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Product Name | (E)-3-(3,4-dichlorophenyl)acrylic acid |
Cas Number | 5680-66-2 |
Formula | C9H6Cl2O2 |
Molar Mass | 217.05 g/mol |
Melting Point | 210-213°C |
Boiling Point | 380.2°C at 760 mmHg |
Density | 1.462 g/cm3 |
Solubility | Slightly soluble in water |
Pka | 4.53 |
Logp | 2.99 |
Vapor Pressure | 0.000328 mmHg at 25°C |
Refractive Index | 1.606 |
Flash Point | 184.9°C |
Appearance | White to beige crystalline powder |
Stability | Stable under normal temperatures and pressures |
Storage Conditions | Store in a cool, dry place |
What are the main applications of (E)-3-(3,4-dichlorophenyl)acrylic acid?
(E)-3-(3,4-dichlorophenyl)acrylic acid has several main applications.
One of its significant applications is in the field of organic synthesis.One of its most important applications is in organic synthesis. It serves as a valuable intermediate for the preparation of various organic compounds.It is a valuable intermediary for the preparation of many organic compounds. Due to the presence of the double bond and the substituted phenyl group, it can participate in a wide range of chemical reactions.It can be used in a variety of chemical reactions due to the double bond and substituted phenyl groups. For example, it can be used in Diels - Alder reactions.It can be used, for example, in Diels-Alder reactions. The double bond in (E)-3-(3,4-dichlorophenyl)acrylic acid can react with appropriate dienes to form cyclic compounds. These cyclic products may have potential applications in the synthesis of pharmaceuticals, agrochemicals, and materials with specific structures.These cyclic compounds may be used in the synthesis pharmaceuticals, agrochemicals and materials with specific structure.
In the area of materials science, this compound can be utilized in the preparation of certain polymers.This compound can be used in the field of materials science to prepare certain polymers. By polymerizing (E)-3-(3,4-dichlorophenyl)acrylic acid or copolymerizing it with other monomers, polymers with unique properties can be obtained. The chlorine atoms on the phenyl ring can influence the physical and chemical properties of the resulting polymers.The chlorine atoms in the phenyl rings can affect the physical and chemical characteristics of the polymers. For instance, they can enhance the polymer's resistance to degradation, such as improving its thermal stability and chemical resistance.They can, for example, improve the polymer's resistance against degradation, such that it has improved its thermal stability and chemical resistant. These polymers may find use in coatings, where they can provide protection against environmental factors like moisture, chemicals, and UV radiation.These polymers can be used in coatings to protect against environmental factors such as moisture, chemicals and UV radiation.
In the pharmaceutical industry, (E)-3-(3,4-dichlorophenyl)acrylic acid can contribute to the development of new drugs. Its structural features can be modified to create molecules with specific biological activities.Its structural characteristics can be altered to create molecules with specific biologic activities. The dichlorophenyl group and the acrylic acid moiety can interact with biological targets in the body.The acrylic acid moiety and the dichlorophenyl group can interact with biological target in the body. Researchers may explore its potential as an inhibitor of certain enzymes or as a ligand for specific receptors.Researchers may investigate its potential as a ligand or inhibitor for certain receptors. For example, it could potentially be developed into an anti - inflammatory agent or a drug for treating certain metabolic disorders by modulating relevant biochemical pathways.It could be developed as an anti-inflammatory agent or drug to treat certain metabolic disorders, for example, by modulating relevant pathways.
In agrochemical applications, it may have the potential to be incorporated into pesticides or plant growth regulators.It may be used in agrochemicals as a plant growth regulator or pesticide. The chlorine - containing phenyl group might contribute to its pesticidal activity, perhaps acting against specific pests like insects or fungi.The chlorine-containing phenyl groups may contribute to its pesticidal action, possibly acting against specific pests such as insects or fungi. As a plant growth regulator, it could influence processes such as plant growth, flowering, or fruit ripening, thereby improving crop yields and quality.It could act as a plant growth regulator to influence processes like plant growth, fruit ripening or flowering. This would improve crop yields and quality. However, further research and development are needed to optimize its effectiveness and ensure its environmental safety in agricultural settings.Further research and development is needed to optimize the effectiveness of this product and ensure its safety in agricultural settings. Overall, (E)-3-(3,4-dichlorophenyl)acrylic acid holds promise in multiple important areas of chemistry and related industries.
What are the key properties of (E)-3-(3,4-dichlorophenyl)acrylic acid?
(E)-3-(3,4 - dichlorophenyl)acrylic acid is a compound with several key properties.
