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5-Chloropyridin-2-amine, chemical formula: C4H4ClN3, CAS 5428-89-7, molecular weight 128.54 g/mol. It is a white to light yellow crystalline or powdered solid. It has good solubility in common organic solvents, such as ethanol, di N-Methylformamide (DMF) and dichloromethane. It is a compound containing chlorine and amine groups. It may have chemical properties similar to other amine or chloride compounds, such as reactivity, Hydroxylation, Substitution reaction, etc. It can be used to synthesize various pesticides, such as insecticides, fungicides, and herbicides. These pesticides have extensive applications in agriculture and can be used to protect crops from pests, pathogens, and weeds. It can also be used for synthetic coatings, rubber additives, electronic chemicals, and surfactants. In addition, it can also be used as the Lead compound of organic photovoltaic materials and organic light-emitting diodes (OLEDs).
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Chemical Formula |
C4H4ClN3 |
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Exact Mass |
129 |
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Molecular Weight |
130 |
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m/z |
129 (100.0%), 131 (32.0%), 130 (4.3%), 132 (1.4%), 130 (1.1%) |
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Elemental Analysis |
C, 37.09; H, 3.11; Cl, 27.36; N, 32.44 |
2-Amino-5-chloropyrimidine is an organic chemical substance with the molecular formula C4H4ClN3, which has a wide range of applications in the fields of medicine and biochemistry, especially as a pharmaceutical intermediate.
Overview of Antiparasitic Drugs
Antiparasitic drugs are a type of medication used to treat and prevent parasitic infections. Parasitic diseases are diseases caused by parasites invading the human or animal body, posing a serious threat to human health and livestock production. The mechanism of action of antiparasitic drugs mainly includes affecting enzymes in the parasite, acting on receptors in the parasite, interfering with parasite metabolism, and affecting ion balance or transport in the parasite.
Classification and effects of antiparasitic drugs
Nematode expelling drugs are mainly used to drive away intestinal nematodes and lung nematodes. Common anti nematode drugs include dichlorvos, levamisole, and benzimidazole.
(1) Dichlorvos:
Dichlorvos is an organic phosphate antiparasitic drug that has the advantages of broad-spectrum, high efficacy, low cost, easy availability, and convenient administration. It inhibits the activity of cholinesterase in the insect body, causing the accumulation of acetylcholine (Ach) in the insect body, leading to excitement, spasms, paralysis, and death. Dichlorvos can not only drive away most intestinal nematodes such as roundworms, whipworms, hookworms, etc., but also drive away certain flukes and external use to drive away mites, flies, and blood sucking insects.
(2) Leflunomide:
Leflunomide is an imidazole thiazide antiparasitic drug with high efficacy, broad spectrum, and low toxicity. It inhibits the enzyme reductase of the insect body, interferes with the sugar metabolism process, leads to ATP deficiency, and thus kills the insect body. Leflunomide is mainly used to drive away various intestinal nematodes such as roundworms, pinworms, and hookworms, as well as lung nematode diseases. It can also be used as a preventive drug for latent mastitis in dairy cows.
The tapeworm expelling medicine is mainly used to expel tapeworms from the human and animal bodies. Common anti tapeworm drugs include chloramphenicol, hesperetin, and thiodicarbonamide.
(1) Chlorambucil:
Chlorambucil, also known as metronidazole, inhibits the absorption of glucose in the insect body and disrupts its oxidation process, resulting in a large accumulation of lactic acid in the insect body and death. Chlorambucil is not only used to treat various tapeworm diseases in livestock and poultry, but also to treat anterior and posterior disc flukes in cattle and sheep, as well as to kill snails (the intermediate host of Schistosoma japonicum).
(2) Hecao phenol:
Hecao phenol is an antiparasitic drug extracted from plants and has the effect of repelling tapeworms. It is mainly used to drive away tapeworms from the human body, including hooked and uncircumcised tapeworms.
The anti fluke medicine is mainly used to expel flukes from the human and animal bodies. Common anti fluke drugs include thiodicarbonamide, praziquantel, nitrochlorophenol, etc.
