Diethyl chlorophosphate – general description and application
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. 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.
This compound is typically prepared by the chlorination of diethylphosphite with carbon tetrachloride, which is called Atherton–Todd reaction. Another option of preparation is reaction of phosphoryl chloride with ethanol in the presence of triethylamine.
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. It is also used in the synthesis of organophosphorus nerve agent mimics. Phosphoroamidate linkages are found in a large array of biologically active natural products for example Microcin C7, Dinogunellin, Phosphoarginine, Phosphocreatine, Phosphoramidon, Phosmidosine and Agrocin.
Product categorization (Chemical groups):
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