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3'-Chloropropiophenone, also known as inter-chlorobenzophenone, is an important organic synthetic intermediate with the molecular formula C9H9ClO. Its appearance is usually white to pale yellow crystals or crystalline powder, and it has a characteristic aromatic odor. In the chemical industry, this compound is mainly used as a key raw material and is widely applied in the fields of pharmaceuticals and fine chemicals, serving as the precursor for synthesizing a series of drugs (such as certain antidepressants, anticonvulsants) and other high-value fine chemicals. The chlorine atom and benzoyl group in its molecular structure have high reactivity and are prone to undergo various reactions such as nucleophilic substitution, reduction, or cyclization. As a chemical substance, its production, storage, and use must strictly follow safety regulations, as it may cause irritation to the skin, eyes, and respiratory tract, and has certain risks to the environment. During transportation and disposal, relevant chemical management regulations must be followed to ensure safe operation and compliance with environmental protection.
| C.F |
C9H9ClO |
| E.M | 168 |
| M.W | 169 |
| E.A |
168 (100.0%), 170 (32.0%), 169 (9.7%), 171 (3.1%) |
| m/z |
C, 64.11; H, 5.38; Cl, 21.02; O, 9.49 |
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3'-Chloropropiophenone (CAS number 936-59-4) is a halogenated aromatic ketone conflate with a unique chemical structure. Its molecule contains both a ketone carbonyl group (- CO -) and a chloropropyl side chain (- CH2CH2Cl). This bifunctional property makes it an important intermediate in the field of organic conflate. Since its discovery in the mid-20th century, 3-chlorophenylacetone has shown extensive application value in fields such as medicine, pesticides, dyes, and materials science, and its uses have continued to expand with the advancement of chemical conflate technology.
1. The cornerstone of the synthesis of antidepressant bupropion hydrochloride
It is a key precursor for the conflate of Bupropion Hydrochloride. Amphetamine is an atypical antidepressant that works by inhibiting the reuptake of norepinephrine and dopamine by neurons. It is suitable for patients with poor efficacy or intolerance to selective serotonin reuptake inhibitors (SSRIs). In its conflate route, the chloropropyl side chain of the substance is introduced into the amino group through nucleophilic substitution reaction, and the ketone carbonyl group is reduced and converted into a hydroxyl group, ultimately forming the core skeleton of bupropion.
Typical process case:
In a patented process, this product is used as the raw material to synthesize bupropion through the following steps:
Side chain modification: react it with tert butyl sulfonamide to generate chiral auxiliary modified intermediates, ensuring the stereoselectivity of subsequent reactions;
Reduction reaction: Use sodium borohydride or lithium aluminum tetrahydroxide to reduce the ketone carbonyl group to a secondary alcohol;
Hydrolysis and purification: The chiral auxiliary is removed by alkaline hydrolysis, and finally the intermediate of bupropion with a purity of ≥ 99.5% is obtained.
This process increases the overall yield to over 85% and significantly reduces production costs by controlling the reaction temperature (0-5 ℃) and catalyst dosage.
2. Synthesis intermediates of other psychotropic drugs
In addition to bupropion and malavir, it can also be used to synthesize the following drugs:
Dapoxetine: a selective serotonin reuptake inhibitor used to treat premature ejaculation. 3-chlorophenylacetone is introduced into the fluorinated benzene ring through side chain modification to form the key intermediate of dapoxetine.
Fluoxetine Hydrochloride: A classic SSRI antidepressant. 3-chlorophenylacetone undergoes oxidation reaction to generate benzoic acid derivatives, which further synthesize the active ingredient of fluoxetine.
Precursors of anti-tumor drugs: Studies have shown that 3-chlorobenzone derivatives can induce tumor cell apoptosis by inhibiting topoisomerase activity, and are currently in the preclinical research stage.
