Dimethyl 3-(3-chlorophenoxy)-2-oxopropylphosphonate
[CAS# 40665-94-9]

Identification

• Classification: Chemical reagent >> Organic reagent >> Phosphonate / phosphonate
• Name: Dimethyl 3-(3-chlorophenoxy)-2-oxopropylphosphonate
• Synonyms: 1-(3-chlorophenoxy)-3-dimethoxyphosphorylpropan-2-one
• Molecular Formula: C₁₁H₁₄ClO₅P
• Molecular Weight: 292.65
• CAS Registry Number: 40665-94-9
• EC Number: 620-947-9
• SMILES: COP(=O)(CC(=O)COC1=CC(=CC=C1)Cl)OC

Properties

• Density: 1.3±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.504, Calc.^*
• Boiling Point: 400.1±30.0 ºC (760 mmHg), Calc.^*
• Flash Point: 303.5±32.2 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319

Discovory and Applicatios

Dimethyl 3-(3-chlorophenoxy)-2-oxopropylphosphonate is a phosphonate derivative utilized in organic synthesis, particularly in reactions requiring the formation of carbon-carbon bonds. The compound belongs to a class of organophosphorus compounds that are versatile intermediates in chemical synthesis. The development of such phosphonates originated from research into the Horner-Wadsworth-Emmons (HWE) reaction, a widely-used method for synthesizing alkenes from carbonyl compounds. The discovery and optimization of these phosphonate reagents significantly advanced the field of stereoselective synthesis.

Dimethyl 3-(3-chlorophenoxy)-2-oxopropylphosphonate is typically synthesized via a nucleophilic substitution reaction between dimethyl phosphite and 3-(3-chlorophenoxy)-2-oxopropanal. The product contains a chlorophenoxy group attached to a phosphonate ester, providing both nucleophilic and electrophilic centers in the molecule. This makes the compound highly reactive and suitable for further chemical transformations in complex synthetic pathways.

In synthetic organic chemistry, dimethyl 3-(3-chlorophenoxy)-2-oxopropylphosphonate is widely used as a reagent in olefination reactions. Its phosphonate group is critical for these reactions, allowing it to form carbon-carbon double bonds, which are crucial in constructing complex molecular structures. The introduction of the 3-chlorophenoxy group provides added versatility, as it can influence the electronic properties and reactivity of the molecule. This makes it a valuable intermediate in the synthesis of pharmaceutical compounds, agrochemicals, and other fine chemicals.

One of the significant applications of dimethyl 3-(3-chlorophenoxy)-2-oxopropylphosphonate is in the pharmaceutical industry. Its ability to participate in stereoselective reactions makes it an essential building block for synthesizing biologically active molecules, where controlling the stereochemistry is crucial for biological efficacy. Additionally, the compound’s chlorophenoxy group can serve as a functional handle for further derivatization, allowing for fine-tuning of the physicochemical properties of the target molecules.

In addition to its role in olefination, the compound is explored in medicinal chemistry as a phosphate mimic. Phosphonate analogs like dimethyl 3-(3-chlorophenoxy)-2-oxopropylphosphonate can interact with enzymes that bind phosphate-containing substrates, making it useful in designing enzyme inhibitors and studying biochemical pathways.

References

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2024. 9-oxa prostaglandin analogs as ocular hypotensives. WO-9857942-A1, Priority Date: 18-Jun-1997.