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4-Amino-2-chloropyridine is an important bifunctional pyridine derivative and an organic synthetic building block. Its structural feature lies in the presence of an amino group (-NH₂) at the 4th position of the pyridine ring and a chlorine atom (-Cl) at the 2nd position. This unique substitution pattern endows the molecule with unique reactivity: the chlorine atom acts as a good leaving group and can undergo nucleophilic substitution reactions (such as with alcohols, amines), or participate in palladium-catalyzed cross-coupling reactions (such as Suzuki, Buchwald-Hartwig couplings), efficiently constructing carbon-carbon or carbon-heteroatom bonds; at the same time, the amine group at the para position has electron-donating effect and nucleophilicity, which can regulate the electron cloud density of the ring, enhance the reactivity of the adjacent chlorine, and directly participate in transformations such as acylation, diazotization, etc., or combine with metal ions as a coordination site. Due to the specific relative positions of the amino group and the chlorine atom, the two can synergistically participate in heterocyclic synthesis (such as constructing a tetracyclic system). This compound is therefore widely used in the design and preparation of pharmaceutical intermediates (especially for the synthesis of antibiotics, anti-tumor drugs), pesticide molecules, and functional materials, and is a key starting material for the development of nitrogen-containing heterocyclic bioactive molecules.
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Chemical Formula |
C5H5ClN2 |
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Exact Mass |
128 |
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Molecular Weight |
129 |
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m/z |
128 (100.0%), 130 (32.0%), 129 (5.4%), 131 (1.7%) |
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Elemental Analysis |
C, 46.71; H, 3.92; Cl, 27.57; N, 21.79 |
4-Amino-2-chloropyridine is an important organic intermediate with a wide range of applications.
1. Pesticide field: it can be used in the manufacture of pesticides such as insecticides, fungicides and herbicides.
2. Dye field: it can be used to synthesize some organic dyes and pigments.
3. Other fields: it can also be used to synthesize polymer materials, electronic materials, catalysts, etc.
4. Pharmaceutical field: it can be used to synthesize some important drugs, such as Lomefloxacin, Enoxacin, Nimesulide, etc.
It should be noted that due to the high toxicity of it necessary safety measures should be taken when using it.
4-Amino-2-chloropyridine, its main uses include the following aspects:
Pharmaceutical intermediates
Treatment of neurological diseases: It has a wide range of applications in the treatment of neurological diseases such as multiple sclerosis.
Broad spectrum antibiotics: 4-Amino-2-chloropyridine is also used as a broad-spectrum antibiotic and can be used to treat various infectious diseases, such as urinary tract infections, intestinal infections, respiratory infections, and skin and soft tissue infections. In addition, it can also be used to treat some gastrointestinal diseases, such as gastritis.
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Pesticide intermediates
As a synthetic raw material or intermediate for pesticides, 4-Amino-2-chloropyridine also plays an important role in the field of pesticide manufacturing. It can participate in the synthesis process of various pesticides, providing effective support for agricultural production.
02
Pigment intermediates
In the pigment industry, 4-Amino-2-chromopyridine is also an important synthetic raw material or intermediate. It can participate in the synthesis process of pigments, improve the performance and quality of pigments, and meet the demand for pigments in different fields.
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Other applications
4-Amino-2-clonopyridine is also an intermediate of the plant growth regulator chlorpropiramine, indicating its broad application prospects in the agricultural field.
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The main applications of 4-Amino-2-chloropyridine are extensive, including the following aspects:
Pharmaceutical field
Drug synthesis: As a synthetic intermediate for various drugs, it plays an important role in drug research and production. Especially for synthesizing compounds with specific pharmacological activities, these compounds may be used to treat neurological diseases, infectious diseases, inflammation, etc.
Antimicrobial agents: Due to their antibacterial activity, 4-Amino-2-chloropyridine or its derivatives may be used to develop new antimicrobial agents for the treatment of various infections caused by bacteria.
01
Pesticide field
Pesticide intermediate: In pesticide manufacturing, it serves as a key raw material or intermediate for synthesizing certain pesticides, helping to produce efficient and low toxicity pesticide products to protect crops from pests and diseases.
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In the field of pigments and dyes
The synthesis of pigments and dyes: Although not as widely used in the fields of medicine and pesticides, 4-Amino-2-chromopyridine may also play a role in the synthesis of certain pigments and dyes, improving their color properties and stability.
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Chemical intermediates
Organic synthesis: As an important raw material or intermediate in organic synthesis, it can participate in various chemical reactions to generate compounds with specific structures and properties, providing support for the development of the chemical industry.
