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3,5-Bis(trifluoromethyl)bromobenzene is an organic compound with CAS 328-70-1 and molecular formula C8H4BrF6. Colorless to light yellow solid with a high melting point. At room temperature, it appears as an amorphous solid without a fixed melting point, but can gradually melt at temperatures above 100 ℃. The relative density (water=1) is 2.07, and the refractive index (n20D) is 1.477. Not easily soluble in water, but can be soluble in most organic solvents such as alcohols, ethers, ketones, esters, etc. This characteristic makes the compound widely used in organic synthesis and extraction. Has high chemical stability. At room temperature, it is not easily oxidized or reduced, and is not sensitive to light and air. However, under high temperatures or specific catalytic conditions, it may undergo dehalogenation or cyclization reactions, generating other types of compounds. Infrared spectroscopy and nuclear magnetic resonance spectroscopy are commonly used analytical methods to identify the structure of this compound. Through these spectra, the functional groups and molecular structure in the compound can be determined. It can also be used in polymer materials such as synthetic rubber, plastics, and fibers. It can be used as a softener, plasticizer, and processing aid to improve the processing and mechanical properties of materials. In addition, it can also be used to prepare special materials such as ion exchange resins and catalyst carriers.
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Chemical Formula |
C8H17NO7 |
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Exact Mass |
239 |
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Molecular Weight |
239 |
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m/z |
239 (100.0%), 240 (8.7%), 241(1.4%) |
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Elemental Analysis |
C, 40.17; H, 7.16; N, 5.86; O, 46.82 |
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The method for synthesizing 3,5-Bis(trifluoromethyl)bromobenzene in the laboratory can be carried out using 3,5-dihydroxybenzyl alcohol as the raw material. The following are the detailed steps of this method:
Step 1: Synthesis of 3,5-dihydroxybenzyl alcohol
The synthesis of 3,5-dihydroxybenzyl alcohol is divided into two steps. Firstly, using o-dimethoxybenzene as the raw material, 2,6-dinitrophenol is obtained through nitration reaction, followed by reduction reaction to obtain 2,6-diaminophenol, which is then condensed with formaldehyde to obtain 3,5-dihydroxybenzyl alcohol.
Under the action of concentrated sulfuric acid and sodium nitrate, o-dimethoxybenzene is nitrated to obtain 2,6-dinitrophenol. This reaction is an electrophilic substitution reaction, resulting in ortho substituted products.
Using iron powder and hydrochloric acid as reducing agents, 2,6-dinitrophenol is reduced to obtain 2,6-diaminophenol. This reaction is a reduction reaction that reduces nitro groups to amino groups.
In sodium hydroxide solution, 2,6-diaminophenol is condensed with formaldehyde to obtain 3,5-dihydroxybenzyl alcohol. This reaction is a condensation reaction, generating an ether bond and a hydroxyl group.
Step 2: Synthesis of 3,5-bis trifluoromethyl bromobenzene
Under the action of anhydrous aluminum trichloride, 3,5-dihydroxybenzyl alcohol was subjected to Friedel Crafts reaction with trifluoromethyl bromide to obtain 3,5-bis trifluoromethyl bromobenzene. This reaction is an electrophilic substitution reaction, resulting in para substituted products.
Synthesis of 3,5-bis (trifluoromethyl) bromobenzene: Under the catalysis of anhydrous aluminum trichloride, 3,5-dihydroxybenzyl alcohol is subjected to Friedel Crafts reaction with trifluoromethyl bromide to produce 3,5-bis (trifluoromethyl) bromobenzene. This reaction is an electrophilic substitution reaction, where trifluoromethyl bromide acts as an electrophilic reagent to attack the para position of 3,5-dihydroxybenzyl alcohol.
Step 3: Purification
Purify the generated 3,5-bis trifluoromethyl bromobenzene through distillation and crystallization methods. The specific purification conditions can be adjusted according to the experimental conditions.
3,5-Bis(trifluoromethyl)bromobenzene as an organic compound, has wide applications in many fields. Among them, being a softener is one of its important uses.
3,5-bis (trifluoromethyl) bromobenzene has good flowability and good solubility with non-polar solvents and certain polar solvents such as ketones, esters, and alcohols. This enables it to effectively penetrate between the molecular chains of polymers, reduce intermolecular interactions, and thereby improve the plasticity and flexibility of polymers. Therefore, 3,5-bis (trifluoromethyl) bromobenzene has been widely used as a softener in fields such as rubber, plastics, coatings, and inks.
Rubber industry:
In the rubber industry, 3,5-bis (trifluoromethyl) bromobenzene can be used as a rubber processing aid. It can interact with the active groups on the rubber molecular chain, improving the plasticity and flowability of rubber. In addition, 3,5-bis trifluoromethyl bromobenzene can also enhance the UV resistance and weather resistance of rubber, and improve the service life of rubber products. By adding an appropriate amount of 3,5-bis trifluoromethyl bromobenzene, the hardness of the rubber can be reduced, making it more flexible and elastic. Therefore, it is widely used in the manufacturing process of rubber products such as tires, rubber hoses, tape, and seals.