First, in terms of its chemical structure, it contains a phenyl ring substituted with two chlorine atoms at the 3 and 4 positions.Its chemical structure consists of a phenyl-ring with two chlorine atoms substituted at the 3rd and 4th positions. The presence of the double bond in the (E) - configuration imparts geometric isomerism to the molecule.The double bond in (E)-configuration imparts geometric isomerism. This double bond also makes the compound reactive towards addition reactions.This double bond also makes this compound reactive to addition reactions. For example, it can undergo electrophilic addition reactions with reagents like bromine or hydrogen halides.It can undergo electrophilic reactions, for example, with reagents such as bromine or hydrogen chlorides. The carboxylic acid functional group (-COOH) at the end of the side - chain is highly polar.The carboxylic functional group (-COOH), at the end of side-chain, is highly polar. This group can participate in acid - base reactions.This group can be involved in acid-base reactions. It can donate a proton in the presence of a base, acting as a Bronsted - Lowry acid.It can donate a proton in the presence a base and act as a Bronsted-Lowry acid. The pKa value of the carboxylic acid group is an important characteristic, determining its acidity in solution.The pKa of the carboxylic group is a key characteristic that determines its acidity in solutions.
Regarding physical properties, (E)-3-(3,4 - dichlorophenyl)acrylic acid is likely to be a solid at room temperature. The presence of the polar carboxylic acid group and the relatively large and non - polar phenyl ring gives it an amphiphilic nature to some extent.The amphiphilic property is due to the presence of the carboxylic acid group, which is polar, and the large non-polar phenyl rings. However, due to the non - polar nature of the dichlorophenyl part, its solubility in water is expected to be relatively low.Due to the non-polar nature of the Dichlorophenyl, its solubility is expected to be low in water. It may be more soluble in polar organic solvents such as ethanol, methanol, or dimethyl sulfoxide (DMSO) because these solvents can interact with both the polar carboxylic acid group through hydrogen bonding and the non - polar phenyl ring through van der Waals forces.It may be more soluble with polar organic solvents like ethanol, methanol or dimethyl sulfoxide because these solvents interact both with the polar carboxylic group through hydrogen bonds and the non polar phenyl ring via van der Waals forces.
In terms of its reactivity, as mentioned, the double bond is a site of reactivity.As mentioned, the double-bond is a reactivity site. It can be hydrogenated to form the saturated derivative, which would change the physical and chemical properties of the molecule.It can be hydrogenated into the saturated derivative which would change both the physical and chemical properties. The carboxylic acid group can be used in various reactions.The carboxylic group can be used for various reactions. For instance, it can be esterified with alcohols in the presence of an acid catalyst to form esters.It can, for example, be esterified in the presence an acid catalyst with alcohols to form esters. These esters may have different physical properties, such as higher volatility and different solubility characteristics compared to the parent acid.These esters can have different physical characteristics, such as higher volatile and different solubility properties compared to the acid parent. Additionally, the chlorine atoms on the phenyl ring can potentially be involved in substitution reactions under appropriate conditions, although the aromaticity of the phenyl ring makes these reactions less straightforward compared to aliphatic halogen - containing compounds.The chlorine atoms of the phenyl rings can also be involved in substitution under the right conditions. However, the aromaticity makes it more difficult to perform these reactions than with aliphatic halogen-containing compounds.
Overall, the combination of the double bond, carboxylic acid group, and dichlorophenyl ring in (E)-3-(3,4 - dichlorophenyl)acrylic acid gives it a unique set of properties that can be exploited in various synthetic and chemical applications.
How is (E)-3-(3,4-dichlorophenyl)acrylic acid synthesized?
(E)-3-(3,4 - dichlorophenyl)acrylic acid can be synthesized through the following general approach.
One common method is based on the Knoevenagel condensation reaction.Knoevenagel condensation is one common method. First, 3,4 - dichlorobenzaldehyde is used as a starting material.As a first step, 3,4-dichlorobenzaldehyde must be used. It is reacted with malonic acid in the presence of a base catalyst.It is then reacted with malonic acids in the presence a base catalyst. A suitable base could be pyridine or piperidine.A base that is suitable could be pyridine, or piperidine. The reaction occurs in a solvent such as ethanol or toluene.The reaction takes place in a solvent like ethanol or toluene.
