diethyl phosphorochloridate
{{Chembox
| ImageFile =diethylchlorophosphate.svg
| ImageSize =
| ImageAlt =
| PIN = Diethyl phosphorochloridate
| OtherNames = {{ubl|Diethylchlorophosphate|Diethoxyphosphorus oxychloride|Diethyl chlorophosphate|Diethyl chlorophosphonate|Diethyl phosphorochloride|Diethoxyphosphoryl chloride|O,O-Diethyl chlorophosphate}}
|Section1={{Chembox Identifiers
| CASNo = 814-49-3
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = F1NZC04LRU
| PubChem = 13139
| SMILES = CCOP(=O)(OCC)Cl
| ChemSpiderID = 12587
| InChI = 1/C4H10ClO3P/c1-3-7-9(5,6)8-4-2/h3-4H2,1-2H3
| InChIKey = LGTLXDJOAJDFLR-UHFFFAOYAA
| StdInChI = 1S/C4H10ClO3P/c1-3-7-9(5,6)8-4-2/h3-4H2,1-2H3
| StdInChIKey = LGTLXDJOAJDFLR-UHFFFAOYSA-N
}}
|Section2={{Chembox Properties
| Formula = {{chem2|(C2H5O)2P(O)Cl}}
| C=4|H=10|Cl=1|O=3|P=1
| Appearance = colorless liquid
| Density = 1.1915 g/cm3
| MeltingPtC =
| BoilingPtC = 60
| BoilingPt_notes = (2 mm Hg)
| Solubility = }}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt = }}
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Diethyl chlorophosphate is an organophosphorus compound with the formula {{chem2|(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.{{Cite web|url=https://hazmap.nlm.nih.gov/category-details?id=4825&table=copytblagents|title=Haz-Map Category Details|website=hazmap.nlm.nih.gov|access-date=2016-07-30}} The molecule is tetrahedral.
Synthesis and reactions
The compound is prepared by the chlorination of diethylphosphite with carbon tetrachloride (Atherton–Todd reaction).{{cite journal|title=Reactions of Dialkyl Phosphites. Synthesis of Dialkyl Chlorophosphates, Tetraalkyl Pyrophosphates, and Mixed Orthophosphate Esters|author=Steinberg, Geo. M.|journal=Journal of Organic Chemistry|year=1950|volume=15|issue=3 |pages=637–47|doi=10.1021/jo01149a031}}
The compound is electrophilic. Controlled hydrolysis gives tetraethyl pyrophosphate. Alcohols react to give phosphate esters:
:{{chem2|(C2H5O)2P(O)Cl + ROH → (C2H5O)2P(O)OR + HCl}}
The reagent is routinely employed in organic synthesis for phosphorylation of carboxylates,{{cite journal|journal=Org. Synth.|title=tert-Butyl Azidoformate|author=Michael A. Insalaco |author2=D. Stanley Tarbell|year=1970|volume=50|page=9|doi=10.15227/orgsyn.050.0009}} alcohols,{{cite journal|journal=Org. Synth.|title=Preparation and Reductive Cleavage of Enol Phosphates: 5-Methylcoprost-3-ene|author=D. C. Muchmore|year=1972|volume=52|page=109|doi=10.15227/orgsyn.052.0109}} and amines.{{cite journal|journal=Org. Synth.|title=Conversion of Amines to Phospho Esters: Decyl Diethyl Phosphate|author=Nick Nikolaides |author2=Ioanna Schipor |author3=Bruce Ganem |year=1995|volume=72|page=246|doi=10.15227/orgsyn.072.0246}}
See also
- [http://www.chemicalbook.com/ChemicalProductProperty_EN_CB3161171.htm Diethyl chlorophosphate] at www.chemicalbook.com.
References
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