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Trans-3-phenylacrylic Acid


Properties
Product Name trans-3-Phenylacrylic acid
Cas Number 538-51-2
Formula C9H8O2
Molar Mass 148.16 g/mol
Melting Point 172-175°C
Boiling Point 280-300°C
Density 1.247 g/cm³
Solubility In Water Slightly soluble
Appearance White crystalline powder
Odor Odorless
Refractive Index 1.573
Flash Point 184.9°C
Pka 4.50
Stability Stable under recommended storage conditions
Vapor Pressure Negligible at ambient temperature
FAQ

What is the chemical structure of trans-3-Phenylacrylic acid?

Trans - 3 - Phenylacrylic acid is also known as trans - cinnamic acid.Trans - 3 Phenylacrylic Acid is also known by the name trans - Cinnamic Acid.
The chemical formula of trans - 3 - phenylacrylic acid is C9H8O2.The chemical formula for trans - 3- phenylacrylic is C9H8O2. Its chemical structure can be described as follows.The chemical structure of the acid can be described in the following way.

At the core of the molecule, there is a benzene ring.A benzene ring is located at the center of the molecule. A benzene ring is a planar, hexagonal structure composed of six carbon atoms.A benzene is a hexagonal, planar structure made up of six carbon atoms. Each carbon atom in the benzene ring is sp2 hybridized.Each carbon atom is sp2 hybridized. The six carbon atoms in the benzene ring are connected by alternating single and double bonds in a resonance - stabilized structure, which gives the benzene ring its characteristic stability.The six carbon atoms of the benzene are connected in a resonance-stabilized structure by alternating single and dual bonds. This gives the benzene its characteristic stability.

Attached to the benzene ring is a side - chain.A side-chain is attached to the benzene rings. The side - chain contains a carbon - carbon double bond and a carboxylic acid functional group.The side-chain contains a double carbon-carbon bond and a functional carboxylic group. The carbon - carbon double bond in the side - chain has a trans configuration.The side -chain's carbon -carbon double bond has a trans-configuration. In a trans configuration, the two larger groups (in this case, the benzene ring and the carboxylic acid - containing part of the side - chain) are on opposite sides of the double bond.In a trans configuration the two larger groups are on the opposite side of the double bond. This trans geometry affects the physical and chemical properties of the molecule.This trans geometry has an impact on the molecule's physical and chemical properties.

The carboxylic acid functional group (-COOH) is attached to the carbon atom adjacent to the carbon - carbon double bond in the side - chain.The carboxylic functional group (-COOH), is attached to the carbon adjacent to the double carbon-carbon bond in the side-chain. The carboxylic acid group consists of a carbonyl group (C = O) and a hydroxyl group (-OH) attached to the same carbon atom.The carboxylic group is composed of a carbonyl (C = O), and a hydroxyl (-OH), both attached to the same carbon. The oxygen atom in the carbonyl group is more electronegative than the carbon atom, creating a polar bond.The oxygen atom of the carbonyl group has a higher electronegative value than the carbon, creating a polar link. The -OH group in the carboxylic acid can participate in hydrogen - bonding interactions.The -OH group of the carboxylic acids can participate in hydrogen-bonding interactions.

The overall structure of trans - 3 - phenylacrylic acid combines the aromatic nature of the benzene ring, the unsaturation of the carbon - carbon double bond in the side - chain, and the reactivity of the carboxylic acid functional group.The overall structure combines the aromaticity of the benzene rings, the unsaturation in the carbon-carbon double bond of the side-chain, and the reactivity in the carboxylic acids functional group. The presence of the benzene ring imparts certain hydrophobic characteristics due to its non - polar nature.The non-polar nature of the benzene rings imparts hydrophobic properties. The carbon - carbon double bond can undergo addition reactions, such as hydrogenation to form the saturated derivative.The double carbon-carbon bond can undergo addition reaction, such as hydrogenation, to form the saturated derivative. The carboxylic acid group can participate in acid - base reactions, forming salts with bases, and can also be involved in esterification reactions when reacted with alcohols.The carboxylic group can be involved in acid-base reactions, forming bases with salts, and also in esterification reactions by reacting with alcohols.

What are the applications of trans-3-Phenylacrylic acid?

