Triethyl phosphonoacetate is a reagent for organic synthesis used in the Horner-Wadsworth-Emmons reaction (HWE) or the Horner-Emmons modification.
Triethyl phosphonoacetate can be added dropwise to sodium methoxide solution to prepare a phosphonate ylide. It has an acidic proton that can easily be abstracted by a weak base. When used in an HWE reaction with a carbonyl the resulting alkene formed is usually the E alkene, and is generated with excellent regioselectivity.
| Name | Triethyl Phosphonoacetate | EINECS | 212-757-6 |
| CAS No. | 867-13-0 | Density | 1.13 g/cm3 |
| PSA | 71.64000 | LogP | 1.81560 |
| Solubility | Slightly miscible with water. | Melting Point | -24 °C
|
| Formula | C8H17O5P | Boiling Point | 287.4 °C at 760 mmHg |
| Molecular Weight | 224.194 | Flash Point | 141.6 °C |
| Transport Information | UN 3082 9/PG 3 | Appearance | colorless to light yellow liquid |
Appearance and properties: colorless and light yellow transparent liquid
Density: 1.13 g/mL at 25 °C(lit.)
Boiling point: 142-145 °C9 mm Hg(lit.)
Melting point: -24°C
Flash point: 165°C
Refractive index: n20/D 1.431(lit.)
Stability: Stable under normal temperatures and pressures.
Storage conditions: Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.
Usage
It can be used as a plasticizer, fire retardant and extractant, etc., and is also an important intermediate for the manufacture of natural compounds such as vitamin compounds, drugs, and insect pheromones.
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