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2-Amino-4-methylpyrimidine is an organic compound. It is a colorless to light yellow crystalline solid with no special odor. It is easily soluble in many organic solvents, such as ethanol, methanol, di N-Methylformamide (DMF), dichloromethane, etc. It has a low solubility in water. The refractive index value may vary at different wavelengths. Taking 20 degrees Celsius as an example, its nD value (sodium yellow light, wavelength 589.3 nm) is approximately 1.578. It is combustible. When heated or ignited, it can burn and release products such as carbon dioxide, nitrogen oxides, and water. Stable compounds are relatively stable at room temperature. But it is necessary to avoid contact with strong oxidizing agents.
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Chemical Formula |
C5H7N3 |
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Exact Mass |
109.06 |
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Molecular Weight |
109.13 |
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m/z |
109.06 (100.0%), 110.07 (5.4%), 110.06 (1.1%) |
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Elemental Analysis |
C, 55.03; H, 6.47; N, 38.50 |
Drug synthesis:
2-Amino-4 methylpyrimidine is an important intermediate for many important drugs. It can be used as the starting material for the synthesis of anticancer drugs such as Fluorouracil and Sunitinib. In addition, it can also be used to synthesize Antiviral drug and antibacterial drugs, such as HIV Reverse-transcriptase inhibitor.
Pesticide synthesis:
It can be used as an intermediate for the preparation of various pesticides, such as pyrimidine pesticides (such as pyrimidin and pyrimidin). These pesticides are widely used for crop protection and have good insecticidal and fungicidal activity against various pests and pathogens.
Sunscreen:
The amino groups in 2-Amino-4 methylpyridine have the ability to absorb ultraviolet rays, making them widely used in sunscreens. It can absorb ultraviolet B (UVB) and some ultraviolet A (UVA), playing a role in protecting the skin from UV damage.
Dye synthesis:
Due to the unique structural properties of 2-Amino-4 methylpyridine, it can be used to prepare dyes with fluorescence or pigment properties. These dyes are widely used in fields such as textiles, ink, and ink.
Polymer material synthesis:
2-Amino-4 methylpyridine can be used as a crosslinking agent or functional monomer for the synthesis of polymers and polymer materials. By reacting with other compounds, polymer materials can be formed, such as polyamide, polyimide and polyurethane. These polymer materials have important application value in fields such as plastics, coatings, adhesives, etc.
Optical and liquid crystal materials:
2-Amino-4 methylpyridine can be used as a precursor for synthesizing optical and liquid crystal materials. Its derivatives are commonly used in the preparation of optical polymers, liquid crystal displays, etc., and have excellent optical and electrochemical properties.
Chemical analysis:
2-Amino-4 methylpyridine can be used as a reagent in chemical analysis to analyze and determine the content, concentration, and properties of different substances. It is widely used in fields such as drug analysis, environmental monitoring, and food safety.
Other applications:
2-Amino-4 methylpyridine can also be used to prepare flexible electronic devices, optoelectronic devices, and functional materials. In addition, due to its unique chemical structure, it also has some potential applications, such as battery materials, photocatalysts, etc.
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Applications in Drug Synthesis
2-Amino-4-methylpyrimidine can serve as a crucial intermediate in the synthesis of heterocyclic compounds, which are often found in various pharmacological agents.
Its amino and pyrimidine rings provide reactive sites for further chemical modifications, enabling the creation of a diverse range of derivatives with potential therapeutic activities.
Certain derivatives have shown antiviral activities, particularly against certain viruses by inhibiting their replication processes.
These compounds can be further optimized to enhance their antiviral efficacy and reduce side effects, making them promising candidates for antiviral drug development.
Some research has indicated that specific modifications can lead to compounds with anticancer properties.
These compounds may target specific molecular pathways involved in cancer cell proliferation and survival, thereby inhibiting cancer progression.
Due to its ability to interact with neurotransmitter receptors and ion channels, it and its derivatives have potential applications in the development of drugs for central nervous system disorders.
These compounds may regulate neuronal activity and improve symptoms associated with conditions such as anxiety, depression, and pain.
Besides the aforementioned applications, it may also find uses in the synthesis of drugs for other therapeutic areas, such as cardiovascular disease, inflammation, and infectious diseases.
