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Product Name | (2E)-3-(4-Bromo-2-chlorophenyl)acrylic acid |
Cas Number | 87017-12-9 |
Formula | C9H6BrClO2 |
Molar Mass | 261.50 g/mol |
Property 1 | Boiling Point: Not available |
Property 2 | Melting Point: 180-182 °C |
Property 3 | Density: Not available |
Property 4 | Solubility: Soluble in organic solvents |
Property 5 | Appearance: Light yellow solid |
Property 6 | pKa: Approx. 4.5 |
Property 7 | Flash Point: Not available |
Property 8 | Refractive Index: Not available |
Property 9 | Storage Conditions: Store at 2-8 °C |
Property 10 | Hazard Statements: H315 (Causes skin irritation) |
What are the applications of (2E)-3-(4-Bromo-2-chlorophenyl)acrylic acid?
(2E)-3-(4-Bromo-2-chlorophenyl)acrylic acid has several important applications.
In the field of organic synthesis, it serves as a valuable building block.It is a useful building block in organic synthesis. Its double - bond and the halogen - substituted phenyl group endow it with unique reactivity.Its double-bond and halogen-substituted phenyl groups endow it with a unique reactivity. The double bond can participate in various addition reactions, such as Diels - Alder reactions.Double bonds can be used in addition reactions such as Diels-Alder reactions. This allows chemists to construct more complex cyclic structures.This allows chemists construct more complex cyclic structure. For example, when reacting with a suitable diene, it can form cyclohexene - based derivatives, which are often key intermediates in the synthesis of natural products and pharmaceuticals.When reacting with suitable dienes, it can produce cyclohexene-based derivatives. These are often key intermediates for the synthesis of pharmaceuticals and natural products.
The halogen atoms, bromine and chlorine, on the phenyl ring are highly reactive for substitution reactions.The halogen atoms on the phenyl rings, bromine and chlorine, are highly reactive in substitution reactions. They can be replaced by different nucleophiles.They can be substituted by different nucleophiles. For instance, a nucleophilic aromatic substitution reaction can be carried out where the bromine or chlorine is replaced by an amino group, a hydroxyl group, or an alkoxy group.Nucleophilic aromatic substitution reactions can be carried out, for example, when the bromine or chloride is replaced by a group of amino, hydroxyl, or alkoxy. This enables the synthesis of a wide range of substituted phenyl - acrylic acid derivatives with potentially diverse biological activities.This allows the synthesis a variety of substituted phenyl-acrylic acid derivatives that may have diverse biological activities.
In the pharmaceutical industry, (2E)-3-(4 - Bromo - 2 - chlorophenyl)acrylic acid can be used as a starting material for the development of new drugs.In the pharmaceutical industry (2E)-3 - (4 - Bromo-2 - chlorophenyl - acrylic acid can be used to develop new drugs. Compounds containing the acrylic acid moiety often show interesting biological properties.The compounds containing the acrylic-acid moiety have many interesting biological properties. The presence of the bromine and chlorine atoms can enhance the lipophilicity of the molecule, which may improve its ability to cross cell membranes.The presence of bromine and chlorine atoms can increase the lipophilicity, which could improve the ability of the molecule to cross cell membranes. This could potentially lead to the discovery of new anti - inflammatory, anti - cancer, or anti - microbial agents.This could lead to the discovery new anti-inflammatory, anti-cancer, or anti-microbial agents. For example, some studies have shown that related phenylacrylic acid derivatives can interact with specific proteins in cells, inhibiting their functions and thus exerting therapeutic effects.Some studies have shown, for example, that related phenylacrylic acids can interact with specific protein in cells, inhibiting the functions of these proteins and exerting therapeutic effects.
In the area of materials science, it can be incorporated into polymers.In the field of materials science it can be incorporated in polymers. The double bond of the acrylic acid group can be polymerized, either alone or in combination with other monomers.The double bond in the acrylic acid group, alone or combined with other monomers, can be polymerized. The resulting polymers may have unique optical or mechanical properties due to the presence of the halogen - substituted phenyl groups.The halogen-substituted phenyl group may give the polymers unique optical or mechanical characteristics. These polymers could be used in applications such as optical coatings, where the halogen atoms can influence the refractive index of the material, or in the development of high - performance plastics with enhanced strength and stability.These polymers can be used for optical coatings where the halogens can influence the material's refractive index, or to develop high-performance plastics with enhanced strength.