The reaction mechanism involves the deprotonation of malonic acid by the base, generating a nucleophilic enolate ion.The reaction involves deprotonation by the base of malonic acid, resulting in a nucleophilic Enolate ion. This enolate ion attacks the carbonyl carbon of 3,4 - dichlorobenzaldehyde, forming an intermediate. Subsequently, a series of proton transfers and elimination steps take place.Then, a series proton transfer and elimination steps are performed. The elimination of a molecule of carbon dioxide from the intermediate leads to the formation of (E)-3-(3,4 - dichlorophenyl)acrylic acid. The (E)-configuration is favored due to the thermodynamic stability of the trans - double bond formed in this process.The (E-configuration is preferred due to the thermodynamic stability of the trans-double bond formed during this process.
Another possible synthetic route could involve the Wittig reaction.The Wittig reaction is another possible route. In this case, 3,4 - dichlorobenzaldehyde is reacted with a phosphonium ylide.In this case, the 3,4-dichlorobenzaldehyde reacts with a phosphoniumylide. The phosphonium ylide can be prepared by reacting a phosphonium salt with a strong base.The phosphonium is prepared by reacting the phosphonium with a strong acid. For example, triphenylphosphine can be reacted with an alkyl halide to form a phosphonium salt, which is then treated with a base like butyllithium to generate the ylide.Triphenylphosphine, for example, can be reacted to an alkyl chloride to produce a phosphonium halide, which is then treated to butyllithium in order to create the ylide. The reaction between the 3,4 - dichlorobenzaldehyde and the phosphonium ylide results in the formation of (E)-3-(3,4 - dichlorophenyl)acrylic acid derivative. The reaction conditions, such as the choice of solvent (usually an aprotic solvent like THF) and reaction temperature, need to be carefully controlled to ensure high yields and selectivity for the desired product.To ensure high yields, the reaction conditions (such as the choice solvent, usually an aprotic one like THF), and the reaction temperature must be carefully controlled.
Purification of the synthesized (E)-3-(3,4 - dichlorophenyl)acrylic acid is typically required. This can be achieved through techniques like recrystallization from an appropriate solvent system, such as a mixture of ethanol and water.Recrystallization can be achieved using a solvent system such as ethanol and water. Column chromatography can also be used to separate the product from any unreacted starting materials or by - products, resulting in a pure sample of (E)-3-(3,4 - dichlorophenyl)acrylic acid.
What are the safety precautions when handling (E)-3-(3,4-dichlorophenyl)acrylic acid?
When handling (E)-3-(3,4 - dichlorophenyl)acrylic acid, several safety precautions are necessary.
Firstly, personal protective equipment should be worn.First, it is important to wear personal protective equipment. This includes appropriate gloves.Gloves are a good example. Chemical - resistant gloves, such as those made of nitrile or neoprene, are essential to prevent skin contact.To prevent skin contact, it is essential to use gloves that are chemical-resistant, such as those made from nitrile or Neoprene. Skin exposure can lead to irritation, redness, and potential allergic reactions.Skin contact can cause irritation, redness and allergic reactions. Additionally, safety goggles or a face shield should be used.Safety goggles or face shields should also be worn. This protects the eyes from any splashes or aerosols of the chemical.This will protect the eyes from any aerosols or splashes of the chemical. Inhalation is also a concern, so a respirator with an appropriate filter for organic chemicals may be required, especially in situations where there is a risk of vapor or dust generation.Inhalation can also be a problem, so a respirator that has an organic chemical filter may be needed, especially if there is a possibility of vapors or dust.
Secondly, proper ventilation is crucial.Second, ventilation is essential. Working in a well - ventilated area, such as a fume hood, helps to remove any potentially harmful vapors or dust.A fume hood or other well-ventilated area is ideal for removing any harmful dust or vapors. If a fume hood is not available, ensure the work area has good general ventilation to prevent the build - up of chemical concentrations in the air.If a fume-hood is not available, make sure the area has adequate ventilation to prevent chemical concentrations from building up in the air. High concentrations of (E)-3-(3,4 - dichlorophenyl)acrylic acid in the air can irritate the respiratory tract, causing coughing, shortness of breath, and other respiratory problems.
Thirdly, when handling the chemical, avoid creating dust.Thirdly, avoid creating dust when handling the chemical. This can be achieved by using techniques that minimize powder dispersion, such as carefully scooping or weighing the solid form.You can achieve this by using techniques to minimize powder dispersion. For example, carefully scooping and weighing the solid. If the chemical is in solution, be cautious when pouring or transferring to prevent splashing.Pour or transfer the solution with caution to avoid splashing.
