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4-(Trifluoromethyl)benzoic acid (CAS 402-50-4) is a versatile aromatic compound with the formula C₈H₅F₃O₂. Structurally, it features a benzene ring substituted with a trifluoromethyl group at the 4-position and a carboxylic acid at the 1-position. The trifluoromethyl (-CF₃) moiety imparts unique physicochemical properties, including high electronegativity and metabolic stability, making it valuable in medicinal chemistry and materials science.
Physically, this compound appears as a white crystalline solid, with a melting point around 130–132°C and limited water solubility. It dissolves in polar organic solvents like DMSO or ethanol. Synthetically, it is prepared via trifluoromethylation of benzoic acid precursors or oxidation of 4-(trifluoromethyl)benzaldehyde. The carboxylic acid group enables diverse reactions, such as esterification, amidation, or coupling reactions, while the trifluoromethyl group enhances lipophilicity and chemical stability.
Applications span pharmaceuticals, agrochemicals, and advanced materials. In drug development, it serves as an intermediate for antifungal agents and kinase inhibitors. Its rigid structure and electron-withdrawing properties also make it useful in liquid crystals and fluorescent probes. Additionally, the compound's robust chemical framework supports its role as a key building block in synthesizing complex molecules with tailored functionalities.
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Chemical Formula |
C8H5F3O2 |
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Exact Mass |
190.02 |
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Molecular Weight |
190.12 |
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m/z |
190.02 (100.0%), 191.03 (8.7%) |
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Elemental Analysis |
C, 50.54; H, 2.65; F, 29.98; O, 16.83 |
Pharmaceutical Industry
4-(Trifluoromethyl)benzoic acid is used as a building block in the synthesis of various pharmaceutical compounds. Its trifluoromethyl group often imparts specific biological activities, such as improved metabolic stability and enhanced binding affinity to target proteins.
- Resistance to Metabolic Degradation: The trifluoromethyl group can enhance the metabolic stability of a drug molecule. Metabolic enzymes often target specific functional groups for degradation, but the electron-withdrawing nature and steric bulk of the trifluoromethyl group can hinder these enzymatic reactions. This results in a longer circulation time of the drug in the body, allowing for improved efficacy and reduced dosing frequency.
- Altered Metabolic Pathways: The trifluoromethyl group can also alter the metabolic pathways of a drug, directing it away from rapid degradation routes and towards more stable metabolites. This can lead to a more predictable pharmacokinetic profile and reduced potential for drug-drug interactions.
- Shape and Electronic Complementarity: The trifluoromethyl group can improve the binding affinity of a drug to its target protein by providing shape and electronic complementarity. The group's steric bulk and electron-withdrawing properties can create a more favorable interaction with the binding site of the protein, leading to stronger and more specific binding.
- Hydrophobic Interactions: The trifluoromethyl group is hydrophobic, which can enhance the drug's ability to interact with hydrophobic regions of the target protein. This can be particularly important in cases where the binding site is buried within the protein structure or contains hydrophobic pockets.
- Conformational Stabilization: The trifluoromethyl group can also stabilize the conformation of the drug molecule, ensuring that it adopts the optimal binding pose when interacting with the target protein. This can further enhance binding affinity and specificity.
- Antibiotics and Antifungals: The derivatives have been used in the development of antibiotics and antifungals, where the trifluoromethyl group can enhance the drug's ability to penetrate bacterial or fungal cell membranes and bind to target enzymes.
- Anti-inflammatory Agents: The compound has also been employed in the synthesis of anti-inflammatory agents, where the trifluoromethyl group can improve the drug's selectivity and potency towards specific inflammatory pathways.
- Central Nervous System (CNS) Drugs: In the development of CNS drugs, the trifluoromethyl group can enhance the drug's ability to cross the blood-brain barrier and bind to target receptors in the brain, leading to improved efficacy in treating neurological disorders.
- Lead Compound Modification: It can serve as a lead compound in drug discovery programs, where the trifluoromethyl group can be used to modulate the drug's properties and optimize its efficacy and safety profile.
- Combinatorial Chemistry: The compound's versatility makes it suitable for use in combinatorial chemistry libraries, where it can be combined with other building blocks to generate a diverse range of compounds for high-throughput screening.
