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Product Name | 2-(Trifluoromethyl)acrylic acid |
Cas Number | 328-45-0 |
Formula | C5H3F3O2 |
Molar Mass | 166.07 g/mol |
Physical State | solid |
Color | white |
Odor | odorless |
Melting Point | 115-117°C |
Boiling Point | 268-270°C |
Density | 1.547 g/cm3 |
Solubility | slightly soluble in water |
Flash Point | 121°C |
What are the main applications of 2-(Trifluoromethyl)acrylic acid?
2 - (Trifluoromethyl)acrylic acid has several important applications.
In the field of polymer materials, it is widely used as a monomer.It is widely used in the field of polymer material as a monomer. Due to the presence of the trifluoromethyl group, polymers synthesized from 2 - (Trifluoromethyl)acrylic acid possess unique properties. The trifluoromethyl group imparts high hydrophobicity, chemical resistance, and weather resistance to the polymers.The trifluoromethyl groups imparts high hydrophobicity and chemical resistance to polymers. For example, in the production of coatings, these polymers can form a protective layer with excellent water - repellent and anti - corrosion properties.These polymers, for example, can be used to create a protective coating with excellent anti-corrosion and water-repellent properties. They can be used on metal surfaces, such as in the automotive industry to protect car bodies from rust and environmental damage.They can be used to protect metal surfaces from rust or environmental damage, as in the automotive sector. In addition, the polymers can also be used in the manufacturing of textiles, providing fabrics with water - and oil - repellent functions without sacrificing breathability.Polymers can be used to make textiles that are water- and oil-repellent without sacrificing breathability.
In the pharmaceutical industry, 2 - (Trifluoromethyl)acrylic acid can serve as a key intermediate. The trifluoromethyl group has a significant impact on the biological activity and pharmacokinetic properties of drugs.The trifluoromethyl groups has a significant effect on the biological activity of drugs and their pharmacokinetic properties. Compounds containing this group often show enhanced lipophilicity, which can improve the permeability of drugs through cell membranes.Compounds that contain this group have an increased lipophilicity. This can improve the permeability through cell membranes of drugs. This property is crucial for drugs to reach their target sites within the body effectively.This property is essential for drugs to reach the target sites in the body. For instance, some anti - inflammatory and anti - cancer drug candidates are synthesized using 2 - (Trifluoromethyl)acrylic acid as a starting material to introduce the trifluoromethyl functionality, aiming to enhance the drug's efficacy and bioavailability.
Another application area is in the synthesis of specialty chemicals.It can also be used to synthesize specialty chemicals. It can participate in various chemical reactions, such as addition reactions and condensation reactions.It can be used in a variety of chemical reactions such as addition reactions or condensation reactions. These reactions can be used to create complex organic molecules with specific structures and functions.These reactions can be used in order to create complex organic molecule with specific structures and function. For example, in the production of fluorinated dyes, 2 - (Trifluoromethyl)acrylic acid can be used to introduce fluorine atoms into the dye molecules. Fluorinated dyes often have better light - fastness and color - fastness compared to their non - fluorinated counterparts, making them suitable for applications in high - quality textile dyeing and printing, as well as in the inkjet printing industry.Fluorinated colors are often more light-fast and color-fast than their non-fluorinated counterparts. This makes them ideal for use in high-quality textile dyeing, printing and inkjet printing.
In summary, 2 - (Trifluoromethyl)acrylic acid plays an important role in polymer materials, pharmaceuticals, and specialty chemical synthesis, contributing to the development of products with improved performance and functionality in these diverse fields.
How is 2-(Trifluoromethyl)acrylic acid synthesized?
2 - (Trifluoromethyl)acrylic acid can be synthesized through several methods. One common approach involves starting from compounds containing the trifluoromethyl group.One common method is to start with compounds containing trifluoromethyl groups.
One route begins with trifluoroacetaldehyde. Trifluoroacetaldehyde can react with a phosphorus ylide, prepared from a phosphonium salt and a strong base. For example, a phosphonium salt like ethyltriphenylphosphonium bromide is treated with a base such as butyllithium to generate the ylide. The ylide then reacts with trifluoroacetaldehyde in a Wittig reaction. In this reaction, the ylide attacks the carbonyl carbon of trifluoroacetaldehyde, leading to the formation of an intermediate betaine. The betaine then undergoes elimination to produce 2 - (Trifluoromethyl)acrylic acid or its corresponding ester, which can be further hydrolyzed to obtain the acid.
