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2-Amino-5-Chlorobenzophenone, yellow crystalline powder, molecular formula C13H10ClNO, CAS 719-59-5, density 1.33g/mL, indicating 1.33 grams of 2-amino-5-chlorodibenzophenone per milliliter. The solubility in methanol is very low, forming a slightly turbid solution; In dimethyl sulfoxide, it has a high solubility. In addition, it has good solubility in organic solvents such as ethanol, ether, and chloroform. The solubility in water is relatively low. Pharmaceutical intermediates. Production of sleeping pills, diazepam and other medications. Toxic substances, flammable; Burning produces toxic nitrogen oxides and chloride smoke, warehouse ventilation, and low-temperature drying. Fire extinguishing agents include dry powder, foam, sand, carbon dioxide and fog water.
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Chemical Formula |
C13H10ClNO |
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Exact Mass |
231 |
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Molecular Weight |
232 |
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m/z |
231 (100.0%), 233 (32.0%), 232 (14.1%), 234 (4.5%) |
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Elemental Analysis |
C, 67.40; H, 4.35; Cl, 15.30; N, 6.05; O, 6.91 |
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Melting point 96-98 ° C (lit.), Boiling point 207 ° C, Density 1.33, Refractive index 1.6000 (estimated), Flashpoint 211 ° C, Storage condition: store below + 30 ° C, Solubility in methanol gives very fault solubility Soluble in DMSO., Acidity coefficient (PKA) 0.06 ± 0.10 (predicted), Morphology crystal powder, Color yellow, BRN 475640, Stable Incompatible with strong oxidizing agents. InChIKeyZUWXHHBROGLWNH-UHFFFAOYSA-N
Prepared by reacting p-chloroaniline with 2-Amino-5-Chlorobenzophenone
Add p-chlorobenzene to a glass lined reaction vessel, and then add anhydrous zinc chloride at a temperature below 70 ℃.
Under stirring conditions, benzoyl chloride is added dropwise. Afterwards, heat up and keep at 195-205 ℃ for 2 hours.
Wash five times with hot water at 90-95 ℃, and the water layer and washing solution can be used to recycle benzoic acid and zinc chloride.
Slowly add sulfuric acid at around 100 ℃, and then keep at 142 ℃ for 40 minutes.
Inject the liquid into water at 05 ℃ while it is hot to precipitate the solid. Under stirring conditions, adjust the pH value to no higher than 1 with liquid alkali, and then filter at 2025 ℃. The filtrate can be used for the recovery of p-chloroaniline.
The filter cake is suspended in water, neutralized to pH 6, filtered and dried, washed with water until neutral, and finally dried to obtain the crude product.
Add 6-7 times ethanol and 6% activated carbon to the crude product, reflux for 30 minutes, filter and crystallize, and dry to obtain high-quality 2-amino-5-chlorobezophenone.
As an important pharmaceutical intermediate, 2-amino-5-chlorobenzophenone's unique chemical structure and properties enable it to participate in various chemical reactions, thereby synthesizing drgs with different pharmacological activities. These drgs have a wide range of applications in the pharmaceutical field, including sedation, hypnosis, anti anxiety, anti depression, anti epileptic, antibacterial, and other aspects. Therefore, in-depth research on the use of pharmaceutical intermdiates is of great significance for promoting the development and innovation of the pharmaceutical industry.
(1) Limianning: Limianning is a commonly used sedative drug, mainly used to treat symptoms such as insomnia and anxiety. It is one of the important intermdiates for the synthesis of levonorgestrel. Through specific chemical reactions, it can be converted into levonorgestrel to meet clinical needs.
(2) Diazepam: Diazepam is another commonly used sedative drug that has various pharmacological effects such as anti anxiety, sedative hypnotic, anticonvulsant, and muscle relaxation. It also plays an important role in the stable synthesis process. Through reasonable chemical steps, it can be converted into stability, providing effective treatment methods for clinical practice.
(3) Shu Le An Ding: Shu Le An Ding is a long-acting benzodiazepine drug with sedative, hypnotic, and anti anxiety effects. It is also synthesized from it as an intermdiate. The therapeutic effect of Shule Anding is long-lasting and the side effects are relatively small, so it has been widely used in clinical practice.
It is a key intermdiate for synthesizing various sedative drgs. Sedatives are a type of medication that can inhibit central nervous system activity, causing feelings of quietness, comfort, and drowsiness in the human body. In the field of medicine, sedatives are widely used to treat symptoms such as insomnia, anxiety, and tension.
(1) Carbamazepine: Carbamazepine is a broad-spectrum antiepileptic drug with various pharmacological effects such as antiepileptic, neuropathic, and anti manic effects. Plays a crucial role in the synthesis process of carbamazepine. Through specific chemical reactions, it can be converted into precursor compounds of carbamazepine, which can then be further reacted to obtain carbamazepine.
(2) Sodium valproate: Sodium valproate is another commonly used antiepileptic drug, mainly used to treat various types of epilepsy symptoms. Although it is not a direct intermdiate for the synthesis of sodium valproate, it may play an indirect role in its synthesis process. For example, through specific chemical reactions, it can be converted into certain compounds, which can then be further reacted to obtain the raw material or intermediate of sodium valproate.
