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3-Bromobiphenyl is an organic compound with the molecular formula C12H9Br, CAS 2113-57-7. It is a light yellow liquid that can be used as a raw material for pesticide fungicides and industrial disinfectants. It is an important industrial raw material and a widely used organic synthesis intermediate, widely used in fields such as pharmaceuticals and liquid crystal industry. In recent years, the export volume of product in China has been increasing, mainly to some LCD display manufacturers in Japan and South Korea. It is also used as a reagent for synthesizing benzene sulfonamide derivatives of 12-LOX inhibitors and for preparing pyrrolidine derivatives of GlyT1 inhibitors.
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C.F |
C10H13N5O4 |
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E.M |
267 |
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M.W |
267 |
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m/z |
267 (100.0%), 268 (10.8%), 268 (1.8%) |
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E.A |
C, 44.94; H, 4.90; N, 26.21; O, 23.95 |
The structure of it can be further decomposed into the following aspects:
◆ Main structure:
Bromobiphenyl is composed of two benzene rings, each containing six carbon atoms and five hydrogen atoms. These two benzene rings are connected by a conjugated bond, resulting in a planar structure of the entire molecule.
◆ Bromine substituents:
On a benzene ring of bromobiphenyl, the position of a hydrogen atom is replaced by a bromine atom. This bromine atom causes the molecule to exhibit partial polarity while also endowing the compound with specific chemical properties.
◆ Conjugate structure:
The two benzene rings in bromobiphenyl are connected by conjugated bonds to form an extended conjugated system. This conjugated system enables molecules to have good electronic conductivity and stability, and affects their behavior in chemical reactions.
◆ Space configuration:
Due to the fact that bromobiphenyl is a planar molecule, there is no chiral center or chiral isomer present. It can rotate freely without affecting the chemical properties of the molecules.
◆ Molecular properties:
Bromobiphenyl has a high melting and boiling point and exists in a solid or liquid state. It is easily soluble in organic solvents, but almost insoluble in water. Its physical and chemical properties make it widely used in fields such as preservatives.
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3-Bromobiphenyl is an organic compound with high antibacterial properties and is widely used in the field of preservatives.
1. Wood preservation:
Bromobiphenyl can be used as one of the components of wood preservatives. Wood is susceptible to damage from fungi, borers, and molds, leading to decay and degradation. Adding bromobiphenyl to wood can effectively inhibit the growth of these microorganisms and extend the lifespan of the wood. It can prevent wood decay, deformation, and loss of structural strength, while reducing adverse effects on the environment.
2. Coatings and adhesives:
Bromobiphenyl can be used as an antibacterial component in coatings and adhesives. Coatings and adhesives are prone to the growth of bacteria and fungi in humid environments, thereby reducing the performance and quality of products. By adding bromobiphenyl, it can effectively inhibit the growth of microorganisms, maintain the stability and anti pollution performance of coatings and adhesives.
3. Textile processing:
Bromobiphenyl can be used as an additive for textile preservatives. Textiles are often attacked by bacteria and mold in humid environments, producing odors and damaging fiber structures. By applying bromobiphenyl in textile treatment, it can effectively inhibit the growth of microorganisms, improve the durability and hygiene performance of textiles.
4. Protection of building materials:
In building materials, the addition of bromobiphenyl can have a anti-corrosion effect. For example, adding bromobiphenyl to building materials such as gypsum boards, insulation materials, and concrete can effectively inhibit the growth of microorganisms, prevent the decay and deterioration of building materials, and extend their service life.
5. Personal care products:
Due to its antibacterial properties, bromobiphenyl can be used in personal care products such as shampoo, shower gel, and hand cream. Adding bromobiphenyl can prevent microbial contamination of products, ensuring their safety and stability.
6. Conductive materials:
Bromobiphenyl can be used as a raw material for preparing conductive materials. By functionalizing with other compounds, materials such as polymers, textiles, and coatings with good conductivity can be prepared. These materials have important applications in the electronics industry and information technology.
Method for preparing 3-bromobiphenyl:
This method uses biphenyl as the raw material and undergoes four steps of nitration, reduction, bromination, and deamination, followed by extraction to obtain bromobiphenyl. This method is simple and the product is easy to separate.
The specific steps are as follows:
1) Nitrification reaction
Dissolve biphenyl in an organic solvent, add a mixture of nitric acid and sulfuric acid dropwise, and react at 55-60 ° C. After the reaction is completed, extract with water, collect the organic phase, and obtain the nitration product; Among them, the molar ratio of biphenyl to nitric acid is 1:1 to 1 6. Among them, 1:1. 2 is the optimal ratio; The organic solvent does not react with sulfuric acid or nitric acid and is not miscible with water;
2) Reduction reaction
Under stirring conditions, add iron powder and catalyst to the water to obtain a mixture of iron powder; Add nitration products dropwise to the mixture of iron powder for reaction; The optimal reaction is at 60 ° C; After the reaction is completed, alkalization is carried out to obtain the reduced product. Among them, the molar ratio of the nitration product to iron powder is 1:1 to 10, with 1:4 being the optimal ratio; The catalyst assists in the catalytic reduction of iron powder;
3) Bromination reaction
Add liquid bromine to the reduction product under stirring conditions and react at room temperature; After the reaction is completed, extract with water to obtain brominated products. Among them, the molar ratio of the reduction product to liquid bromine is 1: 1-4, where I: 1 26 is the optimal ratio;
4) Deamination reaction
Add brominated products to water, then add concentrated hydrochloric acid to the reaction system, and dissolve the generated brominated product hydrochloride under stirring conditions. Cool to o ° C to obtain a mixture of brominated products and salts; Add sodium nitrite to the brominated product hydrochloride mixture for reaction at a temperature not exceeding 5 ° C; After the reaction is completed, add sodium hypophosphate to it and stir until the reaction is complete; Finally, extract with ethyl acetate to obtain product;
Among them, the molar ratio of the brominated product, sodium nitrite, and sodium hypophosphate is 1:1 to 1 5: 5-15, of which 1: 1 2: 10 0 is the optimal reaction condition. Here, the brominated products first react with concentrated hydrochloric acid to generate hydrochloride and dissolve in water, ensuring that the reaction is homogeneous and can proceed smoothly.
