereby improving their safety of use.
Dye field
Ortho bromophenol is an important intermediate for the synthesis of various azo dyes. Azo dye molecules with specific colors and dyeing properties can be efficiently synthesized through diazotization and coupling reactions of ortho bromophenol. These dyes are widely used in industries such as textiles, leather, printing, etc., bringing rich and colorful colors to people's lives. O-Bromophenol can also be used to synthesize various other types of dyes. For example, in the synthesis of certain anthraquinone, phthalocyanine, or metal complex dyes, ortho bromophenol can be used as a starting material or intermediate.
By introducing and converting ortho bromophenol, dye molecules can be structurally modified to improve their dyeing performance or fastness. This is of great significance for improving the quality and market competitiveness of textiles. With the increasing awareness of environmental protection, people have put forward higher requirements for the environmental friendliness of dyes. Through the modification and modification of ortho bromophenol, a new type of dye with low toxicity, easy degradation and other environmental characteristics can be developed.
Plastic and rubber fields
O-Bromophenol can be used to synthesize antioxidants, improve the heat resistance and aging resistance of plastics and rubber. This is of great significance for extending the service life of plastic and rubber products and maintaining their stable performance. By introducing and converting ortho bromophenol, plasticizers with specific plasticizing effects can be synthesized. These plasticizers can improve the processing and physical properties of plastics and rubber.
By modifying and modifying with ortho bromophenol, the physical properties of plastics and rubber, such as hardness, toughness, tensile strength, etc., can be improved. This is of great significance for meeting the demand for plastic and rubber products in different fields. Adding specific functional derivatives of ortho bromophenol to plastics and rubber can endow them with new properties or uses. For example, plastic and rubber products with conductivity, magnetism, or flame retardancy can be synthesized.
Disinfectants and preservatives
2-Bromophenol has effective killing effects on various bacteria, fungi, and viruses. For example, it can effectively kill common pathogenic bacteria such as Escherichia coli, Staphylococcus aureus, Neisseria gonorrhoeae, Vibrio cholerae, as well as viruses such as hepatitis virus and influenza virus. This makes ortho bromophenol have broad application prospects in disinfection of public places, surface disinfection of environmental objects, and disinfection of sanitary ware. O-Bromophenol exhibits strong bactericidal activity at lower concentrations. The bactericidal effect is positively correlated with concentration, and the higher the concentration, the better the bactericidal effect.
However, it should be noted that excessively high concentrations may have adverse effects on the environment and human health, so strict concentration control is necessary when using. Compared to other disinfectants, ortho bromophenol has relatively mild properties. It will not cause significant corrosion or damage to the disinfected items, nor will it cause serious irritation or injury to human skin. This makes ortho bromophenol a safe and reliable disinfectant. Can be used for disinfection of public places, surface disinfection of environmental objects, disinfection of sanitary ware, disinfection of aquaculture, disinfection of industrial water, tap water, domestic sewage, etc.
Application as a preservative
O-Bromophenol has effective inhibitory effects on various bacteria, fungi, and molds. This makes it have broad application prospects in fields such as food, cosmetics, and medicine. For example, in terms of food preservation, ortho bromophenol can be used to extend the shelf life of food and prevent it from spoiling due to microbial contamination; In terms of cosmetic preservation, ortho bromophenol can be used to inhibit microbial growth in cosmetics, maintaining their stability and safety.
Compared to other preservatives, ortho bromophenol has relatively low toxicity and irritation. It will not cause significant harm to human health, nor will it pollute the environment. This makes it a safe and reliable preservative. It has good stability at room temperature and is not easily decomposed or deteriorated. This enables it to maintain a good anti-corrosion effect during storage and use. Can be used for food preservation, cosmetics preservation, pharmaceutical preservation, other industrial preservation, etc.
The discovery of 2-bromophenol can be traced back to the flourishing period of organic chemistry in the 19th century. According to existing literature, German chemist Karl Lehmann first reported in 1856 the possible presence of ortho substituents in the products of phenol bromination reactions. However, due to limitations in analytical techniques at the time, Lehman was unable to accurately identify the structure of ortho bromophenol.
French chemist Charles Friedel first confirmed the molecular formula of o-bromophenol through elemental analysis and melting point determination in his systematic research in the 1870s. Friedel discovered that when phenol reacts with bromine at low temperatures, it mainly produces monobrominated products, with a significant proportion of ortho isomers. This discovery provides early experimental evidence for understanding the regioselectivity of aromatic electrophilic substitution reactions.
At the end of the 19th century, with the improvement of organic structure theory, chemists gradually recognized the particularity of 2-bromophenol. German chemist Victor Meyer proposed in 1888 that the ortho substitution effect of phenolic hydroxyl groups may be related to the formation of intramolecular hydrogen bonds. This insight laid the foundation for later understanding the physical and chemical properties of 2-bromophenol. In the 20th century, the research on ortho bromophenol ushered in an important turning point.
In 1903, British chemist William Henry Perkin Jr. developed a more efficient synthesis method, successfully increasing the yield of ortho bromophenol to over 70% by controlling reaction conditions and brominating agent ratios. This breakthrough has enabled the large-scale preparation of the compound and promoted the in-depth study of its properties.
In 1912, German chemist Otto Diels first determined the crystal structure of ortho bromophenol and found that its molecules formed dimers through hydrogen bonding.
2-Bromophenol is a significant organic compound with diverse applications across various industries, including pharmaceuticals, agrochemicals, dyes, and organic synthesis. Its unique structure and properties make it a valuable intermediate in the synthesis of more complex molecules. However, the handling and use of 2-bromophenol require careful consideration of its safety and environmental impact. By understanding its synthesis methods, physical and chemical properties, applications, safety precautions, and regulatory requirements, industries and researchers can effectively utilize 2-bromophenol while minimizing its potential risks to human health and the environment. As research continues to advance, new applications and safer handling methods for 2-bromophenol may emerge, further expanding its utility and ensuring its sustainable use in the future.
Frequently Asked Questions
What are the safety precautions for using bromophenol blue?
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Use explosion-proof electrical/ventilating/lighting equipment. Ensure that eyewash stations and safety showers are close to the workstation location. OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166. Wear appropriate protective gloves and clothing to prevent skin exposure.
What is the correct common name of 2-bromophenol?
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2.4 Synonyms
2-bromophenol.
o-bromophenol.
ortho-bromophenol.
Why does bromophenol blue turn yellow?
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The color change in Bromophenol Blue is due to the ionization of its molecular structure at different pH levels. In Acidic Solutions (pH < 3.0): The molecule exists in its protonated form, appearing yellow.
Does Bromophenol blue dissolve in water?
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Solvent selection: Bromophenol blue is usually dissolved in water, but can also be dissolved in organic solvents such as ethanol or DMSO depending on the specific experimental needs. 2. Electrophoresis tracking: Bromophenol blue is often used as a tracking dye in gel electrophoresis.
What is the color change of bromophenol?
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It's typically yellow in acidic conditions and transitions to blue as the solution becomes more alkaline. This color shift occurs due to changes in the electronic structure of the molecule as it donates or accepts protons (H⁺ ions), making it a useful tool for tracking pH changes in various laboratory applications.
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