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Diethyl phosphorochloridate

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Diethyl phosphorochloridate
Names
Preferred IUPAC name Diethyl phosphorochloridate
Other names Diethylchlorophosphate; Diethoxyphosphorus oxychloride; Diethyl chlorophosphonate; Diethyl phosphorochloride; Diethoxyphosphoryl chloride; O,O-Diethyl chlorophosphate
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.011.270 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H10ClO3P/c1-3-7-9(5,6)8-4-2/h3-4H2,1-2H3Key: LGTLXDJOAJDFLR-UHFFFAOYSA-N
  • InChI=1/C4H10ClO3P/c1-3-7-9(5,6)8-4-2/h3-4H2,1-2H3Key: LGTLXDJOAJDFLR-UHFFFAOYAA
SMILES
  • CCOP(=O)(OCC)Cl
Properties
Chemical formula C4H10ClO3P
Molar mass 172.54 g/mol
Appearance colorless liquid
Density 1.1915 g/cm
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 , 100 kPa). Infobox references
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. The molecule is tetrahedral.

Synthesis and reactions

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

The compound is electrophilic. Controlled hydrolysis gives tetraethyl pyrophosphate. Alcohols react to vie mixed phosphate esters:

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

The reagent is routinely employed in organic synthesis for phosphorylation of carboxylates, alcohols, and amines.

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: 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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