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L-3-Chlorophenylalanine is an organic compound that is a derivative of phenylalanine, in which the amino acids α There is a chlorine atom on carbon that replaces the benzene ring. Usually present in the form of white crystals or crystalline powders. Its appearance depends on its crystalline form or material state. The molecular weight is 204.65 grams/mole, with formula 9H10ClNO2 and CAS 80126-51-8. It is a solid that exhibits stable properties at room temperature. It has some typical amino acid characteristics, such as containing carboxyl groups, amino groups, and aromatic rings. It has broad application prospects in the synthesis of polymer materials.

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Chemical Formula |
C9H10ClNO2 |
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Exact Mass |
199 |
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Molecular Weight |
200 |
|
m/z |
199 (100.0%), 201 (32.0%), 200 (9.7%), 202 (3.1%) |
|
Elemental Analysis |
C, 54.15; H, 5.05; Cl, 17.76; N, 7.02; O, 16.03 |
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By introducing the L3 Chlorophenylalanine unit, the structure, function, and performance of polymers can be adjusted to meet specific application requirements. These applications cover drug delivery systems, biodegradable polymers, functional polymers, optical materials, hydrogels, environmental protection and other fields. However, further exploration is still needed for specific research and development work to fully utilize its potential value in polymer materials.

L-3-Chlorophenylalanine, as a chiral aromatic ring substituted amino acid derivative, is a key intermediate in the fine chemical industry chain that connects basic amino acid raw materials with high-end pharmaceutical, food, and materials fields due to its unique molecular structure - introducing chlorine atoms at the 3rd position of the benzene ring while retaining the natural amino acid skeleton in the L configuration. It has both chiral recognition activity and chemical modification potential. Unlike ordinary non chiral chlorinated phenylalanine, its chiral purity directly determines the efficacy and safety of downstream products.

Core applications in the field of pharmaceutical intermediates
Pharmaceutical synthesis is its most core application scenario, and the chlorine substituted benzene ring in its molecular structure can bring stronger lipid solubility and targeted binding ability to drug molecules. At the same time, the chiral skeleton of L configuration can perfectly adapt to the recognition sites of enzymes in the human body, greatly improving the bioavailability of drugs. In the synthesis of anti-tumor targeted drugs, it is a key chiral block for multiple protein kinase inhibitors. By introducing it into the active site side chain of the drug molecule.
Some new targeted drugs targeting solid tumors have achieved precise inhibition of drug-resistant cancer cells by introducing this structure. Relevant clinical data shows that targeted drugs containing its structure have a half-life 60% longer in the human body than ordinary phenylalanine modified drugs, greatly reducing the daily dosage of patients.
In the development and production of antidepressant neuropharmaceuticals, it can serve as a chiral precursor for serotonin reuptake inhibitors. The chlorine atom on its benzene ring can precisely regulate the efficiency of drug molecules crossing the blood-brain barrier, increasing the concentration of drugs in the brain by 35% while reducing unnecessary distribution of drugs in the peripheral circulation.

Significantly reducing the common peripheral side effects of traditional antidepressants such as dry mouth and dizziness. In the field of cardiovascular drugs, this substance is a key intermediate for some novel angiotensin receptor antagonists. By introducing its structure through chiral synthesis, the drug's blood pressure stability is significantly improved, avoiding the blood pressure fluctuations that may occur with ordinary sartan drugs. At present, the pharmaceutical grade products of mainstream domestic suppliers have a stable optical purity of over 99.5%, fully meeting the production quality control standards of high-end active pharmaceutical ingredients. The relevant production capacity has covered more than 80% of the downstream pharmaceutical enterprise demand in China.
Functional applications in the fields of biology and food
In the field of biomanufacturing, 3-chloro-L-phenylalanine is a core raw material for enzyme inhibitors and biochemical reagents. It can serve as a specific inhibitor of phenylalanine hydroxylase and accurately regulate the intracellular tyrosine synthesis pathway in molecular biology experiments. It is widely used in metabolic pathway research, protein expression regulation, and other scientific research scenarios. The chromatographic grade standard products launched by multiple domestic biological reagent companies have become the core reference reagents for amino acid metabolomics research in universities and research institutes.