(1) Sulfur Dichlorophenol:
Sulfur Dichlorophenol inhibits energy metabolism in insects, reduces sugar breakdown and oxidation processes, leading to energy (ATP) deficiency and muscle paralysis death. Sulfur dichlorophenol can not only drive away liver flukes, anterior and posterior suction cup flukes, ginger flukes and other flukes, but also drive away various tapeworms.
(2) Praziquantel:
Praziquantel is a broad-spectrum antiparasitic drug that has a killing effect on various parasites such as flukes, tapeworms, and nematodes. It reduces the intake of glucose by the insect body, causing sugar to seep out from the skin, resulting in insufficient energy supply and being driven away. Praziquantel is currently the preferred drug for synchronous chemotherapy in the treatment of schistosomiasis in humans and animals, and can also kill the cysticercus and cercariae of schistosomiasis.
Antigen insecticides are mainly used to treat parasitic diseases caused by protozoa, such as coccidiosis, trypanosomiasis, and pear shaped worm disease.
Anti coccidiosis drugs are mainly used to prevent and treat one of the most important diseases in intensive chicken farming - coccidiosis. According to their different mechanisms of action, anticoccidial drugs can be roughly divided into two categories: polyether ion carrier antibiotics and chemically synthesized anticoccidial drugs. Polyether based ionophore antibiotics such as monensin and salinomycin inhibit the growth and development of insects by interfering with the normal penetration of cations and absorption of nutrients. Chemical synthesized anticoccidial drugs such as sulfaquinoxaline and nicarbazine act on different stages of the parasite's life to achieve the goal of killing the parasite.
Antiparasitic use
1. Inhibit insect metabolism
2-Amino-5-chloropyrimidine, as an organic chemical substance, may have an inhibitory effect on insect metabolism. By interfering with metabolic processes within the insect, such as sugar metabolism, fat metabolism, or protein metabolism, it leads to insufficient energy supply or accumulation of metabolic products, thereby killing or inhibiting the growth and reproduction of the insect.
2. Affects ion balance within the insect body
The ion balance within the insect body is crucial for its normal physiological functions. It may cause physiological dysfunction of the parasite by affecting the ion balance inside the parasite, such as sodium ions, potassium ions, or calcium ions, thereby achieving the goal of anti parasitic treatment.
3. Interference with insect receptor function
The receptors on the surface of the insect are important mediators for the interaction between the insect and the host environment. It may interfere with the interaction between the insect and the host environment, such as nutrient absorption and metabolite excretion, by binding to receptors on the surface of the insect, thereby inhibiting the growth and reproduction of the insect.
4. As an intermediate for synthesizing other antiparasitic drugs
It has a wide range of applications in the fields of medicine and biochemistry, especially as a pharmaceutical intermediate. It may serve as a key intermediate for synthesizing other drugs with anti parasitic activity, and through further chemical modification and modification, new drugs with stronger anti parasitic activity can be obtained.
5-Chloropyridine-2-amine is an important organic compound with broad application prospects in fields such as medicine, pesticides, and materials science. However, due to the particularity of its structure and the complexity of its synthesis path, its synthesis method has always been the focus of researchers.
Synthesis strategy
The strategy for synthesizing 5-choropyridin-2-amine starting from 2-furanic acid can be summarized as follows: carboxyl conversion, cyclization, chlorination, nitration, reduction, and purification. These steps need to be carried out sequentially, and each step requires strict reaction conditions and catalysts.
Detailed steps and chemical equations
Firstly, convert 2-furanic acid into the corresponding ester or amide for subsequent cyclization reactions. Here we choose esterification reaction as an example.
C4H4ClN3 + C4H8O2 → C12H12N2O3 + H2O
For example, using methanol as the alcohol source can yield methyl 2-furanate.
Next, 2-furfurfuryl ester is converted into the precursor of pyridine ring through cyclization reaction. This step usually requires the use of specific catalysts and reaction conditions.
