Linshang Chemical
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1-Chloro-4-Fluoro-2-Iodobenzene
Linshang Chemical
|
HS Code |
763141 |
| Chemical Formula | C6H3ClFI |
| Molecular Weight | 256.44 |
| Appearance | Liquid (presumably, based on similar compounds) |
| Solubility In Water | Low, as it is an aromatic halide |
| Solubility In Organic Solvents | Good solubility in common organic solvents like dichloromethane, chloroform |
| Vapor Pressure | Low, considering its molecular weight and nature of halogens |
As an accredited 1-Chloro-4-Fluoro-2-Iodobenzene factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
| Packing | 1 - chloro - 4 - fluoro - 2 - iodobenzene packaged in 100 - gram bottles. |
| Storage | 1 - Chloro - 4 - fluoro - 2 - iodobenzene should be stored in a cool, dry, well - ventilated area. Keep it away from heat sources, flames, and oxidizing agents. Store in a tightly sealed container, preferably made of corrosion - resistant materials like glass. Avoid exposure to moisture which could potentially initiate unwanted reactions. |
| Shipping | 1 - Chloro - 4 - fluoro - 2 - iodobenzene is shipped in specialized, well - sealed containers. These are designed to prevent leakage. Shipments follow strict chemical transport regulations, ensuring safe transit to the destination. |
Competitive 1-Chloro-4-Fluoro-2-Iodobenzene prices that fit your budget—flexible terms and customized quotes for every order.
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What are the chemical properties of 1-chloro-4-fluoro-2-iodobenzene?
1-Chloro-4-fluoro-2-iodobenzene is an organic halogenated aromatic hydrocarbon. Its chemical properties are unique and unique in many chemical reactions.
First of all, the existence of halogen atoms gives it the activity of nucleophilic substitution reaction. Chlorine, fluorine and iodine atoms all have certain electronegativity, which changes the electron cloud density of the benzene ring. Among them, iodine atoms are easily replaced by nucleophilic reagents in nucleophilic substitution reactions due to their large atomic radius and relatively low C-I bond energy. For example, when sodium alcohol is used as a nucleophilic reagent, nucleophilic substitution can occur, and iodine atoms are replaced by alkoxy groups to produce corresponding aromatic ethers.
Furthermore, the localization effect of halogen atoms on aromatic rings is also significant. Chlorine and fluorine are ortho-para-sites, although they cause the activity of electrophilic substitution of the blunt benzene ring, they guide the electrophilic reagents to attack the ortho-and para-sites of the benzene ring. Although iodine is also an ortho-para-site, the localization effect is slightly weaker due to the combination of electron-giving conjugation effect and electron-withdrawing induction effect. Therefore, in the electrophilic substitution reaction, the new substituent is more likely to enter the ortho-and para-sites of the halogen atom.
In addition, 1-chloro-4-fluoro-2-iodobenzene can For example, with palladium catalysts and suitable organometallic reagents, coupling can occur to achieve the construction of carbon-carbon bonds, which is very important in the organic synthesis of complex aromatic hydrocarbons.
And because it contains a variety of halogen atoms, under specific conditions, it can be selectively dehalogenated. For example, by selecting the appropriate reducing agent and reaction conditions, the iodine atoms can be preferentially removed, while the chlorine and fluorine atoms are retained. This property has important applications in the design of organic synthesis steps and the selective preparation of products.
First of all, the existence of halogen atoms gives it the activity of nucleophilic substitution reaction. Chlorine, fluorine and iodine atoms all have certain electronegativity, which changes the electron cloud density of the benzene ring. Among them, iodine atoms are easily replaced by nucleophilic reagents in nucleophilic substitution reactions due to their large atomic radius and relatively low C-I bond energy. For example, when sodium alcohol is used as a nucleophilic reagent, nucleophilic substitution can occur, and iodine atoms are replaced by alkoxy groups to produce corresponding aromatic ethers.
