Diethyl phosphorochloridate

Chemical compound From Wikipedia, the free encyclopedia

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.

Quick facts Names, Identifiers ...
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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.011.270 Edit this at Wikidata
UNII
  • 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
  • CCOP(=O)(OCC)Cl
Properties
(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).
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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

References

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