Overall, (2E)-3-(4 - Bromo - 2 - chlorophenyl)acrylic acid is a versatile compound with significant potential in multiple scientific and industrial fields, facilitating the creation of new substances with tailored properties and functions.Overall, (2E - 3-(4 – Bromo – 2- chlorophenyl - acrylic acid) is a versatile chemical compound that has significant potential in many scientific and industrial fields. It facilitates the creation of new substances, with tailored properties and functions.
What are the properties of (2E)-3-(4-Bromo-2-chlorophenyl)acrylic acid?
(2E)-3-(4 - Bromo - 2 - chlorophenyl)acrylic acid has several important properties.The properties of (2E)-3(4-bromo-2-chlorophenyl-acrylic acid) are important.
First, in terms of its chemical structure, it contains a phenyl ring substituted with a bromine atom at the 4 - position and a chlorine atom at the 2 - position.Its chemical structure is a phenyl with a bromine at the 4 – position and a chloride at the 2 – position. The presence of the double bond in the acrylic acid moiety gives it the ability to participate in addition reactions.The double bond present in the acrylic acid moiety allows it to participate in addition reaction. For example, it can undergo electrophilic addition reactions with reagents like bromine or hydrogen halides.It can, for example, undergo electrophilic reactions with reagents such as bromine or hydrogen chlorides. The double bond also contributes to its potential for polymerization reactions under appropriate conditions.Under the right conditions, its double bond can also contribute to its polymerization potential.
The carboxylic acid group is highly polar.The carboxylic group is highly polar. This imparts acidic properties to the compound.This gives the compound acidic properties. It can donate a proton in aqueous solutions or in the presence of a base, forming a carboxylate anion.It can donate a protons in aqueous solution or in presence of abase, forming a carboxylate anion. The pKa value of the carboxylic acid group determines its acidity.The pKa of the carboxylic group determines its acidity. Generally, carboxylic acids have pKa values in the range of 4 - 5, and this (2E)-3-(4 - Bromo - 2 - chlorophenyl)acrylic acid is likely to follow a similar trend.Carboxylic acids usually have pKa value in the range 4 - 5. This (2E)-3 - (4 - Bromo-2 - Chlorophenylacrylic acid will likely follow a similar pattern. The acidity allows it to react with bases such as sodium hydroxide to form the corresponding sodium carboxylate salt.Its acidity allows it react with bases like sodium hydroxide to produce the sodium carboxylate salt.
The bromine and chlorine atoms on the phenyl ring are electronegative halogens.The bromine and chlorine atoms are electronegative halogens. They influence the reactivity of the phenyl ring through inductive and resonance effects.They influence the reactivity by inductive and resonance effects. Inductively, they withdraw electron density from the ring, making the ring less electron - rich.Inductively they remove electron density from ring, making it less electron-rich. This can affect the reactivity of the ring towards electrophilic aromatic substitution reactions.This can alter the reactivity towards electrophilic aromatic substitute reactions. For instance, compared to an unsubstituted phenyl ring, the bromine and chlorine substituents will direct incoming electrophiles to the ortho and para positions relative to the stronger electron - withdrawing group among them (usually the bromine due to its higher electronegativity in this case).The bromine and chloride substituents, for example, will direct incoming electron-withdrawing groups to the ortho and par positions relative to an unsubstituted, phenyl ring.
In terms of physical properties, (2E)-3-(4 - Bromo - 2 - chlorophenyl)acrylic acid is likely to be a solid at room temperature.Physically, (2E-3)-4-(4-bromo-2-chlorophenyl-acrylic acid will likely be a solid when it reaches room temperature. This is due to the presence of strong intermolecular forces.This is because of the strong intermolecular force. The carboxylic acid group can participate in hydrogen bonding with other molecules of the same compound.The carboxylic group can participate in hydrogen bonds with other molecules from the same compound. The halogen - substituted phenyl ring also contributes to van der Waals forces.The halogen-substituted phenyl rings also contribute to van der Waals force. These intermolecular forces hold the molecules together in a solid lattice.These intermolecular interactions hold the molecules in a solid lattice.
