Diethyl_chlorophosphate

Diethyl phosphorochloridate

Diethyl phosphorochloridate

Chemical compound

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.

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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 vie mixed 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

  1. [1]
    "Haz-Map Category Details". hazmap.nlm.nih.gov. Retrieved 2016-07-30.
  2. [2]
    Steinberg, Geo. M. (1950). "Reactions of Dialkyl Phosphites. Synthesis of Dialkyl Chlorophosphates, Tetraalkyl Pyrophosphates, and Mixed Orthophosphate Esters". Journal of Organic Chemistry. 15 (3): 637–47. doi:10.1021/jo01149a031.
  3. [3]
    Young, Jonathan R. (2001). "Diethyl phosphorochloridate". E-EROS Encyclopedia of Reagents for Organic Synthesis: 1–3.
  4. [4]
    Michael A. Insalaco; D. Stanley Tarbell (1970). "tert-Butyl Azidoformate". Org. Synth. 50: 9. doi:10.15227/orgsyn.050.0009.
  5. [5]
    D. C. Muchmore (1972). "Preparation and Reductive Cleavage of Enol Phosphates: 5-Methylcoprost-3-ene". Org. Synth. 52: 109. doi:10.15227/orgsyn.052.0109.
  6. [6]
    Nick Nikolaides; Ioanna Schipor; Bruce Ganem (1995). "Conversion of Amines to Phospho Esters: Decyl Diethyl Phosphate". Org. Synth. 72: 246. doi:10.15227/orgsyn.072.0246.
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