Their purity reaches 99.9%, fully meeting the high-precision detection requirements of HPLC high-performance liquid chromatography.
In the field of feed and nutritional supplements, the components that have been strictly purified and can be used as functional amino acid additives can regulate the protein metabolism efficiency of livestock and poultry, improve lean meat conversion rate, enhance the immune ability of livestock and poultry, and reduce the use of antibiotics in the breeding process at a reasonable and safe dosage.
Some export-oriented feed additive production enterprises have added this substance as a characteristic functional component to high-end livestock and poultry feed, significantly enhancing the export competitiveness of their products. With the advantage of a stable domestic supply chain, related products have been exported in bulk to multiple regions such as Southeast Asia and Europe. In the development of formula foods for special medical purposes, they can also be used as special metabolic regulatory components to provide customized nutritional support for patients with specific amino acid metabolism disorders, filling the nutritional gap that cannot be covered by ordinary formula foods.


Expansion and application in the field of fine chemicals and materials
In the field of organic synthesis, l-3-chlorophenylalanine is a key starting material for chiral synthesis. With the three reaction sites of amino, carboxyl, and benzene ring chlorine atoms on its molecule, hundreds of chiral derivatives can be synthesized through multi-step organic reactions, which are widely used in the preparation of chiral catalysts and ligands. The chiral bisphosphine ligand synthesized with it as the skeleton exhibits extremely high catalytic enantioselectivity in asymmetric hydrogenation reactions, and the chiral purity of the catalytic product can reach over 99%.
This type of chiral catalyst is the core support for the green synthesis of high-end fine chemicals, greatly reducing the energy consumption and waste emissions of traditional chiral separation processes.
In the field of functional polymer materials, introducing it as a functional monomer into the molecular chain of degradable polyamino acid materials can accurately adjust the degradation rate and mechanical properties of the materials, increase the hydrophilicity of the materials by more than 2 times, and optimize the cell compatibility of the materials.


These modified polyamino acid materials can be used as the core raw materials for medical surgical sutures and tissue engineering scaffolds. The degradation cycle in the human body can be precisely controlled according to the needs, completely avoiding the risk of inflammation caused by residual ordinary synthetic polymer materials. In the field of optical materials, chiral optical films based on 3-chloro-L-phenylalanine have unique circularly polarized light response characteristics and can be applied to wide viewing angle compensation films for liquid crystal displays to improve the color reproduction accuracy of display devices. Currently, this type of material has entered the testing stage in the development of some high-end display panels.

The following are the detailed steps and corresponding chemical equations for the Strecker synthesis of L 3-Chlorophenylalanine using p-nitrobenzaldehyde and alanine:
React p-nitrobenzaldehyde with alanine to produce L-3-nitrophenylalanine.
C7H5NO3 + C3H7NO2 → C9H10N2O4
Perform a hydrogenation reduction reaction on L-3-nitrophenylalanine to reduce the nitro group to an amino group, resulting in the formation of L-3 Chlorophenylalanine.
C9H10N2O4 + H2 → C9H10ClNO2

The following are the detailed steps and corresponding chemical equations for the synthesis of L 3-Chlorophenylalanine using hydrogenation reduction:
C9H10N2O4 + H2 → C9H10ClNO2
Dissolve L-3-nitrophenylalanine in appropriate solvents, such as alcohol solvents (such as ethanol, isopropanol) or organic solvents (such as dimethyl sulfoxide, dimethylformamide). Ensure that the solution is thoroughly mixed.
Adding suitable hydrogenation reduction catalysts to the reaction system, common choices include platinum (Pt), palladium (Pd), or platinum carbon (Pt/C). The selection and dosage of catalysts should be adjusted according to specific reaction conditions.
At a suitable temperature (room temperature or heating), hydrogen gas (H2) is introduced into the reaction system and sufficient stirring is maintained. The reaction time can be adjusted according to the reaction process, usually requiring a longer time.
After completing the hydrogenation reaction, cool the reaction system to room temperature and purify L-3-Chlorophenylalanine through crystallization or appropriate purification techniques such as solvent crystallization, precipitation, or column chromatography.
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