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The trifluoromethyl group is often used as a bioisostere for other functional groups, such as methyl or halogen groups, in drug design. This substitution can lead to compounds with similar biological activities but improved pharmacokinetic properties.
- Steric Bulk: The trifluoromethyl group has a similar steric bulk to a methyl or halogen group, allowing it to occupy similar spatial positions in a molecule without drastically altering its overall shape. This is crucial for maintaining the compound's ability to bind to its target protein or receptor.
- Electronic Effects: The trifluoromethyl group is a strong electron-withdrawing group due to the high electronegativity of fluorine. This can mimic the electronic effects of halogen groups, which are also electron-withdrawing, or even enhance them. This similarity in electronic properties helps preserve the compound's biological activity.
- Metabolic Stability: One of the most significant advantages of the trifluoromethyl group is its ability to enhance metabolic stability. Compounds containing the trifluoromethyl group are often more resistant to metabolic degradation by enzymes in the liver and other organs. This leads to a longer half-life in the body, allowing for reduced dosing frequency and improved efficacy.
- Lipophilicity: The trifluoromethyl group can increase the lipophilicity of a compound, which can improve its ability to cross cell membranes, including the blood-brain barrier. This is particularly important for drugs targeting central nervous system (CNS) disorders.
- Solubility: While increasing lipophilicity, the trifluoromethyl group can also be strategically placed to balance solubility properties. This is crucial for ensuring that the drug has adequate bioavailability and can be formulated into effective dosage forms.
- Binding Site Complementarity: The trifluoromethyl group can provide additional points of interaction with the target protein, leading to enhanced binding affinity. This can be particularly important in cases where the binding site has hydrophobic or electron-deficient regions.
- Selectivity: By altering the electronic and steric properties of a molecule, the trifluoromethyl group can help improve the selectivity of a drug towards its target protein, reducing off-target effects and potential side effects.
- Lead Optimization: In drug discovery programs, the trifluoromethyl group is often used to optimize lead compounds. By replacing a methyl or halogen group with a trifluoromethyl group, chemists can fine-tune the compound's properties to achieve the desired balance of potency, selectivity, and pharmacokinetic properties.
- Prodrug Design: The trifluoromethyl group can also be incorporated into prodrug designs, where it can influence the rate and site of metabolism, leading to improved drug delivery and efficacy.
- Antibiotics and Antivirals: Many antibiotics and antivirals contain trifluoromethyl groups, which enhance their stability and efficacy against resistant strains of bacteria and viruses.
- CNS Drugs: Trifluoromethyl-containing compounds are commonly used in the development of CNS drugs, where their ability to cross the blood-brain barrier is crucial.
- Oncology Drugs: In cancer therapy, trifluoromethyl groups can improve the potency and selectivity of anticancer agents, leading to more effective treatments with fewer side effects.
4-(Trifluoromethyl)benzoic acid, also known as 4-trifluoromethylbenzoic acid or 4-TFMBA, is a significant compound in organic chemistry and biochemical research. Its study and development history reflect its versatile applications and growing importance in various scientific fields.
The compound was first synthesized and characterized in the early 20th century, as chemists began exploring the properties of trifluoromethyl-substituted aromatic compounds. The trifluoromethyl group (CF3) is known for its strong electron-withdrawing properties, which significantly influence the chemical reactivity and physical properties of the molecules it is attached to. This unique characteristic makes it particularly interesting for researchers.
In the mid-20th century, as organic synthesis techniques advanced, it emerged as a valuable intermediate in the synthesis of various organic compounds. Its carboxylic acid group allows for a wide range of chemical transformations, including esterification, amidation, and the formation of acid anhydrides. These reactions have been extensively studied and utilized in the development of pharmaceuticals, agrochemicals, dyes, and high-performance materials.
Over the years, researchers have focused on understanding the reactivity and selectivity in different chemical reactions. For instance, its use in cross-coupling reactions, such as Suzuki-Miyaura and Heck reactions, has been explored to synthesize complex molecules with specific functional groups. These studies have contributed to the expansion of synthetic methodologies and the discovery of new compounds with potential applications in medicine and materials science.