Furthermore, the localization effect of halogen atoms on aromatic rings is also significant. Chlorine and fluorine are ortho-para-sites, although they cause the activity of electrophilic substitution of the blunt benzene ring, they guide the electrophilic reagents to attack the ortho-and para-sites of the benzene ring. Although iodine is also an ortho-para-site, the localization effect is slightly weaker due to the combination of electron-giving conjugation effect and electron-withdrawing induction effect. Therefore, in the electrophilic substitution reaction, the new substituent is more likely to enter the ortho-and para-sites of the halogen atom.
In addition, 1-chloro-4-fluoro-2-iodobenzene can For example, with palladium catalysts and suitable organometallic reagents, coupling can occur to achieve the construction of carbon-carbon bonds, which is very important in the organic synthesis of complex aromatic hydrocarbons.
And because it contains a variety of halogen atoms, under specific conditions, it can be selectively dehalogenated. For example, by selecting the appropriate reducing agent and reaction conditions, the iodine atoms can be preferentially removed, while the chlorine and fluorine atoms are retained. This property has important applications in the design of organic synthesis steps and the selective preparation of products.
What are the common uses of 1-chloro-4-fluoro-2-iodobenzene?
1-chloro-4-fluoro-2-iodobenzene is 1-chloro-4-fluoro-2-iodobenzene. The common preparation routes are as follows:
Halogenation-based method
1. ** Starting from benzene derivatives **:
- If p-fluoroaniline is used as the starting material. First, p-fluoroaniline is diazotized with sodium nitrite in the presence of hydrochloric acid. This reaction needs to be carried out at a low temperature (usually 0-5 ° C) to prevent the decomposition of diazonium salts. To form p-fluorobenzene diazonate. The reaction formula is:\ (Ar - NH_ {2} + NaNO_ {2} + 2HCl\ xrightarrow {0 - 5 ^ {\ circ} C} Ar - N_ {2} ^ {+} Cl ^ {-} + NaCl + 2H_ {2} O\) (\ (Ar\) represents p-fluorophenyl).
- Subsequently, the diazonium salt is mixed with cuprous chloride and potassium iodide. The diazonium group is replaced by a chlorine atom and an iodine atom, resulting in 1-chloro-4-fluoro-2-iodobenzene. In this process, cuprous chloride and potassium iodide play the role of providing chlorine and iodine, and the reaction conditions are relatively mild, which can better control the substitution position of halogen atoms, and the yield is relatively high.
2. ** Further halogenation with halobenzene as raw material **:
- With p-chlorofluorobenzene as the starting material. In the presence of a suitable catalyst (such as iron or iron salt), react with iodine elemental substance at a certain temperature. Due to the localization effect of chlorine and fluorine atoms on the benzene ring, the iodine atoms will be preferentially replaced in the ortho position (relative to the fluorine atoms), resulting in 1-chloro-4-fluoro-2-iodobenzene. In this reaction, iron or iron salt catalysts can polarize iodine molecules, making it easier to undergo electrophilic substitution reactions. However, attention should be paid to controlling the reaction conditions to avoid excessive halogenation. The reaction temperature is generally around 60-80 ° C, which can be adjusted appropriately according to the specific experimental conditions.
Reaction with metal-organic reagents
1. ** Grignard reagent method **:
- First prepare Grignard reagents for p-chlorofluorobenzene. React p-chlorofluorobenzene with magnesium chips in an ether solvent such as anhydrous ether or tetrahydrofuran to form Grignard reagents. This reaction needs to be carried out in an anhydrous and anaerobic environment, because Grignard reagents are extremely sensitive to water and oxygen. The reaction formula is:\ (Ar - X + Mg\ xrightarrow {anhydrous ether or tetrahydrofuran} Ar - MgX\) (\ (Ar\) represents p-chlorofluorophenyl,\ (X\) is a chlorine atom).
- Then, the generated Grignard reagent is reacted with an iodine substitution reagent (such as iodomethane, etc.) to introduce an iodine atom to generate 1-chloro-4-fluoro-2-iodobenzene. The advantage of this method is that the reaction selectivity is good, and the structure of the product can be precisely controlled by selecting a suitable halogenation reagent, but the preparation and use conditions of Grignard reagent are relatively harsh.