In the plastic industry, 3,5-bis (trifluoromethyl) bromobenzene can be used as a plasticizer. It can interact with active groups on plastic molecular chains, reduce intermolecular forces, and increase the flexibility and plasticity of plastics. By adding an appropriate amount of 3,5-bis trifluoromethyl bromobenzene, the processing performance and product performance of plastics can be improved. It is widely used in the manufacturing process of plastic products such as polyvinyl chloride (PVC), polyethylene (PE), polypropylene (PP), and polystyrene (PS).
Coating industry:
In the coating industry, 3,5-bis trifluoromethyl bromobenzene can be used as a coating additive. It can interact with the active groups in the coating, improving the leveling and wetting properties of the coating. By adding an appropriate amount of 3,5-bis trifluoromethyl bromobenzene, the surface tension of the coating can be reduced, making it easier to wet the substrate surface, and improving the adhesion and uniformity of the coating. In addition, 3,5-bis trifluoromethyl bromobenzene can also enhance the UV resistance and weather resistance of coatings, improve their corrosion resistance and service life. It is widely used in the manufacturing process of coatings such as architectural coatings, automotive coatings, and anti-corrosion coatings.
In the ink industry, 3,5-bis trifluoromethyl bromobenzene can be used as an ink additive. It can interact with the active groups in the ink, improving the rheological properties and stability of the ink. By adding an appropriate amount of 3,5-bis trifluoromethyl bromobenzene, the viscosity of the ink can be reduced, making it easier to print and apply. In addition, 3,5-Bis(trifluoromethyl)bromobenzene can also enhance the UV resistance and weather resistance of ink, improve its adhesion and friction resistance. It is widely used in the manufacturing process of printing ink and coating ink.
What Are The Side Effects Of This Compound?
Pollution to the environment
Water pollution:
This compound is harmful to water bodies. Once leaked, it may contaminate groundwater, surface water, and surrounding water bodies, affecting water quality and ecological environment.
Soil pollution:
If leaked substances enter the soil, they may cause pollution, affecting soil fertility and plant growth.
Potential hazards to human health
Irritation:
This substance is irritating and may cause irritation to the eyes, skin, and respiratory tract, leading to symptoms such as redness, swelling, pain, and difficulty breathing.
Potential toxicity:
Although specific acute toxicity data may not be available, long-term exposure or contact with the substance may have potential toxic effects on human health.
Carcinogenic risk:
Some organic compounds are carcinogenic, although their specific carcinogenicity is not yet clear, long-term exposure may increase the risk of cancer.
Safety precautions
Leakage handling:
In the event of a leak, immediate containment measures should be taken to prevent pollutants from entering water bodies, soil, or air. Inert materials such as sand and activated carbon can be used to absorb the leaked material and transfer it to a safe location for disposal.
Personal protection:
When handling or coming into contact with the substance, appropriate personal protective equipment such as goggles, gloves, masks, etc. should be worn to reduce irritation and injury to the eyes, skin, and respiratory tract.
Storage and transportation:
It should be stored in a cool, ventilated, and dry place, away from sources of fire and heat. During transportation, it is necessary to ensure that the packaging is intact and sealed to avoid leakage and contamination.
Other precautions
Environmental monitoring:
When using this substance, regular monitoring of environmental air quality, water quality, and soil quality should be conducted to promptly identify and address potential pollution issues.
Compliance with regulations:
Relevant national laws, regulations, and standards should be followed to ensure the safety and compliance of the use of the substance.
Other precautions
Leaking extinguishing agent:
Extinguish the fire with water mist, dry powder, foam or carbon dioxide extinguishing agent.
Avoid using direct current water to extinguish the fire. Direct current water may cause the splash of flammable liquid and spread the fire.
Precautions and protective measures for fire fighting:
Firefighters must wear air breathing apparatus and full body fire fighting clothes to extinguish the fire in the upwind direction.
Move the container from the fire site to an open place as far as possible.
If the container in the fire site has changed color or made a sound from the safety pressure relief device, it must be evacuated immediately.
Isolate the accident site and prohibit irrelevant personnel from entering. Collect and treat fire water to prevent environmental pollution.
Precautions for operation:
Operators should receive special training and strictly abide by the operating procedures.
Operation and disposal should be carried out in places with local ventilation or comprehensive ventilation facilities.
Avoid contact with eyes and skin, and avoid inhalation of steam.
Keep away from kindling and heat sources. Smoking is strictly prohibited in the workplace.
Use explosion-proof ventilation system and equipment.
If Canning is required, the flow rate should be controlled, and there should be a grounding device to prevent the accumulation of static electricity.
Avoid contact with prohibited substances such as oxidants.
Handle with care to prevent package and container damage.
Emptied containers may leave harmful substances.
Wash your hands after use and do not eat in the workplace.
Equip with corresponding varieties and quantities of fire-fighting equipment and leakage emergency treatment equipment.
Storage precautions:
Store in a cool and ventilated warehouse.
It should be stored separately from oxidants and edible chemicals, and should not be mixed.
Keep the container sealed.
Keep away from kindling and heat sources.
Lightning protection equipment must be installed in the warehouse.
The exhaust system shall be equipped with a grounding device to conduct and remove static electricity.
Explosion proof lighting and ventilation are adopted.
It is forbidden to use equipment and tools that are easy to produce sparks.
The storage area shall be equipped with leakage emergency treatment equipment and suitable storage materials.
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