Fourthly, storage is important.Storage is also important. Store (E)-3-(3,4 - dichlorophenyl)acrylic acid in a cool, dry place away from sources of heat, ignition, and incompatible substances. Keep it in a tightly sealed container to prevent evaporation and contamination.Store it in a tightly-sealed container to prevent contamination and evaporation. Labels on the storage container should be clear, indicating the chemical name, potential hazards, and safety instructions.Labels should be clearly visible on the container, indicating the chemical's name, any potential hazards and safety instructions.
Finally, in case of an accident, be prepared.Be prepared in the event of an accident. Have an eyewash station and a safety shower readily available in the work area.Keep an eyewash station, and a safety-shower near the work area. If skin contact occurs, immediately wash the affected area with plenty of water for at least 15 minutes.If skin contact occurs immediately wash the area with lots of water for 15 minutes. If eyes are exposed, flush them with copious amounts of water and seek immediate medical attention.If the eyes are exposed, wash them with plenty of water. Seek immediate medical attention. In case of inhalation, move to fresh air and seek medical help if symptoms persist.If you inhale the substance, get to fresh air. Seek medical attention if symptoms persist.
What are the potential environmental impacts of (E)-3-(3,4-dichlorophenyl)acrylic acid?
(E)-3-(3,4 - dichlorophenyl)acrylic acid is an organic compound. Its potential environmental impacts are as follows:Its environmental impact is as follows:
1. Soil ImpactSoil Impact
If (E)-3-(3,4 - dichlorophenyl)acrylic acid enters the soil, it may affect soil organisms. Microbes in the soil play a crucial role in nutrient cycling, decomposition of organic matter, and maintaining soil structure.Microbes play a vital role in soil structure, organic matter decomposition, and nutrient cycling. The presence of this compound could potentially inhibit the growth and activity of these beneficial microbes.This compound may inhibit the growth and activity these beneficial microbes. For example, certain bacteria and fungi that are responsible for breaking down plant residues and releasing nutrients like nitrogen and phosphorus might be disrupted.This could disrupt certain bacteria and fungal species that are responsible for breaking plant residues down and releasing nutrients such as nitrogen and phosphorus. This could lead to a decrease in soil fertility over time.This could eventually lead to a decrease of soil fertility. Additionally, if the compound accumulates in the soil, it could potentially leach into groundwater, carrying with it the risk of contaminating water sources.If the compound accumulates, it can leach into the groundwater and contaminate water sources.
2. Water ImpactWater Impact
When it gets into water bodies such as rivers, lakes, or groundwater, it can have significant effects on aquatic ecosystems.It can have a significant impact on aquatic ecosystems when it enters water bodies like rivers, lakes or groundwater. Aquatic organisms like fish, amphibians, and invertebrates are highly sensitive to chemical pollutants.Chemical pollutants are highly toxic to aquatic organisms such as fish, amphibians and invertebrates. (E)-3-(3,4 - dichlorophenyl)acrylic acid may act as a toxicant, disrupting the normal physiological functions of these organisms. It could interfere with their respiratory systems, reproductive capabilities, and overall growth and development.It could affect their respiratory systems, reproduction capabilities, and growth and development. For instance, it might cause abnormal development in fish embryos, leading to reduced survival rates.It could, for example, cause abnormal development of fish embryos and reduce survival rates. In addition, it can also affect the water quality parameters.It can also have an impact on the parameters of water quality. It may contribute to changes in the pH of the water or interact with other dissolved substances, potentially altering the chemical balance of the aquatic environment.It can alter the chemical balance in the aquatic environment by altering the pH or interacting with other dissolved substances.
3. Air ImpactAir Impact
Although less likely to be present in the air compared to soil and water, if (E)-3-(3,4 - dichlorophenyl)acrylic acid is released during industrial processes as vapors or in aerosol form, it can have implications for air quality. Once in the atmosphere, it may participate in chemical reactions, potentially contributing to the formation of secondary pollutants.Once in the air, it can participate in chemical reactions that could lead to secondary pollutants. These secondary pollutants can have adverse effects on human health and the environment.These secondary pollutants may have negative effects on the environment and human health. For example, they could contribute to the formation of smog, which reduces visibility and can cause respiratory problems for humans and animals.They can, for example, contribute to the formation smog which reduces visibility, and can cause respiratory issues in humans and animals. However, the volatility of this compound needs to be considered; if it has a low vapor pressure, the air - related impacts are likely to be minimal.The volatility of the compound is important to consider. If it has a low vapour pressure, air-related impacts are likely minimal. Overall, understanding its potential environmental fate and impacts is crucial for proper management and protection of the environment.Understanding its potential environmental fate is important for the proper management and protection.