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Triethyl 2-Phosphonopropionate is a chemical compound belonging to the class of organophosphorus compounds. It has the chemical formula C9H21O3P, with a molecular weight of 212.23 g/mol. This colorless to slightly yellow liquid is characterized by its distinct phosphorus-containing functional group, the phosphonate ester, which gives it unique chemical properties and applications.
Structurally, the consists of a propyl chain substituted at the 2-position with a phosphonate (PO3) group. The phosphonate group is further esterified with three ethyl (C2H5) groups. This configuration allows for versatile reactivity, making it a valuable intermediate in synthetic chemistry.
The compound is relatively stable under normal conditions but can undergo hydrolysis, leading to the formation of corresponding alcohols and phosphonic acids. It is soluble in organic solvents such as ether, esters, and ketones, but less so in water.
Due to its unique structure, it finds applications in various fields. In agriculture, it serves as a precursor for the synthesis of certain pesticides and herbicides, leveraging its biological activity. In the pharmaceutical industry, it is employed as a building block for the preparation of drugs targeting specific biochemical pathways. Additionally, its role in materials science, particularly in the synthesis of flame retardants and polymer additives, underscores its industrial significance.
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Chemical Formula |
C9H19O5P |
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Exact Mass |
238.10 |
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Molecular Weight |
238.22 |
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m/z |
238.10 (100.0%), 239.10 (9.7%), 240.10 (1.0%) |
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Elemental Analysis |
C, 45.38; H, 8.04; O, 33.58; P, 13.00 |
Wittig-Horner Reagent
It serves as a key reagent in the Wittig-Horner reaction, which is a well-known and widely utilized chemical transformation.
The Wittig-Horner reaction is particularly significant in the synthesis of acrylic acid and its derivatives. This reaction involves the condensation of aldehydes or ketones with a phosphorus-containing reagent, such as triethyl 2-phosphonopropionate, under specific conditions. The reaction typically proceeds through the formation of an intermediate, which then undergoes elimination to yield the olefinic product, in this case, acrylic acid or a related compound.
The versatility of the Wittig-Horner reaction lies in its ability to convert a wide range of aldehydes and ketones into the corresponding acrylic acids or olefins. This makes it a valuable tool in organic synthesis, especially for the preparation of compounds with specific functional groups and stereochemical configurations.
In summary, its role as a key reagent in the Wittig-Horner reaction underscores its importance in the synthesis of acrylic acid and related compounds, contributing to the diversity and complexity of organic molecules that can be synthesized through this reaction.
About Wittig-Horner reaction
The Wittig-Horner reaction is a variant of the classic Wittig reaction, used primarily for the synthesis of alkenes. It employs phosphonates, specifically α-phosphonates instead of the phosphonium ylides used in the traditional Wittig reaction. The use of phosphonates offers several advantages, including easier preparation and handling, as well as higher yields and stereoselectivity in some cases.
The phosphonate reagent is typically prepared beforehand. This reagent contains a phosphorus atom bonded to an oxygen, which is in turn bonded to an alkyl or aryl group and an ethoxy group (from triethyl phosphite).
In the presence of a base (commonly sodium hydride, NaH, or potassium tert-butoxide, t-BuOK), the phosphonate reacts with an aldehyde or ketone. The base abstracts a proton from the α-carbon of the phosphonate, forming a negatively charged intermediate, known as a ylide.
The ylide is the key intermediate in this reaction. It possesses a negative charge on the carbon atom that was originally attached to the phosphorus, and a positively polarized phosphorus atom.
The ylide then undergoes an intramolecular elimination reaction, where the negatively charged carbon atom attacks the carbonyl carbon of the aldehyde or ketone. This results in the formation of a new carbon-carbon double bond and the elimination of the ethoxy group and the corresponding alcohol (from the aldehyde or ketone). In the case of triethyl 2-phosphonopropionate reacting with formaldehyde, for example, the elimination leads to the formation of acrylic acid and triethyl phosphate as byproducts.
After the reaction is complete, the reaction mixture is typically worked up to isolate the olefinic product. This may involve quenching the reaction, extracting the product, and purifying it through techniques such as distillation or chromatography.
Significance in Synthesis
Mild Conditions
It can be performed under relatively mild conditions, which can be beneficial for heat-sensitive substrates.
Stereoselectivity
In some cases, it offers higher stereoselectivity compared to the classic Wittig reaction.
Functional Group Tolerance
It tolerates a wide range of functional groups, allowing for the synthesis of complex molecules.
Ease of Reagent Preparation
Phosphonates are generally easier to prepare and handle than phosphonium ylides.
Applications in Synthesis of Acrylic Acid and Derivatives
Polymers
They are used in the production of polymers such as polyacrylates, which are found in products like paints, adhesives, and superabsorbents.
Surfactants
Acrylic acid derivatives are used in the manufacture of surfactants for personal care products and industrial applications.
Crosslinking Agents
They serve as crosslinking agents in various materials, enhancing their mechanical properties.
