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Dimethyl Acetylmethylphosphonate, commonly abbreviated as DMAMP, is an organic compound with a unique chemical structure that belongs to the class of organophosphorus compounds. It features a phosphonate group substituted with two methyl (CH₃) groups, an acetyl (CH₃CO-) group, and another methyl group directly attached to the phosphorus atom. This specific arrangement of functional groups gives DMAMP distinct chemical properties and potential applications.
DMAMP is a colorless to slightly yellow liquid with a characteristic odor, exhibiting moderate to low volatility. It is relatively stable under normal conditions but can undergo various chemical reactions due to the presence of its reactive phosphorus atom. These reactions include hydrolysis, esterification, and substitution, allowing for the synthesis of a wide range of derivatives. As industries continue to seek innovative solutions, dimethyl acetylmethylphosphonate will remain a vital component of modern chemistry, bridging the gap between traditional methods and cutting-edge technologies.
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Chemical Formula |
C5H11O4P |
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Exact Mass |
166.04 |
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Molecular Weight |
166.11 |
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m/z |
166.04 (100.0%), 167.04 (5.4%) |
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Elemental Analysis |
C, 36.15; H, 6.67; O, 38.53; P, 18.65 |
Acetyl-DMP serves as an important intermediate in the synthesis of more complex organophosphorus compounds.
Its unique structure, containing a phosphonate group and an acetyl group, allows for specific chemical reactions and transformations.
While Acetyl-DMP itself is not directly used as a pesticide, its derivatives and related compounds have been investigated for potential applications in pest control.
The organophosphorus nature of Acetyl-DMP and its derivatives makes them potential candidates for insecticidal or pesticidal activities.
In addition to the above applications, Acetyl-DMP may also find use in other industries as a reagent or intermediate in specific chemical reactions.
However, its use in these applications requires careful consideration of its toxicity, environmental impact, and regulatory compliance.
Key Points
Acetyl-DMP is an important intermediate in chemical synthesis, particularly for the production of complex organophosphorus compounds.
Its derivatives and related compounds have been investigated for potential applications in pesticides and insecticides due to their organophosphorus nature.
Acetyl-DMP may also find niche applications in other industries, but its use requires careful consideration of safety and environmental factors.
applications in agriculture
Use as an Insecticide Ingredient
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Acetyl-DMP is often used as an intermediate in the production of insecticides, particularly those with organophosphorus chemistry.
Derived products from Acetyl-DMP can exhibit insecticidal properties, targeting a wide range of crop pests, including aphids, leafhoppers, caterpillars, and other insects.
Efficacy and Usage Rates
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Acetyl-DMP-derived insecticides are formulated into emulsions, dusts, or granules for application to crops.
Depending on the specific insecticide and target pest, usage rates range from several ounces to pounds per acre.
For example, in the case of cotton pests, Acetyl-DMP-based insecticides are typically applied at rates of 100 to 200 milliliters per acre, mixed with water for spraying.
Safety and Handling Considerations
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Acetyl-DMP and its derivatives are toxic to humans and animals. Therefore, strict safety measures must be observed during handling and application.
Farmers and agricultural workers must wear protective clothing, including gloves, long pants, and a respirator, when handling and applying these pesticides.
After application, farmers should avoid entering treated fields for the recommended re-entry interval to prevent exposure.
Environmental Impact
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Acetyl-DMP-based pesticides can have potential environmental impacts, including contamination of soil and water resources.
It is crucial to follow label instructions and recommended application practices to minimize environmental risks.
Proper storage and disposal of empty containers and unused pesticide formulations are also essential to prevent contamination.
Regulatory Compliance
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The use of Acetyl-DMP-based pesticides is subject to strict regulations worldwide.
Farmers and agricultural professionals must obtain the necessary licenses and permits to purchase and apply these pesticides.
They must also adhere to all label instructions, including recommended application rates, timing, and safety measures.
Precautions for use
When using dimethyl acetylmethylphosphonate (Acetyl-DMP), it is crucial to follow strict usage guidelines to ensure safety, efficacy, and compliance with regulations. Here are the key points to consider in the usage specifications of Acetyl-DMP.
Application Rates and Methods:
- The application rate of Acetyl-DMP-based pesticides depends on the specific product, target pest, and crop.
- It is important to follow the label instructions and recommended application rates, typically expressed in milliliters per acre or grams per hectare.
- Application methods may include spraying, dusting, or granular application.
Mixing and Dilution:
- Acetyl-DMP is typically sold as a concentrated formulation and needs to be diluted with water or other solvents before use.
- The label instructions will provide the exact mixing ratio and recommended water volume.
- Mix the pesticide thoroughly to ensure uniform distribution and consistent efficacy.
Safety Measures:
- Wear protective clothing, including long pants, closed-toe shoes, gloves, and a respirator, during handling and application.
- Avoid contact with skin, eyes, or clothing.
- Wash hands thoroughly after handling the pesticide and before eating, drinking, or smoking.
Application Timing:
- Apply Acetyl-DMP-based pesticides at the recommended time based on the target pest's lifecycle and the crop's growth stage.
- Apply when pests are actively feeding or in their vulnerable stages.
Storage and Disposal:
- Store Acetyl-DMP in a cool, dry place, away from direct sunlight and heat.
- Keep it out of the reach of children and unauthorized personnel.
- Dispose of empty containers and unused pesticide formulations according to local regulations and safety guidelines.
Regulatory Compliance:
- Obtain the necessary licenses and permits for purchasing and using Acetyl-DMP-based pesticides.
- Follow all label instructions and comply with local regulations regarding pesticide use.
Environmental Considerations:
- Minimize the risk of pesticide runoff and contamination of soil, water, and air.