Emerging application areas: integration of green chemistry and biotechnology
1. Enzymatic asymmetric conflate
With the deepening of the concept of green chemistry, enzyme catalysis technology has shown great potential in the conflate of 3-chlorophenylacetone derivatives due to its advantages of high selectivity and low pollution. For example:
Carbon based reductase catalysis: Using EbSDR8 carbon based reductase, 3-chloroacetone is asymmetrically reduced to (R) -3-chloro-1-phenyl-1-propanol, with an e.e. value (enantiomeric excess) ≥ 99%, providing an efficient pathway for chiral drug conflate;
Lipase catalyzed esterification: By using Candida Antarctica lipase B (CALB) to catalyze the esterification of 3-chlorophenylacetone with alcohols, biologically active ester derivatives can be synthesized for use in the fields of pesticides or fragrances.
2. Functional modification of nanomaterials
The chlorinated side chains can introduce functional groups such as amino and thiol groups through substitution reactions for surface modification of nanomaterials. For example:
Gold nanoparticle modification: 3-chlorophenylacetone is thiolated to generate 3-mercaptobenzene, and its surface is modified with Au-S bonds to improve its biocompatibility for targeted tumor therapy;
Quantum dot functionalization: The substance is converted into 3-aminophenylacetone through an amination reaction, which covalently binds to the carboxyl group on the surface of CdSe quantum dots to prepare fluorescent biological probes.
3'-Chloropropiophenone, as an important organic conflate intermediate, has a wide range of applications in the fields of medicine, pesticides, and materials science. With the deepening of the concept of green chemistry, synthetic processes are gradually developing towards high efficiency, environmental protection, and low cost. The following is a systematic review of its common conflate methods:
Phenylacetone chlorination method: optimization and innovation of traditional process
The phenylacetone chlorination method is the most mature industrial route for synthesizing 3-chlorophenylacetone, and its core principle is to introduce chlorine atoms through the alpha chlorination of phenylacetone.
The typical process flow is as follows:
Chlorination reaction:
Aluminum trichloride (catalyst) and 1,2-dichloroethane (solvent) are added to the reaction vessel, and a solution of phenylacetone is added dropwise while stirring. Selective chlorination is carried out by introducing chlorine gas. The reaction temperature is controlled at 15-70 ℃, and the reaction process is tracked by chromatography. After 6-10 hours, the chlorination is stopped.
Post treatment:
The low-temperature hydrolysis reaction mixture is washed with water to remove inorganic salts, and the crude product is obtained by vacuum distillation. Finally, the product is purified by distillation at 170 ℃, with a purity of 99.7% -99.9% and a yield of 88% -90%.
Technological breakthrough:
Catalyst improvement: Traditional methods use aluminum trichloride, but there are equipment corrosion issues. The patented technology of Shandong Polar Medicine has improved the reaction activity to over 95% by optimizing the catalyst system, while reducing the generation of by-products.
Solvent recovery: The acid water produced by hydrolysis can be recycled and reused, combined with the tail gas treatment system, to achieve closed-loop solvent utilization and reduce environmental pollution.
Chlorobenzoic acid condensation method: a breakthrough in atomic economy
The condensation method of m-chlorobenzoic acid constructs the target molecule through a condensation decarboxylation reaction, with an atomic utilization rate close to 100%, which conforms to the principles of green chemistry. The specific steps are as follows:
Raw material preparation:
M-chlorobenzoic acid is obtained by alkaline hydrolysis and acidification of m-chlorobenzonitrile.
Condensation reaction:
Under the action of a catalyst, m-chlorobenzoic acid condenses with propionic acid to form an intermediate, which is then heated to 180 ℃ for decarboxylation, releasing carbon dioxide and forming the target molecule.
Product separation:
3-chlorophenylacetone is obtained by solvent absorption of the distillate, cooling and crystallization. The yield of this route reaches 82% and does not require the use of heavy metal catalysts.
Technical advantages:
Minimizing waste: The decarboxylation reaction only produces carbon dioxide and water, which is in line with the concept of "zero emissions".
Cost optimization: The raw material m-chlorobenzoic acid can be prepared from industrial by-products of m-chlorobenzonitrile, reducing raw material costs by 30%.
Biocatalysis: The Rise of Enzyme Engineering
With the development of synthetic biology, biocatalysis has gradually emerged due to its high selectivity and low energy consumption advantages.
Typical cases are as follows:
Enzyme screening
Carbon based reductase (EbSDR8) was isolated from soil, which can specifically reduce the ketone carbonyl of 3-chloroacetone to generate (R) -3-chloro-1-phenyl-1-propanol.