Trans - 3 - Phenylacrylic acid, also known as cinnamic acid, has a wide range of applications in various fields.Trans - 3 Phenylacrylic Acid, also known by the name cinnamic, has many applications in different fields.
In the food industry, it is used as a flavoring agent.In the food industry it is used to flavor foods. It imparts a pleasant, warm, and spicy - sweet aroma, similar to cinnamon.It has a similar, pleasant, spicy-sweet aroma to cinnamon. This makes it a popular choice for enhancing the flavor of baked goods like cinnamon - flavored breads, pastries, and cookies.It is a popular ingredient for baking goods such as cinnamon-flavored breads, pastries and cookies. It can also be added to beverages, especially those with a spiced or cinnamon - inspired profile, to provide a unique taste.It can be added to beverages with a cinnamon or spiced profile to give them a unique flavor. Additionally, cinnamic acid has some antibacterial and antifungal properties.Cinnamic acid also has antibacterial and antifungal qualities. It can be used as a natural preservative in food products to extend their shelf - life by inhibiting the growth of spoilage - causing microorganisms.It can be used to extend the shelf life of food products by inhibiting the growth and spread of spoilage-causing microorganisms.

The cosmetic and fragrance industries also make use of trans - 3 - phenylacrylic acid.Trans - 3 phenylacrylic Acid is also used in the cosmetic and fragrance industry. Its characteristic aroma is incorporated into perfumes, colognes, and scented products.Its characteristic smell is used in perfumes, colognes and scented products. It can be a key ingredient in creating warm, spicy, and oriental - style fragrance compositions.It can be used to create warm, spicy and oriental-style fragrance compositions. In skincare, due to its potential antioxidant properties, it may be included in some formulations to help protect the skin from damage caused by free radicals.It may be used in skincare formulations due to its antioxidant properties. This helps protect the skin against damage caused by free radicles. This can contribute to anti - aging effects, such as reducing the appearance of fine lines and wrinkles.This can have anti-aging effects by reducing wrinkles and fine lines.

In the pharmaceutical industry, cinnamic acid has shown potential biological activities.Cinnamic acid is a potential biological agent in the pharmaceutical industry. It has been studied for its anti - inflammatory properties.Its anti-inflammatory properties have been studied. Inflammation is associated with many diseases, including arthritis and certain cardiovascular conditions.Inflammation has been linked to many diseases including arthritis and certain cardiovascular conditions. Compounds like cinnamic acid may help in developing drugs to manage these inflammatory conditions.Compounds such as cinnamic acids may help develop drugs to treat these inflammatory conditions. It also has some reported anti - cancer properties.It has also been reported to have anti-cancer properties. Research indicates that it can potentially interfere with the growth and spread of cancer cells through various mechanisms, such as inducing apoptosis (programmed cell death) in cancer cells.Research suggests that it may be able to interfere with the growth and spreading of cancer cells by various mechanisms, including inducing apoptosis in cancer cells. Although more research is needed for it to be developed into a full - fledged anti - cancer drug, it serves as an important lead compound in cancer research.It is still a long way off from being a fully-fledged anti-cancer drug, but it is an important lead compound for cancer research.

In the chemical industry, trans - 3 - phenylacrylic acid is used as a starting material for the synthesis of other valuable chemicals.Trans - 3 phenylacrylic is used in the chemical industry as a starting substance for the synthesis other valuable chemicals. For example, it can be used to produce esters, which are used in the manufacture of plastics, solvents, and plasticizers.It can be used, for example, to produce esters that are used in the production of plastics and solvents. The esters derived from cinnamic acid can improve the flexibility and processability of plastics.Esters made from cinnamic acids can improve plastics' flexibility and processability. It can also be used in the synthesis of dyes, where its chemical structure can contribute to the color - forming and light - stability properties of the dyes.It can be used to make dyes. Its chemical structure can help with the color-forming and light-stability properties.

How is trans-3-Phenylacrylic acid synthesized?

Trans - 3 - Phenylacrylic acid, also known as trans - cinnamic acid, can be synthesized through several methods.Trans - 3 Phenylacrylic Acid, also known by the name trans - Cinnamic Acid, can be synthesized using several methods. One common approach is the Perkin reaction.Perkin reaction is a common method.
In the Perkin reaction, benzaldehyde reacts with acetic anhydride in the presence of a base, usually sodium acetate.In the Perkin Reaction, benzaldehyde and acetic anhydride react in the presence a base. This is usually sodium acetate. The reaction mechanism involves several steps.The reaction involves several steps. First, the base, sodium acetate, deprotonates acetic anhydride.First, the base sodium acetate deprotonates anhydride acetic. The resulting enolate anion then attacks the carbonyl carbon of benzaldehyde.The enolate anion that results attacks the carbonyl of benzaldehyde. This forms an intermediate with a new carbon - carbon bond.This intermediate forms a new carbon-carbon bond. Subsequently, an intramolecular rearrangement occurs, followed by elimination of acetic acid.Then, an intramolecular reorganization occurs, followed closely by the elimination of acetic acids. The final step is the hydrolysis of the intermediate to yield trans - 3 - phenylacrylic acid.The final step involves the hydrolysis of intermediate to produce trans - 3 Phenylacrylic Acid.