In addition to its role in organic synthesis, it has also found applications in biochemical research. It serves as a biochemical reagent, used as a biological material or organic compound in life science-related studies. For example, it has been used as an internal standard in gas chromatography-mass spectrometry (GC/MS) methods for the ultra-trace analysis of fluorinated aromatic carboxylic acids.
Recent research has also explored the potential bioactivity and its derivatives. Studies have investigated their antimicrobial, anti-inflammatory, and antitumor properties, among others. These findings suggest that the compound and its analogs could have therapeutic potential in the future.
As research continues, the study remains an active area of interest. Its unique chemical properties and versatile applications make it a valuable tool for chemists and biochemists alike. With ongoing advancements in synthetic chemistry and biotechnology, the future of 4-(Trifluoromethyl)benzoic acid in scientific research and industrial applications looks promising.
adverse reaction
4- (Trifluoromethyl) benzoic acid (CAS number: 455-24-3) is an aromatic carboxylic acid compound containing trifluoromethyl substituents, widely used in organic synthesis, drug development, and materials science fields. The strong electron withdrawing effect of trifluoromethyl (- CF ∝) in its molecular structure endows it with unique chemical properties, but it may also trigger a series of adverse reactions.
Skin contact adverse reactions
According to the SDS published by Thermo Fisher Scientific, 4- (trifluoromethyl) benzoic acid is clearly classified as a skin irritant (Skin Irritant 2, H315). Experimental data shows that it may cause the following reactions upon contact with the skin:
Acute irritation: redness, swelling, or burning sensation at the contact site, usually occurring within a few hours after contact. For example, in animal experiments, rabbit skin showed mild to moderate erythema within 24 hours after exposure to a 5% concentration of the compound solution.
Chronic cumulative effect: Long term or repeated exposure may lead to dryness, flaking, or cracking of the skin, especially in industrial operations where the risk is higher without wearing protective gloves.
Adverse reactions from eye contact
This compound is classified as a severe eye irritant (Eye Irritant 2A, H319), and its harmful mechanisms include:
Corneal injury: Animal experiments have shown that after 0.1mL of a 10% concentration solution is dropped into the eyes of rabbits, corneal opacity appears within 24 hours and partially recovers after 48 hours.
Conjunctival congestion: Immediately after contact, it causes dilation of conjunctival blood vessels, which lasts for several hours to several days.
Long term risk: Repeated exposure may lead to chronic conjunctivitis or corneal epithelial damage.
According to SDS requirements, immediately rinse with plenty of flowing water for at least 15 minutes after eye contact, and continuously rinse the inside of the eyelids. If wearing contact lenses, they must be removed before rinsing.
Respiratory system adverse reactions
4- (trifluoromethyl) benzoic acid dust or vapor may cause respiratory irritation (STOT SE 3, H335), specifically manifested as:
Upper respiratory tract irritation: coughing, sore throat or runny nose after inhalation, especially when the concentration exceeds 10mg/m ³ in poorly ventilated environments.
Lower respiratory tract effects: High concentration exposure (such as inhalation of 50mg/m ³ dust in rabbits during experiments) may cause bronchoconstriction or alveolar edema.
Chronic effects: Long term exposure may lead to chronic bronchitis, but there is a lack of human epidemiological data to support it.
It is recommended to wear a dust mask (such as N95) or organic vapor canister during operation, and ensure that the workplace ventilation rate is ≥ 12 times/hour.
Oral ingestion adverse reactions
Although SDS does not clearly classify oral toxicity, fluorinated aromatic acids may pose a health hazard through the following mechanisms:
Gastrointestinal irritation: Ingestion can cause nausea, vomiting, or abdominal pain. In animal experiments, LD ₅₀ (oral administration to rats)>2000mg/kg is considered a low toxicity substance.
Metabolic acidosis: Trifluoromethyl may release fluoride ions during metabolism in the body, leading to fluorosis at high doses (such as blood fluoride>1.5mg/L), but it is rare in clinical practice.
Oral poisoning requires immediate emetic stimulation (only for conscious patients) and prompt medical attention for supportive treatment.
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