Diethyl phosphorochloridate

Diethyl chlorophosphate is an organophosphorus compound with the formula (C₂H₅O)₂P(O)Cl. As a reagent in organic synthesis, it is used to convert alcohols to the corresponding diethylphosphate esters. It is a colorless liquid with a fruity odor. It is a corrosive, and as a cholinesterase inhibitor, highly toxic through dermal absorption.^[1] The molecule is tetrahedral.

Diethyl phosphorochloridate

Names
Preferred IUPAC name Diethyl phosphorochloridate
Other names Diethylchlorophosphate Diethoxyphosphorus oxychloride Diethyl chlorophosphate Diethyl chlorophosphonate Diethyl phosphorochloride Diethoxyphosphoryl chloride O,O-Diethyl chlorophosphate
Identifiers
CAS Number	814-49-3 Y
3D model (JSmol)	Interactive image
ChemSpider	12587
ECHA InfoCard	100.011.270
PubChem CID	13139
UNII	F1NZC04LRU Y
CompTox Dashboard (EPA)	DTXSID4052556
InChI InChI=1S/C4H10ClO3P/c1-3-7-9(5,6)8-4-2/h3-4H2,1-2H3 Key: LGTLXDJOAJDFLR-UHFFFAOYSA-N InChI=1/C4H10ClO3P/c1-3-7-9(5,6)8-4-2/h3-4H2,1-2H3 Key: LGTLXDJOAJDFLR-UHFFFAOYAA
SMILES CCOP(=O)(OCC)Cl
Properties
Chemical formula	(C2H5O)2P(O)Cl
Molar mass	172.54 g·mol−1
Appearance	colorless liquid
Density	1.1915 g/cm3
Boiling point	60 °C (140 °F; 333 K) (2 mm Hg)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Synthesis and reactions

The compound is prepared by the chlorination of diethylphosphite with carbon tetrachloride (Atherton–Todd reaction).^[2]

The compound is electrophilic. Controlled hydrolysis gives tetraethyl pyrophosphate. Alcohols react to give phosphate esters: ^[3]

(C₂H₅O)₂P(O)Cl + ROH → (C₂H₅O)₂P(O)OR + HCl

The reagent is routinely employed in organic synthesis for phosphorylation of carboxylates,^[4] alcohols,^[5] and amines.^[6]

See also

• Diethyl chlorophosphate at www.chemicalbook.com.