Its solubility is an important aspect.Its solubility plays a major role. The polar carboxylic acid group favors solubility in polar solvents such as water, alcohols, and carboxylic acids themselves.The polar carboxylic group is more soluble in polar solvents like water, alcohols and carboxylic acids. However, the relatively large non - polar phenyl ring with halogen substituents reduces its solubility in water compared to simpler carboxylic acids.The relatively large non-polar phenyl rings with halogen substitutes reduce its solubility in the water compared to carboxylic acid. It may have better solubility in organic solvents like dichloromethane, ethyl acetate, or acetone, which can dissolve both the polar and non - polar parts of the molecule through a combination of dipole - dipole interactions and van der Waals forces.It may be more soluble in organic solvents such as dichloromethane or acetone. These organic solvents can dissolve both polar and non-polar parts of the molecules through a combination dipole-dipole interactions and van Der Waals forces.
How is (2E)-3-(4-Bromo-2-chlorophenyl)acrylic acid synthesized?
The synthesis of (2E)-3-(4 - Bromo - 2 - chlorophenyl)acrylic acid can be achieved through the following general steps.The following general steps can be used to synthesize (2E)-3 - (4 - Bromo-2 - Chlorophenyl)acrylic Acid.
First, start with 4 - bromo - 2 - chlorobenzaldehyde as a key starting material.Start with 4 -bromo-2-chlorobenzaldehyde. This aldehyde can react with a reagent containing an active methylene group.This aldehyde reacts with a reagent that contains an active methylene. A common choice is malonic acid in the presence of a base such as pyridine.Malonic acid is a common choice in the presence pyridine or a base. This reaction is known as the Knoevenagel condensation.This reaction is called the Knoevenagel condensate.
In the Knoevenagel condensation, the base in pyridine deprotonates the malonic acid, generating a carbanion.In the Knoevenagel reaction, the base of pyridine deprotonates malonic acid to produce a carbanion. This carbanion then attacks the carbonyl carbon of 4 - bromo - 2 - chlorobenzaldehyde.This carbanion attacks the carbonyl of 4 -bromo -2 - chlorobenzaldehyde. After the nucleophilic addition, an intermediate is formed.After the nucleophilic addtion, an intermediate is produced. Subsequently, a dehydration step occurs.Then, a step of dehydration occurs. The acidic conditions provided by the reaction medium or the action of the base - acid interplay leads to the elimination of a water molecule.The base-acid interaction or the acidic conditions of the reaction medium lead to the elimination of one water molecule. This results in the formation of the double bond, giving (2E)-3-(4 - bromo - 2 - chlorophenyl)propenoic acid, which is the target (2E)-3-(4 - Bromo - 2 - chlorophenyl)acrylic acid.
Another possible approach could involve the use of Wittig - type reactions.A second possible approach would be to use Wittig-type reactions. First, prepare a phosphonium ylide from an appropriate phosphonium salt.Prepare a phosphonium-ylide by first preparing a suitable phosphonium salt. For example, react triphenylphosphine with an alkyl halide containing the appropriate side - chain related to the target molecule.React, for example, triphenylphosphine to an alkylhalide that contains the side-chain related to the target. Then, react this phosphonium ylide with 4 - bromo - 2 - chlorobenzaldehyde.This phosphonium-ylide is then reacted with 4 -bromo-2 - chlorobenzaldehyde. The ylide reacts with the aldehyde in a concerted manner to form an oxaphosphetane intermediate.The ylide reacts in concert with the aldehyde to form an intermediate oxaphosphetane. This intermediate then decomposes to give the desired (2E)-3-(4 - Bromo - 2 - chlorophenyl)acrylic acid along with triphenylphosphine oxide as a by - product.This intermediate decomposes into the desired (2E),-3-(4-Bromo -2 - chlorophenyl),acrylic acid, along with triphenylphosphine as a by-product. The Wittig reaction is highly stereoselective and often gives the E - isomer predominantly, which is the required configuration in (2E)-3-(4 - Bromo - 2 - chlorophenyl)acrylic acid.The Wittig reactions are highly stereoselective, and they often give the E-isomer as the predominant isomer. This is the configuration required in (2E-3)-3-(4-Bromo -2 - chlorophenyl-acrylic acid.