Another possible method is via the reaction of a trifluoromethyl - containing halide.A trifluoromethyl-containing halide can also be used. For instance, a trifluoromethyl - substituted alkyl halide can be reacted with a carbonyl compound in the presence of a suitable base and catalyst.In the presence of a suitable catalyst and base, a trifluoromethyl-substituted alkyl chloride can be used to react with a carbonyl. The reaction might involve a sequence of steps including nucleophilic addition and elimination.The reaction may involve nucleophilic elimination and addition. The halide is first activated by the base, and the resulting carbanion - like species attacks the carbonyl group.The base activates the halide, and the carbanion-like species that results attacks the carbonyl groups. After appropriate rearrangement and elimination steps, the double bond is formed, leading to the synthesis of 2 - (Trifluoromethyl)acrylic acid.
In some cases, a multi - step synthesis starting from simpler trifluoromethyl - containing building blocks might be employed.In some cases a multi-step synthesis may be used, starting with simpler trifluoromethyl-containing building blocks. These building blocks are gradually assembled through reactions such as halogenation, substitution, and condensation reactions.These building blocks are assembled gradually through reactions like halogenation and substitution reactions. For example, starting from trifluoromethane, it can be converted into a trifluoromethyl - containing intermediate through a series of reactions with reagents like halogens and metal - containing compounds.Through a series reactions, trifluoromethane can be converted to a trifluoromethyl-containing intermediate. This intermediate is then further reacted with other organic molecules to form the carbon - carbon double bond and ultimately 2 - (Trifluoromethyl)acrylic acid. Each of these methods requires careful control of reaction conditions such as temperature, reaction time, and the stoichiometry of reactants to ensure high yields and purity of the final product.To ensure high yields, each of these methods must carefully control reaction conditions, such as temperature, time of reaction, and stoichiometry.
What are the physical and chemical properties of 2-(Trifluoromethyl)acrylic acid?
2 - (Trifluoromethyl)acrylic acid is a compound with distinct physical and chemical properties.
Physical Properties
Appearance: It is typically a colorless to slightly yellowish liquid.Appearance: It's usually a colorless or slightly yellowish liquid. This visual characteristic is common for many organic acids in their pure form and can vary slightly depending on purity levels and storage conditions.This visual characteristic is present in many organic acids when they are pure. It can vary depending on the purity level and storage conditions.
Boiling Point: The boiling point of 2 - (trifluoromethyl)acrylic acid is relatively specific, which is important for its separation and purification processes in laboratories or industrial settings. Precise boiling points are crucial in distillation procedures to isolate the compound from reaction mixtures or other substances.In distillation procedures, precise boiling points are essential to isolate the compound.
Melting Point: The melting point of this compound helps to define its phase behavior under different temperature conditions.Melting Point: The melting temperature of this compound is used to determine its phase behavior at different temperatures. Knowing the melting point is useful for understanding how the acid behaves in solid - liquid transitions, which can impact handling and storage.Understanding the melting point can help you understand how the acid behaves during solid-liquid transitions. This can have an impact on handling and storage. For example, if stored at a temperature close to its melting point, the substance may change from a solid to a liquid state.If the substance is stored at a temperature near its melting point, it may become liquid.
Solubility: It shows solubility characteristics in various solvents.It has solubility properties in different solvents. It is likely to be soluble in polar organic solvents due to the presence of the carboxylic acid group, which can form hydrogen bonds with appropriate solvent molecules.It is likely that it will be soluble in organic polar solvents because of the presence carboxylic acid groups, which can form hydrogen bond with the appropriate solvent molecules. Solubility in water is also an important aspect.The solubility of the compound in water is another important factor. The trifluoromethyl group, being highly electronegative, may influence the overall solubility in water.Trifluoromethyl, which is highly electronegative, can influence the overall water solubility. The carboxylic acid group can interact with water through hydrogen bonding, but the hydrophobic trifluoromethyl group may oppose this to some extent.The hydrophobic trifluoromethyl can interfere with the interaction of the carboxylic acid with water.
Chemical Properties
Acidity: As an acrylic acid derivative, 2 - (trifluoromethyl)acrylic acid is acidic. The carboxylic acid functional group (-COOH) can donate a proton in solution, making it react with bases.The carboxylic functional group (-COOH), which is present in the solution, can donate a proton to the acid and cause it to react with bases. The presence of the trifluoromethyl group adjacent to the carboxylic acid group can enhance its acidity compared to unsubstituted acrylic acid.Trifluoromethyl groups can increase the acidity of acrylic acid compared to the unsubstituted form. The highly electronegative trifluoromethyl group withdraws electron density from the carboxyl group, stabilizing the carboxylate anion formed after proton donation.The trifluoromethyl group is highly electronegative and removes electron density from carboxyl groups, stabilizing carboxylate anion after proton donation.
