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(e)-3-(3,5-dimethoxyphenyl)acrylic Acid


Properties
Product Name (E)-3-(3,5-Dimethoxyphenyl)acrylic acid
Cas Number 13601-19-5
Formula C11H12O4
Molar Mass 208.21
Property1 Appearance: White to off-white powder
Property2 Melting Point: 175-177°C
Property3 Solubility: Soluble in organic solvents
Property4 Boiling Point: Not available
Property5 Density: Not available
Property6 Refractive Index: Not available
Property7 pKa: Not available
Property8 Storage conditions: Store in a cool, dry place
Property9 Stability: Stable under recommended storage conditions
Property10 Potential applications: Used in organic synthesis and research
FAQ

What are the applications of (E)-3-(3,5-dimethoxyphenyl)acrylic acid?

(E)-3-(3,5-dimethoxyphenyl)acrylic acid has several applications in different fields.
In the pharmaceutical industry, it can serve as an important intermediate for the synthesis of various bioactive compounds.It can be used as an intermediate in the pharmaceutical industry to synthesize bioactive compounds. Its structure, with the 3,5 - dimethoxyphenyl group and the acrylic acid moiety, provides a framework that can be modified to create molecules with potential biological activities.Its structure with the 3,5-dimethylphenyl group, and the acrylic acid moiety provides a framework which can be modified to produce molecules with potential biological activity. For example, it can be used in the synthesis of drugs targeting specific receptors or enzymes.It can be used to synthesize drugs that target specific enzymes or receptors. Some derivatives might possess anti - inflammatory properties.Some derivatives may have anti-inflammatory properties. The dimethoxy groups on the phenyl ring can influence the molecule's lipophilicity and electronic properties, which in turn can affect its ability to interact with biological targets.The dimethoxy group on the phenyl can influence the molecule’s electronic properties and lipophilicity, which can in turn affect its ability to interact biological targets.

In the area of materials science, (E)-3-(3,5 - dimethoxyphenyl)acrylic acid can be utilized in the preparation of certain polymers. When polymerized, it can introduce specific functional groups into the polymer chain.It can introduce functional groups into polymer chains when polymerized. The acrylic acid part can participate in polymerization reactions, and the 3,5 - dimethoxyphenyl group can endow the polymer with unique optical or electronic properties.The acrylic acid can be used in polymerization reactions and the 3,5-dimethoxyphenyl can give the polymer unique optical or electronic properties. For instance, polymers containing this monomer might show interesting fluorescence or conductivity characteristics, making them suitable for applications in optoelectronic devices such as light - emitting diodes or sensors.Polymers containing the monomer may exhibit interesting fluorescence and conductivity characteristics. This makes them suitable for optoelectronic applications such as light-emitting diodes and sensors.

It also has applications in organic synthesis as a building block.It is also used as a building-block in organic synthesis. Chemists can use it to construct more complex organic molecules.It can be used by chemists to build more complex organic molecules. The double bond in the acrylic acid part can undergo a variety of reactions like addition reactions, allowing for the attachment of different substituents.The double bond of the acrylic acid can undergo different reactions, such as addition reactions, which allows for the attachment of various substituents. The methoxy groups on the phenyl ring can direct further chemical modifications, enabling the synthesis of molecules with precisely tailored structures.The methoxy groups of the phenyl rings can be used to direct further chemical modifications. This allows the synthesis and amplification of molecules with tailored structures. These synthetic molecules can then be used in research to study reaction mechanisms or to develop new compounds with desired properties.These synthetic molecules can be used to study reaction mechanisms and develop new compounds that have desired properties.

In the field of natural product total synthesis, (E)-3-(3,5 - dimethoxyphenyl)acrylic acid can be a key intermediate. Many natural products contain similar structural motifs, and this compound can be used as a starting point to access these complex natural molecules.This compound can be used to access complex natural molecules that have similar structural motifs. By mimicking the biosynthetic pathways or using synthetic strategies, chemists can build up the carbon - skeleton and functional groups of natural products, which can have potential applications in drug discovery, as some natural products have shown remarkable biological activities.By using synthetic strategies or mimicking biosynthetic pathways, chemists are able to build up the carbon-skeleton and functional group of natural products. This can be useful in drug discovery as some natural compounds have demonstrated remarkable biological activity.

What is the synthesis method of (E)-3-(3,5-dimethoxyphenyl)acrylic acid?

