Diethyl phosphorochloridate

Last updated
Diethyl phosphorochloridate
Diethylchlorophosphate.svg
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 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
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
Appearancecolorless 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).

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.

Contents

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

  1. ↑ "Haz-Map Category Details". hazmap.nlm.nih.gov. Retrieved 2016-07-30.
  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. ↑ Young, Jonathan R. (2001). "Diethyl phosphorochloridate". E-EROS Encyclopedia of Reagents for Organic Synthesis. pp. 1–3.
  4. ↑ Michael A. Insalaco; D. Stanley Tarbell (1970). "tert-Butyl Azidoformate". Org. Synth. 50: 9. doi:10.15227/orgsyn.050.0009.
  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. ↑ 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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