Diethyl phosphorochloridate explained

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.

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

See also

Notes and References

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

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