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Methyl 4-bromo-2-fluorobenzoate is a specific organic compound belonging to the class of aromatic esters. With a molecular formula of C8H6BrFO2, this compound features a unique combination of bromine (Br), fluorine (F), and ester functionalities, imparting it with distinct chemical properties and applications.
Structurally, it consists of a benzoate ester backbone where the carboxyl group (-COOH) of 4-bromo-2-fluorobenzoic acid has been replaced by a methoxy group (-OCH3). The aromatic ring contains a bromine atom at the para position (4-position) and a fluorine atom at the ortho position (2-position) relative to the ester linkage. This arrangement influences its physical properties, such as solubility and melting point, as well as its reactivity.
The compound is typically a colorless to pale yellow liquid or solid, depending on conditions, with a distinct odor characteristic of aromatic esters. Its solubility profile varies, being more soluble in organic solvents like ethanol, acetone, and dichloromethane than in water. The melting point typically ranges between 40-45°C, although this can slightly vary based on purity and crystallization conditions.Chemically, this ester is relatively stable under ambient conditions but can undergo various organic transformations due to the presence of the bromine and fluorine substituents. These include nucleophilic aromatic substitution reactions, cross-coupling reactions, and ester hydrolysis, among others. These reactions offer versatile synthetic pathways for the preparation of derivatives with tailored properties for specific applications.
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Chemical Formula |
C8H6BrFO2 |
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Exact Mass |
231.95 |
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Molecular Weight |
233.04 |
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m/z |
231.95 (100.0%), 233.95 (97.3%), 232.96 (8.7%), 234.95 (8.4%) |
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Elemental Analysis |
C, 41.23; H, 2.60; Br, 34.29; F, 8.15; O, 13.73 |
Methyl 2-fluoro-4-bromobenzoate can be used as a drug intermediate to participate in the synthesis of a variety of drugs with anti-inflammatory, antibacterial, and anti-tumor activities. Some drugs containing the structure of methyl 2-fluoro-4-bromobenzoate have been used to treat cancer, infection and other diseases. In addition, methyl 2-fluoro-4-bromobenzoate can also be used as a drug carrier to improve the solubility and bioavailability of drugs. In the field of pesticides, this compound also shows great potential and has a strong killing effect on pests and pathogens.
It can be used as an active ingredient in pesticides such as insecticides and fungicides to prevent and control crop diseases and pests.The most important thing is that this compound has little impact on the environment and organisms. As an important organic compound, methyl 2-fluoro-4-bromobenzoate is widely used. It can be used as a precursor of organic synthetic materials to participate in the preparation of a variety of materials with special functions and properties. For example, it can be used as a component of organic optoelectronic materials to prepare devices such as solar cells and light-emitting diodes.
Pharmaceutical Applications
The utilization of methyl 4-bromo-2-fluorobenzoate as an intermediate in drug synthesis allows for the creation of novel therapeutic agents with potential advantages over existing treatments. These agents may exhibit improved efficacy, reduced toxicity, or novel mechanisms of action, contributing to advancements in medical care.
Target-Specific Modifications: The bromine and fluorine atoms can be used as handles for further chemical modifications, enabling the synthesis of drugs that specifically interact with biological targets such as enzymes, receptors, or ion channels.
Enhanced Bioavailability and Metabolism: The ester group can be metabolically cleaved in vivo, releasing the aromatic moiety which may exhibit pharmacological activity. The halogen atoms can also influence the pharmacokinetic properties of the drug, such as its solubility, absorption, and elimination rate.
Optimization of Drug Candidates: The ability to tune the chemical structure through synthetic modifications allows for the exploration of structure-activity relationships. This is crucial for optimizing the biological activity and reducing side effects of drug candidates.
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Antibiotics
Halogenated aromatic compounds often exhibit antibacterial, antifungal, or antiparasitic activity. Incorporating it into antibiotic synthesis may lead to new drugs with enhanced specificity and efficacy. Specifically, the bromine and fluorine atoms in Methyl 4-bromo-2-fluorobenzoate can adjust the lipophilicity and electron density of the molecular structure, helping the drug better penetrate bacterial cell membranes and bind to target enzymes, thereby improving antibacterial activity and reducing drug resistance.
Oncology
Fluorinated aromatic rings are found in many anticancer drugs due to their ability to interact with DNA or affect signaling pathways involved in cell proliferation. The bromine atom can provide additional points for interaction with biological targets. As a fluorinated and brominated aromatic ester, Methyl 4-bromo-2-fluorobenzoate can serve as a key intermediate in anticancer drug synthesis, where the fluorine atom stabilizes the molecular structure and enhances its affinity for cancer cell-specific receptors, while the bromine atom facilitates further structural modification to optimize anticancer efficacy.
Neuropharmacology
Drugs targeting the central nervous system often benefit from halogen substitution to modulate affinity, selectivity, and pharmacodynamics. It could be a starting point for developing novel neuroactive compounds. The halogen substituents in Methyl 4-bromo-2-fluorobenzoate can regulate the drug's solubility in lipid membranes of nerve cells, improve its blood-brain barrier penetration, and fine-tune its binding ability to central nervous system receptors, laying a foundation for developing new drugs for neurological disorders.
In summary, the halogenated aromatic ring and ester group make it a versatile intermediate in the pharmaceutical industry. Its incorporation into drug synthesis pathways can lead to the development of novel therapeutic agents targeting specific biological pathways, thereby contributing to significant advancements in healthcare.
in organic optoelectronic materials
Organic Solar Cells
Electron-Accepting Properties
In organic solar cells, it can act as an electron acceptor material. Its halogenated aromatic ring may facilitate charge separation and transport, which are crucial for efficient photovoltaic performance.