Purification of the synthesized product is crucial.Purification is essential. It can be achieved through techniques such as recrystallization.Techniques such as recrystallization can be used to achieve this. Dissolve the crude product in a suitable solvent system where the product has different solubility at different temperatures.Dissolve the crude in a solvent system that is suitable for the product. The product will have varying solubilities at different temperatures. For example, a mixture of organic solvents like ethanol - water can be used.You can use a mixture of organic solvants like ethanol and water. Heat the solution to dissolve the product, then slowly cool it.The solution should be heated to dissolve the product and then cooled slowly. The pure product will crystallize out, leaving impurities in the solution.The impurities will remain in the solution, while the pure product crystallizes out. Filtration can then be used to separate the pure (2E)-3-(4 - Bromo - 2 - chlorophenyl)acrylic acid crystals.Filtration is then used to separate pure (2E)-3 - (4 - Bromo-2 - Chlorophenyl-acrylic acid crystals. Characterization of the product can be done using techniques like nuclear magnetic resonance (NMR) spectroscopy to confirm the structure and infrared (IR) spectroscopy to identify functional groups.The product can be characterized using techniques such as nuclear magnetic resonance spectroscopy (NMR) to confirm the structure, and infrared spectroscopy (IR) to identify functional groups.
What are the safety precautions when handling (2E)-3-(4-Bromo-2-chlorophenyl)acrylic acid?
(2E)-3-(4-Bromo-2-chlorophenyl)acrylic acid is a chemical compound that requires certain safety precautions when being handled.
First, personal protective equipment is crucial.Personal protective equipment is essential. Wear appropriate protective clothing, such as a lab coat, to prevent direct contact of the chemical with your skin.Wear protective clothing such as a labcoat to prevent direct skin contact with the chemical. Chemical - resistant gloves, preferably made of materials like nitrile, should be worn.Wear chemical-resistant gloves, preferably made from materials such as nitrile. This helps to avoid skin absorption of the compound, which could potentially lead to skin irritation, allergic reactions, or more serious health effects if the chemical is toxic.This will help to prevent skin absorption, which can lead to skin irritations, allergic reactions or more serious health issues if the chemical in question is toxic. Additionally, safety goggles or a face shield should be used to protect your eyes.Safety goggles or face shields should also be worn to protect your eyes. Even a small splash of (2E)-3-(4-Bromo-2-chlorophenyl)acrylic acid into the eyes could cause severe irritation, damage to the cornea, or other eye - related problems.
Second, work in a well - ventilated area.Second, make sure you are working in an area that is well-ventilated. This chemical may release vapors, and a well - ventilated environment, such as a fume hood, helps to remove these vapors.A well-ventilated environment, such a fume hood or a well-ventilated area, can help remove these vapors. Inhalation of the vapors can irritate the respiratory tract, causing coughing, shortness of breath, or more serious lung problems over time.Inhaling the vapors may cause irritation of the respiratory tract. This can lead to coughing, shortness in breath, or even more serious lung conditions over time. If there is no fume hood available, ensure that the room has good general ventilation to dilute the concentration of any released vapors.If a fume hood is not available, make sure that the room is well ventilated to dilute any released vapors.
When handling the chemical, avoid generating dust.Avoid generating dust when handling the chemical. (2E)-3-(4-Bromo-2-chlorophenyl)acrylic acid in powder form, if applicable, can form dust particles in the air. Inhalation of these dust particles can be as harmful as inhaling the vapors.Inhaling these dust particles is just as dangerous as inhaling vapors. Use proper techniques when transferring the chemical, such as using a scoop or spatula carefully, and avoid any actions that could cause the powder to become airborne.Transfer the chemical using the correct technique, such as a spatula or scoop. Avoid any actions that may cause the powder to become aerosolized.
In case of accidental contact, know the proper first - aid procedures.Know the correct first-aid procedures in case of accidental contact. If it comes into contact with the skin, immediately wash the affected area with plenty of soap and water for at least 15 minutes.If it gets on the skin, wash the area immediately with soap and water. This should last at least 15 minutes. If it gets into the eyes, rinse them thoroughly with clean water for a long time, preferably with an eyewash station, and seek medical attention promptly.If it gets in the eyes, rinse with clean water and for a long period of time, preferably using an eyewash station. Seek medical attention immediately if it is inhaled. If inhaled, move to fresh air immediately.Inhalation should be treated immediately by moving to fresh air. If ingestion occurs, do not induce vomiting unless specifically instructed by a medical professional, and seek emergency medical help right away.If you ingest the substance, do not induce vomiting until you are instructed to by a medical professional. Seek immediate medical attention.
Finally, proper storage is also important.It is also important to store the acid properly. Store (2E)-3-(4-Bromo-2-chlorophenyl)acrylic acid in a cool, dry place, away from heat sources and incompatible substances. Keep it in a tightly - sealed container to prevent leakage and evaporation.Keep it in a tightly-sealed container to prevent leaking and evaporation. Label the container clearly with the chemical name, hazards, and any other relevant information for easy identification and to ensure safe handling by others.Label the container with the chemical name and any relevant information, such as hazards and other relevant information, to make it easy to identify and ensure safe handling.