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Other applications
Plant growth regulator: As previously mentioned, it can also serve as an intermediate for the plant growth regulator Chlorpyriprole, used to promote plant growth and development.
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It should be noted that although 4-Amino-2-chloropyridine has multiple potential uses, its potential environmental and health impacts need to be considered in practical applications.
The synthetic route of 4-Amino-2-chloropyridine can be obtained from 2-chloro-4-nitropyridine through multiple steps such as reduction and ammonolysis. The following is one of the synthetic routes and its detailed steps:
1. Add 2-chloro-4-nitropyridine, Fe, and HCl to cyclohexanone, and react under oxygen oxidation to generate 2-chloro-4-nitropyridine-1-oxide.
2. Reduction of 2-chloro-4-nitropyridine-1-oxide to 2-chloro-4-aminopyridine.
3. React 2-chloro-4-aminopyridine and ferric chloride (FeCl3) in sodium hydroxide (NaOH) aqueous solution to generate 4-chloropyridine-2,6-dione.
4. React 4-chloropyridine-2,6-dione with tetrabutyllithium (Bu4NLi) to generate 4-butylpyridine-2,6-dione.
5. React 4-butylpyridine-2,6-dione with ethyl benzoate in sodium hydroxide (NaOH) aqueous solution to produce ethyl 4-butylpyridine-2,6-dione-4-carboxylate .
6. React ethyl 4-butylpyridine-2,6-dione-4-carboxylate with sodium hydroxide (NaOH) aqueous solution to generate 4-butylpyridine-2,6-dione-4-carboxylic acid Salt.
7. React 4-butylpyridine-2,6-dione-4-carboxylate with hydrogen chloride (HCl) in ethanol to generate 4-butylpyridine-2,6-dione-4-carboxylate -4-Hydroxy.
8. React 4-butylpyridine-2,6-dione-4-formate-4-hydroxyl with ferrous chloride (FeCl2) and hydrochloric acid (HCl) in ethanol to generate 4-chloro-2- (4-Hydroxy-4-butylpyridine-2,6-dione)pyridine.
9. React 4-chloro-2-(4-hydroxy-4-butylpyridine-2,6-dione)pyridine with ammonia water to generate product. It should be noted that you need to pay attention to safe operation in the above steps.
The discovery history of 4-Amino-2-chloropyridine has not been widely documented and reported. However, based on the name of the substance, it can be speculated that it is most likely obtained by chlorination and amination of pyridine molecules. Pyridine is a common nitrogen-containing heterocyclic compound. Because of its active chemical properties, it is widely used in the fields of medicine, pesticide, dye and so on. Chlorination and amination reactions are one of the common methods for preparing pyridine compounds.
At present, the discovery history and research process of product still need further discussion and research.
4-Amino-2-chloropyridine is an organic compound with aromatic and heterocyclic structure, its chemical properties are mainly manifested in the following aspects:
1. Electrophilic substitution reaction: Chlorine atoms and amino groups in it have certain electrophilicity, so electrophilic substitution reactions, such as substitution reactions and amination reactions, are prone to occur.
2. Oxidation reaction: it is easily oxidized by oxidants, for example, it can react with hydrogen peroxide to generate corresponding chloropyridone derivatives.
3. Reduction reaction: it can undergo a reduction reaction with a reducing agent, such as hydrogen, to generate the corresponding 4-aminopyridine derivative.
4. Alkaline reaction: it is an alkaline compound that can react with acid to generate corresponding hydrochloride or other acid salts.
5. Rearrangement reaction: it can also undergo a rearrangement reaction, such as an epoxidation reaction under acidic conditions to generate the corresponding 4-amino-3-pyridinol.
The reaction properties of 4-Amino-2-chloropyridine are mainly manifested in the following aspects:
1. Substitution reaction: Chlorine atoms and amino groups in it have certain electrophilicity and are prone to substitution reactions, such as nucleophilic substitution reactions with alkyl halides, alkyl halides, etc., to generate corresponding substitute product.
2. Amination reaction: it contains amino groups, which can undergo amination reactions with acid chlorides and acid anhydrides to generate corresponding amides and imides.
3. Condensation reaction: it can undergo condensation reaction with aldehydes or ketones, for example, it can condense with acetone to generate the corresponding pyrido[2,3-d]pyrimidine.
It should be noted that since it is an organic compound with certain toxicity and danger, relevant safety operating procedures should be followed during its production and use to ensure the safety of laboratories and production sites.
