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Diethyl (2-oxopropyl)phosphonate(Diethyl acetonylphosphonate) is an organophosphonic acid ester compound with specific chemical properties and potential application value. As an organic compound, it has certain volatility and flammability, so it is necessary to take corresponding safety measures during storage and transport, such as keeping away from ignition sources and avoiding high temperature.
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Chemical Formula |
C7H15O4P |
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Molecular Weight |
194.17 |
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Exact Mass |
194.07 |
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m/z |
194.07 (100.0%), 195.07 (7.6%) |
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Elemental Analysis |
C, 43.30; H, 7.79; O, 32.96; P, 15.95 |
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Boiling point |
126 °C9 mm Hg(lit.) |
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Density |
1.01 g/mL at 25 °C(lit.) |
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Storage conditions |
Inert atmosphere,Room Temperature |
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Form |
Liquid |
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Color |
Clear colorless to light yellow |
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Solubility |
Miscible with tetrahydrofuran, ether, dichloromethane and chloroform. |
Diethyl acetonylphosphonate belongs to the class of organophosphonic acid esters. They usually have special chemical properties and biological activities and are important participants in many chemical reactions and biological processes. Organophosphonates can be used as reaction intermediates or raw materials in organic synthesis, participating in various chemical reactions to prepare target products. In addition, they may have specific biological activities or functionalities, such as antibacterial, antiviral, insecticidal, etc., and thus have potential applications in pesticides, pharmaceuticals and other fields.
in Pharmaceutical Applications
Diethyl (2-oxopropyl)phosphonate may serve as a key intermediate in the synthesis of certain drugs. During drug synthesis, it are often used as intermediates to build complex drug molecular structures due to their unique chemical properties and reactivity. Thus, it has the potential to play a role in the synthesis of drug molecules with specific pharmacological activities.
Although specific information is limited, diethyl acetonylphosphonate may have antibacterial, antiviral, antitumour and other biological activities in some cases. These activities may arise from their interaction with specific molecules in the organism, such as binding to enzymes, receptors or DNA. Thus, it has the potential to be used in the pharmaceutical field as a compound candidate or precursor drug for drugs with these biological activities.
3. Drug carriers or modifiers
In drug delivery systems, diethyl acetonylphosphonate are sometimes used as drug carriers or modifiers to improve drug solubility, stability, targeting and other properties. Although there is no direct evidence that it has a specific application in this area, its chemical structure characteristics may give it potential as a drug carrier or modifier.
In biological and medical research, diethyl acetonylphosphonate are sometimes used as research tools, such as probes and markers. These compounds can help scientists better understand and study various biological processes and mechanisms in living organisms. It has the potential to play a similar role in this field.
It is a clear colorless to light yellow liquid. Its boiling point is reported as 126 °C at 9 mmHg (lit.), 129 °C at 9 mmHg, and 98 °C at 1 mmHg. The variation in values is due to measurements at different reduced pressures; under standard atmospheric pressure, its boiling point is not commonly documented, but the low-pressure data reflect its moderate volatility, consistent with the polar phosphonate and carbonyl groups that give rise to moderate intermolecular forces.
The product has a density of 1.01 g/mL at 25 °C (lit.) and a specific gravity of 1.11 (20/20). This places it as a liquid denser than water (1.00 g/mL), a result of the phosphorus atom and polar functional groups (P=O, C=O) that increase molecular packing efficiency. Its density is consistent with other organophosphonate esters and is important for liquid handling, separation, and formulation processes.
The product has a flash point of >110 °C, 113 °C (235 °F), and >230 °F (>110 °C). These values classify it as a low-flammability liquid, with a flash point well above typical ambient temperatures. This low flammability risk simplifies storage and handling, though standard precautions for organic liquids still apply.
Diethyl (2-oxopropyl)phosphonate is miscible with tetrahydrofuran, ether, dichloromethane, and chloroform. It is soluble in most common organic solvents due to its polar phosphonate and carbonyl moieties, which balance lipophilic ethyl groups. While its solubility in water is not fully documented, its polar character suggests moderate miscibility with polar protic/aprotic solvents, making it versatile for organic synthesis and formulation applications.
The product is chemically stable under recommended storage conditions. It should be stored at room temperature, preferably in an inert atmosphere (e.g., nitrogen) and in a cool, dark place (<15 °C) to avoid hydrolysis or oxidation. The compound is resistant to decomposition under normal handling, but prolonged exposure to strong acids, bases, or high temperatures may cause cleavage of the phosphonate ester or carbonyl group. Its stability supports long-term storage and use as a synthetic intermediate without significant degradation.
For the detection, a variety of analytical techniques can be used, the following are some of the commonly used methods:
Chromatography
High Performance Liquid Chromatography (HPLC): HPLC is a commonly used separation and analysis technique for the separation and quantification of components in complex mixtures. By choosing suitable column, mobile phase and detector conditions, it can be accurately detected and quantified.
Gas Chromatography (GC): Although GC is more commonly used for the analysis of more volatile compounds, it may also be an effective method for the detection of low-boiling compounds such as the product. However, since the compound may contain non-volatile phosphonate groups, appropriate derivatisation methods may be required to increase its volatility in practical applications.
Spectroscopic Methods
Infrared spectroscopy (IR): IR spectroscopy provides information on the functional groups in the compound. By comparing the standard IR spectrogram with the IR spectrogram of the sample to be tested, a preliminary judgement can be made as to whether or not the target compound is contained in the sample.
Nuclear Magnetic Resonance Spectroscopy (NMR): NMR spectra can provide information on the interatomic connection mode and spatial structure in the compounds, which is important for determining the structure and purity.