Its chemical versatility allows for the creation of a wide range of derivatives with different pharmacological profiles, making it a valuable tool in drug discovery and development.
experimental research case
Research on 2-Amino-4-methylpyrimidine has been extensive, with various synthetic and structural studies conducted. One notable case is the synthesis and structural characterization of a series of metal complexes with this compound. In this study, researchers prepared a range of silver (I) and copper (II) complexes by reacting it (amp) with metal salts in methanol solution. The resulting complexes were then characterized using X-ray crystallography, FT-IR, and 1H-NMR spectra. These complexes exhibited unique structural features, with the molecules interlinked through self-complementary double hydrogen bondings to form one-dimensional molecular chains.
Another research case focused on the synthesis of zinc compounds with it. In this study, a series of zinc compounds were prepared and structurally characterized by X-ray crystallography. The compounds exhibited tetrahedral geometries, with the central zinc atom coordinated by two organic ligands and two anions. The molecules were linked through various interactions, such as C–H---X, N–H---X, N–H---N, and π–π stacking, to form two-dimensional structures.
2-Amino-4-methylpyrimidine is an organic compound belonging to the pyrimidine family of heterocyclic molecules. It features a pyrimidine ring structure where the nitrogen atoms occupy positions 1 and 3, while the carbon atoms form the rest of the ring. The specific substitution pattern in it includes an amino group (-NH2) at the 2-position and a methyl group (-CH3) at the 4-position.
This compound exhibits distinct chemical properties, including its ability to form hydrogen bonds through the amino group, which enhances its solubility in polar solvents. The presence of the methyl group influences its physical properties and reactivity, often providing stability and modifying electronic properties.
In the realm of synthetic chemistry, it serves as a valuable intermediate in the preparation of various pharmaceuticals, agrochemicals, and other specialized chemicals. Its versatile structure allows for further derivatization, such as alkylation, arylation, or acylation, to yield a broad spectrum of functionalized pyrimidine derivatives.
Moreover, due to its pyrimidine scaffold, it finds applications in the development of nucleotide analogs and bioconjugates for research purposes in biology and medicine. Its potential as a building block in drug discovery is continually being explored, particularly in areas like anticancer and antiviral therapies.
How to reduce the side effects of this compound?
Measures and suggestions to reduce side effects
To reduce its side effects and potential risks, the following are some measures and suggestions:
- Strengthen research and evaluation: Increase research and development efforts on it, gain a deeper understanding of its chemical properties, biological activity, and toxicological characteristics. At the same time, conduct comprehensive security assessments to provide scientific basis for its safe use in various fields.
- Strict use and management: When using, it is necessary to strictly follow the instructions in the manual to avoid excessive use or abuse. At the same time, strengthen safety management during storage, transportation, and use to ensure that no safety accidents occur.
- Take environmental protection measures: Appropriate environmental protection measures should be taken during use and disposal to avoid pollution to water resources, soil environment, and ecosystems. For example, measures such as wastewater treatment and soil remediation can be taken to reduce its impact on the environment.
- Strengthen monitoring and early warning: Establish a monitoring and early warning mechanism for it, timely discover and deal with potential safety hazards. For example, regular monitoring and analysis of the usage environment can be conducted to assess potential risks and take necessary response measures.
- Carry out science popularization propaganda: Strengthen the science popularization propaganda work on this substance, and enhance the public's awareness and understanding of it. Through popular science promotion, public awareness of safety and environmental protection can be enhanced, thereby reducing the potential risks that may arise during use.
Emergency response measures
- Develop emergency plans: Develop detailed emergency plans, including emergency response procedures, emergency material preparation, emergency personnel training, etc. Regularly conduct emergency drills to improve emergency response capabilities and levels.
- Mastering first aid knowledge: Understand and master the first aid knowledge of 2-amino-4-methylpyrimidine poisoning, such as first aid measures for skin contact, eye contact, inhalation, and ingestion.
Training and supervision
- Train: Provide safety training for researchers and users to understand the properties, hazards, and safe operating procedures of 2-amino-4-methylpyrimidine. Enhance the security awareness and operational skills of researchers and users.