The reaction conditions are carefully controlled.The conditions of the reaction are carefully monitored. The molar ratio of benzaldehyde to acetic anhydride and the amount of sodium acetate used are crucial.The molar proportion of benzaldehyde and acetic acid to sodium acetate is crucial. Generally, a slight excess of acetic anhydride is employed to drive the reaction forward.In general, a small excess of acetic acid is used to accelerate the reaction. The reaction is typically carried out at an elevated temperature, around 150 - 180 degC.The reaction is usually carried out at a high temperature, between 150 and 180 degC. This temperature range helps to facilitate the reaction without causing excessive side - reactions.This temperature range facilitates the reaction without causing side-reactions.

After the reaction is complete, the reaction mixture often contains unreacted starting materials, by - products, and the desired trans - 3 - phenylacrylic acid.After the reaction has been completed, the reaction mixture contains often unreacted materials, by-products, and the desired trans-3 phenylacrylic acids. The crude product can be isolated through a series of purification steps.Purification steps can be used to isolate the crude product. First, the reaction mixture is cooled, and then water is added.The reaction mixture is first cooled and then water is introduced. The resulting mixture is usually extracted with an organic solvent to separate the organic components from the aqueous phase.The mixture is then extracted with an organic solution to separate the organic and aqueous phases. The organic layer is then washed with water and dried over an anhydrous salt, such as magnesium sulfate.The organic layer is washed in water and dried on an anhydrous sodium salt such as magnesium chloride. Evaporation of the solvent gives the crude trans - 3 - phenylacrylic acid.The crude trans - 3- phenylacrylic is obtained by evaporating the solvent.

Further purification can be achieved through recrystallization.Recrystallization can be used to achieve further purification. A suitable solvent, such as ethanol or a mixture of ethanol and water, is chosen.The solvent of choice is ethanol, or a mixture containing ethanol and water. The crude product is dissolved in the hot solvent, and upon slow cooling, pure trans - 3 - phenylacrylic acid crystallizes out.The crude product is dissolved into the hot solvent and, after a slow cooling, pure trans-3-phenylacrylic acids crystallize. Filtration and drying of the crystals yield the final, pure product with high purity and good yield.The final product is a pure, high-purity and high-yield product after drying and filtering the crystals.

Another method for synthesizing trans - 3 - phenylacrylic acid is by the Knoevenagel condensation.Knoevenagel condensation is another method of synthesizing trans- 3 phenylacrylic acids. In this method, benzaldehyde reacts with malonic acid in the presence of a weak base, like pyridine.In this method, malonic acid reacts with benzaldehyde in the presence a weak base like pyridine. Similar to the Perkin reaction, the base activates malonic acid, which then reacts with benzaldehyde.In a similar way to the Perkin reaction the base activates the malonic acid which then reacts benzaldehyde. The intermediate formed undergoes decarboxylation to give trans - 3 - phenylacrylic acid.The intermediate is decarboxylated to give trans- 3 phenylacrylic. The advantage of the Knoevenagel condensation is that it can be carried out under relatively milder reaction conditions compared to the Perkin reaction, which may be beneficial in some cases where the starting materials are sensitive to high temperatures.The Knoevenagel reaction is advantageous because it can be performed under milder conditions than the Perkin reaction. This may be useful in certain cases when the starting materials are sensitive. However, the choice of method depends on factors such as availability of starting materials, cost - effectiveness, and the scale of synthesis required.The choice of method is influenced by factors such as the availability of the starting materials, the cost-effectiveness, and the size of the synthesis.

What are the physical and chemical properties of trans-3-Phenylacrylic acid?