Here is a common synthesis method of (E)-3-(3,5 - dimethoxyphenyl)acrylic acid:
1. Preparation of starting materialsPrepare the starting materials
The synthesis often starts with 3,5 - dimethoxybenzaldehyde as a key starting material. This compound can be obtained through various chemical routes, such as the methylation of 3,5 - dihydroxybenzaldehyde using methylating agents like dimethyl sulfate in the presence of a base.

2. Knoevenagel condensation reaction
The main step for the synthesis of (E)-3-(3,5 - dimethoxyphenyl)acrylic acid is the Knoevenagel condensation. In this reaction, 3,5 - dimethoxybenzaldehyde reacts with malonic acid in the presence of a catalyst. Piperidine is a commonly used catalyst for this reaction.Piperidine is commonly used as a catalyst in this reaction. The reaction is usually carried out in a suitable solvent, such as pyridine.The reaction is carried out in a suitable solvant, such as pyridine.
The reaction mechanism involves the formation of an enolate anion from malonic acid under the action of the base (piperidine).The reaction involves the formation of enolate anion under the action (piperidine) of the base. The enolate anion then attacks the carbonyl carbon of 3,5 - dimethoxybenzaldehyde. Subsequent dehydration occurs, leading to the formation of the (E)-3-(3,5 - dimethoxyphenyl)acrylic acid. The (E) - configuration is favored due to the thermodynamic stability of the trans - double bond in this type of reaction.The (E)-configuration is preferred due to the thermodynamic stability of the trans-double bond in this type reaction.

3. Reaction conditions and work - up3.
The reaction is typically carried out at an elevated temperature, usually around the boiling point of the solvent (pyridine boils at about 115 - 116 degC).The reaction is usually carried out at a high temperature, typically around the boiling point (pyridine boils between 115-116 degC). After the reaction is complete, the reaction mixture is cooled.The reaction mixture is cooled after the reaction has been completed. Then, the product can be isolated by acidifying the reaction mixture with a mineral acid, such as hydrochloric acid.The product can then be isolated by acidifying a reaction mixture with mineral acids, such as hydrochloric. The precipitated (E)-3-(3,5 - dimethoxyphenyl)acrylic acid can be collected by filtration. Further purification can be achieved by recrystallization from an appropriate solvent, like ethanol - water mixture.Recrystallization using an appropriate solvent like ethanol-water mixture can be used to purify the product further. During recrystallization, the impure product is dissolved in a minimum amount of hot solvent, and then slowly cooled to allow the pure compound to crystallize out, leaving impurities in the solution.During recrystallization the impure product dissolves in a small amount of hot solvent and is then slowly cooled, allowing the pure compound crystallize, leaving the impurities behind. This process can improve the purity of the (E)-3-(3,5 - dimethoxyphenyl)acrylic acid product.

What are the physical and chemical properties of (E)-3-(3,5-dimethoxyphenyl)acrylic acid?

(E)-3-(3,5 - dimethoxyphenyl)acrylic acid is an organic compound with the following physical and chemical properties:
Physical Properties

Appearance: It is likely to exist as a solid at room temperature.Appearance: It will likely exist as a solid when at room temperature. Many aromatic carboxylic acids with similar structures are solids due to the presence of strong intermolecular forces, such as hydrogen bonding and van der Waals forces.Many aromatic carboxylic acid with similar structures are solids because of the strong intermolecular interactions, such as hydrogen bonds and van der Waals force. The planar nature of the aromatic ring and the carboxyl group contributes to efficient packing in the solid state.The planar natures of the aromatic ring, and the carboxyl groups, contribute to efficient packing.

Melting Point: The melting point of (E)-3-(3,5 - dimethoxyphenyl)acrylic acid depends on its crystal structure and intermolecular interactions. The methoxy groups on the phenyl ring can influence the melting point.The methoxy groups of the phenyl rings can influence melting point. The electron - donating methoxy groups can change the polarity of the molecule and the strength of intermolecular forces.The electron-donating methoxy group can change the polarity and strength of intermolecular force. Generally, aromatic carboxylic acids with similar substituents have melting points in the range of several tens to a few hundred degrees Celsius.Aromatic carboxylic acid with similar substituents usually have melting points between a few tens and a few hundreds of degrees Celsius.