Reactivity towards Addition Reactions: The carbon - carbon double bond in the acrylic acid structure makes it reactive towards addition reactions.The double carbon-carbon bond in the structure of acrylic acid makes it reactive to addition reactions. It can undergo electrophilic addition reactions with reagents such as halogens, hydrogen halides, and water in the presence of appropriate catalysts.In the presence of catalysts, it can undergo electrophilic reactions with reagents like halogens and hydrogen halides. The trifluoromethyl group may influence the regioselectivity of these addition reactions due to its electron - withdrawing nature, affecting the distribution of electron density in the double bond.Due to its electron-withdrawing nature, the trifluoromethyl can influence the regioselectivity in these addition reactions.
Polymerization: Similar to acrylic acid, 2 - (trifluoromethyl)acrylic acid can participate in polymerization reactions. It can form polymers through radical polymerization processes.It can form polymers by radical polymerization. These polymers can have unique properties due to the presence of the trifluoromethyl groups, such as enhanced hydrophobicity, chemical resistance, and potentially different surface properties compared to polymers derived from unsubstituted acrylic acid.These polymers may have unique properties because of the trifluoromethyl group, such as enhanced hydrophobicity and chemical resistance. They could also have different surface properties than polymers derived by unsubstituted acrylic acid.
Reactivity with Nucleophiles: The carboxylic acid group can react with nucleophiles.Reactivity with Nucleophiles The carboxylic group can react with nucleophiles. For example, it can form esters when reacted with alcohols in the presence of an acid catalyst.It can, for example, form esters in the presence an acid catalyst when it reacts with alcohols. This reaction is important for the synthesis of various organic compounds and can be used to modify the properties of the original acid by introducing different alkyl or aryl groups through the esterification process.This reaction is crucial for the synthesis and modification of organic compounds.
What safety precautions should be taken when handling 2-(Trifluoromethyl)acrylic acid?
When handling 2-(Trifluoromethyl)acrylic acid, several important safety precautions should be followed.
First, personal protective equipment is essential.Wearing personal protective equipment (PPE) is essential. Wear appropriate chemical - resistant gloves, such as those made of nitrile or neoprene.Wear gloves that are resistant to chemicals, such as those made from nitrile or Neoprene. This helps to prevent skin contact, which can lead to irritation, burns, or potential absorption of the chemical into the body.This will help to prevent skin contact that can cause irritation, burns or absorption of chemicals into the body. A lab coat or chemical - resistant apron should also be worn to protect clothing and the body from splashes.Wearing a lab coat or chemical-resistant apron will protect clothing and body from splashes. Additionally, safety goggles with side shields are necessary to safeguard the eyes from any potential splashes or aerosols of the acid.Safety goggles with side-shields are also necessary to protect the eyes from any potential aerosols or splashes of acid.
Second, ensure proper ventilation. Work in a well - ventilated area, preferably under a fume hood.Work in an area that is well-ventilated, preferably under fume hoods. 2-(Trifluoromethyl)acrylic acid may release vapors that can be irritating to the respiratory system. Adequate ventilation helps to dilute these vapors, reducing the risk of inhaling harmful amounts.Adequate ventilation can dilute these vapors and reduce the risk of inhaling harmful quantities. If working in an enclosed space without a fume hood, use local exhaust ventilation to remove the vapors effectively.If you are working in a closed space without a fume-hood, you can use local exhaust ventilation.
Third, be cautious during handling operations.Third, use caution when handling the chemical. When transferring the acid, use appropriate glassware or plastic containers that are compatible with the chemical.Use glassware or plastic containers compatible with the chemical when transferring acid. Avoid sudden movements or rough handling that could cause spills.Avoid sudden movements and rough handling which could cause spills. When measuring the acid, use accurate pipettes or burettes and do so slowly and carefully to prevent splashing.Use accurate pipettes or burettes to measure the acid and proceed slowly and carefully.
Fourth, know the storage requirements.Fourth, be sure to know the storage requirements. Store 2-(Trifluoromethyl)acrylic acid in a cool, dry place away from sources of heat, ignition, and incompatible substances. It should be stored in a tightly - sealed container to prevent evaporation and leakage.Store it in a tightly-sealed container to prevent evaporation. Keep it separate from bases, oxidizing agents, and reducing agents as these can react violently with the acid.Separate it from bases, oxidizing and reducing agents. These can react violently.
