Diethyl phosphorochloridate

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	814-49-3 ;
3D model (JSmol)	Interactive image;
ChemSpider	12587;
ECHA InfoCard	100.011.270
PubChem CID	13139;
UNII	F1NZC04LRU ;
CompTox Dashboard (EPA)	DTXSID4052556 ;
	InChI 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;
	SMILES CCOP(=O)(OCC)Cl;
Properties
Chemical formula	C4H10ClO3P
Molar mass	172.54 g/mol
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). Infobox references

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 + HCl

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

References

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

[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.

[1]

[2]

[3]

[4]

[5]

[6]

Synthesis and reactions

See also

References