Solubility: In terms of solubility, it is sparingly soluble in water.Solubility: It is sparingly water soluble. The hydrophobic nature of the 3,5 - dimethoxyphenyl group dominates over the hydrophilic carboxyl group.The hydrophobic nature is dominant over the hydrophilic carboxyl groups. However, it is more soluble in organic solvents such as ethanol, methanol, and dichloromethane.It is more soluble in organic solvants such as ethanol methanol and dichloromethane. The polar - nonpolar balance of these solvents can interact with the different parts of the (E)-3-(3,5 - dimethoxyphenyl)acrylic acid molecule. The carboxyl group can form hydrogen bonds with polar solvents like alcohols, while the aromatic and methoxy groups can interact with the non - polar parts of the organic solvents.The carboxyl group forms hydrogen bonds with polar organic solvents such as alcohols, whereas the aromatic and methoxy can interact with non-polar parts of these solvents.

Color: It is often colorless or may have a pale - colored appearance.Color: It can be colorless or pale-colored. Aromatic compounds without extensive conjugated chromophores typically do not have intense colors.Aromatic compounds that lack extensive conjugated chromophores do not usually have intense colors. The 3,5 - dimethoxyphenyl and acrylic acid moieties do not contain highly conjugated systems that would absorb visible light strongly, resulting in a relatively colorless compound.The acrylic acid and 3,5-dimethoxyphenyl moieties don't contain highly conjugated systems which would absorb visible light very strongly, resulting a relatively colorless substance.

Chemical Properties

Acidity: The carboxyl group in (E)-3-(3,5 - dimethoxyphenyl)acrylic acid is acidic. It can donate a proton in the presence of a base, forming the corresponding carboxylate anion.It can donate a protons in the presence a base to form the carboxylate anion. The pKa value of the carboxyl group is influenced by the substituents on the phenyl ring.The substituents on phenyl rings influence the pKa of the carboxyl groups. The electron - donating methoxy groups can increase the electron density around the carboxyl group, making it slightly less acidic compared to unsubstituted acrylic acid.The electron-donating methoxy group can increase the density of electrons around the carboxyl groups, making it slightly acidic compared with unsubstituted acrylic acid. This is because the negative charge on the carboxylate anion is less stabilized when there is more electron density around the carboxyl group.This is because there is less stabilization of the negative charge on carboxylate anion when there is a higher electron density around carboxyl group.

Reactivity of the Double Bond: The (E)-configured double bond in the acrylic acid part of the molecule is reactive.Double bond reactivity: The double bond with the configuration (E) in the acrylic acid portion of the molecule has a high level of reactivity. It can undergo addition reactions.It can undergo addition reaction. For example, it can react with electrophiles such as bromine in an electrophilic addition reaction to form a dibromo - derivative.It can, for example, react with electrophiles like bromine in an addition reaction electrophilic to form a dibromo-derivative. The double bond can also participate in polymerization reactions under appropriate conditions, especially in the presence of initiators.Under certain conditions, the double bond can participate in polymerizations, especially when initiators are present. This reactivity is characteristic of alkenes and is useful in the synthesis of polymers or other functionalized compounds.This reactivity, which is characteristic of alkenes, is useful for the synthesis or other functionalized compounds.

Reactions of the Aromatic Ring: The 3,5 - dimethoxyphenyl ring can undergo electrophilic aromatic substitution reactions.Aromatic Substitution Reactions: The 3,5-dimethylphenyl ring is capable of electrophilic aromatic substitution. The methoxy groups are ortho/para - directing groups.The methoxy groups have ortho/para-directing properties. They increase the electron density at the ortho and para positions of the phenyl ring, making these positions more reactive towards electrophiles.They increase the electron densities at the ortho and par positions of the phenyl rings, making them more reactive to electrophiles. Reactions such as nitration, halogenation, or Friedel - Crafts reactions can occur at these activated positions on the aromatic ring.These activated positions can cause reactions such as nitrations, halogenations, or Friedel-Crafts reactions.

Is (E)-3-(3,5-dimethoxyphenyl)acrylic acid toxic?

