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5-Fluoro-2-nitroaniline is an organic compound with the chemical formula C6H5FN2O2, which is in the form of white to light yellow crystals. It is an important intermediate in organic synthesis, often used in the preparation of similar compounds and the development of new drugs. It is a derivative of fluoronitroaniline.
This compound has specific chemical structure and physical properties. This compound has high lipophilicity and is easy to penetrate the cell membrane. In addition, the product has low toxicity, giving it certain advantages in distribution and metabolism in the body. Due to its importance in the field of organic intermediate chemistry, it has become one of the important basic substances in organic chemistry research. Research has shown that it can be used to make high-value compounds such as pharmaceuticals, pesticides and dyes.
|
Chemical Formula |
C6H5FN2O2 |
|
Exact Mass |
156 |
|
Molecular Weight |
156 |
|
m/z |
156 (100.0%), 157 (6.5%) |
|
Elemental Analysis |
C, 46.16; H, 3.23; F, 12.17; N, 17.94; O, 20.50 |
5-Fluoro-2-nitroaniline is an organic compound with a variety of uses, including the following:
1. Radiopharmaceutical synthesis: In nuclear medicine, radiopharmaceuticals with specific biological activities are often used for diagnosis and treatment. 5-fluoro-2 nitroaniline can be used as an intermediate in the synthesis of certain radioactive drugs. For example, radiopharmaceuticals for diagnosing tumors, cardiovascular diseases, and other diseases can be synthesized by labeling specific locations of 5-fluoro-2 nitroaniline.
2. Disease diagnosis: By utilizing the specific biological activity of 5-fluoro-2 nitroaniline, it can be used as a tracer for disease diagnosis. For example, 5-fluoro-2 nitroaniline can be labeled with specific biomolecules for early diagnosis and disease monitoring through its distribution and metabolism in the body.
3. Tumor treatment: In tumor treatment, 5-fluoro-2 nitroaniline can be used directly as a radioactive drug or in combination with other drugs. By launching β Particle or γ Radiation, 5-fluoro-2 nitroaniline, can kill tumor cells and inhibit their growth. This treatment method is commonly referred to as internal irradiation or nuclide therapy.
4. Molecular imaging: Molecular imaging is a non-invasive technique that can observe changes in specific molecules or biological processes in vivo. 5-fluoro-2 nitroaniline can be used as a molecular probe for molecular imaging research. For example, by using positron emission tomography (PET) technology, the distribution and metabolism of 5-fluoro-2 nitroaniline in the body can be tracked, thereby understanding the development process of tumors and other diseases.
5. Pharmacokinetic research: 5-fluoro-2 nitroaniline can also be used to study the absorption, distribution, metabolism, and excretion processes of drugs in the body. By combining 5-fluoro-2 nitroaniline with other drugs, the bioavailability and pharmacodynamic properties of drugs can be evaluated.
6. In vitro diagnosis: In the field of in vitro diagnosis, 5-fluoro-2 nitroaniline is also widely used. For example, it can be used as part of antigen or antibody conjugates to develop in vitro diagnostic kits such as enzyme-linked immunosorbent assay (ELISA). In addition, 5-fluoro-2 nitroaniline can also be used for tissue staining and pathological research.
7. Other applications: In addition to the above applications, 5-fluoro-2 nitroaniline has also been applied in fields such as nuclide tracing and environmental monitoring. For example, labeling 5-fluoro-2 nitroaniline can track the progress of chemical reactions or study the properties of materials.
5-Fluoro-2-nitroaniline is an important nitrogen-containing aromatic compound, which is widely used in pharmaceuticals, dyes, materials and other fields. Various synthetic methods of 5-fluoro-2 nitroaniline will be introduced below.
A chemical reaction process for synthesizing 5-fluoro-2 nitroaniline. The following is a detailed description of the specific steps of this method and its corresponding chemical equations.
1. Prepare reaction raw materials and equipment
The required raw materials include p-fluoronitrobenzene, concentrated nitric acid, sodium nitrate, sodium nitrite, and anhydrous ethanol. The required equipment includes a separating funnel, condensing tube, crystallization vessel, stirrer, electronic balance, etc.
2. Synthesis steps:
2.1 At room temperature, mix sodium nitrate and sodium nitrite in a 1:1 mass ratio, and add an appropriate amount of anhydrous ethanol to dissolve into a mixed solution.
