Diethyl chlorophosphate – general description and application

Unfortunately, this article is currently only in English language. We are working on a translation. Thank you for understanding.

General description of Diethyl chlorophosphate:

Diethyl chlorophosphate [814-49-3] or diethyl phosphorochloridate is a colorless to faith yellow clear liquid with the fruity odor and the boiling point of 60 °C/2 mmHg.^[1] It acts as an cholinesterase inhibitor. It has high oral (LD₅₀ = 11 mg/kg, rat) and very high dermal toxicity (LD₅₀ = 8  μL/kg, rabbit), it is also toxic by inhalation.^[2]

This compound is typically prepared by the chlorination of diethylphosphite with carbon tetrachloride, which is called Atherton–Todd reaction.^[3] Another option of preparation is reaction of phosphoryl chloride with ethanol in the presence of triethylamine.^[4]

Application of Diethyl chlorophosphate:

By using this substance, some ketones can be converted to enol phosphates which can be reduced to alkenes/alkanes or coupled with organometallic reagents to form substituted alkenes. Following enol phosphates can be then converted into β-keto phosphonates, useful for Horner-Emmons homologation.^[5] It is also used in the synthesis of organophosphorus nerve agent mimics.^[6] Phosphoroamidate linkages are found in a large array of biologically active natural products for example Microcin C7, Dinogunellin, Phosphoarginine, Phosphocreatine, Phosphoramidon, Phosmidosine and Agrocin.^[7]

Product categorization (Chemical groups):

Main category:

• Phosphorus reagents

______________________________________________________________________________________