Whole cell catalysis
Introducing enzyme genes into Escherichia coli to construct a whole cell catalyst. In a 5L fermentation tank, when the bacterial concentration reaches OD600=20, 3-chlorophenylacetone is added for conversion. After 12 hours, the e.e. value (enantiomer excess value) of the product is ≥ 99%, and the yield is 85%.
Application prospects:
Chiral drug conflate: Biocatalytic method has been used for asymmetric conflate of key intermediates of bupropion, reducing chemical separation steps and lowering production costs.
Sustainable production: Enzyme catalyzed reactions are carried out at room temperature and pressure, reducing energy consumption by 60% compared to chemical methods and meeting carbon neutrality goals.
Other innovative methods: interdisciplinary integration
Photocatalytic chlorination: Using phenylacetone as the raw material, under visible light irradiation, photocatalysts (such as Ru (bpy) ∝² ⁺) activate chlorine gas to achieve alpha selective chlorination. The reaction conditions of this route are mild, and the utilization rate of chlorine atoms is close to 100%, but 3'-Chloropropiophenone is currently in the laboratory stage.
Electrochemical conflate: By electrolyzing a mixed solution of phenylacetone and sodium chloride, chlorine radicals are generated on the electrode surface to directly attack the alpha site of phenylacetone. This route does not require the addition of oxidants and has an atomic economy of 95%, but the lifespan of the electrode material needs to be further optimized.
3'-Chloropropiophenone is a chlorinated aromatic ketone compound. Its chemical properties can be summarized as follows:
Physical state and appearance: At room temperature, it appears as a white to light yellow or light orange crystalline solid, with a specific crystalline form.
Melting point and boiling point: The melting point ranges from 43 to 47 degrees Celsius, and at low pressure conditions (such as 14 mmHg), the boiling point is 124 degrees Celsius, indicating that its volatility is affected by pressure.
Solubility: It is soluble in organic solvents such as methanol, but insoluble in water. This property limits its application in aqueous-phase reactions, but the reaction can be carried out in an organic solvent system.
Chemical stability: It remains stable under normal storage conditions (sealed, dry, at room temperature), but it should be protected from strong oxidants, strong bases, and humid environments to prevent decomposition or adverse reactions.
Reactivity:
Hydrolysis reaction: Under acidic or alkaline conditions, the lactone ring may undergo hydrolysis, generating corresponding hydroxy acids or salt derivatives.
Nucleophilic substitution reaction: The chlorine atom acts as the leaving group and can participate in nucleophilic substitution reactions, being replaced by amino groups, hydroxyl groups, etc., to form various derivatives.
Reduction reaction: With the aid of a catalyst, the carbonyl group can be reduced to an alcohol hydroxyl group, generating compounds such as 3-chlorobenzyl alcohol.
Oxidation reaction: Under the action of a strong oxidizing agent, the benzene ring or side chain may undergo oxidation, generating carboxylic acids or quinone compounds.
Safety warning: This compound is irritating. Contact with the eyes, respiratory system, or skin may cause discomfort. During operation, protective gloves and goggles should be worn, and it should be carried out in a well-ventilated environment.
FAQ
1. What is 3 Chloropropiophenone used for?
3'-Chloropropiophenone is an aromatic ketone intermediate used as a building block in CNS-active pharmaceutical synthesis, heterocyclic compound formation, and fine chemical development.
2. What is 3 chloro propiophenone synthesis?
3'-Chloropropiophenone synthesis
3'-Chloropropiophenone is a key intermediate in the synthesis of drugs such as bupropion hydrochloride, dapoxetine and maraviroc, and can be mainly used in laboratory organic synthesis and chemical production processes.
3. What are the chemical properties of 3'-Chloropropiophenone?
3'-Chloropropiophenone (CAS number: 34841-35-5) is a chlorinated aromatic ketone with the molecular formula C₉H₉ClO and a molecular weight of 168.62. Its structure consists of a chlorinated benzene ring and a propionyl group. It is highly reactive and can easily participate in nucleophilic substitution, reduction reactions, etc. It is a key intermediate for synthesizing complex organic molecules (such as drugs, fragrances, pesticides).
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