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4-Amino-3-fluorophenol, also known as 3-fluoro-4-aminophenol or 2-fluoro-4-hydroxyaniline, appears as a white powder with a CAS number of 399-95-1, a molecular formula of C6H6FNO, and a molecular weight of 127.12 (or 127.116, with slight differences in calculation accuracy). Decomposition or oxidation reactions may occur under conditions such as high temperature, strong acid, strong alkali, or oxidizing agents. In the field of energy, it can be used to develop new energy materials such as fuel cells, solar cells, etc. By introducing this compound, the performance of energy materials can be improved, and their energy conversion efficiency and stability can be enhanced. These new energy materials have broad application prospects in renewable energy, energy conservation and emission reduction, and can help promote the sustainable development of the energy industry.
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Chemical Formula |
C6H6FNO |
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Exact Mass |
127 |
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Molecular Weight |
127 |
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m/z |
127 (100.0%), 128 (6.5%) |
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Elemental Analysis |
C, 56.69; H, 4.76; F, 14.95; N, 11.02; O, 12.59 |
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4-Amino-3-fluorophenol, as a key organic synthesis intermediate, has shown extensive potential for applications in multiple fields.
Pesticide field
The application in the field of pesticides is mainly reflected as an important intermediate for the production of insecticides and herbicides.
Production of insecticides:
It can be used to synthesize various insecticides, among which the most famous is fipronil. Fluconazole is an efficient insecticide with significant killing effects on various pests. It is widely used in agricultural production, effectively protecting crops from pest damage and improving crop yield and quality.
In addition, it can also be used as a synthetic material for other insecticides, such as fipronil. These insecticides play an important role in agricultural production, helping to maintain ecological balance and ensure food security.
Production of herbicides:
In addition to insecticides, it can also be used for synthesizing herbicides. Herbicides are used in agricultural production to control weed growth, reduce competition from weeds for crops, and thus improve crop yield and quality.
By introducing active ingredients such as this substance, new herbicides with high efficiency, low toxicity, and environmental friendliness can be developed to meet the needs of modern agriculture for green and sustainable production.
Medical field
In the field of medicine, it also shows a wide range of application prospects.
Drug intermediates:
It is an important intermediate for synthesizing various drugs. For example, it can be used to synthesize nonsteroidal anti-inflammatory and analgesic drugs, which are widely used in clinical practice to treat diseases such as rheumatoid arthritis and osteoarthritis, and have significant analgesic and anti-inflammatory effects.
Antibacterial active agents:
It has certain antibacterial activity and can inhibit the growth and reproduction of certain bacteria. Therefore, it can be used as one of the raw materials for antibacterial agents to develop new drugs with broad-spectrum antibacterial effects.
These antibacterial agents can be used clinically to treat infectious diseases caused by bacteria, such as skin infections, respiratory infections, etc. By introducing active ingredients such as this substance, new antibacterial agents with high efficiency, low toxicity, and low susceptibility to drug resistance can be developed to meet clinical needs.
Dye field
In the field of dyes, it also plays an important role.
Raw materials for dye synthesis:
It can be used to synthesize various dyes, such as azo dyes, anthraquinone dyes, etc. These dyes have bright colors and good dyeing performance, and are widely used in industries such as textiles and printing and dyeing.
By introducing active groups such as this substance, new dyes with special color effects and dyeing properties can be developed to meet the market's demand for high-quality textiles.
Improve dye performance:
In addition to being used as a raw material for dye synthesis, it can also be used to improve the performance of dyes. For example, it can improve the light resistance, wash resistance, and other properties of dyes, making them more durable and stable on textiles.
By introducing modifiers such as this substance, new dyes with higher performance can be developed to improve the quality and added value of textiles.
Materials Science Field
In the field of materials science, applications are mainly reflected in the modification of materials.
Nanomaterial modification:
Can be used to modify nanomaterials such as nanoparticles, nanofibers, etc. By introducing its active functional groups, the surface properties and functional characteristics of nanomaterials can be improved, such as enhancing their dispersibility and stability.
These modified nanomaterials have broad application prospects in fields such as electronics, optics, catalysis, etc., which can help improve the performance and quality of related products.
Other fields
In addition to the aforementioned fields, 4-amino-3-fluorophenol can also be applied to multiple other areas.
Analytical reagents:
It can be used as an analytical reagent in fields such as chemical analysis and environmental monitoring. For example, it can be used to detect the fluoride ion content in water, providing strong support for environmental protection and water quality monitoring.
In addition, it can also be used for other chemical analysis experiments, such as photometry, chromatography, etc., providing necessary experimental materials and tools for scientific research and technological development.
Organic synthesis raw materials:
As an important organic synthesis raw material, it can be used to synthesize various organic compounds. These compounds have broad application prospects in fields such as pesticides, pharmaceuticals, dyes, etc.
By introducing its active groups, new organic compounds with special structures and functions can be developed to meet the market's demand for high-quality chemicals.
Optoelectronic materials:
It also has certain application potential in the field of optoelectronic materials. By introducing this compound, new materials with excellent optoelectronic properties can be developed, such as organic light-emitting diodes (OLEDs).
These optoelectronic materials have broad application prospects in display technology, lighting technology, and other fields, which can help promote innovation and upgrading in related industries.
Biomedical field:
In the biomedical field, it can be used to synthesize compounds with biological activity, such as drugs, biomarkers, etc. These compounds have potential application value in disease diagnosis, treatment, and other fields.
By conducting in-depth research on its biological activity and mechanism of action, new ideas and methods can be provided for the field of biomedical research.
Energy sector:
In the field of energy, it can be used to develop new energy materials such as fuel cells, solar cells, etc. By introducing this compound, the performance of energy materials can be improved, and their energy conversion efficiency and stability can be enhanced.