- Regulatory supervision: Establish and improve safety supervision mechanisms to regulate the use, storage, and transportation of 2-amino-4-methylpyrimidine.Regularly inspect and evaluate the safety operations of researchers and users to ensure the effective implementation of various safety measures.
Safety Assessment
Acute Toxicity Data
The LD50 for intravenous injection in rats is 730 mg/kg, indicating that the acute toxicity is at a moderate level. During operation, direct skin contact or inhalation of dust should be avoided. It is recommended to wear a gas mask, goggles and protective gloves, and conduct the experiment in a fume hood.
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Skin and Eye Irritation
This compound is classified as a skin irritant (category 2) and an eye severe irritant (category 2A). If skin contact occurs, it is necessary to immediately rinse with a large amount of soapy water; if eye contact occurs, it is necessary to rinse with flowing water for at least 15 minutes and seek medical assistance.
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Respiratory Protection
Inhalation of dust or vapor may cause respiratory irritation. The operation site should be equipped with a local exhaust system and the concentration of the compound in the air should be regularly detected to ensure it is below the occupational exposure limit (currently there is no clear OEL, it is recommended to refer to the 10 mg/m³ short-term exposure limit for similar pyrimidine compounds).
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Environmental Hazards
It has mild toxicity to aquatic organisms and leakage to water sources should be avoided. Waste disposal should follow the Basel Convention and be handled by professional institutions through incineration (the incineration temperature should be ≥ 1200°C to ensure complete decomposition).
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Stability Analysis
Physical Stability
At room temperature (25°C) and in a dry environment, 2-amino-4-methylpyrimidine can be stably stored for at least 2 years. Its melting point is 158-160°C and its boiling point is 283.4 ± 33.0°C, indicating that it is not prone to decomposition under routine experimental conditions. However, note:
Light Sensitivity: Long-term exposure to ultraviolet light may lead to isomerization, and it is recommended to store it in a dark place.
Thermal Stability: A deamination reaction may occur above 150°C, generating 4-methylpyrimidine, and the heating temperature should be strictly controlled.
Chemical Stability
Oxidant Reaction: Contact with strong oxidants (such as potassium permanganate, hydrogen peroxide) may trigger a violent reaction, and the compound should be stored separately and kept away from such substances.
Acid and Base Stability: It is stable within the pH range of 4-9, but it may hydrolyze in strong acids (pH < 2) or strong bases (pH > 12), generating 2-amino pyrimidine and formic acid.
Metal Ion Influence: Contact with transition metal ions such as copper and iron may form complexes, reducing the compound's activity. It is recommended to store it in glass or polyethylene containers.
Optimized Storage Conditions
Temperature: The optimal storage temperature is 2-8°C, which can significantly extend the shelf life to more than 3 years.
Humidity: Relative humidity should be kept below 60% to prevent moisture absorption and caking.
Packaging: Use double-layer sealed packaging (inner layer is an aluminum foil bag, outer layer is a high-density polyethylene barrel), which can effectively block moisture and oxygen.
Risk Control Measures
Operation Specifications
Use a negative pressure weighing hood during weighing to avoid dust dispersion.
When transferring liquids, use inert gas protection (such as nitrogen) to reduce the risk of oxidation.
After the experiment, all equipment that has come into contact with the compound should be soaked in 5% sodium bicarbonate solution and then cleaned.
Emergency Handling of Leakage
Small-scale leakage: Cover with adsorption cotton (such as diatomaceous earth) and collect for professional disposal.
Large-scale leakage: Build a dike, use a non-explosive pump to transfer to a tanker, and spray disinfectant with hypochlorous acid solution on site.
Personal Protective Equipment (PPE)
Basic Protection: N95 mask, chemical protective goggles, nitrile gloves.
Advanced Protection (large-scale operation): A-level chemical protective suit, positive pressure air respirator.
Stability Cases in Industry Applications
In the pharmaceutical industry, 2-amino-4-methylpyrimidine is often used in the synthesis of antiviral drug precursors. A certain enterprise optimized the storage conditions (temperature 4°C, humidity 30%) and increased the purity of the raw material drug from 98.5% to 99.2%, and reduced the content of deamination products in the impurity spectrum from 0.8% to 0.1%, significantly improving product quality.
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