Finally, in case of an emergency, be prepared.Be prepared in the event of an emergency. 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 rinse the affected area with plenty of water for at least 15 minutes and seek medical attention.If skin contact occurs immediately rinse the area with lots of water for 15 minutes. Seek medical attention. In case of eye contact, flush the eyes with copious amounts of water for a prolonged period and get immediate medical help.If you have eye contact, rinse your eyes with a lot of water and for a long time. Seek immediate medical attention. If inhalation occurs, move to fresh air and seek medical advice.In the event of inhalation, seek medical attention and move to a fresh area. If ingestion happens, do not induce vomiting but seek immediate medical treatment.In the event of ingestion, do not induce vomiting. Instead, seek immediate medical attention. By following these safety precautions, the risks associated with handling 2-(Trifluoromethyl)acrylic acid can be significantly minimized.
What are the typical uses of 2-(Trifluoromethyl)acrylic acid in different industries?
2 - (Trifluoromethyl)acrylic acid has several important applications across different industries.
In the polymer industry, it serves as a valuable monomer.It is a valuable monomer in the polymer industry. When incorporated into polymers, it imparts unique properties.It imparts unique properties when incorporated into polymers. The trifluoromethyl group significantly enhances the polymer's resistance to chemicals, weathering, and solvents.The trifluoromethyl groups significantly improves the polymer’s resistance to chemicals and weathering. For instance, polymers made with 2 - (trifluoromethyl)acrylic acid can be used in coatings for industrial equipment. These coatings are highly durable and can withstand harsh environmental conditions, protecting the underlying metal from corrosion and chemical degradation.These coatings are extremely durable and can withstand harsh conditions. They protect the metal beneath from corrosion and chemical degradation. They are also used in the production of high - performance adhesives.These coatings are also used to produce high-performance adhesives. The presence of the trifluoromethyl group improves the adhesive's adhesion to various substrates and its resistance to moisture and heat, making it suitable for applications in the automotive and aerospace industries where reliability under extreme conditions is crucial.The presence of trifluoromethyl improves the adhesive’s adhesion and resistance to heat and moisture, making it ideal for applications in the aerospace and automotive industries where reliability is critical.
In the pharmaceutical industry, this compound is utilized as an intermediate in the synthesis of certain drugs.This compound is used as an intermediate in the pharmaceutical industry to synthesize certain drugs. The unique chemical structure of 2 - (trifluoromethyl)acrylic acid can be modified to create molecules with specific biological activities. The trifluoromethyl group can influence a drug molecule's lipophilicity, which affects its ability to cross cell membranes.The trifluoromethyl can affect a drug's lipophilicity which impacts its ability to cross cell walls. This property is useful in the development of drugs that need to penetrate cells to exert their therapeutic effects.This property is helpful in the development and testing of drugs that must penetrate cells to exert therapeutic effects. It can also enhance the metabolic stability of drug candidates, prolonging their half - life in the body and potentially reducing the frequency of dosing.It can also improve the metabolic stability of drug candidate, extending their half-life in the body and possibly reducing the frequency dose.
In the agrochemical field, 2 - (trifluoromethyl)acrylic acid can be part of the synthesis of pesticides and herbicides. The trifluoromethyl - containing compounds often exhibit enhanced biological activity against pests and weeds.Trifluoromethyl-containing compounds are often more effective against pests and weeds. Their unique chemical properties can improve the compound's binding to specific target sites in pests or plants, increasing the efficacy of the agrochemical.Their unique chemical properties increase the compound's ability to bind to specific target sites on pests or plants. This increases the agrochemical's efficacy. Additionally, the presence of the trifluoromethyl group can contribute to the compound's environmental persistence in a controlled manner, ensuring long - lasting protection of crops without causing excessive environmental harm.Trifluoromethyl groups can also contribute to the compound’s environmental persistence, in a controlled way, ensuring long-lasting protection of crops, without causing excessive harm to the environment.
In the field of materials science, it can be used to create functional materials.It can be used in the field of materials to create functional materials. For example, in the preparation of ion - exchange membranes.In the preparation of ion-exchange membranes, for example. The acidic group in 2 - (trifluoromethyl)acrylic acid can participate in ion - exchange processes, and the trifluoromethyl group can improve the membrane's chemical stability and hydrophobicity. These membranes have applications in fuel cells, where they need to selectively transport ions while being resistant to the harsh chemical environment within the cell.These membranes are used in fuel cells where they must be able to transport ions selectively while also being resistant to the harsh chemistry within the cell.