By utilizing the Wittig-Horner reaction, chemists can efficiently synthesize these acrylic acid derivatives with high yields and stereoselectivity, contributing to the development of new materials and technologies.
One-Pot Chemoenzymatic Synthesis of γ-Butyrolactone:
γ-Butyrolactone is an important intermediate in the synthesis of various chemicals and pharmaceuticals. Triethyl 2-phosphonopropionate can be used in a one-pot chemoenzymatic process to synthesize γ-butyrolactone. This process combines chemical and enzymatic steps, where the phosphonate serves as a precursor for the formation of the lactone ring through a series of transformations, including phosphorylation, reduction, and lactonization.
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Enantioselective Synthesis of Spiroindanedicarboxylic Acid by Asymmetric Hydrogenation:
The phosphonate group is critical as it can influence the stereoselectivity of subsequent reactions, particularly asymmetric hydrogenation.
Prior to asymmetric hydrogenation, it may undergo a series of chemical transformations to incorporate the spiroindane scaffold and the carboxylic acid functionalities. These transformations could include arylation, condensation, and esterification reactions.
For asymmetric hydrogenation, a chiral catalyst is essential. This catalyst can be a rhodium, ruthenium, or iridium complex ligated with a chiral ligand, such as a diphosphine or a monodentate phosphoramidite. The phosphonate moiety attached to the substrate can interact with the chiral catalyst, potentially guiding the stereoselective reduction of the olefin or other unsaturated bond present in the precursor. This interaction helps in achieving high enantioselectivity, favoring the formation of one enantiomer of the spiroindanedicarboxylic acid over the other.
Stereoselective Intramolecular Diels-Alder Reaction:
The phosphonate group in triethyl 2-phosphonopropionate can stabilize either the dienophile or the diene component of the reaction. This stabilization typically arises from electronic effects, where the negative charge density on the oxygen atoms of the phosphonate can influence the electronic properties of adjacent carbon-carbon double bonds.
Intramolecular reactions inherently provide better control over stereoselectivity compared to intermolecular reactions, as the reactants are covalently tethered. This proximity reduces the entropy cost associated with bringing the reactants together and can favor the formation of a single stereoisomer. The ability to form six-membered rings intramolecularly allows for the construction of complex molecular architectures where the new ring is integrated seamlessly into the existing molecular framework.
In some cases, the reaction can be catalyzed by Lewis acids, which can further enhance the stereoselectivity by coordinating to the phosphonate group and modulating the electronic properties of the reacting moieties. The Diels-Alder reaction generally proceeds under mild conditions, making it compatible with a wide range of functional groups and sensitive substrates.
Products Description
Triethyl-2-Phosphatopropionate (CAS number 3699-66-9) is an organic phosphorus compound commonly used in organic synthesis reactions (such as Horner Wadsworth Emmons reaction, Diels Alder reaction, etc.) and the preparation of pesticides and pharmaceutical intermediates.
Acute toxic reaction
Oral toxicity
Animal experiments have shown that Triethyl 2-phosphanopropionate has significant oral toxicity. Consuming less than 150 grams may be fatal or cause serious harm to health. The toxic mechanism may be related to the inhibitory effect of organic phosphorus compounds on acetylcholinesterase, leading to the accumulation of acetylcholine in the synaptic cleft and causing cholinergic hyperfunction, manifested as gastrointestinal symptoms such as nausea, vomiting, abdominal pain, diarrhea, and in severe cases, respiratory failure, circulatory failure, and even death.
Inhalation toxicity
Inhaling its vapor or aerosol may cause respiratory irritation, symptoms including coughing, difficulty breathing, chest tightness, etc. High concentration exposure may lead to chemical pneumonitis or pulmonary edema, especially in enclosed spaces or poorly ventilated environments where the risk is higher. At present, there is no clear data on the lethal dose of human inhalation, but animal experiments have shown that its toxic effects are positively correlated with concentration and exposure time.
Skin and eye contact
Skin irritation: Direct contact may cause skin redness, itching, rash, and even chemical burns. Long term or repeated exposure may lead to contact dermatitis, characterized by dry, cracked, and flaky skin.
Eye irritation: Splashing into the eyes can cause severe irritation, manifested as eye pain, tearing, photophobia, conjunctival congestion, and even corneal damage. If not rinsed in a timely manner, there may be residual effects such as visual impairment.
Chronic and Long term Health Risks
Central nervous system inhibition
Long term or repeated exposure may lead to central nervous system dysfunction, manifested as headaches, dizziness, fatigue, drowsiness, and lack of concentration. High dose exposure may cause coma, convulsions, and even respiratory center paralysis. The mechanism may be related to the interference of organic phosphorus compounds on the neurotransmitter system.
Environmental and ecological toxicity
Triethyl 2-phosphanopropionate may be degraded in the environment through hydrolysis, photolysis, and other pathways, but the degradation products (such as phosphine, carbon monoxide, phosphorus oxides, etc.) may be toxic or irritating. If discharged in large quantities into water bodies or soil, it may have toxic effects on aquatic organisms (such as fish and algae) and soil microorganisms, disrupting ecological balance.
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