( E ) - 3 - ( 3, 5 - dimethoxyphenyl ) acrylic acid is a chemical compound.Chemical compound ( E )- 3 – ( 3, 5 – dimethoxyphenyl) acrylic acid. Information regarding its toxicity can be found through scientific literature, experimental data from in - vitro and in - vivo studies, as well as safety assessments.You can find information about its toxicity in scientific literature, experimental results from in-vivo and in-vitro studies, and safety assessments.
In in - vitro studies, researchers often expose cell lines to the compound to evaluate its effects on cell viability, proliferation, and metabolism.Researchers expose cell lines to the substance in in-vitro studies to determine its effects on cell viability and metabolism. If ( E ) - 3 - ( 3, 5 - dimethoxyphenyl ) acrylic acid causes significant cell death or disrupts normal cellular functions at relatively low concentrations, it can be considered potentially toxic at the cellular level.If ( E ), - 3 ( 3, 5 – dimethoxyphenyl) acrylic acid causes significant cellular death or disrupts normal cell functions at relatively low levels, it can be regarded as potentially toxic. However, the results from in - vitro studies may not directly translate to the in - vivo situation.The results of in-vitro studies may not be directly applicable to the in-vivo situation.

For in - vivo toxicity studies, animals such as rats or mice are commonly used.In - vivo studies of toxicity are often conducted using animals like rats or mice. These studies assess different aspects of toxicity, including acute toxicity (effects observed shortly after a single exposure), sub - chronic toxicity (effects over a longer period with repeated exposure), and chronic toxicity (long - term effects).These studies evaluate different aspects of toxicology, including acute toxicity and sub-chronic toxicity. If, in acute toxicity studies, high doses of the compound lead to symptoms like lethargy, changes in body weight, or organ damage in the test animals, it indicates acute toxicity.In acute toxicity tests, if high doses of a compound cause symptoms such as lethargy, weight changes, or organ damage, this indicates acute toxicity. In sub - chronic and chronic studies, continuous exposure might show cumulative effects on organs such as the liver, kidneys, or the immune system.In sub-chronic and chronic studies, continuous exposition may show cumulative effects on organs like the liver, kidneys or immune system.

Available scientific reports on this specific compound are crucial for a definite conclusion on its toxicity.It is important to have access to the scientific reports that are available on this compound in order for you reach a definitive conclusion about its toxicity. If there are limited data, it becomes more challenging to accurately determine its toxicity profile.It is more difficult to accurately determine a compound's toxicity profile if there are few data. In general, many organic acids and their derivatives can have a range of toxicological effects depending on their chemical structure and the way they interact with biological systems.Many organic acids and their derivates can have a variety of toxicological effects, depending on their chemical structures and how they interact with biological system. Some may be relatively benign and even have potential beneficial properties, while others can be harmful.Some organic acids may be benign or even beneficial, while others are harmful. Without comprehensive and specific toxicity data on ( E ) - 3 - ( 3, 5 - dimethoxyphenyl ) acrylic acid, a precise statement about its toxicity cannot be made.It is impossible to make a precise assessment of its toxicity without comprehensive and specific data. But by following the general principles of toxicology research and evaluating similar compounds, we can infer that proper safety precautions should be taken when handling it until more detailed toxicity information is available.By following the general principles in toxicology research, and evaluating similar substances, we can deduce that it is best to take safety precautions when handling this compound until more detailed information about its toxicity is available.

What is the stability of (E)-3-(3,5-dimethoxyphenyl)acrylic acid?

(E)-3-(3,5 - dimethoxyphenyl)acrylic acid is a compound with certain stability characteristics.
I. Molecular Structure and Intrinsic StabilityI. Molecular structure and intrinsic stability

The stability of (E)-3-(3,5 - dimethoxyphenyl)acrylic acid is significantly influenced by its molecular structure. The presence of the 3,5 - dimethoxyphenyl group attached to the acrylic acid moiety plays a crucial role.The presence of the 3,5-dimethylphenyl group on the acrylic acid moiety is crucial. The methoxy groups (-OCH3) on the phenyl ring are electron - donating groups.The methoxy groups on the phenyl rings (-OCH3) are electron-donating groups. Through the +M (mesomeric) effect, they can donate electron density to the phenyl ring.They can donate electron density through the +M (mesomeric effect). This electron - donating property helps to stabilize the conjugated system of the molecule.This electron-donating property helps stabilize the conjugated system in the molecule. The conjugation in the molecule extends from the double bond in the acrylic acid part to the phenyl ring, which overall contributes to the stability of the molecule.The conjugation extends from the double bonds in the acrylic acid to the phenyl rings, which contributes to the overall stability of the molecules. The resonance forms that can be drawn due to this conjugation allow for the delocalization of electrons, reducing the electron - rich or electron - deficient regions within the molecule and thus enhancing its stability.This conjugation allows for the delocalization electrons. It reduces the electron-rich or electron-deficient regions in the molecule, and enhances its stability.