C12H12N2O3 + catalyst → pyridine ring precursor+by-products
The specific reaction conditions and catalyst selection for this step need to be optimized based on experimental data and literature reports.
After obtaining the pyridine ring precursor, it is necessary to perform a chlorination reaction to introduce chlorine atoms. This step usually requires the use of chlorination reagents such as chlorine gas, chlorinating agents, or sodium hypochlorite.
Pyridine ring precursor+chlorine gas/chlorinating agent → 5-chloropyridine precursor+by-products
The specific conditions and catalyst selection for chlorination reaction need to be optimized based on experimental data and literature reports.
After obtaining the precursor of 5-chloropyridine, it is necessary to carry out nitration reaction to introduce nitro group. This step usually requires the use of nitration reagents such as concentrated nitric acid and concentrated sulfuric acid.
5-Chloropyridine precursor+concentrated nitric acid+concentrated sulfuric acid → 5-Chloro-2-nitropyridine+water
The nitration reaction needs to be carried out at low temperatures, and the reaction time and temperature need to be controlled to prevent the generation of by-products.
Finally, the nitro group in 5-chloropyridine-2-nitropyridine is reduced to an amino group through a reduction reaction, resulting in the target product 5-chloropyridine-2-amine. This step usually requires the use of reducing agents such as iron powder, sodium sulfide, or hydrogen gas.
5-Chloro-2-nitropyridine+reducing agent → 5-Chloropyridine-2-amine+byproduct
The specific conditions of the reduction reaction and the selection of reducing agents need to be optimized based on experimental data and literature reports.
After obtaining the target product, purification is required to remove impurities and improve the purity of the 5-Chloropyridin-2-Amine. Purification methods typically include recrystallization, distillation, extraction, and chromatographic separation.
Purification steps (example):
Filter the reaction mixture to remove insoluble impurities.
Distillation of the filtrate to remove solvents and volatile impurities.
Use appropriate solvents for extraction to remove remaining impurities.
Perform chromatographic separation on the extraction solution to further purify the target product.
Adverse reactions
Human exposure pathways and potential risks
Occupational exposure
Inhalation risk: During the synthesis or processing of 5-Chloro-2-Pyridine, dust or vapor may enter the human body through the respiratory tract, causing coughing, chest tightness, and pulmonary edema.
Skin contact: Long term exposure to unprotected skin may lead to contact dermatitis, manifested as erythema, blisters, and flaking.
Eye contact: Direct contact with the eyes may cause conjunctivitis, corneal damage, and in severe cases, vision loss.
Environmental exposure
Water pollution: 5-Chloro-2-Pyridine may enter the environment through industrial wastewater discharge, causing acute toxicity to aquatic organisms such as fish and algae.
Food chain enrichment: This compound may accumulate in organisms and be transmitted to humans through the food chain, increasing the risk of long-term low-dose exposure.
Special focus on adverse reactions of 5-Chloro-2-Pyridine amine
Potential risks of long-term low-dose exposure
Although 5-Chloro-2-Pyridine has high acute toxicity, long-term low-dose exposure may cause chronic toxic effects such as liver fibrosis, kidney damage, and immune system suppression.
Animal experiments have shown that rats given low doses (10 mg/kg/d) of 5-chloro-2-pyridamine for six consecutive months exhibit fibrotic lesions in their liver tissue, suggesting its potential carcinogenic potential.
Synergistic toxicity with other substances
5-Chloro-2-pyridamine may exhibit synergistic toxicity with other chemicals such as heavy metals and organic solvents, enhancing damage to living organisms.
For example, combined exposure with benzo [a] pyrene can significantly increase the incidence of lung cancer in mice.
Sensitivity of special populations
Children and pregnant women: Due to its reproductive and developmental toxicity, pregnant women and children are more sensitive to 5-Chloro-2-Pyridine and should avoid contact.
Elderly people: Elderly people have decreased liver and kidney function, reduced metabolism and excretion ability of 5-chloro-2-pyridamine, and are prone to accumulation poisoning.
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