What are the side effects of this compound?
3-Bromobiphenyl is an organic compound with a specific chemical structure and properties. Regarding its side effects, there is relatively little research on its direct impact on human health, as it is mainly used as a chemical raw material and synthetic intermediate and does not come into direct contact with the human body under normal circumstances. However, from the general properties of chemical substances and the toxicity of similar substances, we can speculate and analyze to a certain extent the possible side effects they may have. The following is a detailed explanation of its possible side effects:
◆ Potential side effect analysis
Skin and eye irritation
As a chemical substance, it has certain irritants and corrosives. In direct contact with the skin or eyes, it may cause skin inflammation, redness, pain, as well as symptoms such as eye pain and tearing. Long term exposure or exposure to high concentrations may also cause more severe skin lesions or eye damage.
Impact on respiratory system
Its volatility may cause it to form harmful gases in the air, causing damage to the respiratory system. Long term inhalation of the vapor produced by this substance may lead to respiratory diseases such as respiratory inflammation and bronchitis. In addition, harmful substances in steam may also irritate the throat and nasal cavity, causing symptoms such as coughing and sneezing.
Impact on the nervous system
Although there is limited research on its direct impact on the nervous system, the toxic effects of similar chemicals typically include interference with the normal transmission of neurotransmitters and dysfunction of the nervous system. Therefore, it may have adverse effects on the nervous system, leading to symptoms such as headache, dizziness, drowsiness, and lack of concentration. In extreme cases, it may even lead to more severe neurological disorders.
Effects on the digestive system
If accidentally ingested, it may have adverse effects on the digestive system. It may damage the gastrointestinal mucosa, causing symptoms such as nausea, vomiting, abdominal pain, diarrhea, etc. Long term intake may also lead to chronic digestive diseases such as gastritis and gastric ulcers.
Effects on the reproductive system
Certain chemicals can interfere with the normal development and differentiation of reproductive cells, thereby affecting fertility and reproductive health. Although there is limited research on its specific impact on the reproductive system, given its chemical properties, we cannot rule out the possibility of potential harm to the reproductive system. Long term exposure or exposure to high concentrations may lead to decreased sperm quality in males and menstrual irregularities in females.
Impact on the immune system
The immune system is an important defense line for the human body to resist the invasion of external pathogens. However, chemicals may inhibit the activity of immune cells and reduce the function of the immune system. Some components in this substance may have this immunosuppressive effect, making the human body more susceptible to infection and slower in recovery after infection.
Liver and kidney damage
The liver and kidneys are important metabolic and excretory organs in the human body. After entering the human body, chemicals need to be metabolized and excreted through the liver and kidneys. However, harmful substances may have toxic effects on liver and kidney cells, leading to impaired liver and kidney function. Long term exposure or exposure to high concentrations of substances may increase the risk of liver and kidney diseases such as hepatitis and nephritis.
Carcinogenic risk
Certain chemicals are carcinogenic, capable of damaging DNA, causing genetic mutations, and leading to cellular carcinogenesis. Although there are few specific studies on its carcinogenicity, we cannot completely rule out the possibility of its carcinogenicity due to its chemical properties and the carcinogenic risk of similar substances. Long term exposure or exposure to high concentrations should raise awareness of the risk of cancer.
◆ Safe use and protective measures
Given its potential side effects and risks, the following are some suggestions for safe use and protective measures:
Strengthen personal protection
When in contact, appropriate personal protective equipment should be worn, such as protective gloves, protective clothing, eye protection, and respiratory protective equipment. These devices can effectively reduce direct contact between harmful substances and the skin and eyes, and lower the risk of inhaling harmful vapors.
Maintain good ventilation
In places where this substance is used, good ventilation should be maintained to ensure air circulation. This helps to reduce the concentration of harmful substances in the air and minimize the risk of inhaling harmful vapors.
Strictly control the contact time
Try to minimize contact time with it and avoid prolonged exposure to high concentrations. During the operation, regular rest should be taken to reduce the accumulation of harmful substances in the body.
Storage and transportation safety
It should be stored in a cool, dry, well ventilated warehouse, away from sources of fire and heat. During transportation, it is necessary to ensure that the container is well sealed to avoid leakage and environmental pollution.
Waste disposal
The discarded substance should be properly disposed of in accordance with local regulations to avoid indiscriminate dumping or discharge into the environment. Appropriate waste disposal methods should be chosen, such as incineration, landfill, or chemical treatment, to ensure safe disposal of hazardous substances.
Regular health monitoring
Long term contacts should undergo regular health monitoring, including blood tests, liver and kidney function tests, etc. This helps to promptly identify and address potential health issues.
3-Bromobiphenyl is a critical intermediate with diverse applications in pharmaceuticals, LCDs, and agrochemicals. While its synthesis methods are well-established, ongoing research aims to improve efficiency and sustainability. Strict adherence to safety guidelines is essential to mitigate health and environmental risks. As demand grows, innovations in green chemistry and novel applications will shape the future of this compound.
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