2. ** Lithium reagent method **:
- React with p-chlorofluorobenzene and lithium reagents such as butyl lithium at low temperature (such as -78 ° C) to form an aryl lithium reagent. This step also needs to be carried out under anhydrous and anaerobic conditions. The aryl lithium reagent has high activity and can react with iodine elemental or iodine-containing electrophilic reagents to obtain 1-chloro-4-fluoro-2-iodobenzene. This method has a fast reaction speed, but requires high reaction equipment and operation, and requires precise control of the reaction temperature and reagent dosage.
Halogenation-based method
1. ** Starting from benzene derivatives **:
- If p-fluoroaniline is used as the starting material. First, p-fluoroaniline is diazotized with sodium nitrite in the presence of hydrochloric acid. This reaction needs to be carried out at a low temperature (usually 0-5 ° C) to prevent the decomposition of diazonium salts. To form p-fluorobenzene diazonate. The reaction formula is:\ (Ar - NH_ {2} + NaNO_ {2} + 2HCl\ xrightarrow {0 - 5 ^ {\ circ} C} Ar - N_ {2} ^ {+} Cl ^ {-} + NaCl + 2H_ {2} O\) (\ (Ar\) represents p-fluorophenyl).
- Subsequently, the diazonium salt is mixed with cuprous chloride and potassium iodide. The diazonium group is replaced by a chlorine atom and an iodine atom, resulting in 1-chloro-4-fluoro-2-iodobenzene. In this process, cuprous chloride and potassium iodide play the role of providing chlorine and iodine, and the reaction conditions are relatively mild, which can better control the substitution position of halogen atoms, and the yield is relatively high.
2. ** Further halogenation with halobenzene as raw material **:
- With p-chlorofluorobenzene as the starting material. In the presence of a suitable catalyst (such as iron or iron salt), react with iodine elemental substance at a certain temperature. Due to the localization effect of chlorine and fluorine atoms on the benzene ring, the iodine atoms will be preferentially replaced in the ortho position (relative to the fluorine atoms), resulting in 1-chloro-4-fluoro-2-iodobenzene. In this reaction, iron or iron salt catalysts can polarize iodine molecules, making it easier to undergo electrophilic substitution reactions. However, attention should be paid to controlling the reaction conditions to avoid excessive halogenation. The reaction temperature is generally around 60-80 ° C, which can be adjusted appropriately according to the specific experimental conditions.
Reaction with metal-organic reagents
1. ** Grignard reagent method **:
- First prepare Grignard reagents for p-chlorofluorobenzene. React p-chlorofluorobenzene with magnesium chips in an ether solvent such as anhydrous ether or tetrahydrofuran to form Grignard reagents. This reaction needs to be carried out in an anhydrous and anaerobic environment, because Grignard reagents are extremely sensitive to water and oxygen. The reaction formula is:\ (Ar - X + Mg\ xrightarrow {anhydrous ether or tetrahydrofuran} Ar - MgX\) (\ (Ar\) represents p-chlorofluorophenyl,\ (X\) is a chlorine atom).
- Then, the generated Grignard reagent is reacted with an iodine substitution reagent (such as iodomethane, etc.) to introduce an iodine atom to generate 1-chloro-4-fluoro-2-iodobenzene. The advantage of this method is that the reaction selectivity is good, and the structure of the product can be precisely controlled by selecting a suitable halogenation reagent, but the preparation and use conditions of Grignard reagent are relatively harsh.
2. ** Lithium reagent method **:
- React with p-chlorofluorobenzene and lithium reagents such as butyl lithium at low temperature (such as -78 ° C) to form an aryl lithium reagent. This step also needs to be carried out under anhydrous and anaerobic conditions. The aryl lithium reagent has high activity and can react with iodine elemental or iodine-containing electrophilic reagents to obtain 1-chloro-4-fluoro-2-iodobenzene. This method has a fast reaction speed, but requires high reaction equipment and operation, and requires precise control of the reaction temperature and reagent dosage.
What are 1-chloro-4-fluoro-2-iodobenzene synthesis methods?
