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Dimethylphosphine Oxide (DMPO) is an important organic phosphorus compound, with the molecular formula (CH₃)₂P(O)H. It can be regarded as a derivative of phosphorus oxide (PH₃O) in which two hydrogen atoms have been replaced by methyl groups. The core structural feature of this molecule is its highly polar phosphorus-oxygen double bond (P=O), which has a high bond energy and strong polarity. This bond not only endows the compound with extremely high thermal stability and a high boiling point, but also makes it soluble in water and various polar organic solvents. The molecule as a whole has a tetrahedral configuration. Due to the strong electronegativity of the oxygen atom, the phosphorus atom carries a significant partial positive charge, while the hydrogen atom directly connected to it exhibits unique reactivity, enabling it to act as both a hydrogen bond donor and a receptor. This unique electronic structure makes it an excellent Lewis base and ligand, particularly outstanding in forming stable complexes with transition metals. Therefore, it is widely used in homogeneous catalysis for the preparation of various phosphorus ligands. Additionally, it is a key intermediate in organic synthesis, applied in the synthesis of phosphorus-containing drugs, flame retardants, and functional materials. Its significant polarity also makes it suitable as an analytical solvent or reference substance in nuclear magnetic resonance (NMR) studies.
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Chemical Formula |
C2H7OP, |
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Exact Mass |
78.05 |
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Molecular Weight |
78.05 |
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m/z |
78.02 (100.0%), 79.03 (2.2%) |
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Elemental Analysis |
C, 30.78; H, 9.04; O, 20.50; P, 39.68 |
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Additional information of chemical compound: Boiling point 65-67 °C(Press: 6 Torr), Storage conditions Keep in dark place, Inert atmosphere,2-8°C, Appearence Liquid, Color white solid to light yellow, Sensibility Air sensitive.
It molecules contain strong P=O bonds, which have high electronegativity, giving them a certain degree of polarity. Therefore, the solubility of this substance is higher in polar solvents, while it is lower in non-polar solvents. The electronegativity of the P=O bond is high, and it is easily oxidized by oxygen to form oxides, thereby affecting the chemical properties and stability of dimethyl phosphine oxide. Therefore, when using this compound, it is necessary to avoid contact with air and store it in a dry and sealed container.
Dimethylphosphine oxide, also known as 2-cyano-3,3-diphenylacrylate isooctyl ester, is an oil soluble ultraviolet absorber widely used in various fields.
Organic synthesis field
In the field of organic synthesis, as an organic phosphine compound, it has a wide range of applications.
Intermediate application:
It is a key intermediate in various organic synthesis reactions. The P=O bond in its molecule has a high electronegativity, which makes the substance more soluble in polar solvents and easier to participate in various nucleophilic substitution, addition and other reactions.
For example, in the synthesis of certain organic compounds containing phosphines, they can be used as starting materials to introduce phosphonyl groups through a series of reactions, thereby obtaining the target product.
Synthesis of phosphine ligands:
In the synthesis of organic phosphine ligands, phosphonyl groups can be introduced through reactions for the preparation of chiral catalysts, metal complexes, etc. These ligands play an important role in asymmetric synthesis, improving the stereoselectivity and yield of the reaction.
Functional material modification:
As a structural modifier for organic functional materials containing phosphine, it can improve the polarity, solubility, and other properties of the material. By introducing the structure of dimethyl phosphine oxide, the potential applications of materials in fields such as electronics and optics can be enhanced.
Medical field
In the field of medicine, dimethyl phosphine oxide and its derivatives are mainly used in drug synthesis and local drug formulations.
Drug intermediates:
It is an intermediate for synthesizing certain anti-cancer and antiviral drugs. For example, ARIAD Pharmaceutical Company used it to prepare the new lymphoma drug Brigatinib. By introducing the structure of dimethyl phosphine oxide, the activity and selectivity of the drug have been improved.
Specifically, brigatinib is a second-generation anaplastic lymphoma kinase (ALK) inhibitor that has been approved in multiple countries and regions for the treatment of ALK positive non-small cell lung cancer.
Hydrogen bond receptor:
As a hydrogen bond receptor, it can participate in the interaction between drug molecules and receptor proteins. By introducing phosphine oxide structure, the LogD value of the compound can be significantly reduced, solubility and metabolic stability can be increased.
For example, in the modification of antihypertensive drugs such as prazosin, the introduction of phosphine oxide structures can greatly improve their water solubility while maintaining drug activity.
Free radical capture:
Has strong ability to capture free radicals. Free radicals are a type of chemical substance with unpaired electrons that play an important role in chemical reactions. By reacting with free radicals, the number of free radicals can be effectively reduced, thereby altering the process and products of the reaction.
This characteristic makes it potentially applicable in the development of antioxidant and anti-inflammatory drugs.
Industrial applications
In the industrial field, DIMETHYLPHOSPHINE OXIDE is mainly used as an intermediate for UV absorbers or flame retardants in materials such as plastics, coatings, and dyes.
