Dimethyl (2-oxo-4-phenylbutyl)phosphonate
[CAS# 41162-19-0]

Identification

• Classification: Chemical reagent >> Organic reagent >> Phosphonate / phosphonate
• Name: Dimethyl (2-oxo-4-phenylbutyl)phosphonate
• Synonyms: 1-dimethoxyphosphoryl-4-phenylbutan-2-one
• Molecular Formula: C₁₂H₁₇O₄P
• Molecular Weight: 256.23
• CAS Registry Number: 41162-19-0
• EC Number: 682-093-3
• SMILES: COP(=O)(CC(=O)CCC1=CC=CC=C1)OC

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.494, Calc.^*
• Boiling Point: 362.7±25.0 °C (760 mmHg), Calc.^*, 120-122 °C (0.5 mmHg)
• Flash Point: 186.8±43.5 °C, Calc.^*

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H302+H332-H302-H315-H318-H332
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P354+P338-P317-P321-P330-P332+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H302
Serious eye damage	Eye Dam.	1	H318
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

Dimethyl (2-oxo-4-phenylbutyl)phosphonate is an organophosphorus compound that plays a significant role in organic synthesis, particularly in the construction of complex molecular frameworks. The compound belongs to the class of phosphonate esters, which have been widely studied for their ability to participate in carbon-carbon bond-forming reactions. The discovery of such phosphonate reagents, particularly for use in the Horner-Wadsworth-Emmons (HWE) reaction, marked a significant advancement in synthetic chemistry, enabling the efficient synthesis of alkenes and other important functional groups with high stereoselectivity.

The synthesis of dimethyl (2-oxo-4-phenylbutyl)phosphonate involves the reaction of dimethyl phosphite with 2-oxo-4-phenylbutanal or similar carbonyl compounds. The resulting phosphonate ester is characterized by the presence of a phenyl group, which imparts distinct electronic and steric properties, making it highly useful in the synthesis of various target molecules. The oxo functionality in the molecule further adds to its versatility by enabling diverse reactivity pathways.

One of the primary applications of dimethyl (2-oxo-4-phenylbutyl)phosphonate is in the field of pharmaceutical chemistry, where it serves as a key intermediate in the synthesis of bioactive molecules. Its ability to participate in olefination reactions makes it particularly valuable for building complex alkenes and related structures. The phosphonate group allows the compound to undergo the HWE reaction, forming carbon-carbon double bonds in a highly controlled manner. This makes the compound useful in the creation of drug molecules that require precise stereochemical control.

In addition to its role in pharmaceutical synthesis, dimethyl (2-oxo-4-phenylbutyl)phosphonate is also utilized in agrochemical research, where it is employed in the design of biologically active compounds for use as pesticides or herbicides. Its reactivity and functional versatility make it a valuable tool in the development of new chemicals aimed at improving agricultural productivity.

The compound’s ability to mimic phosphate groups also finds application in the study of biological processes. Phosphonate derivatives are often used to investigate enzyme interactions, particularly those involving phosphorylated substrates. By acting as phosphate analogs, compounds like dimethyl (2-oxo-4-phenylbutyl)phosphonate can be used to explore enzyme mechanisms and to develop inhibitors that target specific biochemical pathways.

References

2011. The Use of COP-OAc in the Catalyst-Controlled Syntheses of 1,3-Polyols. Synthesis.
DOI: 10.1055/s-0031-1289574

2008. A Stable Synthetic Equivalent of 2,3-Dihydropyridine. Synlett.
DOI: 10.1055/s-2008-1078056

2004. Bimatoprost. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-02-0091