The synthesis of 1-chloro-4-fluoro-2-iodobenzene has attracted much attention in organic synthetic chemistry. There are various synthesis paths, and several common methods are described in detail below.
First, the halogenation reaction path. The chlorine, fluorine and iodine atoms can be gradually introduced by using benzene as the starting material under specific halogenation reaction conditions. For example, chlorine gas and benzene are catalyzed by Lewis acid (such as ferric chloride) to undergo an electrophilic substitution reaction to generate chlorobenzene. Subsequently, p-chlorobenzene reacts with fluorinated reagents (such as potassium fluoride, etc.) under specific conditions to introduce fluorine atoms to generate 4-fluoro-chlorobenzene. Finally, 4-fluoro-chlorobenzene reacts with iodine substitutes (such as iodine elemental substance, cuprous iodide, etc., in the presence of appropriate ligands) to obtain 1-chloro-4-fluoro-2-iodobenzene. Although this path is complex, the reaction conditions of each step are relatively clear, which is conducive to operation and control.
Second, the coupling reaction is catalyzed by metal. Aromatic compounds containing chlorine and fluorine are used as substrates, and the coupling reaction is carried out with iodine substitutes under the catalysis of transition metals (such as palladium, nickel, etc.). For example, the synthesis of 1-chloro-4-fluoro-2-iodobenzene can be achieved by heating 4-fluoro-chlorophenylboronic acid with an iodide reagent in an organic solvent in the presence of a palladium catalyst (such as tetra (triphenylphosphine) palladium, etc.) and a base (such as potassium carbonate, etc.). The metal-catalyzed coupling reaction has the advantages of high selectivity and mild conditions, which can effectively avoid the occurrence of unnecessary side reactions.
Third, the aryl diazonium salt method. First, the corresponding amino-containing aromatic compound is made into a diazonium salt, and then reacts with the nucleophiles of chlorine, fluorine and iodine respectively. Specifically, after using 2-amino-4-fluorochlorobenzene as raw material to prepare diazonium salts, iodine atoms are first introduced into the reaction with potassium iodide, and then the target product 1-chloro-4-fluoro-2-iodobenzene can be obtained after appropriate treatment. This method needs to pay attention to the stability of the diazonium salt and the precise control of the reaction conditions to avoid unnecessary decomposition or side reactions.
The above methods have their own advantages and disadvantages. In the actual synthesis, the optimal synthesis path should be selected according to factors such as the availability of raw materials, cost, and purity of the target product.
First, the halogenation reaction path. The chlorine, fluorine and iodine atoms can be gradually introduced by using benzene as the starting material under specific halogenation reaction conditions. For example, chlorine gas and benzene are catalyzed by Lewis acid (such as ferric chloride) to undergo an electrophilic substitution reaction to generate chlorobenzene. Subsequently, p-chlorobenzene reacts with fluorinated reagents (such as potassium fluoride, etc.) under specific conditions to introduce fluorine atoms to generate 4-fluoro-chlorobenzene. Finally, 4-fluoro-chlorobenzene reacts with iodine substitutes (such as iodine elemental substance, cuprous iodide, etc., in the presence of appropriate ligands) to obtain 1-chloro-4-fluoro-2-iodobenzene. Although this path is complex, the reaction conditions of each step are relatively clear, which is conducive to operation and control.
Second, the coupling reaction is catalyzed by metal. Aromatic compounds containing chlorine and fluorine are used as substrates, and the coupling reaction is carried out with iodine substitutes under the catalysis of transition metals (such as palladium, nickel, etc.). For example, the synthesis of 1-chloro-4-fluoro-2-iodobenzene can be achieved by heating 4-fluoro-chlorophenylboronic acid with an iodide reagent in an organic solvent in the presence of a palladium catalyst (such as tetra (triphenylphosphine) palladium, etc.) and a base (such as potassium carbonate, etc.). The metal-catalyzed coupling reaction has the advantages of high selectivity and mild conditions, which can effectively avoid the occurrence of unnecessary side reactions.