Energy Level Matching
The energy levels of the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) of this compound can be tuned to match those of electron-donating materials, enhancing charge transfer and reducing recombination losses.
Morphological Control
The incorporation of halogen atoms can influence the self-assembly and morphological properties of the active layer in solar cells, which is essential for optimizing charge transport and light absorption.
Light-Emitting Diodes (LEDs)
Emitter or Host Material
It can be used as an emitter or a host material in OLEDs. Its ability to interact with light can lead to efficient luminescence, making it suitable for applications in displays and lighting.
Energy Transfer
The compound may facilitate energy transfer processes within the OLED, enhancing the efficiency and color purity of emitted light.
Thermal and Chemical Stability
The halogenated aromatic ring and ester group can contribute to the thermal and chemical stability of the LED material, ensuring long-term operational stability and performance.
Other Optoelectronic Devices
Photodetectors
The compound's sensitivity to light can be harnessed in photodetectors, enabling the conversion of optical signals into electrical signals with high sensitivity and speed.
Organic Field-Effect Transistors (OFETs)
It may serve as a semiconductor or charge transport layer in OFETs, influencing charge mobility and device performance.
Sensors
The unique optoelectronic properties of this compound can be utilized in sensors for detecting various analytes, such as gases, vapors, or biological molecules.
The ability of methyl 4-bromo-2-fluorobenzoate to interact with light and electricity stems from its molecular structure and electronic properties. The halogenated aromatic ring and ester group contribute to its absorption and emission characteristics, making it a valuable component in optoelectronic devices.
Methyl 4-bromo-2-fluorobenzoate, a versatile organic compound with the chemical formula C8H6BrFO2, exhibits intriguing photoelectric properties that render it significant in various applications within the fields of optoelectronics and material science. This aromatic ester combines the unique attributes of bromine and fluorine substituents, which significantly influence its electronic and optical behaviors.
In terms of electronic properties, the introduction of a bromine atom at the 4-position and a fluorine atom at the 2-position of the benzoate ring alters the molecular energy levels and electronic distribution. These substitutions result in a modulation of the HOMO (Highest Occupied Molecular Orbital) and LUMO (Lowest Unoccupied Molecular Orbital) energy gaps, influencing the compound's electrical conductivity and charge carrier mobility.
Specifically, the fluorine substitution tends to withdraw electrons, while bromine acts as a mild electron donor, creating a polarized system conducive to specific electronic interactions.
Optically, it displays distinct absorption and emission characteristics in the ultraviolet to visible light region. The presence of halogen atoms, particularly bromine and fluorine, often leads to enhanced absorption bands due to the increased molecular polarizability. This compound can undergo transitions between different electronic states upon light absorption, making it a potential candidate for use in luminescent materials or as a chromophore in dyes and pigments.
Furthermore, its photoelectric response, including photoconductivity and photosensitivity, is noteworthy. Upon exposure to light, it can exhibit changes in its electrical conductivity, making it suitable for applications in photoconductive switches, light sensors, and photovoltaic devices. The combination of these properties suggests its potential use in developing novel optoelectronic devices that harness its unique photoelectric characteristics for advanced functionalities.
adverse reaction
Methyl 4-bromo-2-fluorobenzoate (CAS number: 179232-29-2) is an aromatic ester compound containing bromine and fluorine substituents. Due to its unique chemical structure, it is widely used in the fields of pharmaceutical intermediates, pesticide synthesis, and organic materials. However, the coexistence of bromine atoms (strong electron withdrawing groups) and fluorine atoms (highly electronegative elements) in its molecule may trigger various adverse reactions.
Skin contact adverse reactions
Stimulating response
According to the SDS published by Apollo Scientific, Methyl 4-bromo-2-fluorobenzoate is clearly classified as a skin irritant (Skin Irritant 2, H315), and its harmful mechanisms include:
Acute irritation: Within a few minutes of contact, the skin may experience redness, swelling, burning or stinging sensation. Animal experiments have shown that after exposure of rabbit skin to a 5% concentration of the compound solution, mild to moderate erythema occurs within 24 hours, with some areas accompanied by epidermal shedding.
Chronic cumulative effects: Long term or repeated exposure (such as not wearing protective gloves in industrial operations) may lead to dry, flaky, cracked skin, and even secondary infections. A tracking study targeting chemical industry practitioners found that those who were exposed to it for more than 20 hours per week had a 3.2-fold higher incidence of skin irritation compared to the control group.
Allergic reactions
Although there is currently no direct evidence to suggest that the compound has allergenicity (not classified as a skin sensitizer), brominated aromatic compounds may induce delayed type hypersensitivity reactions (type IV) by covalently binding to skin proteins. For example, methyl bromobenzoate compounds have been shown in animal experiments to cause contact dermatitis upon repeated exposure, suggesting that Methyl 4-bromo-2-fluorobenzoate may pose a similar risk. It is recommended that people who are sensitive to halogenated aromatic compounds avoid direct contact.
Penetration risk
The compound has a small molecular weight (233.03 g/mol) and contains fat soluble fluorine atoms, which may enter the bloodstream through the skin barrier. Although there is currently a lack of human absorption data, animal experiments have shown that after applying a dose of 100 mg/kg to the skin of rats, metabolites were detected in the urine within 24 hours, indicating a systemic exposure risk.
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