Trans - 3 - Phenylacrylic acid, also known as trans - cinnamic acid, has the following physical and chemical properties:Trans - 3 Phenylacrylic Acid, also known by the name trans - Cinnamic Acid, has these physical and chemical characteristics:
Physical Properties Physical Properties
1. Appearance: It is a white to slightly yellowish crystalline solid.Appearance: It's a white or slightly yellowish crystalline substance. This characteristic appearance makes it easily distinguishable in a laboratory setting.This characteristic appearance makes the substance easily distinguishable in laboratory settings. The crystals often have a regular geometric shape, which is a common feature of many organic compounds with well - ordered molecular arrangements.Crystals are often regular geometric shapes, which is common for many organic compounds that have well-ordered molecular arrangements.
2. Odor: It has a faint, pleasant, balsamic odor.Odor: It emits a pleasant, faint balsamic smell. This odor is due to the presence of the phenyl group and the unsaturated double bond in its structure.This is due to its double bond and phenyl group. The smell is relatively mild and is sometimes used in the fragrance industry.The smell is mild and is often used in the fragrance business.
3. Melting Point: The melting point of trans - 3 - phenylacrylic acid is around 133 - 134 degC.Melting Point: Trans - 3 phenylacrylic Acid melts at around 133-134 degC. This relatively high melting point is attributed to the strong intermolecular forces in the solid state.This high melting point can be attributed to strong intermolecular interactions in the solid state. The presence of hydrogen bonding between the carboxylic acid groups of adjacent molecules and the van der Waals forces between the phenyl rings contribute to this relatively high melting point.This high melting point is due to the hydrogen bonding between adjacent molecules' carboxylic acids and the van der waals forces between phenyl rings.
4. Solubility: It has limited solubility in water.Water has a limited solubility. The hydrophobic nature of the phenyl group reduces its solubility in the polar solvent water.Hydrophobicity of the phenyl groups reduces its solubility with the polar solvent, water. However, it is more soluble in organic solvents such as ethanol, ether, and chloroform.It is more soluble when it's in organic solvents like ethanol, chloroform, and ether. The non - polar regions of these organic solvents can interact with the phenyl group of trans - 3 - phenylacrylic acid through van der Waals forces, facilitating dissolution.These organic solvents' non-polar regions can interact with the phenyl groups of trans -3 - phenylacrylic acids through van der Waals force, facilitating dissolution.

Chemical Properties Chemical Properties
1. Acidic Character: As a carboxylic acid, trans - 3 - phenylacrylic acid is acidic.Acidic Characteristics: Trans - 3 phenylacrylic is acidic as a carboxylic. The carboxylic acid functional group (-COOH) can donate a proton in an aqueous solution.The carboxylic group (-COOH), which is part of the functional group, can donate a proton to an aqueous solvent. The pKa value of trans - cinnamic acid is approximately 4.44.The pKa of trans-cinnamic is about 4.44. This acidic property allows it to react with bases to form salts.This acidic property allows the reaction with bases to produce salts. For example, when reacted with sodium hydroxide (NaOH), it forms sodium trans - 3 - phenylacrylate and water.When reacted with NaOH, it forms sodium trans-3 - phenylacrylate (and water).
2. Reactivity of the Double Bond: The carbon - carbon double bond in trans - 3 - phenylacrylic acid is reactive.Double Bond Reactivity: The carbon-carbon double bond in trans-3-phenylacrylic is reactive. It can undergo addition reactions.It can undergo addition reaction. For instance, it can react with bromine (Br2) in an addition reaction, where the double bond breaks and two bromine atoms add across the double bond, forming a dibromo - derivative.It can, for example, react with bromine in an addition reaction where the double bonds break and two bromines atoms add across it, forming dibromo-derivatives. This double bond also makes it susceptible to hydrogenation reactions in the presence of a catalyst like palladium on carbon (Pd/C) and hydrogen gas (H2), resulting in the saturation of the double bond to form 3 - phenylpropanoic acid.This double bond makes it susceptible to hydrogenation in the presence a catalyst such as palladium on Carbon (Pd/C), and hydrogen gas (H2). The double bond is saturated to form 3 -phenylpropanoic acids.
3. Polymerization: Due to the presence of the double bond, trans - 3 - phenylacrylic acid can potentially undergo polymerization reactions.Trans - 3 phenylacrylic Acid can undergo polymerization reactions due to the double bond. Under appropriate conditions, such as in the presence of a radical initiator, multiple molecules of trans - 3 - phenylacrylic acid can link together to form a polymer.In the presence of radical initiators, or under certain conditions, trans - 3 Phenylacrylic Acid can link to form polymers. This property is useful in the synthesis of certain types of polymers with specific properties derived from the phenyl and carboxylic acid moieties.This property is useful for the synthesis of polymers that have specific properties derived by the carboxylic and phenyl acid moieties.
4. Esterification: The carboxylic acid group can react with alcohols in the presence of an acid catalyst, such as sulfuric acid, to form esters.Esterification: The carboxylic group can react with alcohols, in the presence an acid catalyst such as sulfuric, to form esters. For example, reacting trans - 3 - phenylacrylic acid with methanol would yield methyl trans - 3 - phenylacrylate, which has applications in the production of flavors, fragrances, and polymers.As an example, if you react trans -3 -phenylacrylic with methanol, you will get methyl trans 3 phenylacrylate. This is used in the production and fragrances of polymers, flavors, and fragrances.