Adverse reactions
The manifestations of adverse reactions
Skin reactions
Skin reactions are one of the more common adverse reactions. Contact individuals may experience symptoms such as skin itching, redness, and rash. These symptoms usually appear within hours to days after exposure, and the severity varies from person to person. The occurrence of skin reactions may be related to their direct irritation to the skin and allergic reactions. For individuals with allergies, they may be more prone to severe skin reactions upon contact.
Eye reactions
Eye contact may cause symptoms such as stinging, redness, and tearing of the eyes. These symptoms may affect vision and, in severe cases, may even lead to eye damage. The occurrence of eye reactions is usually caused by direct stimulation of eye tissues. If it accidentally splashes into the eyes during use, rinse immediately with plenty of water and seek medical attention promptly.
Respiratory reactions
Respiratory contact may cause symptoms such as coughing, wheezing, and difficulty breathing. These symptoms may affect respiratory function and, in severe cases, may even lead to suffocation. The occurrence of respiratory reactions may be caused by the inhalation of 4-Amino-2-chloropyridine into the respiratory tract after volatilization, which stimulates and damages the respiratory mucosa. Using in poorly ventilated environments or not taking appropriate protective measures may increase the risk of respiratory reactions.
Systemic reactions
Long term or high-dose exposure may cause systemic reactions such as headache, nausea, vomiting, insomnia, hand tremors, etc. These symptoms may affect the user's daily life and work. The occurrence of systemic reactions may be related to their accumulation in the body and their impact on the nervous system, digestive system, etc.
Factors affecting adverse reactions
Exposure dose
Exposure dose is one of the important factors affecting its adverse reactions. Generally speaking, the higher the exposure dose, the higher the risk of adverse reactions and the more severe the symptoms may be. During production, use, and processing, the exposure dose should be strictly controlled to avoid high-dose exposure.
Contact time
The duration of contact can also affect the occurrence of adverse reactions. Long term exposure may increase the risk of adverse reactions, especially damage to important organs such as the liver and kidneys. Therefore, contact time should be minimized as much as possible, and methods such as shift work should be adopted to reduce the duration of continuous contact.
Individual Differences
Different individuals have varying sensitivities to it. People with allergies, children, pregnant women, elderly and other special populations may be more prone to adverse reactions. Allergic individuals may experience allergic reactions to certain components, leading to severe skin, respiratory, and other symptoms. Children and the elderly have relatively weaker physical functions, poorer tolerance to drugs, and are more susceptible to their effects. Pregnant women are in a special state during pregnancy, and exposure may have adverse effects on the fetus.
Environmental factors
Environmental factors such as temperature, humidity, ventilation conditions, etc. may also affect the adverse reactions of the substance. High temperature and high humidity environments may promote its volatilization, increase its concentration in the air, and thus increase the risk of exposure. A poorly ventilated environment can cause it to accumulate in the air, making it easier for users to inhale and increasing the risk of respiratory reactions.
Preventive measures for adverse reactions
Strengthen personal protection
When using 4-Amino-2-chloropyridine, users should wear appropriate protective equipment such as gloves, goggles, masks, etc. Gloves can prevent direct skin contact with 4-Amino-2-chloropyridine and reduce the occurrence of skin reactions. Goggles can protect the eyes and prevent 4-Amino-2-chloropyridine from splashing into the eyes. Masks can filter out 4-Amino-2-chloropyridine particles in the air, reducing the risk of respiratory inhalation.
Improving the working environment
The workplace should maintain good ventilation conditions and reduce the concentration of 4-Amino-2-chromopyridine in the air. This can be achieved by installing ventilation equipment, strengthening air circulation, and other methods. At the same time, the temperature and humidity in the workplace should be controlled to avoid high temperature and high humidity environments that promote the volatilization of 4-Amino-2-chromopyridine.
Standardized operating procedures
Develop strict operating procedures to ensure proper use by users. Operators should receive professional training, familiarize themselves with its nature, purpose, adverse reactions, and preventive measures. During the operation, it is necessary to strictly follow the operating procedures to avoid any violations.
Strengthen health monitoring
Regular health checks should be conducted on individuals who come into contact with 4-Amino-2-chloropyridine to promptly detect and manage adverse reactions. Health check ups can include skin examination, eye examination, respiratory system examination, liver function examination, kidney function examination, etc. For personnel who experience adverse reactions, timely treatment measures should be taken and job positions should be adjusted to avoid further contact.
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