2.2 Add p-fluoronitrobenzene to the mixed solution and stir evenly.
2.3 Add concentrated nitric acid to the above mixed solution and stir evenly.
2.4 During the reaction process, it is necessary to control the temperature to prevent overheating or undercooling from affecting the progress of the reaction. Appropriate temperature control can be achieved by adding coolant or adjusting the ambient temperature.
2.5 During the reaction process, continuous stirring is required to promote the reaction. The speed and time of the stirrer need to be controlled to prevent excessive stirring from causing product degradation.
2.6 After the reaction is completed, separate the reaction liquid from the upper clear liquid using a separating funnel to obtain a reddish brown mud.
2.7 Cool the reddish brown mud naturally in a crystallization dish to room temperature to obtain a crude product of 5-fluoro-2 nitroaniline.
2.8 Wash the crude product with an appropriate amount of water multiple times to remove unreacted impurities such as sodium nitrate, sodium nitrite, and anhydrous ethanol. Finally, dry the product to obtain a relatively pure 5-fluoro-2 nitroaniline.
Sodium nitrate reacts with sodium nitrite to generate nitrite: NaNO2+NaNO3 → NaNO2H
Nitric acid reacts with p-fluoronitrobenzene to produce 5-fluoro-2 nitroaniline: C6H4FNO2+HNO2 → C6H4FNO2N2O3
Unreacted sodium nitrate and sodium nitrite react with water to form nitric acid and nitrite: NaNO2+NaNO3+H2O → HNO3+HNO2
The generated nitrite reacts with ethanol to generate acetaldehyde: CH3CH2OH+HNO2 → CH3CHO+HNO3
Acetaldehyde reacts with ethanol to produce acetaldehyde alcohol: CH3CHO+CH3CH2OH → CH3CH2CH(OH)CHO
Dehydration of acetaldehyde alcohol to produce acrolein: CH3CH2CH(OH)CHO → CH2=CHCHO+H2O
Acrolein reacts with ethanol to produce acrolein: CH2=CHCHO+CH3CH2OH → CH2=CHCH(OH)CH3
Dehydration of propylene alcohol to produce acrolein: CH2=CHCH(OH)CH3 → CH3CH=CHCHO+H2O
Acrolein reacts with ethanol to produce acrolein: CH3CH=CHCHO+CH3CH2OH → CH3CH=CHCH(OH)CH3
Dehydration of propylene alcohol to produce acrolein: CH3CH=CHCH(OH)CH3 → CH3CH=CHCHO+H2O
Acrolein reacts with ethanol to produce acrolein: CH3CH=CHCHO+CH3CH2OH → CH3CH=CHCH(OH)CH3
Dehydration of propylene alcohol to produce acrolein: CH3CH=CHCH(OH)CH3 → CH3CH=CHCHO+H2O
The second method is through the nitrification reaction catalyzed by phosphorus pentoxide. The specific operation is to dissolve 2-amino-5-fluorophenol in acetone, and then add a small amount of phosphorus pentoxide. Add nitric acid into the reaction system in a titration form, and maintain the temperature of the reaction system below 0°C during the reaction. After the reaction is completed, the reaction product is washed with water, dissolved with dilute acid and purified by crystallizatids for 5-fluoro-2-nitroaniline, each method has its own advantages and disadvantages, and a suitable synthetic method can be selected according to actual needs. Among them, the cost of synthesis through nitration reaction is low but the safety risk is high, while the synthesis cost of reducti
on to obtain product.
The above are a variety of synthetic metho
on reaction is high but less dangerous, so it needs to be carefully selected.
Safety
Health hazards
Stimulants: Have irritancy to the respiratory tract, eyes and skin. Contact may cause redness, pain or allergic reactions.
Toxicity:
Acute toxicity: Toxic through ingestion, inhalation or skin contact (GHS classification as category 3). Accidental ingestion or inhalation may lead to symptoms such as dizziness, nausea, vomiting.
Long-term exposure: May cause damage to organs (such as liver and kidneys) (GHS classification as category 2, repeated exposure toxicity).
Environmental hazards: Harmful to aquatic organisms, with long-term persistent effects (GHS classification as category 3), need to avoid direct discharge into the environment.
Safety operation guidelines
Personal protection: During operation, wear goggles, protective gloves and laboratory coat to avoid inhalation of dust or vapors.
Ventilation requirements: Conduct operations in a well-ventilated laboratory or industrial fume hood to reduce exposure risks.
Emergency handling:
Skin contact: Immediately rinse with plenty of water, seek medical attention if necessary.
