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What are the chemical properties of 3-chloro-5-fluorobenzyl alcohol?
3-Chloro-5-bromotoluene is an organic compound composed of a benzene ring, which is formed at the 3rd position of chlorine atom, the 5th position of bromine atom, and the 1st position of methyl. This compound has the following chemical properties:
1. ** Electrophilic substitution reaction **: The benzene ring is rich in electrons, has nucleophilicity, and is vulnerable to electrophilic attack. Because its methyl group is an ortho-para-site group, chlorine and bromine are also ortho-para-sites. Under the combined action, the electrophilic substitution reaction mainly occurs in the ortho and para-sites of methyl and halogen atoms. If under the action of a suitable catalyst (such as anhydrous ferric chloride) and heating conditions, it can react with bromine to generate derivatives containing more bromine substituents.
2. ** Halogen atom reaction **:
- ** Chlorine atom reactivity **: Although the chlorine atom is directly attached to the benzene ring, because the lone pair electrons of the chlorine atom form p-π conjugation with the benzene ring, the electron cloud density of the C-Cl bond increases, the bond energy increases, and the reactivity of the chlorine atom decreases relatively. However, under certain conditions, such as high temperature, strong base, and copper catalyst, the chlorine atom can be replaced by hydroxyl and amino groups.
- ** Bromine atom reactivity **: Bromine atom activity is high, under the action of metal magnesium, can form Grignard reagent, which is extremely active and can react with a variety of compounds containing active hydrogen or carbonyl groups, thereby forming carbon-carbon bonds, which are widely used in organic synthesis.
3. ** Methyl reaction **: Affected by the benzene ring, the hydrogen atom activity on the methyl group is enhanced. Under light or high temperature conditions, the hydrogen atom on the methyl group can be replaced by halogen atoms to form halogenated methyl benzene derivatives. If treated with a strong oxidant, such as acidic potassium permanganate solution, the methyl group can be oxidized to a carboxyl group to obtain 3-chloro-5-bromobenzoic acid.
4. ** Aromaticity **: 3-chloro-5-bromotoluene follows the Shocker rule, the benzene ring has 6 π electrons, forms a cyclic conjugated system, is aromatic, relatively stable, and is not prone to addition and oxidation reactions under normal conditions. It is easier to perform electrophilic substitution reactions to maintain the stability of its aromatic system.
What are the physical properties of 3-chloro-5-fluorobenzyl alcohol?
3-Chloro-5-bromotoluene is an organic compound that is widely used in the chemical industry. In ancient Chinese, its physical properties are as follows:
This compound is usually in a liquid state at room temperature. Looking at its form, it has a uniform texture and flows freely. Observing its color, it is mostly colorless or slightly yellowish, clear and transparent, and has no obvious impurities. Close to the fine smell, there is a specific aromatic smell, but this smell is not pleasant, and it may be uncomfortable to smell for a long time.
Its density is higher than that of water. If it is co-placed with water, it can be seen that it sinks to the bottom of the water. In terms of solubility, 3-chloro-5-bromotoluene is insoluble in water, but easily soluble in many organic solvents, such as ethanol, ether, benzene, etc. This property allows it to be fully dispersed and participate in the reaction by means of organic solvents in the construction of the reaction system for organic synthesis.
When it comes to the melting and boiling point, its melting point is low, and it is not a solid state at room temperature. The boiling point is relatively high, and it needs to be heated moderately before it can be converted from a liquid state to a gaseous state. This property allows it to be separated and purified by distillation and distinguished from other substances according to the difference in boiling points.
In addition, 3-chloro-5-bromotoluene is volatile to a certain extent. Although it is less volatile than water, it will gradually decrease when left in an exposed environment for a long time. Its vapor density is greater than that of air. If it leaks in a limited space, the steam may spread close to the ground, so be careful.
What are the common uses of 3-chloro-5-fluorobenzyl alcohol?
3-Bromo-5-fluoroanisole is a commonly used chemical raw material in the field of organic synthesis. It has a wide range of common uses and has made significant contributions to the construction of many drug molecules in the field of medicinal chemistry. In the synthesis process of many drugs with specific biological activities, 3-bromo-5-fluoroanisole is often used as a key starting material. With its unique structural characteristics, it can participate in various chemical reactions, introduce specific functional groups to drug molecules, and then endow drugs with precise pharmacological activity.
It can also be seen in the field of materials science. For example, when preparing organic materials with special photoelectric properties, 3-bromo-5-fluoroanisole can be integrated into the molecular structure of the material through ingenious chemical reactions, so that the material exhibits excellent optical or electrical properties, such as specific fluorescence emission characteristics or good charge transport ability, so as to meet the needs of different high-end material application scenarios.
Furthermore, in the field of fine chemicals, it is an important intermediate and participates in the synthesis of a series of high-value-added fine chemicals. These fine chemicals are widely used in the fragrance, dye and other industries, and play a key role in improving product quality and performance.