Antiepileptic drgs are a type of medication that can suppress epileptic seizures. In the field of medicine, antiepileptic drgs are widely used to treat various types of epilepsy symptoms. As a pharmaceutical intermdiate, it can participate in the synthesis of various antiepileptic drgs.
(1) Fluoxetine: Fluoxetine is a commonly used antidepressant drug with various pharmacological effects such as antidepressant, anti anxiety, and anti compulsive. Although not a direct synthetic intermdiate of fluoxetine, it may play a promoting or assisting role to some extent in its synthesis process. For example, through specific chemical reactions, it can be converted into certain compounds, which can then be further reacted to obtain the raw materials or intermdiates of fluoxetine.
(2) Shequlin: Shequlin is another commonly used antidepressant medication, mainly used to treat symptoms such as depression and obsessive-compulsive disorder. Although not directly involved as an intermediate in the synthesis process of sertraline, it may affect the synthesis efficiency or yield of sertraline in some way. For example, by optimizing its synthesis process or purification method, the quality or purity of Shequlin raw materials can be improved, thereby indirectly improving the synthesis efficiency and yield of Shequlin.
Antidepressants are a type of medication that can improve symptoms of depression. In the field of medicine, antidepressants are widely used to treat psychological disorders such as depression and anxiety. As a pharmaceutical intermdiate, it can participate in the synthesis of various antidepressant drgs.
Synthesis of antibacterial drugs
(1) Cephalosporins: Cephalosporins are drgs with broad-spectrum antibacterial activity, mainly used to treat various bacterial infectious diseases. Although it is not a direct synthetic intermdiate of cephalosporin antibiotics, it may play a promoting or assisting role to some extent during its synthesis process. For example, through specific chemical reactions, certain compounds can be converted, and these compounds can be further reacted to obtain the raw materials or intermdiates of cephalosporin antibiotics.
(2) Quinolone antibiotics: Quinolone antibiotics are a class of drgs with broad-spectrum antibacterial activity, mainly used to treat infections in the respiratory tract, urinary tract, digestive tract, and other areas. Although 2-Amino-5-Chlorobenzophenone is not a direct synthetic intermediate of quinolone antibiotics, it may play a promoting or assisting role to some extent during its synthesis process. For example, by optimizing its synthesis process or purification method, the quality or purity of quinolone antibiotic raw materials can be improved, thereby indirectly improving the synthesis efficiency and yield of quinolone antibiotics.
Adverse effects on the environment
2-Amino-5-Chlorobenzophenone (CAS number 719-59-5) is an important organic synthetic intermediate widely used in the pharmaceutical industry, especially in the production of sedatives such as levonorgestrel and diazepam. With the expansion of its industrial applications, its environmental behavior and potential ecological risks have gradually attracted attention.
Environmental distribution and migration
Release pathway
The environmental release of 2-Amino-5-Chorobenzophene mainly comes from the following pathways:
Industrial production and use: During the synthesis of pharmaceutical intermediates, unreacted raw materials, by-products, and waste may enter water bodies or soil through wastewater discharge.
Waste disposal: Laboratory or industrial waste containing this compound may enter the environment through landfill or incineration if not properly disposed of.
Product degradation: The metabolism or decomposition of drugs containing this compound in the environment may release its active ingredients.
Distribution in environmental media
Water body: Due to its hydrophobicity (logP=3.16), this compound is easily adsorbed onto suspended particles or sediments, resulting in a lower concentration in the water phase, but may accumulate in the sediment. Research has shown that halogenated benzophenone compounds with similar structures can reach concentrations of up to μ g/kg in river sediments.
Soil: A high Koc value (500-2000 L/kg) indicates strong adsorption to soil organic matter, low mobility, and may persist in the surface soil for a long time.
Atmosphere: Low volatility, negligible concentration in the atmosphere, but there may be local pollution in the form of aerosols near industrial areas.
Ecotoxicity
This substance exhibits potential toxicity to both aquatic and terrestrial organisms, and its toxicity mechanism is related to the electronic effects and lipid solubility of amino and chlorine atoms.
Toxicity to aquatic organisms
Fish: The 96 hour LC ₅₀ value for rainbow trout is 1-10 mg/L, indicating that short-term exposure may cause respiratory damage or gill tissue lesions. Long term low concentration exposure (<1 mg/L) may affect fish reproduction or behavior.
Invertebrates: The 48 hour EC ₅₀ value for Daphnia magna is 0.5-5 mg/L, mainly interfering with nerve conduction or energy metabolism.
Algae: Growth inhibitory concentration (IC ₅₀) is about 5-20 mg/L, which may affect algal community structure by inhibiting photosynthesis or disrupting cell membrane structure, thereby disrupting the foundation of the aquatic food chain.
Soil biotoxicity
Microorganisms: Experiments have shown that exposure to soil levels of 10-50 mg/kg can reduce urease activity by 20-40%, inhibit nitrogen cycling processes, and indirectly affect plant growth.
Plants: High concentrations may affect plant physiological functions through soil adsorption or root absorption, but specific toxicity data is still lacking.
Bioaccumulation and Amplification Effect
Although its logP value (3.16) is lower than that of strongly hydrophobic pollutants (such as DDT, logP ≈ 6), the stability of its pyridine ring structure allows it to slowly accumulate in aquatic adipose tissue. The biocontrol factor (BCF) of halogenated benzophenone compounds can reach 10-100, indicating potential food chain transfer risks, especially for benthic organisms and fish.
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