Third, the aryl diazonium salt method. First, the corresponding amino-containing aromatic compound is made into a diazonium salt, and then reacts with the nucleophiles of chlorine, fluorine and iodine respectively. Specifically, after using 2-amino-4-fluorochlorobenzene as raw material to prepare diazonium salts, iodine atoms are first introduced into the reaction with potassium iodide, and then the target product 1-chloro-4-fluoro-2-iodobenzene can be obtained after appropriate treatment. This method needs to pay attention to the stability of the diazonium salt and the precise control of the reaction conditions to avoid unnecessary decomposition or side reactions.
The above methods have their own advantages and disadvantages. In the actual synthesis, the optimal synthesis path should be selected according to factors such as the availability of raw materials, cost, and purity of the target product.
1-chloro-4-fluoro-2-iodobenzene need to pay attention to when storing and transporting
1-Chloro-4-fluoro-2-iodobenzene is an organic compound. During storage and transportation, many matters need to be paid attention to.
First words storage. Because it has certain chemical activity, it needs to be stored in a cool and ventilated warehouse. If the temperature of the warehouse is too high, it is easy to cause its chemical properties to change or cause danger. If the temperature is too high, the compound may accelerate decomposition and release harmful gases. And it should be kept away from fires and heat sources to prevent fire or explosion accidents. Open flames or high temperature heat sources are close, or the compound may react sharply, causing serious consequences.
Furthermore, it should be stored separately from oxidants, acids, bases, etc., and must not be mixed. Due to the contact of 1-chloro-4-fluoro-2-iodobenzene with oxidants, or a violent oxidation reaction; contact with acid and alkali, or cause chemical reactions, resulting in material deterioration, or toxic and harmful products.
In terms of packaging, it is necessary to ensure that it is well sealed. If the packaging is not strict, the compound may evaporate into the air, pollute the environment, and be harmful to human health. If the volatile gas is inhaled by humans, it may damage the respiratory tract, nervous system, etc.
As for transportation, transportation vehicles shall be equipped with corresponding varieties and quantities of fire-fighting equipment and leakage emergency treatment equipment. During transportation, in case of leakage or fire and other accidents, it can be responded to in time. During transportation, it is necessary to prevent exposure to the sun, rain, and high temperature. Summer transportation, if there is no protection, exposure to the sun can cause the temperature in the car to rise, causing dangerous reactions of compounds.
When loading and unloading, light handling is required to avoid damage to packaging and containers. If the package is damaged due to rough operation during loading and unloading, 1-chloro-4-fluoro-2-iodobenzene will pollute the environment, and it is also quite difficult to deal with.
In short, the storage and transportation of 1-chloro-4-fluoro-2-iodobenzene must strictly follow relevant regulations and operate with caution to ensure the safety of personnel and the environment from pollution.
First words storage. Because it has certain chemical activity, it needs to be stored in a cool and ventilated warehouse. If the temperature of the warehouse is too high, it is easy to cause its chemical properties to change or cause danger. If the temperature is too high, the compound may accelerate decomposition and release harmful gases. And it should be kept away from fires and heat sources to prevent fire or explosion accidents. Open flames or high temperature heat sources are close, or the compound may react sharply, causing serious consequences.
Furthermore, it should be stored separately from oxidants, acids, bases, etc., and must not be mixed. Due to the contact of 1-chloro-4-fluoro-2-iodobenzene with oxidants, or a violent oxidation reaction; contact with acid and alkali, or cause chemical reactions, resulting in material deterioration, or toxic and harmful products.
In terms of packaging, it is necessary to ensure that it is well sealed. If the packaging is not strict, the compound may evaporate into the air, pollute the environment, and be harmful to human health. If the volatile gas is inhaled by humans, it may damage the respiratory tract, nervous system, etc.
As for transportation, transportation vehicles shall be equipped with corresponding varieties and quantities of fire-fighting equipment and leakage emergency treatment equipment. During transportation, in case of leakage or fire and other accidents, it can be responded to in time. During transportation, it is necessary to prevent exposure to the sun, rain, and high temperature. Summer transportation, if there is no protection, exposure to the sun can cause the temperature in the car to rise, causing dangerous reactions of compounds.