Mass Spectrometry
Mass spectrometry (e.g., GC-MS or LC-MS) can provide information on the molecular weight, molecular formula, and fragment ions of a compound, and is highly accurate for qualitative and quantitative analyses.
(III) Synthesis of Pharmaceuticals and Bioactive Molecules
As a crucial synthetic intermediate, diethyl (2-oxopropyl)phosphonate is widely applied in the preparation of phosphorus-containing drugs, enzyme inhibitors and receptor modulators, leveraging the biocompatibility and targeted binding capacity of phosphonate and carbonyl groups.
Synthesis of phosphorus-containing drugs: It serves for the production of anti-osteoporosis agents and calcitonin-related phosphonic acid drugs, acting as a side-chain precursor for pamidronate disodium.
The HWE reaction is adopted to introduce unsaturated ketone structures, and the phosphonic acid parent nucleus is ultimately obtained via subsequent reduction and hydrolysis.Development of enzyme inhibitors: It is utilized to synthesize matrix metalloproteinase (MMP) inhibitors and angiotensin-converting enzyme (ACE) inhibitors. The phosphonate group mimics the phosphate ester transition state of enzyme substrates, while carbonyl groups form hydrogen bonds with the enzyme active center, thereby significantly enhancing inhibitory activity.
Antitumor and antibacterial molecules: It is used to prepare phosphonate derivatives of nucleoside antitumor drugs to improve water solubility and cellular permeability. It also acts as a key side-chain intermediate for quinolone antibacterial agents; alkyl groups are introduced through enone addition to optimize the antibacterial spectrum and pharmacological activity.
(V) Applications in Materials Chemistry and Fine Chemical Industry
Polymer modifiers: Used as a functional monomer or crosslinking agent, it participates in the synthesis of polyimide, polyester and polyurethane.
The phosphonate moiety endows polymers with outstanding thermal stability, flame retardancy and mechanical strength, making these materials applicable to high-performance fields such as aerospace, electronics and electrical engineering.Organic dyes and photosensitizers: It enables the synthesis of phosphonate-containing enone dyes and photosensitizers, which feature improved light absorption efficiency and light resistance.
These products are widely used in photosensitive resins, solar cell sensitizers and photoresist materials.
Metal surface treatment agents: Phosphonate groups can form strong coordination bonds with metal surfaces (iron, aluminum, copper) to generate dense protective films. It is commonly applied as a metal corrosion inhibitor, rust preventive agent and surface modifier to effectively enhance the corrosion resistance of metallic materials.
The discovery of diethyl acetonylphosphonate is closely linked to the research progress of organophosphorus chemistry and carbonyl phosphonates.
In the mid-20th century, with the maturation of C–P bond construction methods such as the Michaelis-Arbuzov reaction, research on the synthesis and application of organophosphonate compounds gradually gained momentum.
From the 1950s to the 1960s, researchers focused on the synthetic exploration of β-carbonyl phosphonates. They attempted to prepare compounds with dual functional groups of carbonyl and phosphonate via the reaction between triethyl phosphite and halogenated ketones. As a typical product, diethyl (2-oxopropyl) phosphonate was first synthesized, isolated and characterized.
Early studies confirmed that it is a colorless liquid with a molecular structure containing diethyl phosphonate and acetonyl groups. Its core property is the ability to form stable carbanions under alkaline conditions, making it a potential reagent for the Wittig-Horner reaction.
From the 1970s to the 1980s, the Horner-Wadsworth-Emmons (HWE) reaction system was optimized. Owing to its high selectivity for E-alkene formation and water-soluble byproducts for easy purification, this compound was widely utilized in alkene synthesis.
In 1989, Ohira discovered that it could be converted into the Ohira-Bestmann reagent through diazotization, enabling the efficient conversion of aldehydes to alkynes and further expanding its application value. Since then, it has become a commonly used reagent in organic synthesis and medicinal chemistry, with its industrial production technology gradually maturing.
The mainstream synthesis of diethyl acetonylphosphonate is centered on the Michaelis-Arbuzov rearrangement reaction. Featuring easily accessible raw materials, simple operation and stable yield, this route serves as the primary choice for laboratory research and industrial production.
Classic Arbuzov Reaction Synthesis
Triethyl phosphite and chloroacetone are used as raw materials for one-step rearrangement synthesis. Under anhydrous, oxygen-free and inert gas protection conditions, excess triethyl phosphite (acting as the reaction solvent) is heated to 120–140 °C, followed by slow dropwise addition of chloroacetone, and the mixture is incubated for 4 to 6 hours. During the reaction, nucleophilic substitution occurs between the chlorine atom of chloroacetone and the phosphorus atom of triethyl phosphite to form a quaternary phosphonium salt intermediate, which immediately undergoes rearrangement with C–O bond cleavage, constructing a C–P bond and releasing chloroethane. After the reaction, excess triethyl phosphite and low-boiling impurities are removed by vacuum distillation, followed by high-vacuum rectification (126 °C / 9 mmHg), yielding a colorless transparent liquid product with purity ≥ 98% and a yield ranging from 75% to 85%.
Alternative Synthetic Route
For special application scenarios, the condensation method of diethyl phosphite and acetyl halide is available. Diethyl phosphite reacts with bases such as sodium hydride (NaH) or triethylamine to generate phosphide anions, which then react with chloroacetyl bromide or bromoacetyl chloride at 0–25 °C. The target product is obtained through hydrolysis, extraction and rectification. This route features mild reaction conditions yet suffers from high raw material costs and complicated post-treatment procedures, only suitable for small-batch customized synthesis. Both synthetic routes require strict anhydrous conditions to prevent raw material hydrolysis. The final product shall be stored in a sealed and light-proof environment to avoid oxidative deterioration.
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