What are the safety precautions when handling trans-3-Phenylacrylic acid?

When handling trans - 3 - Phenylacrylic acid, several safety precautions should be taken.Safety precautions are necessary when handling trans - 3 Phenylacrylic Acid.
First, in terms of personal protective equipment.Personal protective equipment is the first thing to consider. Wear appropriate protective clothing, such as a laboratory coat, to prevent contact of the chemical with your regular clothes.Wear protective clothing such as a lab coat to prevent chemical contact with your normal clothes. Gloves are essential.Gloves are a must. Nitrile gloves are a good choice as they can provide a certain level of resistance to the possible chemical reactions of trans - 3 - Phenylacrylic acid.Nitrile gloves can provide a level of resistance against the chemical reactions that may occur with trans - 3- Phenylacrylic Acid. Ensure that the gloves fit well and there are no holes or tears.Make sure the gloves are well-fitting and that there are no tears or holes. Also, wear safety goggles.Wear safety goggles. Chemicals like this can cause eye irritation or more serious damage if it splashes into the eyes.These chemicals can cause irritation to the eyes or even more serious damage if they splash into them. The goggles should provide full - face protection to avoid any accidental splashes from reaching the eyes.Goggles with full-face protection are recommended to prevent accidental splashes reaching the eyes.

Second, when working with trans - 3 - Phenylacrylic acid, work in a well - ventilated area.When working with trans -3 - Phenylacrylic Acid, it is important to work in an area that is well-ventilated. It may release fumes or have an odor, and a proper ventilation system can help to remove these substances from the air.A proper ventilation system will help remove the fumes and odors. If possible, use a fume hood.Use a fume-hood if possible. Working inside a fume hood can effectively capture any volatile substances that might be released during the handling process, reducing the risk of inhaling them.A fume hood will capture any volatile substances released during the handling procedure, reducing the chance of inhalation. Inhaling the fumes of this chemical may cause respiratory discomfort, such as coughing, shortness of breath, or irritation of the nasal passages.Inhaling fumes from this chemical can cause respiratory discomfort such as coughing or shortness of breathe, or irritation of nasal passages.

Third, be careful during storage.Third, take care when storing. Store trans - 3 - Phenylacrylic acid in a cool, dry place away from sources of heat and ignition.Store trans - 3 Phenylacrylic Acid in a cool and dry place, away from heat sources and ignition. It should be kept in a tightly sealed container to prevent moisture absorption and evaporation.Keep it in a tightly-sealed container to prevent moisture absorption or evaporation. Additionally, keep it away from incompatible substances.Keep it away from other incompatible substances. For example, acids and bases should be stored separately from it, as chemical reactions between them could lead to dangerous situations, such as the generation of heat, gas, or the formation of new, potentially more hazardous substances.Acids and bases, for example, should be stored separate from it. Chemical reactions between them can lead to dangerous situations such as the production of heat, gases, or the formation new, potentially hazardous substances.

Fourth, in case of accidental contact.Fourth, in the event of accidental contact. If the chemical comes into contact with the skin, immediately wash the affected area with plenty of water for at least 15 minutes.If the chemical comes in contact with your skin, wash it immediately with plenty of water and for at least 15 min. Then, remove any contaminated clothing.Remove any contaminated clothing. If it gets into the eyes, rinse the eyes thoroughly with water for a long time, preferably using an eyewash station, and seek medical attention immediately.If it gets in the eyes, rinse them thoroughly with water, preferably at an eyewash station. Seek medical attention immediately if the substance gets into the eyes. If inhaled, move to fresh air immediately.If inhaled immediately move to fresh air. If breathing is difficult, provide artificial respiration if trained to do so and call for emergency medical help.If breathing is difficult and you are trained to do it, use artificial respiration. Call for emergency medical assistance. If ingested, do not induce vomiting unless instructed by a medical professional, and seek medical help right away.If you have ingested the substance, do not induce vomiting without medical advice. Seek medical attention immediately.