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diethyl phosphite
Sign in to saveAlso known as diethyl phosphonate, diethyl hydrogenphosphite, diethyl hydrogen phosphite, phosphorous acid diethyl ester, Diethylphosphite
Diethyl phosphite 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. Diethyl phosphite is a colorless liquid. The molecule is tetrahedral.
Chemical data
- Formula
- C4H11O3P
- Molecular weight
- 138.1 g/mol
- IUPAC name
- 1-ethoxyphosphonoyloxyethane
- SMILES
- CCOP(=O)OCC
- InChIKey
- MJUJXFBTEFXVKU-UHFFFAOYSA-N
- XLogP
- 0.2
- Polar surface area
- 35.5 Ų
- H-bond donors
- 0
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- chemical compound
- Has part
- hydrogen
- Mass
- 138.04458084200002
Show 3 more facts
- canonical SMILES
- CCOP(=O)OCC
- chemical formula
- C₄H₁₁O₃P
- Commons category
- Diethyl phosphonate
Sources (3)
via Wikidata · CC0
~3 min read
Encyclopedic overview
7 sectionsContents
- Synthesis and properties
- Reactions
- Hydrolysis and alcoholysis
- P-alkylation
- Hydrophosphonylation
- See also
- References
Diethyl phosphite 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. Diethyl phosphite is a colorless liquid. The molecule is tetrahedral.
==Synthesis and properties== The compound was probably prepared in the 1850s by combining phosphorus trichloride and ethanol, but intentional preparations came later. It arises as follows: PCl3 + 3 C2H5OH → (C2H5O)2P(O)H + 2 HCl + C2H5Cl Under similar conditions but in the presence of base, triethyl phosphite results: PCl3 + 3 EtOH + 3 R3N → P(OEt)3 + 3 R3NH + 3 Cl−
Excerpted from Wikipedia’s “diethyl phosphite” article, available under the CC BY-SA 4.0 licence.