Triethyl phosphonoacetate

Triethyl phosphonoacetate is an organophosphorus compound with the chemical formula C_8H_17O_3P. It is used primarily in organic synthesis as a Horner-Wadsworth-Emmons reagent, facilitating the formation of carbon-carbon double bonds adjacent to carbonyl groups. This compound plays a crucial role in the synthesis of various alkenes, making it a valuable reagent in the field of organic chemistry, particularly in the synthesis of vitamins, hormones, and pharmaceuticals.

Properties

Triethyl phosphonoacetate is a colorless liquid at room temperature, with a boiling point of 215-216 °C and a density of 1.069 g/cm^3. It is slightly soluble in water but highly soluble in organic solvents such as ethanol, diethyl ether, and chloroform. Its molecular weight is 194.20 g/mol.

Synthesis

The compound is typically synthesized through the Michaelis-Arbuzov reaction, where triethyl phosphite reacts with ethyl bromoacetate in the presence of a base. This reaction produces triethyl phosphonoacetate along with the by-product, bromide ion.

Applications

Triethyl phosphonoacetate is widely used in organic synthesis, particularly in the Horner-Wadsworth-Emmons (HWE) reaction. The HWE reaction is an important method for the synthesis of alkenes, allowing for the formation of carbon-carbon double bonds in a controlled and efficient manner. This reagent is especially useful in the synthesis of compounds with specific stereochemistry, as it can be used to create both E and Z isomers of alkenes.

In addition to its use in the HWE reaction, triethyl phosphonoacetate is also employed in the synthesis of phosphonates, which are important intermediates in the production of various organic compounds, including pharmaceuticals and agrochemicals.

Safety

Triethyl phosphonoacetate should be handled with care, as it is a flammable liquid and can cause irritation to the skin and eyes. Appropriate safety measures, including the use of personal protective equipment (PPE) such as gloves and goggles, should be taken when handling this chemical. It should be stored in a cool, dry place, away from sources of ignition.

See Also

• Organophosphorus compound
• Michaelis-Arbuzov reaction
• Horner-Wadsworth-Emmons reaction
• Alkene synthesis