Diethyl chlorophosphate is an

organophosphorus compound Organophosphorus compounds are organic compounds containing phosphorus. They are used primarily in pest control as an alternative to chlorinated hydrocarbons that persist in the environment. Some organophosphorus compounds are highly effective in ...

with the formula (C₂H₅O)₂P(O)Cl. As an reagent in

organic synthesis Organic synthesis is a special branch of chemical synthesis and is concerned with the intentional construction of organic compounds. Organic molecules are often more complex than inorganic compounds, and their synthesis has developed into one o ...

, it is use the convert

alcohol Alcohol most commonly refers to: * Alcohol (chemistry), an organic compound in which a hydroxyl group is bound to a carbon atom * Alcohol (drug), an intoxicant found in alcoholic drinks Alcohol may also refer to: Chemicals * Ethanol, one of sev ...

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 Aryl, aromatic substituents. They can be conside ...

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. This increases the amount of the acetylcholine or butyrylcholine in the syn ...

, highly toxic through dermal absorption. The molecule is tetrahedral.

Synthesis and reactions

The compound is prepared by the chlorination of

diethylphosphite Diethylphosphite is the organophosphorus compound with the formula (C2H5O)2P(O)H. It is a popular reagent for generating other organophosphorus compounds, exploiting the high reactivity of the P-H bond. Diethylphosphite is a colorless liquid. The ...

with

carbon tetrachloride Carbon tetrachloride, also known by many other names (such as tetrachloromethane, also IUPAC nomenclature of inorganic chemistry, recognised by the IUPAC, carbon tet in the cleaning industry, Halon-104 in firefighting, and Refrigerant-10 in HVAC ...

(

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 pho ...

). 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 carri ...

. Controlled hydrolysis gives

tetraethyl pyrophosphate Tetraethyl pyrophosphate, abbreviated TEPP, is an organophosphate compound with the formula . It is the tetraEthyl group, ethyl derivative of pyrophosphate (P2O74-). It is a colorless oil that solidifies near room temperature. It is used as an ins ...

. 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.

References

{{reflist Ethyl esters

Synthesis and reactions

See also

References