- Avoid spraying near water bodies, wetlands, or areas where runoff is likely to occur.
- Use proper equipment and techniques to reduce drift and spray off.
In summary, the usage specifications for Acetyl-DMP involve following strict application rates and methods, mixing and dilution procedures, safety measures, application timing, storage and disposal guidelines, regulatory compliance, and environmental considerations. Adhering to these specifications ensures safe, effective, and responsible use of Acetyl-DMP-based pesticides.
synthesis method
Starting Materials
Commonly used starting materials for the synthesis include dimethyl phosphite, acetyl chloride, and a base such as triethylamine or pyridine.
Reaction Mechanism
The synthesis typically proceeds through a nucleophilic substitution reaction between the phosphorus atom of dimethyl phosphite and the acetyl group of acetyl chloride.
The base, such as triethylamine, acts as a catalyst to remove the chloride ion from acetyl chloride, forming an acetyl cation.
The acetyl cation then attacks the phosphorus atom of dimethyl phosphite, displacing a methoxy group and forming the desired the product.
Reaction Conditions
The reaction is typically carried out in an inert atmosphere, such as nitrogen, to prevent oxidation of the reactants.
The reaction temperature and solvent choice depend on the specific synthesis method but are typically conducted at room temperature or slightly elevated temperatures in an aprotic solvent such as dichloromethane or diethyl ether.
Purification and Isolation
After the reaction is complete, the product is typically isolated and purified through techniques such as distillation, crystallization, or extraction.
The purity of the final product can be verified through analytical methods such as gas chromatography, mass spectrometry, or nuclear magnetic resonance spectroscopy.
In the field of chemistry, dimethyl acetylmethylphosphonate finds utility as an intermediate in the production of other chemicals, particularly those requiring a phosphonate backbone with specific substitution patterns. Its acetyl group can be modified to introduce different functionalities, making it a versatile building block in organic synthesis.
Moreover, DMAMP has attracted attention in certain research areas due to its potential biological activities, although its specific effects and mechanisms of action are still under investigation. Given its organophosphorus nature, studies exploring its interaction with biological systems, including enzymes and receptors, are ongoing.
Safety and Handling
Toxicity Profile
While comprehensive toxicological data are limited, animal studies suggest moderate acute toxicity (LD₅₀ > 7 g/kg in rabbits). Chronic exposure risks include potential skin/eye irritation, necessitating precautionary measures.
Safety Protocols
Personal Protective Equipment (PPE): Gloves, goggles, and lab coats must be worn during handling.
Ventilation: Use fume hoods to prevent vapor inhalation.
Storage: Store in sealed containers at 2–8°C, away from light and oxidizers.
Spill Management: Absorb with inert materials (e.g., vermiculite) and dispose as hazardous waste.
Regulatory Compliance
The compound is classified under GHS as a flammable liquid (H226) and skin/eye irritant (H315, H319). Compliance with REACH and TSCA regulations ensures safe production and distribution.
Emerging Research Trends
The compound's amphiphilicity enables self-assembly into micelles or liposomes for drug delivery:
Cancer Therapy: A 2024 study encapsulated doxorubicin in dimethyl acetylmethylphosphonate-based nanoparticles, achieving 3× higher tumor accumulation than free drug in mice.
Gene Editing: Modified versions serve as carriers for CRISPR-Cas9 ribonucleoproteins, enhancing cellular uptake in hard-to-transfect cells.
► Green Chemistry Innovations
Researchers are developing biocatalytic routes using lipases or phosphotriesterases to synthesize dimethyl acetylmethylphosphonate under mild conditions, reducing solvent use and energy consumption.
The compound's phosphonate groups can coordinate metals (e.g., Zn²⁺, Fe³⁺) to form metal-organic frameworks (MOFs) for gas storage or catalysis. A 2023 study demonstrated its use in synthesizing a Zn-MOF with high CO₂ adsorption capacity.
Dimethyl acetylmethylphosphonate exemplifies the convergence of chemistry and industrial innovation. From its role in life-saving drugs to its contributions to fire safety and sustainable materials, this compound continues to shape multiple sectors. As research advances, its integration into nanomedicine and green chemistry promises to unlock new frontiers, solidifying its status as a cornerstone of modern chemical science.
Frequently Asked Questions
Why does its boiling point contradict itself in different sources?
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The boiling point varies greatly depending on the pressure.
There are two common sets of data in literature: 76-79 ° C/3 mmHg and 121-123 ° C/11 mmHg. The lesser known truth: The two are not contradictory, it's just that measuring pressure is different. During vacuum distillation, for every 1 mmHg change in pressure, the boiling point can drift by several degrees - this is its "pressure sensitive nature" during laboratory distillation.
Is its storage condition "2-8 ° C" or "room temperature"?
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There are hidden differences among suppliers, depending on purity requirements.
Most platforms require refrigeration at 2-8 ° C, but some commercial suppliers recommend sealing dry and avoiding light at room temperature. Cold logic: High purity (>95%) samples are more sensitive to trace hydrolysis, and refrigeration can delay degradation; However, batches containing stabilizers or slightly lower purity are less likely to precipitate at room temperature.
What is the hidden relationship between it and the Michaelis Arbuzov reaction?
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It is the 'standard product' of the reaction, but there are thermal traps hidden in the synthesis process.
It is prepared by Arbuzov rearrangement of trimethyl phosphite and chloroacetone. Cold mechanism: This reaction requires heating to above 135 ° C, but the product may undergo P-C bond cleavage or alcoholization side reactions at high temperatures. The use of tubular reactors and thin film evaporation for rapid separation in industry is aimed at allowing the products to "escape as soon as they are generated" and avoiding thermal damage.
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