Diethyl chlorophosphate is an
organophosphorus compound
Organophosphorus chemistry is the scientific study of the synthesis and properties of organophosphorus compounds, which are organic compounds containing phosphorus. They are used primarily in pest control as an alternative to chlorinated hydrocarbo ...
with the formula . As a reagent in
organic synthesis
Organic synthesis is a branch of chemical synthesis concerned with the construction of organic compounds. Organic compounds are molecules consisting of combinations of covalently-linked hydrogen, carbon, oxygen, and nitrogen atoms. Within the gen ...
, it is used to convert
alcohol
Alcohol may refer to:
Common uses
* Alcohol (chemistry), a class of compounds
* Ethanol, one of several alcohols, commonly known as alcohol in everyday life
** Alcohol (drug), intoxicant found in alcoholic beverages
** Alcoholic beverage, an alco ...
s to the corresponding diethyl
phosphate ester
In organic chemistry, organophosphates (also known as phosphate esters, or OPEs) are a class of organophosphorus compounds with the general structure , a central phosphate molecule with alkyl or aromatic substituents. They can be considered a ...
s. It is a colorless liquid with a fruity odor. It is a corrosive, and as a
cholinesterase inhibitor
Cholinesterase inhibitors (ChEIs), also known as anti-cholinesterase, are chemicals that prevent the breakdown of the neurotransmitter acetylcholine or butyrylcholine by cholinesterase. This increases the amount of the acetylcholine or butyryl ...
, highly toxic through dermal absorption. The molecule is tetrahedral.
Synthesis and reactions
The compound is prepared by the chlorination of
diethylphosphite with
carbon tetrachloride
Carbon tetrachloride, also known by many other names (such as carbon tet for short and tetrachloromethane, also IUPAC nomenclature of inorganic chemistry, recognised by the IUPAC), is a chemical compound with the chemical formula CCl4. It is a n ...
(
Atherton–Todd reaction
The Atherton-Todd reaction is a name reaction in organic chemistry, which goes back to the British chemists F. R. Atherton, H. T. Openshaw and A. R. Todd. These described the reaction for the first time in 1945 as a method of converting Dialkyl ph ...
).
The compound is
electrophilic
In chemistry, an electrophile is a chemical species that forms bonds with nucleophiles by accepting an electron pair. Because electrophiles accept electrons, they are Lewis acids. Most electrophiles are positively charged, have an atom that carr ...
. Controlled hydrolysis gives
tetraethyl pyrophosphate. Alcohols react to give phosphate esters:
:
The reagent is routinely employed in organic synthesis for phosphorylation of carboxylates, alcohols, and amines.
See also
Diethyl chlorophosphateat www.chemicalbook.com.
References
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Ethyl esters