When loading and unloading, light handling is required to avoid damage to packaging and containers. If the package is damaged due to rough operation during loading and unloading, 1-chloro-4-fluoro-2-iodobenzene will pollute the environment, and it is also quite difficult to deal with.
In short, the storage and transportation of 1-chloro-4-fluoro-2-iodobenzene must strictly follow relevant regulations and operate with caution to ensure the safety of personnel and the environment from pollution.
1-chloro-4-fluoro-2-iodobenzene impact on the environment and people
1 - chloro - 4 - fluoro - 2 - iodobenzene is an organic halogenated aromatic hydrocarbon. This substance has potential effects on both the environment and human body.
First talk about the impact on the environment. It has a certain stability and is difficult to degrade rapidly in the natural environment. If it flows into the soil, it will cause soil pollution, affect the structure and function of soil microbial communities, and interfere with the material cycle and energy conversion of soil ecosystems. For example, it may inhibit the growth and reproduction of some beneficial microorganisms, which in turn affects the absorption and growth of nutrients by plants. If it enters the water body, it will spread with the water flow and endanger aquatic organisms. Because it is fat-soluble, it is easy to accumulate in aquatic organisms, and it is transmitted and amplified through the food chain, causing greater harm to high-nutrient organisms. For example, it can affect the nervous system and reproductive system of fish, resulting in abnormal behavior and decreased fertility. And in the atmosphere, it will participate in photochemical reactions after volatilization, affect air quality, and may generate harmful secondary pollutants.
Let's talk about the impact on the human body. If the human body ingests this substance through breathing, skin contact or accidental ingestion, it will endanger health. It may be toxic to the human nervous system, causing headaches, dizziness, fatigue, memory loss and other symptoms. Because it contains halogen atoms, it may also interfere with the human endocrine system, affect the normal secretion and regulation of hormones, and cause reproductive and developmental problems. Long-term exposure will increase the risk of cancer, because the structure of halogenated aromatics may cause cancer in human cells. For example, some workers engaged in related chemical production who have been exposed to the environment containing this substance for a long time may have a higher risk of cancer than ordinary people.
In conclusion, 1-chloro-4-fluoro-2-iodobenzene has many potential hazards to the environment and human body, and it needs to be strictly controlled and properly handled during production, use and disposal to reduce its negative effects.
First talk about the impact on the environment. It has a certain stability and is difficult to degrade rapidly in the natural environment. If it flows into the soil, it will cause soil pollution, affect the structure and function of soil microbial communities, and interfere with the material cycle and energy conversion of soil ecosystems. For example, it may inhibit the growth and reproduction of some beneficial microorganisms, which in turn affects the absorption and growth of nutrients by plants. If it enters the water body, it will spread with the water flow and endanger aquatic organisms. Because it is fat-soluble, it is easy to accumulate in aquatic organisms, and it is transmitted and amplified through the food chain, causing greater harm to high-nutrient organisms. For example, it can affect the nervous system and reproductive system of fish, resulting in abnormal behavior and decreased fertility. And in the atmosphere, it will participate in photochemical reactions after volatilization, affect air quality, and may generate harmful secondary pollutants.
Let's talk about the impact on the human body. If the human body ingests this substance through breathing, skin contact or accidental ingestion, it will endanger health. It may be toxic to the human nervous system, causing headaches, dizziness, fatigue, memory loss and other symptoms. Because it contains halogen atoms, it may also interfere with the human endocrine system, affect the normal secretion and regulation of hormones, and cause reproductive and developmental problems. Long-term exposure will increase the risk of cancer, because the structure of halogenated aromatics may cause cancer in human cells. For example, some workers engaged in related chemical production who have been exposed to the environment containing this substance for a long time may have a higher risk of cancer than ordinary people.
In conclusion, 1-chloro-4-fluoro-2-iodobenzene has many potential hazards to the environment and human body, and it needs to be strictly controlled and properly handled during production, use and disposal to reduce its negative effects.
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