Plastics and Coatings:
As an intermediate for UV absorbers or flame retardants, it can be used to prepare high-performance plastics and coatings, enhancing their weather resistance and flame retardancy.
For example, adding bis (2-carboxyethyl) methyl phosphine oxide (CEMPO) to flame-retardant PA66 plastic can significantly improve the material's flame retardant rating.
Dyes and fragrances:
In the dye industry, participate in the synthesis of certain acidic dyes and functional dyes. These dyes have good color fastness and vividness, which can meet the needs of different fields.
In the spice industry, the derivatives of this substance can be used to prepare special essence. These essence have unique fragrance and lasting fragrance effect, which can enhance the added value of the product.
Catalyst preparation:
Ligands that can be used to prepare metal catalysts. By introducing phosphonyl groups, the activity and selectivity of catalysts can be enhanced, thus playing an important role in fields such as petrochemicals and fine chemicals.
Agriculture and Environmental Protection
In the fields of agriculture and environmental protection, applications are gradually receiving attention.
Pesticide synthesis:
Derivatives of dimethyl phosphine oxide can be used for the synthesis of insecticides, fungicides, and other pesticides. These pesticides have good insecticidal and bactericidal effects, which can improve the disease and pest resistance of crops, thereby ensuring food security and agricultural product quality.
Environmental Protection Treatment:
Can be used for the removal of heavy metal ions in wastewater treatment. Due to its unique structural characteristics, it can undergo complexation reactions with heavy metal ions, forming precipitates that are easy to remove from wastewater.
In addition, it can also be used as a photocatalyst to degrade organic pollutants. Under light conditions, active oxygen species with strong oxidizing properties can be generated to oxidize and decompose organic pollutants into harmless substances.
It is produced by hydrolysis of chlordimethylphosphine:
Me2PCl + H2O→Me2P(O)H + HCl
Methanol instead of ethanol can also be used instead of water, and the byproduct is chloromethane.
DMHO is used as an intermediate in organic synthesis, such OLED.
At room temperature, slowly drip sodium bis (trimethylsilyl) amide (solution in dried tetrahydrofuran) into a degassed solution of dimethyl phosphine oxide (50 mg, 0.64 mmol) in dried tetrahydrofuran while stirring. Then stir the obtained reaction mixture at room temperature for 15 minutes. The observed solution became turbid due to the formation of phosphonyl anions. Slowly adding a mixed solution of 5-chloro-6- (chloromethyl) benzo [d] [1,3] dioxane (119.4 mg, 0.58 mmol) in dry tetrahydrofuran to the phosphonyl anion mixture, a white precipitate can be observed slowly forming in the reaction mixture. Stir the reaction mixture at room temperature for 16 hours, then add an equal amount of water to the reaction mixture to quench it. Extract the mixture five times with equal volume of dichloromethane, dry and filter the combined organic matter on Na2SO4, and concentrate the resulting filtrate under vacuum to remove the solvent. The target product can be obtained by cleaning the residue with chloroform/n-hexane to remove impurities and salts.
Remark: BLOOM TECH(Since 2008), ACHIEVE CHEM-TECH is the subsidiary of us.
Dimethylphosphine oxide is an organic compound with multiple uses.
When synthesizing dimethyl phosphine oxide, the following two methods are usually used:
1. Methyl oxidation method
Methyl oxidation method is a commonly used method for synthesizing dimethyl phosphine oxide. This method involves reacting methanol and oxygen under the action of a catalyst to produce formaldehyde, which then reacts with sulfur trioxide to produce dimethyl phosphine oxide. The reaction equation is as follows:
2CH3OH + O2 → 2HCHO + H2O
2HCHO + SO3 → CH3OCH2O2SO3H
The main reaction conditions of this method are acidic environments, so sulfuric acid needs to be added as a catalyst during the reaction process. However, excessive sulfuric acid can inhibit the reaction, so it is necessary to control the amount of sulfuric acid used. In addition, the price of methanol is relatively low, so this method is more economical.
2. Oxidation phosphating method
Oxidative phosphating method is another method for synthesizing dimethyl phosphine oxide. This method involves reacting trichloromethane with phosphorus pentoxide in a solvent to produce dimethyl phosphine oxide. The reaction equation is as follows:
PCl3+2CHCl3 → CH3OCH2OPOCl2+2HCl
The main advantages of this method are mild reaction conditions and easy operation. Meanwhile, the price of trichloromethane is relatively low, which is beneficial for reducing production costs. However, phosphorus pentoxide has high toxicity and corrosiveness, so this method requires high requirements for operators and corresponding safety measures need to be taken.
Overall, both methods can be used to synthesize dimethyl phosphine oxide. The methyl oxidation method reacts in acidic environments with simple operation and low raw material cost; The oxidative phosphating method requires a reaction in anhydrous chloride, with mild operating conditions and relatively low raw material costs. In the actual production process, suitable synthesis methods can be selected based on production needs and equipment conditions. It should also be noted that the waste liquid, exhaust gas, and residue generated by these methods should be treated reasonably to ensure environmental and production safety.
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