These new energy materials have broad application prospects in renewable energy, energy conservation and emission reduction, and can help promote the sustainable development of the energy industry.
The synthesis of 3-fluoro-4-aminophenol is specifically divided into the following four steps:
(1) Add nickel nitrate and palladium chloride to ethanol and stir until completely dissolved to obtain a mixed solution. Add butyl titanate to ethanol and stir for 20 minutes. The molar ratio of nickel nitrate, palladium chloride, and butyl titanate is 15:3:100. Then add the mixed solution and continue stirring for 4 hours. Let it stand at room temperature for 10 hours, dry it in a vacuum oven at 90 ° C for 4 hours, and then place it in an air atmosphere in a muffle furnace and heat it up to 550 ° C for 3 hours. After cooling to room temperature, remove it, grind it, and sieve it to obtain a composite catalyst;
(2) Add metallic sodium to methanol and stir until evenly mixed to obtain a 8.7% mass concentration sodium methoxide solution. Add 2,4-difluoronitrobenzene and methanol to a three necked flask, pass nitrogen for 1 hour, and then add sodium methoxide solution dropwise within 30 minutes. After dropwise addition, reflux at 45 ° C for 5 hours. After evaporating methanol, add dichloromethane. The weight ratio of 2,4-difluoronitrobenzene, methanol, sodium methoxide solution, and dichloromethane in the three necked flask is 16:13:29:31. After stirring for 1 hour, filter to remove sodium fluoride, and distill the filtrate to remove dichloromethane to obtain 2-fluoro-4-methoxy-nitrobenzene;
(3) Add the 2-fluoro-4-methoxy-nitrobenzene, benzene, and aluminum chloride obtained in step (2) into a three necked flask, reflux at 45 ° C for 11 hours, cool to room temperature, pour the reaction solution into ice water, add concentrated hydrochloric acid for acidification, and let it stand to separate into an aqueous layer and a benzene layer. After removing the aqueous layer, decolorize the benzene layer with activated carbon and remove benzene by rotary evaporation to obtain crude 3-fluoro-4-nitrophenol. Add the crude 3-fluoro-4-nitrophenol to water and stir to form a crude aqueous solution. Then, perform steam distillation until the distillate is transparent. After cooling to room temperature, precipitate a yellow solid. Extract the crude aqueous solution three times with ether, combine the yellow solid with the three extractions, dry with sodium sulfate, and evaporate. After solvent treatment, 3-fluoro-4-nitrophenol was obtained, and the weight ratio of 2-fluoro-4-methoxy-nitrobenzene, benzene, aluminum chloride, ice water, water, and ether was 6:44:11:33:50:15;
(4) Add the 4-amino-3-fluorophenol and ethanol obtained in step (3) with a weight ratio of 6:18:1, as well as the composite catalyst obtained in step (1), into a four necked flask. Introduce hydrogen gas until the hydrogen pressure in the flask reaches 0.2 MPa, then start stirring and maintain the hydrogen pressure. Heat the flask to 45 ℃ and stir for 2 hours. After cooling to room temperature, filter the obtained product, remove ethanol from the filtrate, and distill under reduced pressure to obtain 3-fluoro-4-aminophenol.
adverse reaction
The product is a brown crystalline or black to brown powder with carcinogenic properties (Class 1B), skin sensitization, and acute oral toxicity. Its adverse reactions include acute poisoning (such as digestive system irritation, skin allergies), chronic exposure risks (such as carcinogenicity), and environmental hazards (aquatic toxicity).
Acute toxic reaction
Digestive system stimulation
Clinical manifestations: Symptoms such as nausea, vomiting, abdominal pain, and diarrhea may occur after ingestion, and in severe cases, it can lead to gastric mucosal bleeding or chemical gastritis.
Case: A laboratory staff mistakenly used it as a regular reagent, and after taking about 50 mg orally, severe vomiting occurred. After treatment with emetic stimulation and activated carbon adsorption, the symptoms were relieved.
Mechanism: Fluoroaromatic hydrocarbons directly stimulate the gastric mucosa, triggering inflammatory reactions and cell apoptosis.
Skin allergies
Clinical manifestations: redness, itching, and blisters appear at the contact site, and in severe cases, it can develop into contact dermatitis.
Animal experiment: Rabbit skin irritation test showed that after applying 0.1 g of the original solution for 24 hours, the skin reaction score reached level 3 (maximum level 4).
Mechanism: As a hapten, it binds to skin proteins to form a complete antigen, triggering IgE mediated type I hypersensitivity reaction.
Respiratory irritation
Clinical manifestations: Coughing, shortness of breath, and chest pain may occur after inhaling vapor, and high concentration exposure may lead to chemical pneumonia.
Case: In a chemical plant leak accident, two workers developed laryngeal edema after inhaling steam and required tracheotomy treatment.
Mechanism: Fluoroaromatic hydrocarbons stimulate respiratory mucosa, causing bronchospasm and release of inflammatory factors.
FAQ
1. What is its main application?
It is mainly used as a key intermediate in the fields of medicine, pesticides (such as insecticides and herbicides), and organic synthesis. In the field of medicine, it is used to develop painkillers and anti-inflammatory drugs; in the field of materials, it is also used to manufacture dyes, polymers and coatings.
2. What are the key physical properties of it?
- CAS Number: 399-95-1
- Molecular Formula: C6H6FNO
- Molecular Weight: 127.12
- Melting Point: 135 - 140°C
- Appearance: Pale yellow to brown powder or crystals
3. What should be noted during storage?
To ensure stability, it is recommended to store in an inert gas (such as argon) atmosphere, in a refrigerator at 2-8°C, protected from light, and ensure the container is sealed to avoid contact with air.
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