What is the stability of (2E)-3-(4-Bromo-2-chlorophenyl)acrylic acid?
(2E)-3-(4 - Bromo - 2 - chlorophenyl)acrylic acid is an organic compound.It is an organic compound. Its stability is influenced by several factors.Its stability can be affected by a number of factors.
First, the molecular structure plays a crucial role.The molecular structure is crucial. The presence of the phenyl ring, substituted with bromine and chlorine atoms, contributes to the compound's overall stability.The presence of a phenyl ring substituted with chlorine and bromine atoms contributes to the overall stability of the compound. The aromatic nature of the phenyl ring provides a certain degree of electronic delocalization.The aromatic nature of phenyl rings allows for a certain amount of electronic delocalization. The bromine and chlorine atoms, being electronegative halogens, can affect the electron density distribution in the ring.Electronegative halogens such as bromine and chlorine can influence the electron density distribution within the ring. Electron - withdrawing groups like these can influence the reactivity of the adjacent double bond and the carboxylic acid group.These electron-withdrawing groups can affect the reactivity and double bond of the carboxylic group.
The double bond in the acrylic acid moiety is also important.The double bond within the acrylic acid moiety also plays a role. In (2E)-3-(4 - Bromo - 2 - chlorophenyl)acrylic acid, the E - configuration of the double bond imparts a specific geometric stability.The E-configuration of the double bond in (2E)-3 - (4 - Bromo-2 - Chlorophenyl-acrylic acid confers a particular geometric stability. This configuration allows for more efficient packing of the molecule in the solid state or in solution, which can enhance its overall stability compared to the Z - isomer.This configuration allows a more efficient packing of a molecule, whether in solid state or solution. This can increase its overall stability when compared to the Z-isomer.
The carboxylic acid group can participate in various interactions.The carboxylic group can be involved in a variety of interactions. It can form hydrogen bonds with other molecules in the environment, such as water molecules if in an aqueous medium.It can form hydrogen bond with other molecules, such as water molecules in an aqueous environment. These hydrogen - bonding interactions can either stabilize or destabilize the compound depending on the surrounding conditions.These hydrogen-bonding interactions can either destabilize or stabilize the compound depending on surrounding conditions. For example, in a polar solvent, the formation of hydrogen bonds between the carboxylic acid group and the solvent molecules can solubilize the compound and contribute to its stability in solution.In a polar solution, for example, the formation between the carboxylic acids and the solvent molecules of hydrogen bonds can solubilize and contribute to the stability of the compound in solution.
Thermally, the compound's stability depends on the strength of its chemical bonds.The strength of the chemical bonds in the compound determines its thermal stability. The carbon - halogen (C - Br and C - Cl) bonds in the phenyl ring are relatively strong, but they can be broken under high - energy conditions such as high temperatures or in the presence of strong reducing or oxidizing agents.The carbon-halogen (C- Br and C- Cl) bonds of the phenyl rings are relatively strong. However, they can be broken by high-energy conditions such as high temperature or the presence of strong reducing agents or oxidizing substances. The double bond can also be prone to addition reactions under certain circumstances, which would change the structure and thus the stability of the compound.Under certain conditions, the double bond is also susceptible to addition reactions that can change the structure of the compound.
In terms of photostability, the presence of the aromatic ring and the double bond can make the compound sensitive to light.The presence of an aromatic ring or a double bond can increase the compound's photostability. Photons can excite electrons in the conjugated system, potentially leading to bond cleavage or isomerization reactions.Photons may excite electrons within the conjugated system and lead to bond cleavages or isomerizations. However, the presence of the halogen atoms can also have a moderating effect on photochemical reactivity.The presence of halogen atoms may also have a moderating impact on photochemical reactivity.
Overall, the stability of (2E)-3-(4 - Bromo - 2 - chlorophenyl)acrylic acid is a complex interplay of its molecular structure, the nature of its functional groups, and the environmental conditions it is exposed to.Overall, the stability (2E)-3 - (4 - Bromo-2 - chlorophenylacrylic acid is a complex interaction of its molecular structures, its functional groups and the environmental conditions to which it is exposed. While it has some inherent stability due to its aromatic and conjugated structure, it can also be reactive under specific chemical, thermal, or photochemical conditions.It has some inherent stability because of its aromatic and conjugated structures, but it can also be reactive under certain chemical, thermal or photochemical conditions.