Synthesis of this compound, the usual method is to use the corresponding phenolic compounds as starting materials, introduce bromine and fluorine atoms through halogenation reaction, and then through etherification reaction to successfully prepare 3-bromo-5-fluoroanisole. This synthetic path, with its relatively mature reaction conditions and high yield, is very popular in industrial production and laboratory preparation.
What are the synthesis methods of 3-chloro-5-fluorobenzyl alcohol?
3-Bromo-5-fluoroacetophenone is an important intermediate in organic synthesis. The common synthesis methods are as follows:
** Benzene is used as the starting material **:
First, benzene and bromine undergo an electrophilic substitution reaction under the action of catalysts such as iron tribromide to generate bromobenzene. This reaction needs to be carried out in an anhydrous environment to ensure the activity of the catalyst. Next, bromobenzene and magnesium chips are reacted in anhydrous ether to form Grignard's reagent phenyl magnesium bromide. This step requires strict anhydrous and anaerobic requirements for the reaction system to prevent Grignard's reagent from failing. Then, phenylmagnesium bromide is reacted with 3-bromo-5-fluorobenzoyl chloride, and after hydrolysis, 3-bromo-5-fluorobenzophenone can be obtained. This route has a little more steps, but the raw material benzene is widely sourced and the cost is relatively low.
** Benzoic acid is used as the starting material **:
Benzoic acid is first reacted with thionyl chloride to convert to benzoyl chloride. This reaction condition is relatively mild, and the thionyl chloride can be slightly excessive to promote the reaction in the direction of generating benzoyl chloride. Subsequently, under the catalysis of aluminum trichloride, benzoyl chloride and bromine undergo Fu-gram acylation reaction, and bromine atoms are introduced at specific positions in the benzene ring to generate 3-bromobenzoyl chloride. Then 3-bromobenzoyl chloride is subjected to halogen exchange reaction with fluoride to obtain 3-bromo-5-fluorobenzoyl chloride. Finally, 3-bromo-5-fluorobenzoyl chloride reacts with methyl format reagents and is acidified to obtain the target product 3-bromo-5-fluorobenzophenone. There are also many steps in this path, but the reaction selectivity of each step is good, which is conducive to the separation and purification of the product.
** Using m-bromofluorobenzene as the starting material **:
m-bromofluorobenzene and acetyl chloride under the catalysis of aluminum trichloride undergo Fu-gram acylation reaction to directly generate 3-bromo-5-fluorobenzophenone. This method has short steps, high atomic economy and relatively mild reaction conditions. However, the price of m-bromofluorobenzene is high, resulting in an increase in cost. If the cost factor is considered, the synthesis method of m-bromofluorobenzene can be optimized to reduce the overall cost.
What are the precautions for the storage and transportation of 3-chloro-5-fluorobenzyl alcohol?
3-Bromo-5-chloroacetophenone is a valuable chemical with specific properties. When storing and transporting, many key precautions need to be followed carefully:
Storage
1. ** Environmental selection **: It should be placed in a cool, dry and well-ventilated place. This substance is sensitive to heat, and high temperature can easily cause it to decompose or cause chemical reactions, so it is necessary to avoid heat sources and direct sunlight. Humid environments may also react with it, causing deterioration, and it is essential to keep it dry.
2. ** Container selection **: Corrosion-resistant sealed containers, such as glass containers, should be selected because of their stable chemical properties, which can effectively prevent the leakage of substances and the intrusion of external substances. Storage containers need to have good sealing to prevent volatilization and air contact, so as to avoid oxidation and other reactions.
3. ** Isolated storage **: Do not mix with oxidants, acids, alkalis and other substances. Because of its active chemical properties, contact with the above substances may cause violent chemical reactions, or even explosions, must be classified and stored to ensure a safe distance.
Transportation
1. ** Tight packaging **: Make sure that the packaging is firm and tight before transportation. Use suitable cushioning materials to wrap the container to prevent the container from breaking due to collision and vibration during transportation. At the same time, the warning label should be clearly marked on the outside of the package to indicate its dangerous characteristics.
2. ** Transportation tool adaptation **: Select a transportation tool that meets the requirements for the transportation of hazardous chemicals. The transportation vehicle must be equipped with fire and explosion-proof devices to ensure the safety of the transportation process. And avoid violent actions such as sudden braking and sharp turning of the vehicle during transportation to reduce the impact on the goods.
3. ** Professional personnel **: The person responsible for transportation needs to be professionally trained and familiar with the characteristics of 3-bromo-5-chloromethylacetophenone, emergency treatment methods, etc. During transportation, it is necessary to regularly check the status of the goods, such as whether the packaging is in good condition and whether there are any signs of leakage. If any abnormalities are found, timely measures should be taken to deal with them.