Eye contact: Rinse with flowing water for at least 15 minutes, and seek medical help.
Inhalation or ingestion: Quickly transfer to an area with fresh air, keep breathing unobstructed, and contact emergency personnel immediately.
Storage and transportation
Storage conditions: Store in a sealed, cool and dark place, away from strong oxidants to prevent violent reactions.
Transport requirements: Transport as a hazardous chemical, label with "irritant" and "toxic", prevent collision and high temperatures.
Stability
Chemical stability
At normal temperature and pressure: Stable at room temperature, but avoid mixing with strong oxidants (such as potassium permanganate, concentrated nitric acid) to prevent violent reactions.
Thermal stability: Melting point 96-100°C, boiling point 295.5±20.0°C. May decompose at high temperatures, releasing toxic gases (such as nitrogen oxides, hydrogen fluoride).
Light sensitivity: Long-term exposure to light may lead to decomposition, need to store in a dark place.
Reactivity
Nucleophilic substitution reaction (SNAr): The strong electron-withdrawing effect of nitro and fluorine atoms activates the benzene ring, and the fluorine atom is easily replaced by nucleophilic reagents (such as sodium azide, ammonia water), generating derivative products.
Reduction reaction: Nitro can be reduced to amino (such as using dichlorosilicon/tartaric acid or hydrogen/palladium catalyst), generating 5-Fluoro-1,2-benzenediamine.
Potential risks: May undergo hydrolysis under acidic or alkaline conditions, generating fluoride or nitrobenzamide compounds, need to control reaction conditions.
Compatibility
Prohibited substances: Avoid mixing with strong reducing agents (such as sodium metal), strong acids (such as concentrated sulfuric acid) or strong bases (such as sodium hydroxide) to prevent explosion or release of toxic gases.
Solvent selection: Soluble in organic solvents such as ethanol and ether, but pay attention to the boiling point and flash point of the solvent to prevent fire.
FAQ
Why does the presence of fluorine, nitro, and amino trisubstitutements in this molecule abnormally weaken the strong electron withdrawing induction effect of adjacent nitro groups when the fluorine at position 5 is present?
A: Conventional fluorine is strongly electron withdrawing induced and weakly electron donating conjugated; The 5-F and 2-nitro groups form a cross ring electron compensation effect, and the lone pair electrons of the fluorine p orbital neutralize the strong electron deficient electrons of the nitro group through the conjugated part of the benzene ring, resulting in a decrease in the polarization of the entire aromatic ring electrons. Compared to fluorine free 2-nitroaniline, its acidity and electrophilic reactivity are significantly reduced, making it a rare electron depolarization structure in multi substituted halogenated nitroaniline.
What are the obscure rules for the protonation/deprotonation selectivity of amino and nitro groups in this compound under different acid-base environments?
A: Strong acidic conditions prioritize amino protonation, but the electron withdrawing effect of 5-F significantly reduces amino basicity, making protonation much more difficult than ordinary ortho nitroaniline; In alkaline environments, nitro isomerism into acidic structures does not occur. The space and electron shielding of fluorine atoms block the negative ion resonance stability of nitro oxygen, making it more chemically stable in strong alkaline systems and less prone to hydrolysis and degradation.
Compared to other monofluoronitrobenzenes, what special weak bond interactions exist in their solid-state stacking?
A: The molecule simultaneously possesses strong N-H... O hydrogen bonds, weak C-F... H-C hydrogen bonds, and local π - π dislocation stacking of nitro aromatic rings; The high electronegativity of fluorine atoms can form a unique organic fluorine weak hydrogen bonding network, which inhibits the tight stacking of molecules. The crystal has no obvious solvent encapsulation and a narrow range of thermal sublimation, making it suitable as an intermediate for vapor deposition of organic small molecules. This crystallization characteristic is rarely mentioned in textbooks.
What are the differences in niche reactions caused by the combined action of 2-ortho nitro and 5-fluoro in diazotization reactions?
A: The ortho nitro group stabilizes the diazonium salt of aniline, but the electron withdrawing effect of the 5-fluoro group further reduces the electron cloud density of the aromatic ring, making the diazonium salt highly stable at low temperatures and less prone to spontaneous denitrification and decomposition; At the same time, the superposition of steric hindrance and electronic effect can directionally control the site selectivity of subsequent coupling, hydrolysis and halogenation, which is suitable for the preparation of fluorinated aromatic fine chemicals modified by a single site.
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