Dimethyl [2-oxo-3-[3-(trifluoromethyl)phenoxy]propyl]phosphonate
[CAS# 54094-19-8]

Identification

• Classification: Chemical reagent >> Organic reagent >> Phosphonate / phosphonate
• Name: Dimethyl [2-oxo-3-[3-(trifluoromethyl)phenoxy]propyl]phosphonate
• Synonyms: 1-dimethoxyphosphoryl-3-[3-(trifluoromethyl)phenoxy]propan-2-one
• Molecular Formula: C₁₂H₁₄F₃O₅P
• Molecular Weight: 326.21
• CAS Registry Number: 54094-19-8
• EC Number: 807-854-0
• SMILES: COP(=O)(CC(=O)COC1=CC=CC(=C1)C(F)(F)F)OC

Properties

• Density: 1.3±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.454, Calc.^*
• Boiling Point: 378.6±42.0 ºC (760 mmHg), Calc.^*
• Flash Point: 182.8±27.9 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319
• Precautionary Statements: P264-P264+P265-P280-P302+P352-P305+P351+P338-P321-P332+P317-P337+P317-P362+P364

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319

Discovory and Applicatios

Dimethyl [2-oxo-3-[3-(trifluoromethyl)phenoxy]propyl]phosphonate is a phosphorus-containing organic compound that has gained attention in the fields of medicinal chemistry and agrochemicals. Its unique structure, featuring a phosphonate moiety along with a trifluoromethyl phenoxy group, imparts distinct chemical properties that make it suitable for various applications. The compound was first synthesized in the late 20th century as part of broader efforts to explore phosphorus derivatives with biological activities and potential therapeutic applications.

The discovery of dimethyl [2-oxo-3-[3-(trifluoromethyl)phenoxy]propyl]phosphonate emerged from research aimed at developing novel phosphonates that could serve as intermediates in the synthesis of bioactive compounds. Researchers found that introducing a trifluoromethyl group into the phenoxy ring significantly enhanced the lipophilicity and biological activity of the resultant compounds. This modification is crucial, as it allows for improved membrane permeability and potential interactions with biological targets, increasing the compound's efficacy.

The synthesis of this phosphonate typically involves a multi-step process, starting with commercially available precursors. The key steps often include the formation of the carbonyl group, introduction of the trifluoromethyl phenoxy substituent, and subsequent phosphonation. The final product exhibits a unique combination of properties derived from both the phosphonate and the aromatic components, making it a valuable building block for further chemical transformations.

In medicinal chemistry, dimethyl [2-oxo-3-[3-(trifluoromethyl)phenoxy]propyl]phosphonate has been investigated for its potential as a prodrug or a precursor in the synthesis of more complex pharmaceutical agents. Its ability to undergo enzymatic conversion into bioactive forms enhances its profile as a candidate for drug development. Furthermore, the compound’s structure allows it to serve as a template for the design of inhibitors or modulators targeting various biological pathways, particularly those related to inflammation and cancer.

In the agricultural sector, the compound has potential applications as a pesticide or herbicide. Its ability to interact with specific enzyme systems in plants and pests makes it a candidate for developing environmentally friendly agrochemicals that target unwanted organisms while minimizing harm to beneficial species. Researchers continue to explore the structure-activity relationships of dimethyl [2-oxo-3-[3-(trifluoromethyl)phenoxy]propyl]phosphonate to enhance its effectiveness in agricultural applications.

Overall, the compound represents a significant contribution to the field of organophosphorus chemistry, showcasing the importance of phosphorus-containing compounds in drug design and agricultural science. Its distinctive structural features provide a foundation for continued research aimed at uncovering new biological activities and applications.

References

2024. A Comprehensive Exploration of the Synergistic Relationship between DMSO and Peroxide in Organic Synthesis. Topics in Current Chemistry (Cham), 72(11).
DOI: 10.1007/s41061-024-00482-9

2024. Efficient and selective oxidation of alcohols and hydrocarbons catalyzed by oxovanadium(IV) unsymmetrical salophen complex supported on silica-coated CoFe2O4 magnetic nanoparticles. Journal of the Iranian Chemical Society, 46(11).
DOI: 10.1007/s13738-024-03128-1

2024. Schiff Base-Based Molybdenum Complexes as Green Catalyst in the Epoxidation Reaction: A Minireview. Topics in Current Chemistry (Cham), 72(10).
DOI: 10.1007/s41061-024-00480-x