The (E) - configuration of the double bond in the acrylic acid part also affects stability.The configuration (E) of the double bond within the acrylic acid part can also affect stability. The (E) - isomer (where the two larger groups are on opposite sides of the double bond) is generally more stable than the (Z) - isomer due to reduced steric hindrance.The (E), (Z) and (Z) isomers are more stable due to the reduced steric hindrance. In (E)-3-(3,5 - dimethoxyphenyl)acrylic acid, the phenyl group and the carboxylic acid group are arranged in a way that minimizes steric interactions around the double bond, contributing to the overall stability of the molecule.

II. Stability in Different EnvironmentsStability in different environments

1. Thermal Stability
In terms of thermal stability, the molecule can withstand a certain range of temperatures before decomposition occurs.Thermal stability is the ability of a molecule to withstand a range of temperatures without decomposition. The presence of the conjugated system and the relatively stable aromatic and carboxylic acid functional groups contribute to its ability to resist thermal degradation to some extent.The conjugated system, as well as the relatively stable aromatic and carboxylic acids functional groups, contribute to its ability resist thermal degradation. However, at high temperatures, bond - breaking reactions can occur.At high temperatures, however, bond-breaking reactions can occur. For example, the carboxylic acid group might undergo decarboxylation, losing carbon dioxide and forming a new, potentially less stable product.Decarboxylation of the carboxylic group, for example, can result in carbon dioxide being released and a new product that is potentially less stable. The exact temperature at which significant thermal decomposition begins would depend on factors such as the purity of the compound and the presence of any catalysts or impurities in the system.The exact temperature where thermal decomposition occurs depends on factors like the purity of the compound, and whether there are any catalysts or other impurities present in the system.

2. Stability in SolutionStability of Solution
In solution, the stability of (E)-3-(3,5 - dimethoxyphenyl)acrylic acid can be affected by the nature of the solvent. Polar solvents can interact with the polar functional groups of the molecule, such as the carboxylic acid group.Polar solvents may interact with the polar functional group of the molecule. In an acidic or basic solution, the molecule may undergo reactions.In acidic or basic solutions, the molecule can undergo reactions. In an acidic solution, the carboxylic acid group remains in its protonated form, but in a basic solution, it will be deprotonated to form a carboxylate ion.In an acidic environment, the carboxylic group will remain in its protonated state, but in a base solution, it is deprotonated and becomes a carboxylate. The carboxylate ion may be more reactive towards certain electrophiles or may participate in different solubility - related and reaction - based behaviors compared to the protonated form of the carboxylic acid.The carboxylate is more reactive to certain electrophiles, or it may have different solubility-related and reaction-based behaviors than the protonated carboxylic acid. Additionally, the molecule may be subject to hydrolysis in the presence of water and certain catalysts, especially if the conditions are favorable for breaking the bonds in the molecule.The molecule can also be hydrolyzed in the presence water and certain catalysts if conditions are right for breaking bonds.

3. Photochemical Stability
When exposed to light, (E)-3-(3,5 - dimethoxyphenyl)acrylic acid may also experience changes in its stability. The conjugated system can absorb light energy, promoting electrons to higher energy levels.The conjugated system absorbs light energy and promotes electrons to higher levels of energy. This can potentially lead to photochemical reactions such as cis - trans isomerization (although the (E) - form is more stable initially), or even bond - cleavage reactions if the absorbed light energy is sufficient to break the chemical bonds within the molecule.This can lead to photochemical processes such as cis-trans isomerization, (although the (E ) - form initially is more stable), or even bond-cleavage reactions, if the absorbed energy is enough to break the chemical bond within the molecule. The presence of certain sensitizers or impurities in the environment can further accelerate these photochemical processes.These photochemical reactions can be accelerated by the presence of certain impurities or sensitizers in the environment.

Overall, while (E)-3-(3,5 - dimethoxyphenyl)acrylic acid has some inherent stability due to its molecular structure and conjugation, its stability can be significantly altered by external factors such as temperature, the nature of the surrounding medium, and exposure to light.